The 25 Best Roadside Attractions in Illinois
Ranked by Roadtrippi users — the people who've actually been there. Updated June 2026. Roadtrippi catalogs 774 roadside attractions in Illinois.
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1. Diamond Mine Disaster Monument
Diamond, IL
Melting snow plus heavy rain equals mine collapse; most of the dead remain entombed in it.
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2. Al Capone's Hideaway and Steakhouse (Closed)
St. Charles, IL
An old speakeasy -- a reported haunt of Al in his heyday -- displays a lot of the exhibits from the defunct Al Capone Museum in Chicago. Closed in early 2012.
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3. Tilt!
Chicago, IL
A mechanical contraption tilts a section of a 94th floor skyscraper observation deck out and down 30 degrees. You hold onto steel grab bars.
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4. Bobby Hull and Stan Mikita Statues
Chicago, IL
Chicago Blackhawks hockey legends Bobby Hull and Stan Mikita are sculpted for posterity in front of the stadium where they played.
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5. Madonna of the Trail
Vandalia, IL
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6. Clown Lips Doorway
Chicago, IL
Stand on the tongue mat of sidewalk doorway transformed to resemble an open mouth and massive pair of lips.
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7. Charlie Birger Gallows and George Harrison Artifacts
Benton, IL
Charlie was executed in a public hanging in Illinois in 1928. George visited Benton in 1963, and got the radio station to play a record by a strange new group named The Beatles.
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8. Charles Lindbergh Crash Site #2
turn west onto E. 1000 North Rd/Stringtown Rd/Hwy 32. Drive west 3.8 miles, IL
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9. Ladies Room Jail Cells
Sandwich, IL
The City Hall and Opera House in town have transformed the city's old jail cells into ladies' rest rooms.
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10. Rose Water Tower
Rosemont, IL
A water tower painted to resemble a rose has been the symbol of the Village of Rosemont for decades.
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11. Wolfy's Vienna Beef Sausage
Chicago, IL
Hoisted above the street, a red Vienna sausage held permanently in place by a light bulb-outlined giant fork.
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12. Woolly Mammoth: Curiosity Cabinet
Chicago, IL
Small shop of taxidermy, oddities and quirky collectibles. Two-headed calf, human skulls, a chipmunk riding a horse, and a caricature of Hitler drawn by John Wayne Gacy. You get the idea.
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13. Future City
Cairo, IL
A little hamlet with an official green highway sign. It has spectacularly failed to live up to its optimistic name.
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14. Two-Cell Jail: Shutterbugs Welcome
Gardner, IL
Built in 1906, it's now a serve-yourself photo-op for Route 66 travelers who yearn for behind bars vacation snapshots. Press the button to hear the message.
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15. Tug Fest - East Side of Mississippi River Tug-of-war
Port Byron, IL
Unique competition pits two states on opposite banks of the Mississippi River against each other in an annual tug-of-war. Illinois currently leads Iowa 19 to 11.
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16. Henry's Drive-In: Hot Dog Topped With Fries
Cicero, IL
A giant french-fry "slammed" Chicago Hot Dog graces the sign to Henry's Drive-In. "It's a Meal in Itself."
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17. Darth Naper
Naperville, IL
Joseph Naper was an obscure land surveyor until this statue was unveiled in 2013. Its melodramatic pose seems better suited to the world's most famous space opera.
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18. Grave of King Neptune the Pig
Mount Pleasant, IL
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19. Lincoln Casket, Two-Headed Pig
Carthage, IL
The collection of the now-closed Museum of Funeral Customs is now here, including the world's most perfect replica of President Lincoln's casket. Kibbe has some unusual exhibits of its own, such as a woman's muff made from monkey hair and a two-headed pig.
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20. Peter Toth Giant Indian Head
Oglesby, IL
Artist Peter Toth carved this head of Indian chief Walks-with-the-Wind, part of his Whispering Giants series.
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21. Chicago Fire Survivor Water Tower
Chicago, IL
Made of stone and filled with water, the tower was one of the few structures to survive Chicago's Great Fire of 1871.
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22. Mighty Mouse and Elephant
Malta, IL
Mighty Mouse protects all customers of a pizzeria from evil cats and sneaky wolves. Restaurant is full of pop culture items.
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23. Ten-Person Swing (Gone)
Granite City, IL
Built out of logs by Brian Depauli, its official name is "Giant Swing For All My Friends."
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24. Wabash Turntable
Forrest, IL
An old railroad turntable has been restored on the grounds of a local model train museum, which was a former depot. Also here: an old caboose.
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25. Cardiff Memorial: Mine Explosions
Dwight, IL
A small memorial recalls a series of mine disasters that shrank the population of Cardiff, a town that now no longer exists.
Browse all 774 attractions in Illinois on Roadtrippi.