Embark on one of the monumental journeys of America in our Chicago to Yellowstone road trip
From the grand spectates of Chicago to the natural wonders of Yellowstone, discover the best of America’s wilderness, expansive landscapes, and deep forested areas. Considered one of the experiential journeys, Chicago to Yellowstone road trip is a journey of a lifetime. It’s a culmination of America’s finest states and finest attractions. This road trip brings to life some niche experiences & discoveries you could never imagine.
About Chicago and Yellowstone National Park
Chicago, the urban dense city, is one of the most populated areas of America. It’s the largest city in the Midwest, housing more than 2.7 million people. When you consider a town of this size, it’s easy to guess that Chicago boasts unique touristic experiences, homely culture, and a variety of things to do. Furthermore, Chicago’s world-class museums, historical landmarks, architectural gems, and luxury boutiques make the city fun to explore.
On the other hand, Yellowstone marks a symbol of tranquillity, peace, and calmness. The wilderness and rugged landscapes of the national park make Yellowstone one of the must-visit destinations in the United States. The park is also home to lush green valleys, canyons, and exciting natural wonders that amaze visitors with their awe-inspiring fascinations.
We’ve got a couple of handy in-depth starter guides to help you understand the beautiful landscape of Yellowstone National Park:
Yellowstone Itinerary: Find out how to spend one to five days in Yellowstone National Park.
Yellowstone Lodging & Cabins: Discover where to stay affordably in Yellowstone.
Yellowstone Experiences & Attractions: Explore 19 amazing things to do in Yellowstone NP with kids.
Chicago to Yellowstone Road Trip
The drive to Yellowstone National Park from Chicago is pretty extensive. You will know the drive time & routes in the below sections. However, the entire journey comprises three short road trips in itself. They are namely: Chicago to Sioux Falls, South Dakota to Mount Rushmore (204 miles), and Mount Rushmore to Yellowstone (385 miles).
Pro Tip: If you want to avoid long road trips, we suggest picking up one of the routes to explore the region. South Dakota to Mount Rushmore is the most preferred and scenic route out of all.
How to Plan Chicago to Yellowstone Road Trip
This section will brief you on all the important aspects of planning a perfect Chicago to Yellowstone road trip. From understanding the drive routes to driving times for each of the routes, you’ll get a thorough idea of how to reach Yellowstone comfortably.
Best Route to Reach Chicago to Yellowstone
The drive from Chicago to Yellowstone cuts through four American states Wisconsin, Minnesota, South Dakota, and Wyoming. As you start from Chicago, take the I-90 W to reach Sioux Falls. Continue driving down I-90 W till you reach Mount Rushmore. To continue toward Yellowstone National Park, there are three primary routes to choose from: the Beartooth Highway, Cloud Peak Skyway, and the Bighorn Scenic Byway. I highly recommend taking the Beartooth Highway, as it’s one of the most scenic drives from Mount Rushmore to Yellowstone.
Find out more | Mount Rushmore to Yellowstone – An In-depth Guide.
Driving Times for Chicago to Yellowstone
The drive from Chicago to Yellowstone is 1340 miles (2156 km). If you were to drive non-stop, arriving would take approximately 21hr 15mins. The route cuts through the scenic landscapes of Wisconsin, Minnesota, South Dakota, and Wyoming. Since you’ll be stopping at several stops to enjoy the state’s attractions, we recommend spanning your journey seven to ten days.
Pro tip: To cover a road trip like Chicago to Yellowstone, you need ample time. Most people say you can cover this route within three to five days (including pit stops), but we do not recommend that. Consider spending a minimum of seven days exploring the best of each American state. The maximum you can spare for this journey is ten days.
How to Rent a Car
To rent a car for your Chicago to Yellowstone road trip, I suggest Rentalcars.com. I’ve personally used their service and have found it incredibly affordable compared to other rental operators. With max safety assurance, you can be sure of booking the right vehicle for your entire journey.
Chicago to Yellowstone National Park Map
Here’s a driving route map to reach Yellowstone National Park –
Best Chicago to Yellowstone Road Trip Stops
Explore Urban Chicago
From serious adventures to fun-seeking thrills, there’s always something special that you’d find in Chicago. If you’re visiting this Midwestern metropolis for the first time, then you’ll have the time of your life. The city is home to unique green spaces like Grant and Millennium Park, landmarks such as the Chicago Bean sculpture and Buckingham Fountain, and many world-class museums, pubs, and cafes.
