Travel Itinerary: Road Trip from Chicago to Badlands, Glacier, Yellowstone, and Grand Teton with Two Kids Under Two

Update February 2025: The National Park Service has required timed-entry reservations to drive the scenic Going-to-the-Sun road in Glacier National Park over the last four years due to increased visitor traffic. This is still in effect as of 2025 if you want to enter the park between 9am and 3pm. Tickets become available four months in advance on a rolling basis, and the reservation costs two dollars. This is in addition to the National Park fee. Vehicle reservations will become available on February 13th, 2025, at 8pm MST. Next-day vehicle reservations will be available at 7 pm MST for next-day entry starting on June 12, 2025, on a daily rolling basis. Visit this page for updated information on Glacier National Park, including reservation information.

Leisure travel was far different in 2020 compared to the previous three-plus decades of my life due to the global pandemic caused by COVID-19. Doing your due diligence in every aspect of trip planning was necessary. It was also essential to assess whether the risk-benefit analysis favored flying or driving, and depending on your personal health or those around you at home, if traveling for leisure should have been done at all. Considering these considerations, my family (wife, toddler, and infant son) took a road trip to four national parks. Initially, we had booked a round-trip flight on American Airlines since both legs of the trip had a half-empty plane. However, as we got closer to departure, the Chicago to Bozeman, Montana flight started getting increasingly crowded. Two days before our flight, I received a courtesy message from American Airlines that the flight was expected to be full. They gave me two options: A) I could get my miles refunded without any cost to reinstate them, or B) I could book another flight for the same day, which routed me through Dallas. With Dallas being a hotbed for COVID during that time and the uncertainty of the severity of the virus if one of us were to get it, we did not want to put ourselves at risk. We took option A and decided to rent a one-way car and then fly back from Jackson Hole, Wyoming. This would also be a test run to see how our 22-month-old and 4-month-old (at the time) would handle a lengthy drive. Driving also allowed us to add Badlands National Park and Mt. Rushmore in South Dakota to our itinerary since we wouldn’t drive 1,500 miles from Chicago to Glacier National Park in Montana in one shot.

Day One: Chicago to Mitchell, South Dakota

So it began. We left Chicago at 10 a.m. with the GPS showing us an ETA of 8:03 p.m. at Mitchell, South Dakota. Factor in diaper change stops, gas stops, and venturing out of the car for a scenic viewpoint; we knew 10-10:30 pm was the more realistic time frame. We chose this town since it wasn’t too close to Badlands National Park (204 miles), where overcrowding could be an issue, but close enough to drive over and get there in under three hours. We took I-90 West and made our first stop to explore the Minnesota side of the Mississippi River at Great River Bluffs State Park. We did a relatively short hike here with the kids and got panoramic views of the Mississippi River. The hike wasn’t challenging and was a perfect way to stretch out after being in the car for nearly five hours.

After spending about an hour here, we continued our journey further west to South Dakota, where we’d spend the night. We stayed the night at AmericInn (a Wyndham brand), and the hotel was perfect for a one-night stay. It was clean and comfortable, and they had a bagged breakfast to go.

Day Two: Badlands National Park and Mt. Rushmore

On our second day of the trip, we had Badlands National Park on our agenda as the first stop, followed by Mt. Rushmore. We made it a point to get up early and get to Badlands National Park as early as possible. It took about 2 hours and 45 minutes, and as soon as we got through the gates, I felt like our decision to drive was validated. The scenery and rock formations here are unreal, and there is also some wildlife. We saw bison, big horn sheep, and pronghorn. You can hike several trails at Badlands, but due to our time constraints, sweltering heat, and an infant and toddler in tow, we decided to focus primarily on lookout points and drive through the park.

After six hours at Badlands, we headed 75 minutes west to Mt. Rushmore. It’s not as majestic and grand as I thought, but the precision and detail necessary to carve out four U.S. Presidents is incredible. In hindsight, if I had to choose between spending more time at Badlands and visiting Mt. Rushmore, I would have stayed longer at Badlands National Park. Mt. Rushmore is a bucket list item for many people, so I understand not wanting to skip it if you’re already in South Dakota.

We finished Mt. Rushmore at around 7:15 p.m., and now it was time to make the 366-mile drive to Billings, Montana, where we would spend the night. We stopped at Black Hills National Forest to take in the views. This was a very underrated place that deserved more than the 35-40 minutes we spent here. It was beautiful, and I should have done my homework before visiting. But hey, you can learn from my mistake.

We didn’t reach Billings, Montana, until nearly 1 a.m. Fortunately, both kids were asleep almost the entire way, and the 80 MPH speed limit in South Dakota and Montana didn’t hurt.

