10 Amazing Midwest Tourist Attractions (2024)

Iconic Gateway Arch on a sunny day framed by lush green trees, with a clear blue sky overhead, a perfect stop on a Midwest road trip.

Are you looking for the best Midwest tourist attractions?  There are so many to choose from! 

As a Midwest local, I created a round-up guide of some of the best tourist attractions for every travel style. 

This list is not all conducive (because there is no way I could include all of the details necessary in just one article!) but it’s the perfect starting point for learning about the best attractions of the area. 

From the shimmering reflection of the skyline on The Bean in Chicago to the bustling aisles of Milwaukee’s Public Market, the Midwest offers tons of experiences for every traveler.

Imagine yourself strolling through the vibrant, art-filled streets of Chicago, where Cloud Gate (affectionately known as The Bean) offers stunning, mirror-like views of the city skyline and the sky above.

Then, venture north to Milwaukee to savor artisanal foods and unique gifts at the renowned Public Market. But the Midwest charm doesn’t stop at city borders.

Picture a serene getaway to the quaint small towns scattered throughout the region, like the picturesque Lake Geneva, where tranquility meets adventure.

Let’s get planning!

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1. The Bean

A vibrant group of visitors gathered around the Cloud Gate sculpture, reflecting the clear blue sky and Chicago skyline, a popular spot for photo ops during a girls weekend in Chicago.

The Bean is by far one of the greatest tourist attractions in Chicago.  Formally renamed as the “Cloudgate”, the 33-foot-tall sculpture is a Chicago icon.  It’s definitely touristy.  I know some Chicago locals who haven’t even been here yet.  But it’s one of those “You can’t leave Chicago until you’ve been here” type of things. 

Located in Millenium Park, the towering sculpture is walking distance from other Chicago attractions like Grandt Park and the Art Institute of Chicago. 

⏐💲Price: Free ⏐

2. Navy Pier Ferris Wheel

The Ferris Wheel at Navy Pier is one of Chicago’s most iconic attractions for all ages.    Take a ride on the towering wheel to see breathtaking views of Lake Michigan and the city skyline.

Navy Pier is not just about the Ferris Wheel; it’s a bustling hub of entertainment, shopping, and dining options that cater to every taste.

First-time visitors will be delighted to find that aside from the rides, there are often seasonal and cultural events taking place.

This makes Navy Pier a versatile attraction where one can enjoy not just the scenic views of Chicago’s skyline but also immerse in the local culture and festivities. With its easy accessibility and wide array of activities, Navy Pier is a must-visit destination for anyone exploring Chicago for the first time.

⏐💲Price: $18 ⏐

3. Skydeck

Woman in a blue shirt laying on a glass ledge high above the city at the Skydeck. There are exhilarating views of Chicago skyscrapers beneath her, adding thrill to a girls weekend.

The Skydeck is one of Chicago’s newest can’t-miss activities.  Stand inside of a glass box on top of a ledge overlooking the entire city of Chicago… from over 1,300 feet in the air! 

If the box itself isn’t your thing, there are tons of views from the top floor of The Skydeck too.  They also have a newly renovated interactive museum on your way up to the Skydeck.  I loved snapping silly photos with friends and learning some new facts about Chicago history. 

It’s honestly great for all ages. 

⏐💲Price: Free ⏐ 🎫Tickets

Read Next: Chicago Itinerary

🏨Chicago Hotel Recommendation: Felix Hotel


4. Milwaukee Public Market

Milwaukee Public Market is one of my favorite attractions in all of Milwaukee!  Not only do I love a good local market, but this one overlooks Milwaukee’s Lakefront.  You can conveniently experience local food, take a walk along the lake, and go shopping in the historic Third Ward district all in an afternoon’s time. 

Extend your stay in Milwaukee for Midwest vacation or even a long weekend!

🏨Milwaukee Hotel Recommendation: Plaza Hotel

Small Town

5. Historic Route 66

Historic Route 66 is famous for many reasons!  The route traditionally begins in Chicago, and sweeps road trippers through small farm towns and a few bigger cities until it ends in California.

The nearly 2,500-mile route could be spread over several weeks, but for the sake of this guide, let’s focus on the top stops in the Midwest.