However, this uplifting atmosphere of Chicago can easily overwhelm a tourist. Below are some of the recommended activities which you should definitely see or do on your first-ever visit –
Take a boat ride on Lake Michigan
Across four states of America: Illinois, Indiana, Michigan, and Wisconsin – Lake Michigan is a sheer beauty in terms of recreational activities and shimmering beaches. And with the backdrop of Chicago’s tall skyscrapers, the lake shines even more magnificently.
Read more | A Beginner’s Guide to Lake Michigan
One of the best ways to enjoy the city’s urban life is to take a boat ride around Lake Michigan. It’s a preferred way to explore the town while avoiding the busy summer crowds. Moreover, these scheduled boat trips run throughout the day, and they take you across the historical landmarks of Chicago. Some special boat trips always try an extra effort to give you a different perspective of Chicago.
Book activities | Recommended, most popular Lake Michigan tours.
Visit Chicago Observation Deck
The most touristy thing to do in Chicago is to visit the observation deck on the 94th floor of John Hancock Centre. Undoubtedly, it’s a recommended activity for those visiting the city for the first time. The panoramic views of Chicago’s urban jungle are a sight to behold.
Go on an architecture cruise
This is an experiential activity, as few visitors venture into the city to marvel at its architectural landmarks. And to gasp at historical grandeurs is worth spending money on and speaking of vantage points to view these gems? There’s none. But, the best way to explore them in their entirety is to travel waterways via the Chicago River
Must-Do Activity | Book a 1.5-hour guided Architectural Cruise of Chicago.
This guided tour’s notable structures include: Marina City Goldberg, Merchandise Mart, Willis Tower, Chicago Board of Trade Building, Lake Point Tower, and much more. The tour also includes hospitality of food & drinks.
There’s no better place than Navy Pier in Chicago to relax and unwind. This iconic waterfront space houses renowned restaurants and cafes that serve multinational global cuisine. Apart from culinary scenes, visitors will thoroughly enjoy the shopping atmosphere. With luxury brands & boutiques lining up the pier, there’s no way you would go back empty-handed. Further to this exploration, countless walking & boat trips are scheduled throughout the day to take you in & around Chicago.
Where to stay: The Royal Sonesta Chicago Downtown | Millennium Knickerbocker | Hyatt Place Chicago
Looking for culinary food tours across Chicago?
Chicago’s Craft Brewery Tour: Experience the hippest breweries in Chicago.
Chinatown Food Walking Tour: Explore Chinatown in this 2.5-hour guided tour.
Chicago’s Gourmet Tour: Admire serene sets of Lake Michigan on this cruise gourmet tour.
Pro tip: Do take small halts during a long road trip
It’s highly advisable to take small pit stops while on a long, extensive road journey. For our road trip, the first distance i.e. Chicago to Sioux Falls is 574 miles. Hence, to break this route – we will be taking a stop at Rockford and Madison (Wisconsin).
Visit the towns of Rockford & Madison
A visitor passing through the state must notice the two famous towns of Wisconsin, Rockford, and Madison. Both these towns form an integral part of Wisconsin’s tourism and have been driving crazy amounts of tourists for over a decade.
Madison has five lakes, gourmet restaurants, 270 green parks, free museums, and amazing biking trails. Any outdoor person would absolutely love exploring Madison and experiencing its abundance of things. Below are some of the recommended things to do in Madison:
Explore Five Lakes: If you’ve got the time, look no further than its alluring lake beauty. Mendota, Monona, Wingra, Waubesa, and Kegonsa cover 15,000 acres of land filled with water-bound activities and experiences.
Hiking & Biking: Madison is known for its outdoors. Home to over 270 parks and 200 miles of bike trails, bring out your inner adventure to extensively explore the landscape of Madison.
Arts & Culture: Thumping beats are loud here at Madison. The bustling rock concerts, the peaceful art shows, and the peaceful museum exploration all add up to your experience.
