My wife and I got to experience this beautiful property courtesy of our AMEX free weekend night certificates. Unfortunately, the American Express Hilton Honors Ascend Card no longer has this benefit on the cardmember anniversary. You have to spend $15,000 in a given year to get the free night, and I don’t think it’s worth forgoing points with Chase or AMEX Platinum/Gold to pursue a free night with Hilton in most instances. Since my wife and I have the AMEX Hilton Honors Ascend Card, we combined our free nights into a weekend stay. The nightly rate for our room was $450, so we got $900 worth of value plus $50 credit toward dining for the annual fee we paid for both cards ($95 per card).
Check-In
Walking into the hotel, take the elevator to the third floor. There is no second floor; the third floor is where the check-in desk, lounge, restaurant, and lobby are located. Upon checking in, the receptionist verified our Hilton Gold status, courtesy of the AMEX card, and upgraded us to a room on the 9th floor. We could choose 1,000 Hilton points or a $50 dining credit as Hilton Gold members. We took the dining credit (I don’t recommend taking the points in this scenario). The receptionist was kind enough to give us a mini-tour of the hotel, Estuary restaurant, and some of the amenities this hotel offers.
The circular lamp changes color each hour.
My first impression when walking in was that this hotel did not have many 90-degree angles. The architect made a concerted effort to make the interior as curvy as possible. The lobby was beautiful, and since the hotel was only 45 days old when we stayed, it still had that brand-new scent.
Looking down from the 10th floor to the lobby below.
Room
Our room was on the 9th floor, with a nice view of New York Street below. Keeping up with the theme, the room was curvy but spacious and very comfortable.
Coffee and snacks
As an avid coffee drinker, I always appreciate it when a hotel provides a Keurig-type machine with pods. The coffee was complimentary, per usual, but the snacks were completely overpriced. If you need snacks, there is a CVS across the street where you can get the same offerings for 1/4 of the price.
The bathroom provided two sinks and a separate blurred door to the toilet so two people could use the bathroom simultaneously while still having some privacy.
The toiletries were Shanghai Tang, and the scent was very nice—not too overpowering but not too light either. The room also provided slippers, a safe, laundry bag, iron, and bathrobes.
Estuary and Estuary Bar
Estuary is the restaurant on the premises on the 3rd floor. We went there for breakfast on Saturday morning and ordered a custom-made omelet and buttermilk pancakes. Both were delicious, albeit smaller in portion than your typical brunch diner.
The Estuary Bar area was spacious, and seating was plentiful during the day. If an event is going on at the hotel, it’ll likely get packed in the evening and into the late night.
Third Floor Terrace and Rooftop Bar
Since the hotel was only 45 days old during our stay, the Rooftop Bar was not officially open to guests, so I could only take pictures from behind the glass door. The 3rd-floor terrace was open for use.
View from the Rooftop BarThe Terrace on the 3rd-floor
Fitness Center
The fitness center was one of the better ones I had seen at a hotel. Upon entering, guests are greeted with towels, earphones, and apples.
There are multiple treadmills, elliptical machines, and stationary bikesIf you’re into lifting, they have that covered as well.
Concluding Thoughts
Although I forgot to measure the internet speed, I had no speed or Wi-Fi connectivity issues. If you plan to park your car at the Conrad, parking in their garage is $36 a day. I used the ParkWhiz app and found a garage two blocks away, allowing me to park for $14. There is also metered parking on the street, but it has a three-hour time limit during business hours and is free overnight. One of the most appealing aspects of staying at Conrad DC is that the National Mall, White House, Capitol building, Smithsonian, and many other points of interest are only 10-15 minutes away by walking. I also want to acknowledge the receptionists on the 3rd floor who always gave us complimentary bottles of water whenever we walked by. The staff made an excellent stay that much better.
We had a layover in Boston during a recent trip from NYC to Chicago, so we decided to stop by The Lounge at Logan International Airport. It was rather convenient since we would depart from Terminal C, the same terminal where The Lounge is situated. This lounge is part of the Priority Pass network but also serves as a business class lounge for Aer Lingus and TAP Portugal as they depart from Terminal C. I didn’t have any issues getting in since it wasn’t full. Still, I have heard of incidents where Priority Pass cardholders were denied access when The Lounge expected a large influx of business class travelers flying on Aer Lingus or TAP Portugal. Since it is the only lounge in Terminal C, hours between 4 p.m.-8 p.m. are not sure for Priority Pass card holders.
Receptionist Desk at The Lounge
Upon entering, I showed my Priority Pass card, and the receptionist scanned it and told my wife and me we were good to go. The lounge was 3/4 full and filling up when we entered, which is unsurprising considering that we arrived on a Friday at 6 p.m.
If you’re a business traveler who needs a plug outlet, I highly recommend going to the back of the lounge. There, you’ll find outlets and a semi-partition that will give you privacy.
Once we got situated, I went to see the food offerings. I wasn’t hungry, but for the sake of the review, I helped myself with small portions of a few things. They had pasta salad, hummus with pita, a veggie sandwich that consisted of cream cheese and cucumbers, vegetables, salad, soup (clam chowder), and snacks. The pasta salad was ok but nothing special. The hummus was decent and might have been the best item they had out there. The veggie sandwich was simple but surprisingly not terrible. I didn’t have the turkey sandwich, so the jury is out. It seems like their benchmark was just good enough not to be bad. The refrigerator had no shortage of cold drinks, though. That was a big plus.
