Chicago Road Trip: Roadside Attractions in Chicago

This summer I took a road trip around “Illinois” (believe me, you’ll hear all about it in the coming months). If you are from around here you know that “Illinois” and “Chicago” are two very different things so last weekend my friend Emily and I decided to take a Chicago road trip to find all the best roadside attractions in Chicago and the surrounding area.

OK, OK. So I don’t know if it really counts as a “road trip” if you are gone for less than twelve hours and travel no further than forty-five miles from where you live…but it was still an awesome time and we found so many Chicago roadside attractions!

Here was our Chicago road trip itinerary:

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You should feel free to recreate the day and check out all of these Chicagoland attractions for yourself. Although I recommend doing it in summer (when the McDonald’s Museum is actually open) and on any day but Sunday (a few things are closed on Sunday…) But fear not, Silly America, for all the wonders we did not get to thoroughly explore, we will definitely return to in the future. Here’s a quick recap of all the weird Chicago attractions we found.

Roadside attractions in Chicago:

Mr. Bendo Muffler Man in Chicago, Illinois

Mr. Bendo Muffler Man

The first stop on our road trip was about a mile west of Humboldt Park on Grand and Pulaski: Mr. Bendo. This trip was all about the Muffler Man as we saw a few of these babies. This one was curious to me because his one arm was down instead of both being (as tradition dictates) out in front.

World's Largest Radio Flyer Wagon in Elmwood Park, Illinois

Giant Wagon

We then took off down Grand further into Elmwood Park to find the Radio Flyer Factory and a frickin huge wagon! It was huge! Being Sunday it was, unfortunately, closed and gated off, but we parked in the strip mall across the street to take pics.

Leaning Tower of Niles in Niles, Illinois - Leaning Tour of Pisa Replica

Leaning Tower of Niles

Then it was on to Italy…errr…I mean Niles…for the Leaning Tower of Niles! This replica of Italy’s Leaning Tower of Pisa is roughly half-sized (94 feet vs. 177 feet) and leans about 7’4″ off plum (Pisa has a 15 foot tilt) and sits in front of a YMCA. Being holiday season the tower was decked out for Christmas in garland and bows. Considering I was too food poisoned to want to take a train ride to the real thing last summer, this made a nice substitution. (Want another taste of Italy in America? Check out the Venetian Gondola Rides in Las Vegas.)

Hidden Trout Fisherman Statue, a roadside attraction in Niles/Des Plaines, Illinois

Trout Fisherman

Of all the elusive roadside attractions near me that I didn’t expect to find, this was it. This large trout fisherman statue was left over from an old mini golf course that used to be on the property. Now they are building condos around it, so who knows if it will still be there for long…but it looks pretty safe and sound for the time being!

Big She at Square Deal Shoe Store in Des Plaines

Robert Wadlow’s Shoe?

Square Deal Shoe Store in Des Plaines supposedly has a pair of Robert Wadlow’s shoes on display…Robert Wadlow was the world’s tallest man and so he had some very big shoes. The shoe store was closed, so we couldn’t go in to check it out, but they had this giant shoe in the window.

McDonald's #1 Store Museum in Des Plaines, Illinois

McDonald’s Museum and Store No. 1

Des Plaines is also home to the first McDonald’s! While the restaurant no longer sells food, it’s been restored to its original glory and houses a museum…which, unfortunately, is only open during the summer 🙁 We forwent eating at the working regular ole McDonald’s across the street and instead ate at…

Choo-Choo Diner: Hamburgers on Wheels in Des Plaines, Illinois - Train Themed Restaurant

Choo Choo Restaurant

The Choo Choo restaurant is a tiny little diner. What makes this stop road trip worthy? Going through the kitchen and all around the counter is a toy choo choo train that delivers your food. How rocking is that? Em and I secured spots right at the counter so we could watch it in action. They had a really yummy chocolate shake and a good cheeseburger. And a train! And I even saw the train almost catch fire once! Awesome.

Ferris Bueller's Day Off Garage in Highland Park, Illinois

Ferris Bueller Garage

Does this garage look familiar?

If you have ever seen a small independent art film called “Ferris Bueller’s Day Off ” it should. This is the garage where they kept and crashed the fancy car. It is on someone’s house in Highland Park. Because it is November and there are no leaves it made it easy to see. Finally, one point for visiting all these roadside attractions in Illinois on the chosen day!

Muffler Man and Bessie the Cow in Libertyville, Illinois

Muffler Man and Bessie the Cow

Another muffler man AND a cow statue! This one is at Lamb’s Farm in Libertyville. We were a little confused at first because we say the cow, but not the muffler man. Turns out that the cow is even bigger than the man. We didn’t get too close because they were kind of closed. But I’m sure I will return to see these Illinois roadside attractions again some day.