Looking for more activities in Madison? Read this in-depth guide to find out more experiential activities best suited across all seasons. This will help you plan better in terms of visiting Madison in the right season.
As energetic as Madison is, Rockford is a quaint, peaceful town boasting calm surroundings, beautiful gardens, and world-class museums. It’s also one of the best places in Wisconsin to relax and unwind before you continue your journey toward Yellowstone National Park.
Visit the Anderson Japanese Gardens: One of the ‘to-do’ things in Rockford is to explore the tranquillity of Anderson Japanese Gardens. Set in a serene environment, the gardens are home to tiny waterfalls, pavilions, tea houses, and stone-paved paths.
Cruise on the Rock River: Since Rockford is situated on the banks of the Rock River, one of the fun things to do is to take a short boat ride to explore the sights. The onboard guide will tell you about the town’s intriguing history and culture.
Where to stay: Radisson Hotel & Conference Center | Hampton Inn Rockford | Hampton Inn & Suites Madison
Discover the charm of Sioux Falls
Sioux Falls is among the most incredible places to stop by during your Chicago to Yellowstone road trip. It’s an important tourist destination in the entire South Dakota region and across the central states of America. In addition to its importance, visitors absolutely love staying at Sioux Falls. From exploring the town’s museums and historical landmarks to venturing out to discover the wilderness and beautiful hikes – there are plenty of things to do in Sioux Falls.
Sioux Falls can ultimately overwhelm you with its abundance of attractions & experiences. We thought of shortlisting them so that you spend time visiting only the best ones. Here are some of the must-do things during your first visit to Sioux Falls –
Visit Falls Park
Are you wondering why the name Sioux Falls is? Well, there’s a reason behind it. And this reason is pretty valid.
Sioux Falls is home to ancient rock formations through which a series of waterfalls passes. On average, 7400 gallons of water rush through these craggy rocks. Visitors can marvel at this raw landscape generated by South Dakato’s amazing geology setting.
To explore this waterfalls series, you must visit Falls Park. There are plenty of observation decks and 360-degree view platforms to make your viewing experience more pleasing. Those who love adrenaline fun can take bike rides across the trails spread across Falls Park. These biking trails offer tourists a closer look into the waterfalls. Towards the end of the course, a cafe is built amidst the remnants of an old power company.
Venture out on Sioux Falls Bike Trails
The only best way to explore Sioux Falls is through hiking & biking. These two are the most popular activities, and they justify every sightseeing venture you will do. Moreover, it’s an affordable source of exploration that can get you closer to all hidden gems spread across Sioux Falls.
Rent a bike through a local operator and get your adventure started. All bike trails are paved orderly, leading to some of the most beautiful sights of Sioux Falls. These loop trails cover almost 30 miles and circuit around the town. The most popular route is the Sioux Falls Bike Trail Loop. Considered for beginners, it’s a must-explore trail for all those who want to go easy on their adventure.
Explore Downtown Sioux Falls
After an exploration packed with beautiful scenery, it’s time to hit Downtown Sioux Falls. This bustling area houses some of the best restaurants, cafes, pubs, local museums, art galleries, and more. I personally like to sit and relax at a cafe while watching tourists hustling & shopping across the boutiques on the streets.
Where to stay: ClubHouse Hotel & Suites | Hilton Garden Inn | Hyatt Place Sioux Falls
Explore the rugged Badlands National Park
Badlands National Park is one of the epic and underrated spots of South Dakota. The spellbinding scenery, gorgeous terrain, and sharp pinnacles create one of the most dramatic sights in America. Whether you’re an explorer, a hiker, or a photographer – you can spend weeks exploring the abundance of Badlands National Park.
Not to forget, the drive from Sioux Falls to Badlands National Park across the densely forested areas is truly remarkable. The journey itself justifies the beauty of South Dakota. Visitors will find this route extremely special.
Pro tip: Be ready for Badland’s rough terrain
Badlands National Park is known for its extreme summers and harsh winters. It’s advisable to carry essential clothing items and hiking equipment for your trip to Badlands. Furthermore, always keep a booster (energetic drink) or dry snacks to keep yourself pumped.