I don’t partake in drinking alcohol, but for those of you who do, the bar looked like it was stocked pretty well.
Bar area
My biggest gripe during my time here was this lounge’s lack of dedicated WiFi. You are forced to use Logan’s public WiFi, and the speed is painfully slow. It’s certainly not business traveler-friendly. The bathrooms were clean, which was a nice plus. I would rate this place a 3.2/5. If you happen to be in Terminal C, being at this lounge would still be sitting in the gate area. However, if you’re departing from a different terminal, I would not recommend visiting Terminal C just to visit this lounge.
Maui was the first of two islands my wife and I visited during this trip to Hawaii. The second island we visited was Kauai, which you can read about here. Our last trip to Hawaii (Feb 2019) covered The Big Island, and if you are interested in reading about our time there, you can do so here. Maui, also known as the Valley Isle, is the second largest island in Hawaii and has endless beauty. Our three days didn’t cover everything, but it covered most of the main attractions. We had seven days in Hawaii (the first day was more like a half day), three of which we spent in Maui and four in Kauai. The question a lot of people ask is if 3 days is enough to see most of the main sights in Maui. It was enough for us for two reasons: First, we woke up at dawn and started our day early. This is absolutely crucial. It’ll be difficult if you’re not in your car by 8 a.m. daily. The weather was the second thing out of our control, but it worked in our favor. We had sunshine all 3 days, and that’s just us gambling on great weather for 3 days and getting lucky. Ideally, you want to have one or two extra days as a buffer for rain.
How We Got There
You’ll probably notice a trend with just about every itinerary I post. We rarely use cash to reach our destination, and this trip was no different. Remember that my wife and I have schedules that mostly allow us to take these trips during peak travel season. This trip to Hawaii happened to be during the last 9 days of December, which is high season in Hawaii. Likewise, the number of miles airlines require to get to Hawaii is double that of most cities. United usually charges 22.5k miles a person one-way to get to Maui. That redemption rate from Chicago, Newark, and D.C. was 45k miles per person one-way. Fortunately, Denver still had the saver award redemption at 22.5k miles, so we decided to spend two days there (we had never visited Denver) and depart to Maui from Denver International Airport.
Arrival
Even though this was technically our first day, we arrived too late to do anything significant. Our flight to Maui arrived at 4:35 p.m., and by the time we deplaned, got our bags, and picked up our rental car, it was close to 5:45pm. At this point, we only had about 15 minutes of daylight left. We checked into our hotel, the Napili Shores by Outrigger, ate an early dinner, and decided to sleep at 8pm. The next day was going to be very long.
Day One: Haleakala National Park & Papawai Scenic Lookout
If you’re visiting Maui, you simply can’t leave without witnessing the sunrise at Haleakala National Park. It can’t be replicated elsewhere, and it’s magical. The ideal day is when a layer of clouds below you allows the sun to rise above that layer. Sometimes, it can get cloudy enough that there is little to no visibility, and that’s the type of day you want to avoid. Your best bet is to keep an eye on the weather. You must pay $25 per car at the entrance and make a reservation for $1.50 if you go there at sunrise. The ticket for the sunrise is valid for three days and can be purchased up to 60 days in advance. My wife and I got there 2 hours before sunrise to ensure a good parking spot. You should aim to get there no later than an hour before sunrise, or the desirable parking spots and viewing areas will fill up quickly. It’s a relatively slow 45-minute with steep curves and hairpin turns after hairpin turns. It requires your full attention, and if you’re the type that gets distracted by a cell phone easily while driving, turn it off until you’re at the top. If you run into fog, it can get a little challenging, but fortunately for us, it was clear all the way through during our drive to the top.
View of the sunrise at Haleakala National Park
A few important things to keep in mind. When you’re at the viewpoint, you are at an elevation of about 10,000 feet. Not only is it cold, it is very windy! You will need a warm jacket and ear covers, or it won’t be pleasant. The air is obviously much thinner, so If you’re sensitive to elevation or have had trouble breathing in elevation before, please reconsider. Once you’re done with the sunrise, you can stop at other viewpoints on the way down. There are fantastic picture opportunities of the surrounding craters and landscape.
View of the craters from one of the scenic lookouts on the way down
Papawai Scenic Lookout
On our way back to Lahaina, we decided to stop at the Papawai Scenic Lookout. Locals recommended this spot as a great place to watch whales from the land. During the winter months, mother humpback whales will birth their calves and teach them essential behaviors in the waters of Maui. It took a little patience, but it paid off, and we got a show of a lifetime. About 15 minutes after arriving, we noticed a water mist sprayed about a quarter mile offshore. And there it was, a baby humpback whale under the watchful eye of its mother practicing breaching behaviors. At first, the calf needed some support to breach halfway.
This was as far as the calf could go the first few times.
After about eight attempts to get halfway up, it completely breached the water. I kept my camera in rapid-fire mode and was fortunate to capture a memorable moment.
The lookout provides excellent photo opportunities even if you don’t see whales.
At night, we walked around Lahaina Town and stumbled upon one of the best ice cream shaves we ever had. It’s called Ululani’s Hawaiian Ice Shave, and they have over 50 flavors. I had the ‘Haleakala,’ a coconut, leche, and condensed milk mix. I wish I had taken a picture to post here, but I guarantee you’ll find whatever you want.
