Planning a Midwest Thanksgiving vacation? This is the guide for you!
Thanksgiving break is an ideal time to travel due to the natural time off.
As a Midwest local, I’ll take you through some of my favorite spots.
There are tons of drivable destinations throughout the Midwest offering holiday events to make the most of your November!
Whether you are looking for nature and hiking, urban exploration, or small-town vibes, there is something to suit each travel interest.
Some of the best Midwest Thanksgiving vacations are Chicago, Milwaukee, Indiana Dunes, Starved Rock, Custer State Park, and Detroit.
7 Midwest Thanksgiving Vacations
Cities
1. Chicago
Best for: Big City Holiday
Chicago is one of my favorite cities, and I really love it any time of year.
There are tons of pre-holiday festivities throughout the city that make Chicago an awesome Thanksgiving vacation.
Iconic Chicago holiday activities like the Lightscape at Chicago Botanic Garden, Macy’s holiday windows, and the annual Millennium Park Christmas Tree Lighting take place in November.
You can also enjoy a vantage point of the city from the famous Centennial Wheel at Navy Pier or Skydeck Chicago.
Looking for a traditional Thanksgiving dinner? Several restaurants across the city can serve you up!
If the weather is right, you might even catch the end of some fall foliage in the urban cityscape.
You can also get out of the city for a day trip to places like Starved Rock or Indiana Dunes for some of the best places to hike near Chicago.
⭐Popular Chicago Hotels
2. Milwaukee
Best for: Lowkey Urban
If you are looking for an Urban vacation but want something smaller than Chicago, Milwaukee might be the Midwest Thanksgiving vacation for you.
Similar to Chicago, there are tons of city holiday events beginning around Thanksgiving and running through Christmas.
Candy Cane Lane and the Christmas Carnival of Lights show are two big light shows in Milwaukee each year.
The Christmas Carnival of Lights is a drive-through light show.
It is open from November 22nd – December 31st in 2025. The event is located in Caledonia, Wisconsin, 20 minutes by car from Milwaukee.
Check the official website for any closures before attending.
⭐Highly Rated Milwaukee Tours
Please check Milwaukee news publications for the most up-to-date information.
Other classic things to do in Milwaukee you can enjoy during Thanksgiving vacation include the Pabst Mansion, Milwaukee Public Market, and strolling the Milwaukee Riverwalk.
The Milwaukee Public Market is a personal favorite of mine, and makes for one of the best Midwest tourist attractions!
Milwaukee is an ideal Thanksgiving vacation and Midwest weekend getaway.
3. St. Louis
Best for: Gateway to The West
If you’re looking for a terrific Thanksgiving getaway in the Midwest, head to St. Louis, Missouri!
Spending Thanksgiving in St. Louis, Missouri, offers holiday travelers a delightful blend of the city’s history, culinary traditions, and festive cheer.
Start turkey day with the beloved Thanksgiving Day Parade, a St. Louis tradition with colorful floats, giant helium balloons, and the rhythms of marching bands.
It’s a perfect outing for families. Spoiler alert—Santa will make an appearance!
For those who like to blend their holiday festivities with a bit of exercise, the Turkey Trot races provide the ideal opportunity. Choose the historic 8K run through downtown St. Louis.
⭐Popular St. Louis Tours
Reward yourself with some tasty local foods!
I love the food in Mound City! Make sure to try the foods St. Louis is known for, like St. Louis ribs and gooey butter cake.
But on Thanksgiving Day, we have a great option for a traditional meal. The Thanksgiving Dinner River Cruise offers a unique dining experience aboard a riverboat on the mighty Mississippi River.
Feast on a traditional holiday spread while the stunning riverfront views of St. Louis serve as your backdrop.
Contributed by Denise of Chef Denise
4. Detroit
Best for: Americana Nostalgia
Detroit is an underrated destination for a Thanksgiving getaway in the Midwest because it’s a bit off the beaten path and unlike any other city in the US in its contrasts.
Visually, you’ll be struck by the mix of blight and urban decay alongside shiny and new buildings and homes.