Here’s a brief info on the must-do things to see & experience in Badlands National Park –
Badlands National Park Loop Road
If you’ve only got a half-day to explore the sights of the Badlands, take the Badlands National Park Loop Road. Spanning over 30 miles, this circuit is one of the most-driven routes of the park. The amount of things to see across the loop road is simply magical. While it may take you only an hour to complete the loop, it will take you much longer (probably 5-6 hours) once you realize the amount of sightseeing stops this loop road has.
Badlands Loop Road is a proper, structured paved route that is easy to drive and follow. Once you start your journey, you’ll soon hit overlook points, scenic vantage platforms, and boardwalk trails. Make plenty of stops along the way to soak in the rugged interior charm of this backcountry.
Some notable places (overlooks) you shouldn’t miss include Pinnacles Overlook (known for incredible views), Yellow Hills of the Badlands (known for its yellow-coloured hill display), Yellow Moulds Overlook (known for its fossils & geological features), and Panorama Point (can’t miss this for sunrises and sunsets).
Please be a careful explorer while driving Badlands Loop Road. Road kills are common at this juncture. It’s advisable to maintain a safe distance (minimum 100ft) between your vehicle and the animal.
Hike the Notch Trail
Notch Trail is naturally built for kids and families. Being one of the best things to do in Badlands National Park, Notch Trail is a 1.5-miles round trip packed with exciting things to see. This facilitated trail runs across a scenic canyon, steep climb-up trails, ancient rock formations, and fossils. Furthermore, the area around the Notch Trail is indeed striking for sunset admirers. The slopes of Badlands mountains get completely bathed in orange hues.
Discover the Fossil Exhibit Trail
The Fossil Exhibit Trail takes you back in time by letting you discover the fossil exhibits of extinct creatures who once lived in this national park. The trail is the only place to learn about these discoveries while gaining meaningful knowledge about the fossils. The Fossil Exhibit Trail runs 2.5 miles long, with accessible boardwalks and paved routes, making it one of the must-explore areas.
Visit Homestead Overlook
Apart from all the overlooks you might’ve already seen from Badlands Loop Road, there’s one in particular that you should definitely see. Homestead Overlook is one of the natural gems of Badlands National Park. In contrast to the blue skies, the orange shades of the mountain slopes are a sight to admire! Oh, and you can also spot plenty of prairie in this region.
As mentioned, Badlands National Park is not limited to only the four experiences listed above. There’s a plethora of things to see & do. Here are some notable ones (you should definitely take time to explore): visiting Hay Butte Overlook, watching the sunsets from Big Badlands Overlook, spotting the Badlands Wall, and hiking the Door Trail.
How do I book hotels for this road trip?
Travel Realms partners with two of the leading hotel booking platforms: Booking.com & Hostelworld. For a traveller looking for a varied accommodation option, I suggest exploring stays at Booking.com. For those who prefer budgeted rooms, visit Hostelworld.
Wander the beautiful Custer State Park
Custer State Park is one of the awe-inspiring destinations of our Chicago to Yellowstone road trip. Nestled in the Black Hill region of the United States, the entire state park is filled with natural landmarks, towering peaks, scenic drives, and abundant wildlife.
Interestingly, Custer State Park is still known to a lot of people. It is less popular than Badlands National Park or Mount Rushmore in South Dakota. Even during summer, you won’t find its hiking trails crowded like the others. So easy; you can spend a couple of days exploring the majestic Custer State Park.
Some of the must-do activities in Custer State Park include:
Drive the Needles Highway
You absolutely can’t miss doing one thing in Custer State Park. And that’s driving the scenic Needles Highway. This 14-mile loop road forms part of the central South Dakota Highway 87. As the name implies, this picturesque circuit allows visitors to view world-famous granite zeniths. The entire Highway is adorned with narrow curves, long tunnels, and panoramic vantage points. Honestly, you’ll always need more of the views here.
Circle the Wildlife Loop Road
The Wildlife Loop Road is another must when visiting Custer State Park for the first time. It’s a long, stretched circuit road that cuts through pine-covered hills and grasslands. Since the road runs through the park’s forested areas, expect to see a wide range of unique wildlife. Some of them which you can spot are prairies, bison, bighorn sheep, coyotes, eagles, and hawks.