Day Two: Road to Hana
Along with Haleakala National Park, the Road to Hana is another excursion you simply cannot leave Maui without experiencing. It has black sand beaches, waterfalls, bamboo forests, flower gardens, and breathtaking ocean views, and it was one of the highlights of our stay in Hawaii. The Road to Hana from start to finish is about 52 miles. It is a journey that will take most of the day if you factor in the time you will stop at various stopping points. There are over 600 hairpin turns and 54 bridges (46 of which are one-lane), and you will have to concentrate while driving as the roads can get very narrow at certain points. My wife and I had a rental car, so if there were certain stop points we liked better, we could spend more time. You can take a tour bus, but then you’re on their time. If you are driving there, fill up your tank before you start. The last town before starting this journey is Paia, and the gas prices there are high. You’re better off filling up in Kahului. There no gas stations between Paia and Hana. If you are driving yourself, I highly recommend downloading Gypsy Guide – Road to Hana on your iPhone or Android.
It cost me $5, the best $5 I have ever spent on a narration app. The app will recommend which points of interest are worth stopping for, which don’t require much time, and which should be skipped altogether. It felt like we had an actual person with us, and the app even told us about approaching food shacks and cafes. The great thing about this app is that it worked even when we lost data connectivity. On the way back, the app tells you more about the cultural significance of different points in Maui. These are the places we stopped in chronological order:
1. Garden of Eden Arboretum
This is one of the only points of interest on the Road to Hana, where you have to pay to get in since it is privately owned. The cost is $15 for adults, $5 for children, and infants are free. They do offer student and AAA discounts. My wife and I found it worth it, and you can budget about 30 minutes here. They have numerous native and indigenous plants, many of which you might have never seen, and they also offer some great photo opportunities. The garden also has a smaller waterfall, and you’ll see peacocks on the premises.
Garden of Eden Arboretum
2. Waikamoi Ridge Trail
This was a hike that really stimulated your senses. The best thing about this trail? There are mango trees all around, and it smells like heaven. They also have one of my favorite trees, the rainbow eucalyptus tree, which looks like the bark has been colored by a pastel. The trail can get extremely muddy, so if you’re wearing flip-flops or don’t want to get your shoes destroyed, it wouldn’t be a bad idea to skip this and spend more time at Twin Falls (which we skipped).
This fruit looks like pineapple, but it is not.
Rainbow-eucalyptus tree
3. Halfway to Hana Stand
They’re known for their banana nut bread, which is delicious. I wouldn’t recommend stopping here if it wasn’t worth the hype. It won’t take long, and you can park on the side of the road.
4. Upper Waikani Falls
There is only room for a couple of cars on the side of the road to see this trio of waterfalls, but they are undoubtedly beautiful and worth stopping at if parking is available.
4. Nahiku Market Place
Two words: fish tacos. This was the perfect place to have lunch. The fish tacos were super fresh and delicious. I wish I had a picture, but I inhaled them before realizing I’d forgotten.
5. Wai’anapanapa State Park
This is one of the places where you absolutely have to stop. It is a beautiful black sand beach with an abundance of volcanic rock. There is also a cave that takes you to the waters, where you can go for a swim. The waves are powerful, so keep that in mind. We spent a solid hour here and honestly wished we could have spent more. As of 2022, you must reserve a time to visit this beach.
Black sand beach and volcanic rocks
There’s a story behind this cave, but I won’t ruin it. Download the app above, and it will tell you all about it
6. Wailua Falls
Another point of interest that you should definitely stop by is that you can park on the side of the road and walk down to the base of the falls. I even saw a few people swimming near the base who seemed comfortable doing so. I don’t know how deep it is, so please be cautious if you go in the water. It’s a beautiful waterfall and probably the largest one on The Road to Hana.
7. Oheo Gulch (7 Sacred Pools)
This was our last stop on The Road to Hana. Unfortunately, due to mudslides, access to these pools was closed during our visit to Maui. We could see some of the falls from the trail, but no one was allowed to swim at the base. Oheo Gulch is located 15 minutes past the town of Hana. Here are significant details to keep in mind. If you go beyond this point in your rental car and if something terrible were to occur, your insurance becomes void! Even your credit card coverage would be voided.  The road beyond this point is mostly gravel and dirt; the major rental companies have written this out explicitly in the contract agreement. Many tourists will risk it because some beautiful sites exist beyond Oheo Gulch. But even something as minuscule as a flight tire means you’re alone.
Oheo Gulch
Day Three: Napili Bay
Maui has plenty of amazing beaches where you can spend your day. You can even go beach hopping and taste almost all of them. Since our hotel was at Napili Bay, we decided to spend the day on the beach. This was an excellent spot for snorkeling and seeing marine wildlife. I saw plenty of colorful fish and was lucky enough to see a few sea turtles, one of which was getting by with a missing flipper. You can see the video below.
You can see me snorkeling in the distance with the island of Moloka’i in the background.
If you are in the Lahaina area, I recommend stopping by Gazebo Restaurant for breakfast. Their white chocolate macadamia nut pancakes with homemade whipped cream were terrific, and they were also very generous with their portions.