Day Three: Bozeman, MT, and White Fish, MT (Glacier National Park Area)

Our goal on day three was to get to Whitefish, Montana, with a stop in Bozeman. Whitefish was going to be our home base to explore Glacier National Park. If you recall, our flight from Chicago was booked to Bozeman, MT, where we had initially booked our rental car. We found an excellent car rental deal through Budget, and even though it was non-refundable, we went ahead and made the booking since prices were increasing each day. Since we canceled our flight, I realized Bozeman would have to be incorporated into our trip. With that in mind, we booked our one-way rental from Chicago to Bozeman, and I aligned the drop-off and pickup times so that we could drop off the car we rented from Chicago and pick up the SUV we originally booked in Bozeman. It took two hours to get there from Billings and another five hours to drive north to Whitefish, which would serve as our gateway to Glacier National Park. The entire drive was scenic and beautiful, and long drives don’t seem long and burdensome when surrounded by beauty. We stayed at the Pine Lodge on Whitefish River, a hotel I will review.

Day Four: Glacier National Park

This was our day to explore as much of Glacier National Park as possible. We entered Glacier National Park from the west entrance and immediately got on Going-to-the-Sun Road. This road connects the eastern and western sides of the park and offers stunning views at just about every turnout. There are many trails worth hiking at Glacier National Park, but I strongly suggest going in groups of four or more due to the presence of bears. If you’re traveling with an infant or toddler or need wheelchair access, Trail of the Cedars is what you want to do. It is an ADA-accessible loop trail with no climbing, steep declines, or challenging scrambles. This is a very popular trail for families with younger children, so I strongly recommend getting there early, as the parking area near the trailhead can get packed after 9 a.m.

Continue driving on Going-to-the-Sun Road and prepare your camera for several pullouts offering some of North America’s best scenery.

Going-to-the-Sun Road will eventually lead you to Logan Pass, the country’s continental divide. This is where the watershed draining into the Atlantic Ocean is separated from the watershed draining into the Pacific Ocean.

There is a visitor’s center here, and the parking lot tends to attract several bighorn sheep. It may be tempting, but do not feed them if you encounter them. They will follow you and are capable of doing damage.

The sunsets at Glacier National Park are gorgeous. If you want the best spot for viewing, there is a stretch of Going-to-the-Sun Road about a quarter mile from Logan Pass that will give you the best vantage point. There are also car pullouts in that area.

Day Five: Drive to Gardiner, Montana-Yellowstone National Park

We slept in on day five and made the six-hour drive about 400 miles south to Gardiner, Montana. Our toddler was most restless in this segment due to the long drive and spotty cell phone data coverage. My wife did a great job keeping him entertained, and he did a great job not throwing a tantrum. Ridgeline Hotel was our home base for the next two days and is near the park’s north entrance. Ridgeline is part of the Ascend Collection of hotels under the Choice Hotels network. We called it an early night and prepared for a more extended day tomorrow.

Day Six: Yellowstone National Park

If you enter from the North Entrance of Yellowstone, Mammoth Hot Springs will be among the first sights. I highly recommend getting there early as parking can fill up quickly, and parking along the road is illegal (many tourists ignore this warning). There are some stairs to climb, but a wooden walking path and ramp will take you right to the springs.

Once you’re done here, you can either head south towards Grand Prismatic, Old Faithful, and other geothermal hot springs or east towards Lamar Valley. If you want to view wildlife, including wolves, bears, and bison, Lamar Valley is where you want to be. We saw wolves from a distance and several bears, pronghorn deer, elk, coyote, red fox, and other native animals. If you leave your car to take a picture of a bear or wolf, you should maintain 100 yards of distance and 25 yards of distance from animals such as bison or elk. The photos below were taken using a 200 mm zoom lens with more than 100 yards of distance between me and the bear and more than 50 yards between me and the bison. Bison may seem docile and gentle, but if you get near them, they may charge you and can potentially kill you.

Except for wolves, we could see all of the animals above from the comfort and safety of our car. This is ideal if you’re traveling with younger children and would rather not bring them along for a hike. I allowed my 2-year-old son to walk on a trail with me, and I ensured it wasn’t near the tree line or thick shrubs that could be used as a hiding spot for a mountain lion or bear.

It’s important to note that seeing certain animals, such as bears and wolves, in Yellowstone does require patience. It’s not as simple as you drive there and the animals just show up. The longer you stay in Lamar Valley, the higher your chances. The more days you spend in Yellowstone, the higher the likelihood that you will see most, if not all, the animals. There is a 20-mile stretch of Lamar Valley, which we drove back and forth several times. It took about two hours before we saw our first bear. Bison and elk are plentiful; you can count on seeing them with minimal effort. We spent the entire day here and were rewarded for it. Bring plenty of food and water if you plan on doing the same. Also, remember to bring binoculars. One crucial tip: bison may look docile, but if you get too close, they will charge and try to gore you. People get hurt every year trying to get too close to take that perfect picture. Giving them their space is a great idea, especially if you see calves.