Gold Pyramid House in Wadsworth, Illinois

Golden Pyramid House

“The largest 24-karat gold-plated object ever created” is the private home of a rich Armenian garage builder and his family. Seriously, this giant pyramid is someone’s house. And right next to it on either side are normal looking houses. The place looks kind of run down and like it is maybe under construction…I don’t know when it was built, but I know it was a while ago. It also started snowing while we were here. Who expects there to be snow when visiting the pyramids?

Giant Cigar Store Indian in Oak Lawn, Illinois

30-ft Tall Cigar Store Indian

After the Pyramid we hopped on the highway back to pick up my workaholic friend Matt, who was seriously working on a Sunday. It was about an hour drive, which was the longest stretch between places. We probably could have spaced out our stops at llinois road trip attractions better, but we definitely wanted to be in Des Plaines for lunchtime. With Matt in tow, we then hopped back in the car for more roadside America. The next stop was this big ole Cigar Store Indian in Oak Lawn.

Shiny muffler man in Evergreen Park, Illinois.

Muffler Man – Bunyan

This muffler man in Evergreen Park was very very shiny. That is because he was painted in Du Pont Chroma base auto paint after having a weather-related accident.

63rd Street Indian

Imagine the scene: you are on the south side of Chicago…in the lane going straight…look up…notice that the Indian you are looking for is on that corner…so you slide into the turn lane…end up turning as it’s going to red…pull over into an unpaid metered space, partially in a tow zone…get out to snap a bunch of pics…and then notice the cop car on the corner who then turns and slows down next to your car…as MK put it “they just gave me a look like I’m the guy forced to hold his girlfriends purse and smiled like they understood.” hehe. Anyways. So this Indian Muffler Man was creepy. Mostly because he had big white eyes that made him look blind…all while advertising a vision correction center 🙂

Giant Hot Dog Topped with Fries at Henry's in Cicero, Illinois

Giant Hot Dog Topped with Fries

This was just a hot dog topped with fries on a sign for Henry’s Drive-In, a Route 66 fast food joint. Not too exciting because it is neither freakishly large nor edible. Next.

The Spindle - Car Kabob - in Berwyn, Illinois

The Spindle

I’ve seen the Spindle a million and a half times. But it is a true American icon and my favorite Chicago roadside attraction. And they are trying to take it away from me and build a Walgreens which is just blasphemous, so I try to go and pay my respects as often as possible. I’ll be sure to keep you updated on that.

The Spindle is probably better known as “cars on a spike” or the “car-ca-bob”. It’s at Cermak Plaza in Berwyn and had a starring role in the movie Wayne’s World. It also rocks. I will miss the Spindle terribly when it is gone.

So that, in a nutshell, is Chicagoland. At least, the weird, kooky, roadside of Chicago. Of course, there is much much more silly American sites to see, but a short road trip around Chicago was a good way to spend the day and we managed to soak in a lot in less than twelve hours.

Wonder what other roadside attraction in Chicago, Illinois we would have seen with another twelve?

Date: October 28, 2007

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Chicago Road Trip itinerary and map with stops at all the weird roadside attractions in Chicago and nearby! Including a Ferris Bueller Garage, Golden Pyramid House, world's largest wagon, and more. Add taking a Chicago road trip to your travel bucket lists!
#IllinoisRoadsideAttractions #IllinoisRoadsideAttraction #RoadsideAttractions #RoadsideAttraction #RoadTrip #IllinoisRoadTrip #IllinoisRoadTripItinerary #IllinoisRoadTripMap #IllinoisRoadTripTravel #WeirdRoadsideAttractions #ChicagoRoadTrip
Chicago Road Trip itinerary and map with stops at all the weird roadside attractions in Chicago and nearby! Including a Ferris Bueller Garage, Golden Pyramid House, world’s largest wagon, and more. Add taking a Chicago road trip to your travel bucket lists!

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Valerie Bromann

Founder & ROad Trip Expert

Valerie Bromann is a a website manager, content creator, and writer from Chicago, Illinois (currently living in Dallas, Texas). As an avid road tripper who has visited hundreds of roadside attractions, Val always pull over for a world’s largest thing. Founder of Silly America and author of The Road Trip Journal & Activity Book, she visits, photographs, and writes about all the weird tourist destinations she visits and offers road trip planning advice and inspiration based on her own travels so you can hit the road for yourself.

World's Largest Mailbox in Casey, Illinois roadside attraction

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The Road Trip Journal & Activity Book - Everything You Need to Have and Record an Epic Road Trip! By Valerie Bromann

The Road Trip Journal & Activity Book

Everything You Need to Have and Record an Epic Road Trip!

BY Valerie Bromann

Enjoy fun games and challenges to pass the time on your next road trip and have a keepsake to look back on for years to come with this entertaining must-have for your next vacation.

The road trip you’ve been dreaming of starts here! Journal about your stops and get to know your fellow passengers with activities and exercises designed to pass the time and bring you closer together. Instead of “Are we there yet?” you’ll find yourself asking, “We’re there already?”. Complete with prompts you can turn to while driving between locations, this journal will one day be a memento of your life-changing trip.