So, this was Maui for us in a nutshell. We wish we could have stayed longer, but that meant subtracting a day from Kauai. We felt pretty satisfied with our three days here (excluding travel) and thought we accomplished almost everything we wanted to achieve. If you continue reading about Kauai or the Big Island, scroll to the top of this page, and you will find the links. Thank you for reading.
It had been a while since I used an award redemption for a first class ticket on a domestic route. I wasn’t really left with much of a choice since I needed to get home to Chicago and I had the following options if I wanted to book with American Airlines:
Spend $381 for a one-way ticket in economy
Spend $511 for a one-way ticket in first class
Use 25k American Advantage miles to book in economy
Use 12.5k British Airways Avios (transferrable from Chase or AMEX) to book in first class
Given the options above, using British Airways Avios to book first class on this flight was a no-brainer. Had economy tickets been available for redemption using B.A., it would have only cost 7.5k miles. For whatever reason, American didn’t make economy seats available to British Airways. Still, this is a great redemption and one which I’m getting greater than 4 cents per point. As I’ve mentioned before, this is one of the sweet spots when using BA to book on American.
My flight was on an Embraer-175 regional jet operated by Envoy Air, one of American Airlines’ regional partners. Generally speaking, people will roll their eyes when they hear their flight is on a regional jet as opposed to a mainline aircraft. This is especially true when flying in economy. In a surprising twist, I found the first class cabin to be more comfortable in the E-175 relative to a Boeing 737 or Airbus A320/321. One big advantage with the E-175 if you’re flying solo is the left side of the plane in first class is configured with only a single seat. You get to look out the window and not have to worry about asking people to move if you have to use the lavatory. The right side of the plane has the traditional two adjacent seats.
The seat was spacious and comfortable and since I was fortunate enough to have seat 1A, I had more leg room than I needed to stretch out.
There are only a few routes such as Dallas to Chicago where American Airlines will serve a full dinner on their regional jets for flights under 900 miles. Since we were under that threshold, I was served a snack box with hummus, pita chips, and Fannie May chocolate (Chicago folks are familiar with this).
The hummus and pita chips were decent, certainly better than the normal mini-pretzel bag served in economy. The flight attendants came by multiple times during the two-hour flight to ask if I wanted anything to drink so they were certainly attentive. If you’re a T-Mobile customer, don’t forget that you get an hour of free wifi on American Airlines when flying within the U.S. and Canada. You are also able to text throughout the flight for free by turning on your wifi calling.
American Airlines serves 3-course meals on all first-class flights over 900 miles. They have certain routes under 900 miles where they will still serve a 3-course meal in first class.
If you find yourself booking between Chicago and any of the cities above, you would get enhanced value with the 12.5k Avios redemption for first class because dinner is included. Since BA has a distance based award chart, you can travel as far 1,150 miles from your departure city to get the 12.5k redemption in first class.
One of my friends asked me a pretty good question regarding Ultimate Rewards point transfers into partner programs: Which one should he avoid? While I’ve gone through many of the transfer partners that provide excellent value, I haven’t really addressed the transfer partners or scenarios that provide poor value and thus should be avoided. There are also certain situations where even a good frequent flyer program won’t provide good value if you transfer Ultimate Rewards points into the program. At the very least, you want to get a value of 1.25 cents per point if you’re using the Chase Sapphire Preferred (CSP) and 1.5 cents per point if you’re using the Chase Sapphire Reserve (CSR). How did I arrive at those numbers? If you book through Chase’s UR portal, that’s how much value you would get. For example, by booking a flight using the Chase Ultimate Rewards portal, a ticket worth $150 will require 10,000 UR points if you have the CSR. $150/10,000 = 1.5 cents per points. That same ticket would require 12,000 UR points if you have the CSP $150/12,000 = 1.25 cents per point. Here is what you should do to ensure you get the best value using your points: Make a comparison of the number of UR points required if you were to book through the Chase portal, the number of points required if you were to book through the hotel or frequent flyer program, and the dollar amount required if you were to pay with cash. For certain programs, the answer will be obvious and you will get a clear idea of what not to do. For others, there might be a tie and you won’t come out on the losing end either way. Let’s take a look at some transfer partners and see what type of value they might provide…
IHG
I’m going to use IHG hotels, the least valuable of all transfer partners in my opinion, as the first example. Ultimate Rewards points can be transferred into IHG on a 1:1 transfer ratio in increments of 1,000. Among the brands that are under the IHG umbrella are Holiday Inn, Intercontinental, Indigo, Kimpton, and Candlewood Suites. Let’s say you wanted to stay in Downtown Chicago between June 29th and July 1st at the Intercontinental Hotel on Michigan Avenue….
This would cost $233 a night. If you were to book as a CSR card holder straight through the Ultimate Rewards portal…..