Day Seven: Yellowstone and Grand Teton National Park

Like most other days, we got up early with ambitions to cover two parks in one day. We started our day early in the morning (I can’t thank the kids enough for cooperating) and drove south to view the geysers. Old Faithful is the one that everyone wants to see, and the parking situation can be impossible if you don’t get there early enough. The same can be said for Grand Prismatic, a hot spring that is the largest in the U.S. and the third largest globally. Grand Prismatic is part of the Midway Geyser Basin, also home to Excelsior Geyser, Turquoise Pool, and Opal Pool. It’s essential to stay on the pathway and not jump over the fence to “feel the temperature.” People have fallen to their deaths by getting too close to geysers at Yellowstone.

Grand Prismatic is the size of three football fields, so a little hiking is required to get a panoramic view or a picture that would fit its entirety. If you look straight ahead in the photo above, you will spot people (they’re very tiny in the picture) who have made the hike congregated in an area that allows them to get a bird’s eye view from elevation. Doing this hike with small children on a sweltering day was not an option for us, but if that’s not a concern for you, do it. Once we finished the Midwest Geyser Basin, it was off to Grand Teton National Park in Wyoming.

The southern entrance of Yellowstone and the northern entrance of Grand Teton are only 31 miles apart. While Yellowstone covers over 3,500 square miles, Grand Teton is much smaller, at about 484 square miles. Grand Teton National Park has stunning mountain views and also plenty of wildlife. We arrived around 4 p.m., giving us time to drive around Jackson Lake, Jenny Lake, and Leigh Lake and take in the park’s various viewpoints.

We didn’t have much luck spotting wildlife other than bison on this day. We did enjoy the beautiful sunset and then called it a day. We stayed in Jackson Hole, Wyoming, at the Hampton Inn for this portion of our trip. The summer-time $400/night pricing was exorbitant, and I used 131k Hilton points to book two nights. This was an average redemption rate, but the property was very nice, and the décor fit its Wyoming location. It was one of the best Hampton Inn properties we had ever stayed at. We had one more full day left in Grand Teton National Park before it was time to fly home.

Day Eight: Grand Teton National Park

On the final day of our trip, we woke up early and started driving around the park early in the morning. When we got to a particular area of the Snake River, we were told by park rangers that three grizzlies had killed an elk overnight and consumed some of the carcass about 600 yards off the road. They said it was possible, even likely, that the grizzlies would return later to finish off the carcass. With that in mind, we drove around other parts of the park with a plan to return to that area a couple of hours before sunset when the grizzlies were likely to return. We could spot the elk carcass from our vantage point, but park rangers did not allow anyone to get within 500 yards of the downed elk. So we took in the beauty of other parts of the park, but were excited for what may ensue later in the day.

At about 6 p.m., we drove back to the Snake River area where the elk carcass was situated. By this time, several other groups had gotten word from park rangers about the potential for a grizzly sighting, and the shoulder of the road was packed with cars. After about 30 minutes of waiting, we saw a grizzly running through the meadow and heading straight for the elk carcass. It consumed whatever it could for about 10 minutes before returning to the trees.

Observing nature in action was the perfect way to cap off our trip. Over 2,500 miles driven, countless hours in the car, and cooperation by both kiddos made this trip possible. A very special thanks to my wife, who initially thought I was crazy for proposing this trip but eventually bought in. She did a great job keeping our 22-month-old occupied while ensuring our 4-month-old was constantly fed. This trip would have been difficult without her kid/baby management skills. We’re always asked how we made this trip with an infant and toddler, and if other couples with young kids can do something similar. Our 4-month-old spent most of his time sleeping, which was pretty easy. To keep our 22-month-old busy, we had several educational videos and interactive games uploaded to our phones. We also bought puzzles, Etch-A-Sketch, and other toys to keep him busy. The most important part of the trip was keeping our 22-month-old (Now 32 months old) engaged and educating him. If we saw a specific type of animal or landscape, we’d identify it for him and then ask him to identify it for us if we saw it later. This added to his vocabulary and gave him experiences he can look back on and look forward to. We’re not huge fans of providing much screen time, but trips like this are an exception. These trips may seem daunting, but you can do more than you think. It does take a complete buy-in from both parents, but once you have that, make a game plan and execute it as best you can.

Day Nine: Departure from Jackson Hole Airport to Chicago

One of the unique things about Jackson Hole Airport in Wyoming is that it is the only airport in the U.S. located inside a national park, in this case, Grand Teton. This makes for some spectacular views upon takeoff and landing. Even plane spotting with the backdrop of the mountains is very cool. Thank you for reading. If you found this post helpful, please subscribe for alerts on the latest itineraries.