Uncover Unique Roadside Attractions Near Chicago

There are many famous (and wacky) landmarks across our country, from Route 66 to the World’s Largest Ball of Twine in the middle of nowhere Kansas. But if you’ve never taken the time to check out some of Chicagoland’s weird and wonderful roadside attractions, well, you’re just not doing your road trip right.

Whether your kids are interested in history or mega fans of Home Alone or Wizard of Oz, there’s a fun stop along the road for everyone.

Note: Some of these attractions may be on private property. Check before you head out, and remember it’s never OK to climb on art installations unless there’s a sign that specifically says you can. Admission prices are subject to change in 2025.

Animals of Safari Land

• Address: Safari Land, 701 W. North Ave., Villa Park

See the larger-than-life fiberglass animals outside of Safari Land, a family-owned amusement and arcade park. There are elephants and giraffes to take pictures with.

Exhausted Paul Bunyan 

• Address: 1 University Parkway, University Park

This 25-foot-tall and lifelike statue of Paul Bunyan is different from others in the U.S. Instead of looking strong, he looks tired and hunched over.

Frankenmufflerman

• Address: Haunted Trails, 7759 S. Harlem Ave., Burbank

This attraction is a mix of a Muffler Man and Frankenstein. It stands 20 feet tall and is located inside the park.

Giraffe Bursts Through Roof 

• Address: Grand Dental, 1780 N. Farnsworth Ave., Aurora

This pediatric dental office features a long-necked, smiling giraffe head coming out of their roof. Kids will think this one is so cool!

Home Alone House

• Address: 671 Lincoln Ave., Winnetka

See one of the most famous houses in Chicagoland, the Home Alone house. Even without all of the Christmas décor, it is still pretty recognizable. This is a home residence, so make sure to be courteous and not stay too long.

Lifesize Mastodon Statue

• Address: Phillips Park Zoo, 1000 Ray Moses Drive, Aurora

Admission is free to Phillips Park Zoo so families can pop over to see this lifesized Mastodon statue. It actually marks the area where Mastodon bones and fossils were first uncovered in 1934. The park is open 9 a.m.-5 p.m. daily.

Michael Jordan Statue

• Address: United Center, 1901 W. Madison St., Chicago

The statue is now located indoors. Visitors must enter through inside the gift shop to view it. It is a 17-foot-tall bronze statue of Michael Jordan dunking the basketball on a nameless opponent.

Mr. Beef

• Address: 666 N. Orleans St., Chicago

After the popularity of the hit Hulu TV show, The Bear, Mr. Beef has become a well-known roadside attraction. The Bear has filmed scenes at Mr. Beef and the sandwich shop in the show (The Original Beef) was actually inspired by Mr. Beef. Their menu includes Italian beef sandwiches, Chicago dogs, fries and more.

Muffler Man and Bessie the Cow 

• Address: Lambs Farm, 14245 W. Rockland Road, Libertyville

See the 15-foot-tall Paul Bunyan Muffler Man statue with a giant ax alongside a cow, who is apparently named Bessie. In case there was any doubt you’re in farm country, there’s also a large milk bottle statue nearby. The figures make for great pictures, and the train rides, mini golf and petting zoo at Lambs Farm make the trip to Libertyville more than worth it.

Par-King Skill Golf 

• Address: 21711 N. Milwaukee Ave., Lincolnshire

Check out one of the coolest outdoor mini golf courses in Chicagoland and see the great, tall pink suburban castle. Children must be 48 inches tall to play or even enter the golf course.

Superdawg Drive-In

• Addresses: 6363 N. Milwaukee Ave., Chicago; 333 S. Milwaukee Ave., Wheeling

This drive-in hot dog joint has been around for decades, so you might have spotted the restaurant’s hot dog mascots, Maurie and Flaurie, on the rooftop before.

The Bean

• Address: Millennium Park, S. Michigan Ave., Chicago

It may be the most basic of the roadside attractions, but living in Chicago, it is the most popular to visit. If you’re with someone from out of town, it is a must-see. Standing at 66 feet long and 33 feet tall, this giant bean is a great photo opp.

The Leaning Tower of Niles

• Address: 6300 W. Touhy Ave, Niles

If you can’t quite shell out the funds for a trip to Italy, not to worry. Just 15 minutes northeast of O’Hare, there’s a replica of the famous Leaning Tower of Pisa. Although it stands at about half the height of the real thing, it still makes for great photo ops. Plus, there’s also a fountain and reflecting pool to give the attraction an ultra-authentic Italian feel.

Wizard of Oz Statues

• Address: Oz Park, 2021 N. Burling St., Chicago

See statues of Dorothy, Scarecrow, Tin Man, Cowardly Lion and Toto from the movie, The Wizard of Oz. Also, be sure to check out Dorothy’s Playground while you’re there with your kids. It underwent a major upgrade and features ADA-accessible ramps, slides, a rock climbing wall, jungle gym and more.

World’s Largest Covered Wagon and Big Lincoln

• Address: Best Western, 1750 Fifth St., Lincoln

See a 12-foot-tall Abraham Lincoln on a 24-foot-tall covered wagon. It is the Guinness Book of World Records’ largest covered wagon and is a must-see roadside attraction on Route 66.

World’s Largest Wagon

• 

  Address: 6515 W. Grand Ave., Chicago

If you love Radio Flyer, then you have to stop and snap a photo next to the company’s largest wagon ever on Chicago’s West Side. This massive Radio Flyer stands in front of the company’s headquarters. If the gates are open, you can walk up and take an up-close photo of the 27-foot long wagon. It still holds the Guinness World Record.

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