A good redemption of just over 16k points a night. This is a value of 1.5 cents per point and the litmus test you should use if you’re a CSR card holder booking through Chase. Last but not least, let’s see how many points you would have to transfer into IHG’s program from Chase if you were to use their loyalty program to book this hotel:
A ridiculous 50,000 points per night, meaning you’d have to transfer a total of 150k UR points for 3 nights. If you’re reading this, please don’t ever transfer 150,000 Ultimate Rewards points to make a booking like this in which you’re getting absolutely ripped off. If you do the math, $233/50,000 = 0.4 cents per point. You read that right. You’re getting less than a penny per point value if you transfer 150,000 UR points to book 3 nights at the Intercontinental Chicago on Michigan Avenue when the cash price is $233 per night. It’s unfortunate but these types of redemptions are the norm when using IHG points to book hotel stays. This particular redemption is so bad, you would be better off exchanging 69,900 UR points for $699 cash and then using the cash to book the 3 nights at the hotel. For this scenario, we would book straight through the Chase portal at just over 16k points per night. The only scenario you should consider transferring Ultimate Rewards points into IHG is if you need to top off your account and you’re just 5k or fewer points away from getting an award night at a higher redemption level. For example, if you’re at 29k IHG points and 30k would get you an award night, go ahead and transfer that 1k from Chase. The more you need to transfer, the more you’re losing value.
Marriott
Another transfer partner which provides terrible value when transferring points from Chase Ultimate Rewards is Marriott. Ultimate Rewards points can be transferred into Marriott on a 1:1 ratio in increments of 1,000. Don’t get me wrong, they have a very nice portfolio of properties which include upscale brands such J.W. Marriott and Ritz Carlton. But when you’re redeeming points, it’s all about getting maximum value and getting the most for your redemptions. Let’s say you wanted to stay in the Miami area from March 29th-March 31st in a location close to the airport:
The TownPlace Suites would cost $175/night or a ridiculous 50k Marriott points per night for a total of 150k points. This redemption is even worse than the one we saw above. Please do not, and I repeat do not transfer 150,000 UR points for this type of redemption. $175/50,000 = 0.35 cents per point redemption (lol). To put it into perspective, 60k UR points when transferred into United can get you a round-trip ticket to Europe. 60k UR points when transferred into FlyingBlue can get you two round-trip tickets to Hawaii. If you were to book straight from the Chase portal…..
A far more palatable redemption of nearly 12k per night, giving you the baseline value of 1.5 cents per point if you were a CSR credit card holder. If you carried the CSP instead, your redemption would require approximately 14,300 points per night for a value of 1.2 cents per point. In this scenario just like the one above, booking directly from the Chase Ultimate Rewards portal rather than transferring points into Marriott is the way to go.
Hyatt
On the opposite end of the spectrum, I’m going to use Hyatt, one of my favorite transfer partners and one that provides excellent value as an example. Let’s say you wanted to make a booking at the Hyatt Place in Downtown Chicago between June 29th-July 1st. Here is the cash price you would have to pay per night: At the very minimum, $531 per night (!!).
If you were to book straight through the Chase Portal as a Chase Sapphire Reserve card holder:
At the very minimum, you’re spending 26,509 points per night. This gives you a redemption rate of 1.5 cents per point, the value you would get when booking through Chase as a CSR card holder. And finally, let’s see how many Hyatt Points would be required to make this booking…..
We have our clear winner. For 12k Hyatt points per night, you can find yourself in a room that would cost you $531 per night were you to pay with cash. If you do the math, $531/12,000 = 4.4 cents per point. This would qualify as a fantastic redemption and one where it would be a no-brainer to transfer your points from Chase UR into Hyatt. Prior to transferring into Hyatt, make yourself a World of Hyatt account on their website. This is free and you will get an account number which you will need to link with Chase in their Ultimate Rewards Transfer Portal. Below is just a simple schematic showing you where to go to transfer UR points.
When you click on your point balance, this will be the first page you see. Bring the cursor to “use points” and click on “transfer to travel partners”
Click on World Of Hyatt and transfer the total number of points you would need. Since Hyatt requires 12k points per night for our redemption and we searched for 3 nights, we would transfer a total of 36k UR points into Hyatt. The cash price for those 3 nights would have been nearly $1,600. The only downside of Hyatt is it’s relatively small footprint. They only have about 750 properties worldwide so finding a location where you can take advantage of this value can be challenging, particularly if you’re looking at international destinations.
   Airline Transfers
Generally speaking, transferring to the frequent flyer program of Chase’s airline partners provides very good to excellent value. A prime example of this would be transferring to British Airways Avios for domestic flights on American Airlines or transferring to FlyingBlue, the frequent flyer program of KLM/Air France for a round-trip ticket to Hawaii on Delta Airlines. However, there are certain situations where you’re better off booking a ticket by redeeming UR points through the Chase portal or using cash rather than transferring the points into a frequent flyer account to book a ticket. For this example, I’ll use a round-trip ticket from Chicago (ORD) to New York City (LGA) from April 28th-May 1st.
Pretty good price for a round-trip ticket between Chicago and NYC. Keep in mind, these are economy seats, not basic economy which can be had for $129 round-trip but with limitations such as no carry-on bags and no advanced seat assignments. Now if you wanted to use United miles for this trip…..
25k miles for a round-trip itinerary. How much value would you get if you transferred 25k UR points into United? $169/25,000 = 0.67 cents per point. This would be a terrible way to use UR points since you’re getting less than a cent worth of value per point. If you were to hold a Chase Sapphire Reserve and you booked through the Chase Ultimate Rewards portal, your redemption would require…..
Just 11,240 UR points for a round-trip ticket. You would save yourself nearly 14,000 points, or enough for possibly another round-trip ticket by using Chase’s portal versus transferring into United. If you had the Chase Sapphire Preferred, your redemption would be about 13,500 UR points, a significant number of UR points saved.