Thanksgiving is an off-peak time to visit Detroit, so flights and accommodations are often more affordable. Stay in the stylish and modern Sonder Gabriel Richard, which is conveniently located near the top attractions.
Unless you’re staying very central and not traveling around much, a car is essential. After all, Detroit is The Mobile City!
To learn more about Detroit’s history, swing by the Henry Ford Museum.
⭐Popular Detroit Tours
For memorable eats, start with a slice of Detroit-style pizza at Buddy’s Pizza. It’s similar to Sicilian pizza but cheesier – nothing like nearby Chicago-style pizza.
Also, don’t miss a vegetarian-friendly brunch at Spacecat V-stro.
Pick a day of your trip and drive out to Ann Arbor, where you can explore the charming downtown and the University of Michigan campus.
Contributed by Amber from Amber Everywhere
Nature
5. Northern Indiana
Best for: Small Town Nature
If you are looking for an outdoor Thanksgiving vacation this fall, Indiana Dunes might be the spot for you!
Declared one of the newest national parks of the United States, Indiana Dunes boasts plenty of reasons to visit during Thanksgiving. The smooth, hilly sand dunes make for some of the best hikes in the Midwest.
Thanksgiving is off-season at the park, so you are likely to find fewer crowds during your vacation, amidst the lovely foliage. (Note that peak foliage time changes annually due to weather conditions).
The Indiana Dunes Visitor Center is closed on Thanksgiving Day, but the park itself remains open.
There are plenty of holiday activities to enjoy throughout the Northern Indiana region! Ice skating rinks are generally open Thanksgiving week.
Fair Oaks Farm and Harvest Tyme Family Farm host light show events.
You can also attend an annual tree-lighting ceremony on the Friday after Thanksgiving in Hammond, Indiana.
6. Starved Rock and Matthiessen
Best for: Unexpected Adventure
Starved Rock and Matthiessen State Park provide the perfect combined vacation!
These two Illinois state parks feature sandstone rock formations and seasonal waterfalls (depending on weather).
Visiting feels like you have stepped far outside the Midwest, and it surprises me every time I visit that I am only 2 hours from Chicago!
Guided hikes and lunches are offered through the Starved Rock Lodge on various weekends in November. Check the website calendar for specific dates and times this November.
The Starved Rock Lodge hosts an annual Thanksgiving Buffet. You can purchase tickets in advance to attend!
You can also enjoy the holiday festivities of the small neighboring town of Utica, only 5 minutes away from the park.
7. Custer State Park
Best for: Nature and Wildlife Lovers
Custer State Park in South Dakota is an ideal Thanksgiving destination for nature and wildlife lovers.
It’s off-peak season in Custer, with chilly weather and some snow.
Dress warmly to enjoy the state park and surrounding attractions without the crowds.
Driving the 18-mile wildlife loop is one of my favorite things to do in Custer State Park. Be on the lookout for bison, antelope, elk, deer, and the begging burros.
Don’t miss a visit to the Needles Highway and the famous Needle’s Eye tunnel. If the highway is closed due to snowfall, park at Sylvan Lake and hike 1.25 miles up to the Needle’s Eye.
You can generally find great deals on flights to Rapid City and on lodging in November. Rent a car for the 45-minute drive from Rapid City to the park.
The Holiday Inn Express & Suites Custer-Mt. Rushmore puts you close to Custer’s restaurants and a short drive to Custer State Park, Crazy Horse Memorial, and Mount Rushmore.
Book a few months in advance for the best rates.
Top off your experience with a unique Thanksgiving dinner at the Laughing Water Restaurant at Crazy Horse Memorial.
Contributed by Sonia of Carey On Travels
Conclusion
These Midwest Thanksgiving vacations present a range of delightful options for all types of travelers.
Whether it’s Custer State Park in South Dakota or the cozy charm of small-town getaways, the Midwest offers a unique blend of experiences.
Taking a Midwest road trip can be an ideal way to see several Midwest sights this fall, and perhaps even catch the end of the region’s fall foliage.
Embrace the season and consider these fantastic spots for an unforgettable Thanksgiving adventure!
