19 Roadside Attractions Near Chicago You Must See

A summer road trip isn’t complete without a stop at one of the sometimes quirky (but always interesting) roadside attractions near Chicago, Michigan, Indiana, and Wisconsin. These top spots provide a fun place to stretch your legs, take pictures, and make hilarious family memories your kids will always remember.

Whether you’re headed to Wisconsin and need a stop at the Cheese Castle or are staying local and are pining for an Italian vacation, this list has something no matter which direction you want to go. Pack your bags, hit the road, and prepare for an amazing adventure!

For more road trip fun, check out these weekend road trip ideas and these car games for kids. 

 
Superdawg Drive-In! Photo courtesy of Superdawg

The Best Roadside Attractions in Illinois

1. World’s Largest Wagon: Radio Flyer enthusiasts must visit the company’s headquarters on Chicago’s West Side, where you’ll find the world’s largest wagon. This massive Radio Flyer is 27 feet long and can hold up to 75 children. It's one of the must-see roadside attractions near Chicago, and it'll be hard to resist the urge to climb in yourself! 

2. Route 66 Begin Sign: If you love road trips, this one is for you—iconic Route 66 Begin Sign—found at the intersection of Adams Street and Michigan Avenue in Chicago. Along this historic route, you’ll find quirky attractions designed to lure travelers to local towns, from whimsical landmarks to unique restaurants and even a rabbit ranch.

Top roadside attractions along Route 66 include the Standard Oil Gas Station in Odell, which was built in 1932 and showcases the classic architectural style of its era, and the Oakland Automobile Museum in Pontiac, which displays Pontiac car models from the early 20th century. 

3. The Leaning Tower of Niles: Don't have plans to visit Italy this summer? The Leaning Tower of Niles might be able to scratch that itch. Just 15 minutes northeast of O’Hare, you’ll find a replica of the famous Leaning Tower of Pisa. Standing at about half the height of the original, this charming landmark offers excellent photo opportunities, complete with a fountain and reflecting pool to enhance its Italian ambiance. 
 
4. The Home Alone House: "Kevin!" The iconic Georgian-style home still looks the same as in 1994, minus the Wet Bandits’ damage, of course. Given its fame, the house likely receives many visitors, so a quick visit is best as it is still a private residence. 
 
5. Paul Bunyan and Bessie the Cow: Standing outside Lambs Farm is a 15-foot-tall Paul Bunyan Muffler Man statue wielding a giant ax, accompanied by a cow named Bessie. The statues make for a great photo op and the nearby train rides, mini golf, and petting zoo at Lambs Farm make the trip to Libertyville worthwhile.
 
6. The Largest Collection of Big Things: Casey, Illinois, boasts 12 Guinness World Records for its giant attractions, and there are a ton of fun photo ops including:
 
- World's Largest Wind Chime
- World's Largest Golf Tee
- World's Largest Pitchfork
- World's Largest Rocking Chair
- World's Largest Wooden Shoes
- World's Largest Mailbox
- World's Largest Gavel
- World's Largest Truck Key
- World's Largest Barbershop Pole
- World's Largest Teeter Totter
- World's Largest Golf Driver
- World's Largest Swizzle Spoon
 
7. Kaskaskia Dragon: In Vandalia, Illinois, you’ll encounter the 35-foot Kaskaskia Dragon, modified to spit fire. Purchase a special dragon coin to activate the flames; you'll get about 10 seconds of fiery spectacle. It's absolutely worth it to see the look on the kids' faces. 
 
8. Superdawg Drive-In: This iconic drive-in hot dog joint has been a staple for decades, with its hot dog mascots, Maurie and Flaurie, adorning the rooftop. Fun fact: the mascots are named after the original couple, Maurie and Flaurie Berman, who founded the business in 1948. 
 
9. Wizard of Oz Park: Located in Chicago, the Wizard of Oz Park, established in the 1950s, features statues of characters from "The Wizard of Oz," written by Chicago native Frank Baum. Let the kids burn off steam in Dorothy's Playlot and stroll the garden to see the rest of the Oz gang. 

 
Horseshoe Mound Preserve is worth the trek. Photo by Maureen Wilkey
 
10. Horseshoe Mound Preserve: In Galena, Illinois, this 40-acre preserve offers stunning views of three different states! You might consider spending the whole weekend in Galena, so check out 22 things to do with kids there before you go. 

The Best Roadside Attractions in Michigan

11. The Mystery Spot: Head to St. Ignace, Michigan, and experience the baffling phenomena of the Mystery Spot. Explore this gravity-defying area where the laws of physics seem to be distorted. If you have extra time, check out the zipline course and mini golf!

12. Mackinac Bridge: As you cross the mighty Mackinac Bridge, stop at one of the designated viewpoints for breathtaking views of Lake Michigan and Lake Huron. This iconic bridge is a must-see attraction in Michigan.

13. Paul Bunyan and Babe the Blue Ox in Oscoda: Another version of the American folktale hero, this iconic statue stands over 30 feet tall and is a tribute to Michigan's lumberjack heritage.

 
The Pink Elephant, a Fortville landmark. Photo by Clayton Parker, via Flickr

The Best Roadside Attractions in Indiana

14. The Pink Elephant: If you find yourself near Fortville, Indiana make sure to see the largest pink elephant in the state. Located outside Elite Beverages, this pink elephant can be found on a trailer bed sipping from her blue martini glass. Cheers!

15. World's Largest Ball of Paint: Make a pit stop in Alexandria, Indiana, to witness the quirky wonder that is the World's Largest Ball of Paint. Even better, you can watch as layers of colorful paint are added to this ever-growing attraction.

16. Flick Stature: If you have seen the iconic film A Christmas Story, you likely remember the infamous scene where Flick licks the frozen flag pole and his tongue gets stuck. Outside the South Shore Welcome Center in Hammond, you can see a bronze statue of Flick licking the pole just like in the film. 

17. Giant Santa Claus: For a little taste of the holiday spirit any time of the year visit Santa Claus, Indiana to see the giant statue of the big man himself. It's the oldest statue of Santa Claus in the U.S. and goes along with the year-round cheer this town displays. 

 
The House on the Rock in Spring Green, Wisconsin. Photo by Lorie Shaull, via Flickr

The Best Roadside Attractions in Wisconsin

18. House on the Rock: Venture to Spring Green, Wisconsin, and step into a world of eccentricity at the House on the Rock. Explore the bizarre collections and architectural marvels, like the Heritage of the Sea, which boasts a 200-foot-long sea creature, and the Inifinti Room, a room that extends 218 feet over the valley with over 3,000 pieces of glass. 

19. Mars Cheese Castle: They aren't kidding when they call it a castle It is quite literally, a castle filled with a treasure everyone can appreciate—cheese! Indulge in some cheesy goodness at Mars Cheese Castle in Kenosha, Wisconsin. Sample a variety of cheeses, meats, and other gourmet treats at one of Wisconsin's most beloved roadside attractions.