The Route is not necessarily one attraction, but a road trip filled with several attractions.  The most iconic Route 66 stop in Illinois is the sign representing its starting point at the Northwest corner of Michigan Avenue and Adams Street in Downtown Chicago. 

My favorite small town stop on the Midwest leg of Route 66 is Ewing Manor Preserve in Bloomington, IL.  It’s so beautiful, it doubles as a wedding venue! 

6. Galena

A winding road cuts through a dense forest of radiant autumn hues in Galena, Illinois, highlighting the quintessential fall foliage in the Midwest.
Galena by Austin Goode via Unsplash

Galena, Illinois, stands out as a quintessential Midwest attraction due to its well-preserved 19th-century buildings and rich history.

This small town, nestled among rolling hills, offers visitors a unique glimpse into the past with its charming Main Street, home to more than 100 independent shops.

Galena’s scenic beauty, combined with its historical significance and array of outdoor activities, makes it a must-visit destination for those seeking a peaceful getaway with a touch of nostalgia.

Galena is a quaint, historic town located in Western Illinois.  It is characterized by its rolling hills, ski resorts, wineries, and charming town center.

Bonus: Galena makes for a quaint, Midwest weekend getaway for couples.  

🏨Galena Hotel Recommendation: Cloran Mansion Bed & Breakfast

7. Lake Geneva

Lake Geneva is one of the top day trips from Chicago, and one of the top tourist attractions near the city. 

Visitors love to get away for a day or weekend at the small lake town with an adorable Downtown. 

Its beach and marina allow this small town to double as a favorite lake town among locals.  Rent your boat of choice for the day, or take a boat tour!  If you’re looking for an adrenaline rush, tourists also enjoy the local Zipline and hot-air balloon attractions.  I haven’t tried one of these myself (ziplined once in Costa Rica). 

🏨Lake Geneva Hotel Recommendation: Harbor Shores 

National Parks

8. Indiana Dunes

Indiana Dunes is the Midwest’s newest National Park! 

It’s also conveniently located less than one hour by car from Chicago.  There is also a public transportation option that brings you directly from Ogilvie Transportation Center to Indiana Dunes. 

Indiana Dunes is known for miles of lakeshore beaches along Lake Michigan and miles of hiking trails. 

My favorite Indiana Dunes trails are the Dunes Succession Trail and the 3 Dune Challenge.  You feel like a kid all over again climbing to the top of a giant sand mound, and tumbling to the beach at the bottom!  It never gets old. It’s some of the best hiking near Chicago.  

⏐💲Price: $25 or free with the America the Beautiful Annual Pass

🏨Indiana Dunes Hotel Recommendation: Spring House Inn

9. Mackinac Island

Midwest road trip to a serene lakeside in Mackinac Island, Michigan. There is a white lighthouse overlooking the clear blue waters, flanked by vibrant greenery and a no trespassing white picket fence.
Mackinac Island by Vincent Yuan via Unsplash

Mackinac Island is unique because the entire park is on an island!  That’s right, you need to hop on a ferry to this pearl gem in the Midwest.

It was originally declared as the second national park ever (just behind Yellowstone) but has since been moved to state park status. 

You can find some of the best Midwest hiking here!  

10. St. Louis Gateway Arch

Iconic Gateway Arch on a sunny day framed by lush green trees, with a clear blue sky overhead, a perfect stop on a Midwest road trip.
St. Louis Arch by Chris Hardy via Unsplash

The Gateway Arch was declared one of the country’s newest national parks in 2018!  Combine your visit with a city trip through St. Louis. 

The St. Louis Gateway Arch stands as a symbol of the city’s role as the “Gateway to the West” and offers an unparalleled view from its observation area.

Its stainless steel arch, reaching 630 feet, is a classic architectural marvel.

Visitors can learn about America’s westward expansion in the museum at its base, making it a must-visit for history buffs and architecture enthusiasts alike.


Ready to experience the vibrant culture, breathtaking landscapes, and warm hospitality of the Midwest

Start planning your trip today and immerse yourself in the unique attractions that make the Midwest a must-visit destination.

From the architectural marvels of Chicago to the peaceful retreats in charming small towns, your adventure awaits.

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As a full time employee who loves her job, learn how I honor my wanderlust while working a 9:00-5:00 (because I want to!) This blog welcomes all, and specifically provides resources for those seeking travel intertwined into a busy schedule (3 days to 5 weeks).