1.Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting

★★★★★★★★★★5.0 · 962 reviews · 1 hour 30 minutes (approx.) · from $35Our pick

Chicago’s Medieval Torture Museum: 90 minutes with audio guide and ghost-hunting app, plus wax scenes and interactive torture devices.

“If you're looking for something odd, bizarre, and unique this is a very small intimate but extremely detailed museum of torture macabre. I went a few days before Halloween and it was icing on the cake for me. Perfect for a date where the two of you are both weird, but in a good way.. lol”

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2.Eastside Chicago The Heist Exploration Game and Tour

★★★★★★★★★★4.0 · 10 reviews · 1 hour 35 minutes (approx.) · from $7

Play a self-guided heist game through Millennium Park and Grant Park with offline clues at Cloud Gate, Crown Fountain, Buckingham Fountain, and more for $7.20.

“Prepare to walk a lot, so wear comfortable shoes! The instructions were clear, and the highlights were interesting if you want to learn about some of the city's iconic landmarks.”

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3.Chicago Self-Guided Audio Tour

★★★★★★★★★★4.0 · 9 reviews · 3 to 9 hours (approx.) · from $6Best value

A low-cost self-guided audio tour of Chicago’s top sights, from Union Station to the Riverwalk, using easy mobile links.

“Very informative and interesting. The guide spoke articulately and loud enough for everyone to hear and he had interesting forklore and stories.”

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4.Chicago’s Gold Coast Hidden History: A Self-Guided Audio Walk

★★★★★★★★★★4.5 · 7 reviews · 50 minutes (approx.) · from $7

A budget-friendly self-guided Gold Coast audio walk with offline GPS, local-history storytelling, and stops at surgery museum and Zebra Lounge.

“Tour was informative. The use of visitor was klunky. Had to order the tour twice to use. Viator has committed refund one of the unneeded purchases. Walk and auto play needs some work. Price was right.”

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5.Chicago Riverwalk Self-Guided Walking Tour

★★★★★★★★★★4.0 · 6 reviews · 1 to 2 hours (approx.) · from $14

A self-guided Chicago Riverwalk audio walk with offline GPS. See iconic bridges and towers at your own pace for $14.99.

“Overall a great review of Chicago's history and architecture! The walk along the river is very enjoyable!”

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6.Haunted Chicago Exploration Game and Tour

★★★★★★★★★★4.0 · 6 reviews · 2 hours (approx.) · from $7

A $7.20, phone-led Haunted Chicago scavenger hunt across Lincoln Park landmarks, with clues, flexible pacing, and helpful 24/7 support.

“This was worth the little money it cost. The download and getting ready was a bit of a hassle still worth it. We really enjoyed all of it up until the last clue that was not accessible anymore. However the help menu and chat from the app let us know what happened at the end. Would probably liked a big finish. Still lots of interesting facts and places we would have missed on our trip. I did report the issue so hopefully others won’t get to the last chapter and not be able to complete it as well.”

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7.Chicago Millennium Park Self-Guided Walking Tour

★★★★★★★★★★4.5 · 5 reviews · 1 to 2 hours (approx.) · from $14

Self-guided audio walk through Millennium Park’s top sights, with offline maps and lifetime access for $14.99 in Chicago.

“Self paced walking tour so we could stop & listen, check side info. or just stop for a hot dog and lemonade between spots. Only complaint is when it says only run the tour, it really is only the tour. The couple times I toggled over to take a photo it stopped & I had to re-start it. No big deal, it picked up with where we were.”

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8.Chicago’s Storied Neighborhood: An Audio Tour

★★★★★★★★★★3.0 · 4 reviews · 40 minutes to 1 hour (approx.)

Self-guided Hyde Park audio tour with Bill Ayers. Offline VoiceMap, landmark pass-bys, and flexible pacing in 40–60 minutes.

“I loved having the app so that the talking started at the correct spot. Mr Ayers personal stories really enhanced the experience. I wish there was more talking during the longer stretches of walking:”

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9.Self-Guided Chicago Loop Tour Explore the City at Your Own Pace

★★★★★★★★★★5.0 · 3 reviews · 2 hours to 2 hours 30 minutes (approx.) · from $9

Self-guided Chicago Loop walk with GPS audio, free sights, and flexible timing from DuSable Bridge to Willis Tower for $9.99.

“This was a great way to see downtown Chicago at our own pace. We saw things we would have missed on our own. And could spend time taking photos and exploring. Instead of two hours we spent 4 or 5. Well worth it!”

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10.Michigan Avenue Rendezvous Walking Tour with Smartphone App

★★★★★★★★★★3.2 · 3 reviews · 2 hours · from $17

Michigan Avenue app-led walking tour turns landmarks into a trivia scavenger hunt. Private, self-paced, 2 hours for $17.

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11.Chicago Haunted Ghost Tour GPS Self-Guided Walking Tour

★★★★★★★★★★4.5 · 3 reviews · 1 hour to 1 hour 15 minutes (approx.) · from $9

GPS self-guided haunted walking tour through Chicago’s Riverwalk, Death Alley, and historic hotel lobbies, ending at Congress Plaza.

“The stories were great and informative. The narrator was fun to listen to. Lots of walking meant great exercise.”

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