Fun Fact: Custer State Park was acclaimed as one of the World’s Top Ten Wildlife Destinations. Due to its incredible array of unique animal and bird species, the park has been a paradisical place for all wildlife photographers and explorers. The state park also has a dedicated wildlife reserve.
Visit Sylvan Lake
Nestled amidst the giant rock formations of Custer State Park, Sylvan Lake is popularly known for its striking beauty and contrasting setting. The lake water shines brightly during the day, reflecting the blue hues of the clear skies. From a different angle, it looks as if the rock formations are holding out the water from spilling out.
Most visitors pass the Needles Highway, making it a quick pit stop for Sylvan Lake. However, it’s worth spending some time admiring the terrain that surrounds the water. The lake has a swimming beach and a beautiful 1-mile walking trail leading you to impressive scenic points. Other activities like kayaking, paddle boarding, and picnicking are common.
Marvel at Mount Rushmore National Monument
Mount Rushmore is truly one of the monumental landmarks of our Chicago to Yellowstone road trip. It houses one of the world’s largest sculptures featuring the United States’ four presidents. The completion of the work was done by 1941, however, these 60-ft tall sculptures look as if they were recently carved.
Visitors often have Mount Rushmore National Monument listed down in their American bucket list experiences. And I think it should be for all, as the sight of these sculptures itself is so glorious. As a matter of fact, over 3 million tourists pay a visit here to view this patriotic site.
Popular things to do around Mount Rushmore National Monument:
Hike the Presidential Trail
This beginner-level walking trail is perfect for families travelling with kids. The whole path is filled with scenic vantage points that provide different angle views of the national monument. Moreover, walking the Presidential Trail takes you away from the hustle & bustle of the busy tourist crowd. It’s also relatively quieter during the mornings.
Join a Guided Excursion
The best way to explore Mount Rushmore in its entirety is to join a guided ranger tour. Led by expert rangers, these excursions offer deeper engagement and perspective into the political and environmental history of the area. The tour stops at several points covering explanations on various topics. You can visit the Visitor Centre at Mount Rushmore to book these tours.
Further Resource | These are some of the best accommodation options in Mount Rushmore.
Visit Devils Tower National Monument
Devil’s Tower National Monument is one of the important landmarks in the United States. This iconic site is sacred and holy to the Native Americans, as their tribal connections are strong to this monument. Annually, rituals and ceremonies are held by these tribal communities, where prayers are offered in remembrance of a person.
Well, apart from all its history, Devil’s Tower is a sight to marvel at. Being the first national monument in the U.S., the place has been a long-standing beauty to all visitors and locals. What makes the landmark more interesting is the fact that it has got numerous theories & mysterious stories. (I’ll leave this surprise for your exploration).
Two of my favourite things to do around Devils Tower National Monument include:
Hike the trails
If you could do one thing during your visit to the Devil’s Tower, it should be to explore the site’s amazing hiking trails. From beginner to moderate and difficult ones, there are routes designed for every adrenaline level. Of course, the most difficult ones require you to be physically fit – but it also guarantees you splendid views of the tower. Some of the options to try include: the Tower Trail (1.3 miles), Red Beds Trail (2.8 miles), South Side Trail (0.6 miles), and Joyner Ridge Trail (1.5 miles).
Go stargazing
Devil’s Tower National Monument is located in northeastern Wyoming, which is remotely away from any town or city, This eventually means the site is well protected from pollution. And nothing could be perfect than having a clear sky to gaze at the stars. During summers, the park officially launches its ranger-led night tours. Book them to experience one of the memorable nights.
How much time do you need?
Ideally, two to three hours is more than enough to spend at Devils Tower National Monument (unless you partake in activities like hiking or stargazing). This gives you ample time to explore the surroundings, marvel at the pinnacles of the landmark, capture photos, plus visit the visitor’s centre.
Discover Yellowstone National Park
We finally hit the last stop of our road trip i.e. Yellowstone National Park.
Yellowstone National Park is a breathtaking wonderland of geothermal activity, brimming with gorgeous terrain and abundant wildlife. It’s one of America’s most visited places year-round, with millions of tourists travelling & discovering the best sights within the park.
