7 Weird and Wonderful Roadside Attractions In and Around 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 summer vacation right.

Whether your kids are interested in history or mega fans of Home Alone (I mean, aren’t we all?), there’s a fun stop along the road for everyone. Here’s to making new discoveries close to home.

NOTE: Due to COVID-19 concerns, some locations may be closed or only offer limited access with extra precautions. Please check each location’s website (if available) for more information.  

The Leaning Tower of Niles

If you can’t quite shell out the funds for trip to Italy, not to worry. Just 15 minutes northeast of O’Hare, there’s a replica of the famous Leaning Tower of Pisa that stands at about half the height of the real thing, but still makes for great Instagram ops. Plus, there’s also a fountain and reflecting pool to give the attraction an ultra-authentic Italian feel. How cute would a photo of grandma pretending to hold the tower up be?

The Home Alone House

The Georgian-style home, located at 671 Lincoln Ave., still looks the same as it did in 1994, minus all of the damage from the Wet Bandits’ break-in. I’m sure the house gets thousands of looky-loos each year, so I would suggest keeping your visit brief (the home is still a residence, after all). But since new generations of children discover the film each year, your kids will probably find this stop to be cooler than your average trip to the suburbs.

Paul Bunyan and Bessie the Cow

Outside Lambs Farm stands an imposing 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.

World’s Largest Wagon

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 that can fit up to 75 children.

Par-King Skill Golf

When your kids set eyes on this great, tall pink suburban castle, they might actually believe a princess lives there. It’s actually home to Par-King Skill Golf. If it’s outdoor mini golf season, head inside for some putt putt to see some more of the quirky decorations, like a mini wooden rollercoaster and a Super Looper.

Big Monster Door

Behind this massive yellow door is Big Monsters Toys, a toy and game design studio in the West Loop. We could only imagine the exciting things that go on inside! In the meantime, you can snap a picture outside the door. Extra points if you’re able to hang on from the door knob!

Superdawg Drive-In

This drive-in hot dog joint has been around for decades, so you’ve might have spotted the restaurant’s hot dog mascots, Maurie and Flaurie, on the rooftop before. Fun fact: They’re named after the original couple, Maurie and Flaurie Berman, who opened their business in 1948! How cute is that?


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This story originally published on June 1, 2018. It has been updated with the most recent information. 

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