Chicago · GUIDED

The 15 Best Guided Tours in Chicago

38 tours  ·  from $6 a head

The 15 best guided tours, each with what it costs, how long it takes and who it suits. Start with number one; it sits there for a reason.

Chicago River: 1.5-Hour Guided Architecture Cruise - Marina City and the river’s north and south branches
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Chicago River: 1.5-Hour Guided Architecture Cruise

1.Chicago River: 1.5-Hour Guided Architecture Cruise

★★★★★★★★★★4.8 · 8,046 reviews · 1h 30m · from $44Our pick

Cruise Chicago’s main river and north and south branches for 90 minutes, passing landmarks from the Wrigley Building to Marina City and Willis Tower. An English-speaking guide brings the skyline’s 130-year story to life, while you choose an open deck or climate-controlled seating. Local drinks and Garrett’s Popcorn are available to buy onboard.

“This cruise is definitely worth doing. John our guide was first class, very funny and entertaining as well as being informative.”

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Chicago: Gangsters and Ghosts Guided Walking Tour - The Riverwalk and Death Alley
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Chicago: Gangsters and Ghosts Guided Walking Tour

2.Gangsters and Ghosts Guided Walking Tour

★★★★★★★★★★4.7 · 1,697 reviews · 2 hours · from $36

Join an English-speaking historian guide for a 1.5-mile walk through Chicago’s South Loop, where Prohibition-era gangsters and ghost legends meet at landmarks including the Riverwalk, Palmer House and Congress Hotel. The $36 tour includes entry inside the Palmer House and Congress Hotel, plus a midway break at a former gangster hangout.

“Tanner was really nice Guide. It was a good interesting tour, with much of deap facts.”

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Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting - The ghost-hunting app: extra fun, not the main event
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Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting

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

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

At Chicago’s Medieval Torture Museum, you’ll see hundreds of devices and wax scenes spanning punishment, restraint, interrogation and execution. The roughly 90-minute visit is self-guided, with an audio tour and a ghost-hunting app you can use as you go. Expect dim lighting, interactive displays and grim subject matter. Admission costs $35.83 per person.

“I was pleasantly surprised at how much I enjoyed this museum. I went because by daughter wanted to see it. Very informative audio tour. You go at your own pace.”

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2-Hour Guided Segway Tour of Chicago - The Riverwalk route and Chicago’s bridges
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2-Hour Guided Segway Tour of Chicago

4.2-Hour Guided Segway Tour of Chicago

★★★★★★★★★★5.0 · 442 reviews · from $65

Spend about two hours on a guided Segway ride through downtown Chicago. After a short lesson and safety gear fitting, a group of no more than eight follows either a Grant Park and Museum Campus route or a Riverwalk route past Navy Pier, the bridges, Michigan Avenue, and Millennium Park. Guides have included Mike and Captain Segway.

“It was a great tour, Mike Artur guide was awesome funny and very informative. We would totally recommend it”

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Skip-the-line: Art Institute of Chicago Guided Tour - What the art stops add to the visit
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Skip-the-line: Art Institute of Chicago Guided Tour

5.Skip-the-line: Art Institute of Chicago Guided Tour

★★★★★★★★★★5.0 · 417 reviews · 2 hours 30 minutes (approx.) · from $71

Meet your English-speaking guide at the Art Institute of Chicago at 10:30 am for a small-group highlights tour of 12 people or fewer. With admission included and the museum’s major works as your focus, expect stories about artists such as Van Gogh, Seurat, Hopper, and O’Keeffe, plus help finding your way through the galleries.

“Joel's knowledge and enthusiasm for art and the city of Chicago was infectious! Highly recommend 👌🏽”

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Private Art Institute of Chicago Skip-the-Line Guided Tour - What makes the storytelling useful
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Private Art Institute of Chicago Skip-the-Line Guided Tour

6.Private Art Institute of Chicago Skip-the-Line Guided Tour

★★★★★★★★★★5.0 · 275 reviews · 2 hours 30 minutes (approx.) · from $85

Spend 2.5 hours at the Art Institute of Chicago with an English-speaking guide and admission included. The route can be adjusted to your interests, with time for major works, art movements and less familiar corners. Guides named in recent feedback include Heath, Spiro, Samantha and Mandy, but your guide is not guaranteed.