 Recap
Prior to transferring into a program, evaluate whether you’re getting at least 1.5 cents per point if you’re a Chase Sapphire Reserve holder or 1.25 cents per point if you’re a Chase Sapphire Preferred holder. This is done by taking the cash price/the points required by the loyalty program.This should always be your litmus test prior to transferring. If you’re value matches or exceeds those numbers, transfer the points into the loyalty program. If not, then book directly through the Chase portal. The wildcard is if you happen to have status with a hotel chain. From my experience, hotels won’t extend status benefits if you don’t make the reservation through their own website or toll-free number. What what I do? I would still forego the benefits for IHG and Marriott if it means I’m going to get killed on the redemption when transferring UR points into either of those two brands. A free breakfast or room upgrade is not worth sacrificing a round-trip ticket to Europe, South America, or two round-trip tickets to Hawaii. If you want to read about the transfer partners that can provide tremendous value, you can read that here and here.
Some of you have been kind enough to request referral links and I am very appreciative of that. If you happen to come across this page, you certainly aren’t obligated to use my referral links to sign up for any credit card or service such as Airbnb. But I will be very grateful if you do.
Airbnb: Click Here. Airbnb is a great alternative to hotels in many locations around the world. If you use my referral link, you also get $40 off your first booking of $75 or more. You can read my post about Airbnb here
Chase Freedom: Click Here The benefits of this card is the rotating quarterly categories that gives you 5 points per dollar on the first $1,500 spent on that category. For this quarter, the category is restaurants. Any restaurant, cafe, fast food place, etc will qualify for the 5 points per dollar. You can combine these points with the Chase Sapphire Reserve or Preferred if you have either. Having either of the latter two will allow you to transfer the points to one of many transfer partners that Chase has.
Chase Freedom Unlimited: Click here The benefits of this card is that it awards you 1.5 points per purchase on every single purchase. I use this card for utilities, car maintenance,  trips to Walmart (very unusual to find a credit card that offers more than 1 point per dollar at Walmart), and other categories which don’t fall in travel or dining. These points can also be combined with the Chase Sapphire Reserve or Chase Sapphire Preferred to maximize your benefits.
American Express Platinum: Click Here This card has a hefty annual fee of $550 but if you know how to use the benefits, you still come out ahead. This awards a 60k bonus after $5k spending over the first 3 months so unless you know you will be hitting that threshold, do not apply for the card. Receiving the bonus is a big deal since you can transfer the points to many airlines and hotels. You get $100 global entry credit or $85 TSA pre-check credit. This card gives you complimentary access to Priority Pass lounges, Delta lounges, and Centurion lounges. One day passes for these lounges cost at least $50. You can also bring two guests with you. You get $200 credit to Uber annually, $200 travel credit to a designated airline, membership to Boingo Hotspot, and gold status at Hilton, Marriott, and Starwood hotels. I already detailed how having gold status for Hilton netted me greater than $700 in value from the Conrad Maldives Rangali Island. You can read about that here and you can read about all the benefits of the card here.
American Express Hilton Honors Surpass: Click Here and you can read about it here
We have all heard horror stories from friends and family about flying Spirit Airlines. The much maligned “ultra low cost carrier” gets a bad rap for being the pioneer among U.S. carriers for excessive fees. Bringing an overhead carry-on into the cabin? That will set you back $37 if you pay for it during the booking process, $57 if you declare it during  check in at the airport, and a ridiculous $65 if you declare it at the gate. Forgot to print your boarding pass at home? Having them print your boarding pass at the airport will cost you $10 (although Spirit does have kiosks at some airports which allows you to print for free). Thirsty while on the plane? You’re not getting a complimentary beverage. I literally had to get a rundown of all the rules from a friend so they wouldn’t have that “gotcha” moment with me. Love them or hate them, this is Spirit’s business model and Wall Street will tell you it’s been a relatively successful one. In fact it’s been so successful that American, United, and Delta have all dedicated the rear of their cabin to basic economy where customers can purchase a similar no frills ticket at a cost that competes with Spirit and Frontier. When I fly an airline for the first time, I really look forward to the experience if they are known for excellence in customer service. Admittedly, I also look forward to flying an airline for the first time when the customer service is on the opposite end of the spectrum.
Morbid curiosity on whether my experience would affirm the hellish experience of others led me to book a flight on Spirit in January. It also helped that I was looking for a late flight from NYC to Chicago and Spirit offered the last flight to Chicago, a 10 pm departure. The one way fare was $59, or $20 cheaper than what the legacy carriers were charging for the same route. I didn’t check in any bags or have any item that was large enough to be classified as a carry-on. I purchased a rolling bag that was small enough to fit under the seat, but big enough to fit five days worth of clothes. I made sure to print out my boarding pass at home and wasn’t assigned a seat until I got to the airport (Spirit charges $5 if you want to select your seat).  For those of you traveling with children,  Spirit will try their best to seat families together but there is no guarantee without paying for advanced seat assignments. Checking in at LaGuardia was hassle free and off I went to my gate.
One  of the many warnings to pay for your carry-on prior to arriving at the gate.