Though you may have visited some of the best stops on this road trip, but there’s nothing like Yellowstone. This national park is a culmination of all nature-based activities, making you indulge in them thoroughly. I’ve been to Yellowstone National Park a couple of times, and every time the place had a different experience stored for me. And that’s what I love the most about this park. No matter which season, you always have the fruitful joy of visiting Yellowstone.
I’ll list down a few things which should ultimately be on your bucket-list adventures. For a detailed experiential list, check out our 19 Friendly Things to Do in Yellowstone National Park with Kids.
Grand Prismatic Spring
The rainbow-coloured shades of Grand Prismatic Spring are a spectacular sight to watch. Being one of the main highlights of Yellowstone National Park, this geothermal pool has been a crowd-puller for ages. It’s also the most photographed landmark of the park. What’s more unique is the fact that Grand Prismatic Spring changes its colour every season. And to watch this sight, I suggest either taking the Boardwalk Trail through Midway Geyser Basin or heading to Grand Prismatic Spring Overlook.
Old Faithful Geyser
One of the most recognizable landmarks of Yellowstone – the Old Faithful Geyser – is a natural hot spring that erupts at every 90 minutes interval. Even though it’s 150 years old, the eruption timings are pretty accurate. Usually, Old Faithful Geyser is always crowded. So, it won’t be a nice spectate to see the eruption. Instead, hike to the Observation Point to get overlooking views of the eruption. It’s a 1.1-mile trip, with an uphill that is moderate to walk upon.
Lamar Valley
Lamar Valley is a paradise located within Yellowstone National Park. The scenic drives, the majestic landscapes, and the abundant wildlife make this valley one of the must-visit places in the park. It’s often overlooked by travellers, as it’s located far away from the central sights, but if you make an effort – I promise you’ll be rewarded with surprising views. Alternatively, you can also look at these guided activities which take you in & around Lamar Valley. Well, you certainly won’t need to drive and you can keep yourself occupied marvelling at the outdoor wildlife.
Where to stay: Kelly Inn-West Yellowstone | Explorer Cabins at Yellowstone | Best Western Desert Inn
How to Plan Chicago to Yellowstone Road Trip Itinerary
Planning a road trip is pretty straightforward. What isn’t so simple is its execution. Even to date, I sometimes struggle to compile everything and put it in a single plan. However, if researched and planned well, execution may seem like a cakewalk.
To help you out with your efforts, I’ve curated a sample 7-day itinerary for Chicago to Yellowstone road trip. Customize the below plan as per your requirement, preference and choice. But, more importantly, keep your plan flexible so that the entire road journey isn’t tiresome.
Chicago to Yellowstone National Park Itinerary
Day 1
Explore Chicago (sightseeing & exploration)
Chicago to Rockford, IL (1hr 33mins)
Rockford to Madison, WI (1hr 18mins)
Overnight at Madison.
Day 2
Depart Madison
Madison to Sioux Falls (6hr 35mins) – option to stay at Rochester
Explore Sioux Falls
You can either spend a day or two at Sioux Falls. Recommended duration is two days.
Day 3
Depart Sioux Falls
Sioux Falls to Badlands National Park (3hr 57mins)
Visit Badlands & surroundings
Overnight at Rapid City.
Day 4
Rapid City to Custer State Park (56 minutes)
Spend a day exploring the state park
Day 5
Head to Mount Rushmore National Monument (45 minutes)
Spend full-day exploring Mount Rushmore
Overnight at Keystore.
Day 6
Mount Rushmore to Yellowstone (9 hours)
Rest/ Overnight stay at Gardiner or Montana
Day 7
Explore Yellowstone National Park’s sights & wonders
Recommend stay at Yellowstone National Park is three days.
Voila! You’ve got your road trip set and your itinerary planned. It’s time to explore accommodation. Visit Booking.com to find affordable & luxury options for our Chicago to Yellowstone road trip.
Popular Guided Tours & Excursions
Our partnership with GetYourGuide brings out exclusive tours & experiences for you to choose from. Below are some of the recommended activities and guided excursions which perfectly compliments our Chicago to Yellowstone trip. Book them in advance and plan an exciting journey in the United States.
Further Readings & Resources
American road trips are fun, aren’t they? So, I’m sure you’ll love our other curated trips as well.
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