As I was waiting at the gate, Â the thought occurred that this might not be terrible after all. I haven’t seen anyone get slugged, they haven’t had their “gotcha” moment with me, and I might get to Chicago in a timely manner. And then 10 minutes after that thought, I hear a Spirit gate agent announce “Good evening ladies and gentleman, Spirit flight 331 that was scheduled to depart for Chicago O’Hare at 10 pm is now scheduled to depart at 10:40 pm.” Okay then. I can live with a 40 minute delay. Â This was something I expected prior to booking so I was not all that annoyed or disappointed. You see, Spirit Airlines is routinely ranked dead last among all U.S. carriers in on time performance. While many airlines structure their schedules to comfortably deplane, clean the plane, and board again, Spirit does not. Â Their goal is to land and turn the plane around to their next destination as soon as possible. Their entire motto is if the plane is sitting idle, it is isn’t making money so more time in the air is good, more time on the ground is very bad. This works fine throughout the day if weather and maintenance issues don’t creep up. But if something goes wrong earlier in the day, the domino effect is felt all the way until the last flight takes off. And that is precisely what occurred with my flight (as well as the flight scheduled to depart before mine). But again, 40 minutes was not the end of the world. It can be a whole lot worse.
Spirit is usually at the bottom for on time performance among U.S. carriers
Now it was time to board the flight. The Spirit gate agents eyeballed everyone’s carry-on luggage and checked to see if anything that wasn’t fitting in the personal item bin had been paid for as a carry-on item. This is the step when people who don’t pay attention to the rules or have never flown Spirit end up wasting away the savings they got on their low fare. If your carry-on was not paid for or your personal item is too big for the bin, you’re paying $65 at the gate. No ifs, ands, or buts about it. I looked to see if any unwitting passenger got caught and fortunately no one did. It seemed like everyone on the flight was either a Spirit veteran or a rookie who knew the rules.
If your personal item does not fit in this bin, I can assure you the rest of your day will not be pleasant.
When I boarded the flight I braced myself for the industry low leg room that Spirit offers. Once I was seated, it certainly felt more spacious than that. It’s quite possible that the smaller seat size created an artificial feeling of extra leg room but it felt like any other airline seat in coach. The one catch? Spirit seats do not recline. This is fine for a 90 minute flight. I couldn’t imagine the discomfort on a transcontinental flight.
I had plenty of legroom with space to spare. Your miles might vary depending on your height
Once on the flight, Spirit did not offer any complimentary beverages or snacks but they did make them available for purchase  There was no WiFi (free or paid) or seat-back entertainment. They managed to get me home safely and that was all that I expected.
Would I recommend flying Spirit? Yes, but with a few caveats. Â Above all, you would have to score a really cheap fare. A lot cheaper than the competition. If you scored a really cheap fare and you are on a leisure trip where you can afford to be late by several hours in case of the inevitable delay, go for it. If you are on a route that isn’t between two airports that suffer from chronic delays, you might also fare better.
When should you avoid Spirit? If you are flying on the day of a wedding, an interview, a meeting, a funeral, or if you are flying in the winter months to or from a cold weather city. If you are planning to use Spirit to connect to a different airline on the same day, think long and hard about it.
Here are a few odd facts about Spirit Airlines: If you go to the airport and book your flight, you will save on the passenger usage fee which is usually around $15-$18. Â It seems odd that in 2017, an airline would discourage booking online vs booking in person but that’s what Spirit does. Â Spirit also charges MORE for a carry-on than they do for a checked-in bag. So if you have a rolling bag that’s too large to be a personal item and doesn’t contain anything of significant value, you’re better off just checking it in. It costs $32 when you pay for it during booking (this increases to $52 if you pay for it at the airport) and your bag can be as heavy as 40 lbs.
I have heard from friends that if you ask to be seated in an exit row seat at the gate, Spirit agents will put you there at no cost if it’s available. This will give you plenty of leg room if you can score a seat. It doesn’t hurt to ask and the worse thing that can happen is them saying “no.”
Spirit also has a frequent flier program called Free Spirit. Any flight you take with them will earn miles. In addition to that, they have a unique program called the $9 fare club which gives you access to lower fares and cheaper check-in fees for a cost of $59 per year. I suppose if you are really loyal to Spirit and fly them multiple times per year, it’s a program which might benefit you.
Boston to Dubai, via Toronto: 40k United Mileage Plus miles redeemed per person
First leg of our trip to Dubai was on an Embraer 190 flown by Air Canada. This redemption cost 40k miles per person. When I signed up for the Chase Sapphire Reserve back in September, they had a limited time offer of 100,000 bonus miles upon spending $4k in the first 3 months. Thanks to tuition, I hit that threshold pretty quickly. If you have the Chase Sapphire Reserve or Preferred, you can transfer your points on a 1:1 ratio to United and then use one of their Star Alliance partners to fly. This is exactly what we did.
 2nd leg: Toronto to Dubai
This leg of our trip was on the Boeing 787 Dreamliner flown by Air Canada in economy class. Â This was part of the redemption above. Air Canada is a Star Alliance partner of United.
When using United MileagePlus miles, you can redeem them on any of their Star Alliance partners above.
Abu Dhabi to Male, Maldives: 30k American Airlines miles redeemed per person
My wife and I both signed up for the American Airlines Platinum Select credit card by Citi a few years back and received the bonus 50k miles after hitting the minimum spend threshold (that tuition again). American Airlines is part of One World Alliance but they also have several partners outside the alliance where you can find great redemptions. Etihad happens to be one those partners outside of One World. Others include, Hawaiian Airlines, Jet Airways, Alaska Airlines, and WestJet. One World partners are all below.
American Airlines AAdvantage miles can be redeemed on any of the airlines listed above. This is in addition to several that are not part of the One World Alliance
Male to Rangali Island: TransMaldivian Airways. Â Partial cost offset by 55,000 American Express points.
When you book a trip to Maldives, there are two ways to get your island: by an expensive speedboat transfer or a ridiculously expensive seaplane transfer. Unfortunately, the sea plane transfer is offered by a single company, TransMaldivian Aiways, which allows them to price the 30 minute flights for as much as they desire. They are not affiliated with any airline alliance so you can’t book them using miles. And it costs $546(!!) per round trip ticket to get to your island if it is only accessibly by seaplane. Since we booked the Conrad in Rangali Island, Maldives using Hilton points, our only option was taking the seaplane transfer. Since I couldn’t use miles and I wanted to reduce the cost burden of the seaplane transfer, I redeemed 55,000 American Express Premier Gold points for $550 in statement credit. AMEX Premier Gold has 20 airline transfer partners as well as the highly coveted Starwood hotels program as a transfer partner. Transferring to almost any of the programs would have given me significantly more value than the 1 cent per point I received by redeeming the points for statement credit. But I also hated the idea of spending $1,092 in cold hard cash for a 30 minute round trip flight. Redeeming the points made it a more palatable $273 round-trip per person. As for the experience itself, it was a very unique and scenic flight. The plane seats about 14 passengers in relatively narrow seats. The plane flies at around 4,500 feet so you get a great view of many islands with their over-water villas on the way to Rangali Island.
I’m not quite sure I’ll ever have another redemption in my life that will require as many points as I needed for the Conrad Maldives. This redemption took a lot of planning and required meeting multiple Hilton Card bonuses to have enough points for an award redemption. Back in 2015, My wife and I both applied for and got the Hilton Honors American Express credit card. It had no annual fee and the bonus was 75,000 Hilton points for spending $1,000 over the first 3 months. In 2016, we both got the Citi Hilton Honors Visa card. This offer was 75,000 points if you spend $2,000 over the first 3 months. I timed my car maintenance expenses and college expenses in a manner which I was able use the Citi Hilton card and get the bonus. My wife’s card was used in a similar manner. So if you’re keeping track, that is now 320,000 Hilton points we have accumulated between the two of us. Then earlier this year, American Express had a 100,000 point offer on their Hilton Surpass card. The annual fee was $75 but it came with automatic Hilton Gold Status. The benefit of having Gold status was significant. It ended up paying for the annual fee many times over. Both of us were able to achieve the 100k bonus due to miscellaneous spending + partial tuition. Â Point count: 535,000 between the two of us. At this point, we had enough for 3 nights but due to the unpredictability of the weather (it was technically going to be rainy season in July), we really really wanted to get that in that 4th night. It was around this time that Hilton started a new feature in their Hilton Honors program in which you were now able to combine your points with 10 other people. Â This was the break we needed. I asked my mom and dad if one of them was willing to apply for the no annual fee Hilton Honors AMEX card and get the 75k bonus after spending $2k in the first 3 months. Since they had a relatively large expense upcoming, they obliged and received the bonus. I was able to transfer those points into my account. Point count: Â ~ 620,000. Â Now we had enough points for 4 free nights at one of the best accommodations in the Maldives. Nightly rate if paid for in cash? $670. But the best part of this redemption is the Hilton Gold status that came with having the AMEX Hilton Surpass card. As Hilton Gold members, Conrad upgraded us from the superior over-water villa that we had booked to a retreat over-water villa. The cash value of the upgrade per night is about $130 a night. Multiply that by 4 and the upgrade is worth about $520. Hilton Gold members also had other benefits at the hotel such as free tea, biscuits, and lunch sandwiches between 4 and 5 pm and free mocktails between 5 and 6 pm. Buying lunch or mocktails at the Conrad with cash is not cheap. I’d peg this value at about $60 per day between two people. Multiply that by 4, that’s an additional $240 in value. For paying a total of $150 of annual fees between the two Hilton AMEX Surpass cards ($75 each), we derived about $760 in value. In addition, we both get a free night during our card member anniversary.
Male, Maldives to New York City, via Dubai
This was the part of our trip that really helped in reducing the overall miles/cash expenditure of our entire vacation. Sometimes you just get a little lucky. Back in early May, one of the travel blogs I follow sent out an alert on twitter about a mistake fare for a 1 way ticket from Maldives to NYC on Emirates. The mistake fare was $201 per person (!!!) for the 1 way ticket with dates extending as far out as December. Since Maldives was a trip I had been planning anyway, I thought I’d book the ticket and wait and see if Emirates would honor it. 24 hours after booking, I received an e-mail from Emirates that our tickets had been cancelled and that they would not be honoring the mistake fare. I was slightly disappointed but was prepared for this outcome. One week later, I received a call from Emirates asking me if I was still interested in that one way ticket. I told the rep I absolutely was. The booking/reservations agent informed me that there was a reversal in their decision and that they would be honoring the mistake fare. $201 per ticket from the Maldives to NYC is a steal. To put this into context, this flight would have cost $1,400 in cash per person or 70,000 Emirates miles (which I did not have)  and additional $100+ in taxes person. Once this domino fell, everything else fell into place. Sometimes you just get a little lucky.
Miles for places 