“Very informative guide. Passionate about Art and it came through. Offered flexibility but we went with his program and hit all the highlights. I will take this tour agin if I ever return to Chicago. Excellent job Arnold! Thanks.”

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Chicago River: Guided Sunset Cocktail & Architecture Tour - A cocktail, with a few details to check
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Chicago River: Guided Sunset Cocktail & Architecture Tour

7.Chicago River: Guided Sunset Cocktail & Architecture Tour

★★★★★★★★★★4.6 · 203 reviews · 1h 30m · from $68

Spend 90 minutes on the Chicago River as an English-speaking docent explains the design and history of more than 50 buildings. You’ll pass century-old bascule bridges and see downtown as daylight fades. Depending on your ticket option, one or two alcoholic drinks are included; coffee, soda, and bottled water are free.

“The tour was fantastic. Everyone was friendly, and the guide lady was very knowledgeable and attentive. I highly recommend it for first-timers in Chicago.”

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Big Bus Chicago: Sunset Tour by Open-Top Bus with Live Guide - The Magnificent Mile and the Wrigley Building
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Big Bus Chicago: Sunset Tour by Open-Top Bus with Live Guide

8.Big Bus Chicago: Sunset Tour by Open-Top Bus with Live Guide

★★★★★★★★★★4.0 · 165 reviews · from $49

Take a guided evening loop past Navy Pier, the Magnificent Mile, Millennium Park, the Loop, and the Museum Campus on an open-top double-decker. The 90-minute tour has live commentary in English or Spanish, with seats on both decks offered first come, first served. Guides have included Matt, Matty, Bernie, and Mike, though your guide will vary.

“Excellent way to get a good overview and history of Chicago, especially if this is your first time here. Extremely knowledgeable guide.”

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Chicago River: 1.5-Hour Guided Architecture Riverboat Tour - The boat ride is a practical way to cover ground
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Chicago River: 1.5-Hour Guided Architecture Riverboat Tour

9.Chicago River: 1.5-Hour Guided Architecture Riverboat Tour

★★★★★★★★★★4.7 · 93 reviews · 1h 30m · from $57

Cruise the Chicago River aboard a classic 200-passenger boat for 90 minutes of live English narration on more than 50 buildings, from Art Deco and Gothic towers to modern skyscrapers. You can sit on the open-air top deck, and coffee, lemonade, soft drinks, and snacks are included. Guides have included Jim and Ed. An optional minibus tour is available with select bookings.

“What a great way to spend an hour and a half! Out on the river with front row seats to the majestic and historic buildings of Chicago. Ed was a delightful and knowledgeable guide, mixed with just the right level of humor. Boat was comfortable, expertly handled and staff were polite. Bonus bar afloat! Highly recommended!”

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Art Institute of Chicago Private Expert Guided Tour - What a good guide adds
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Art Institute of Chicago Private Expert Guided Tour

10.Art Institute of Chicago Private Expert Guided Tour

★★★★★★★★★★5.0 · 84 reviews · 2 hours (approx.) · from $215

Spend about two hours at the Art Institute of Chicago with a private English-speaking guide and skip-the-line entry. You can shape the route around your interests, ask questions, and see major works such as Nighthawks, American Gothic, and A Sunday on La Grande Jatte. Guides have included Joe, Colleen, Marlin, and Heath. Morning tours include early admission.

“Joe was an amazing guide. Informative and very interesting! Explained the history of the artist as well as the painting.”

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Chicago: Sunset Tour by Open-top Bus with Live Guide - From Clark Street into River North
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Chicago: Sunset Tour by Open-top Bus with Live Guide

11.Sunset Tour by Open-top Bus with Live Guide

★★★★★★★★★★4.3 · 69 reviews · from $50

Ride an open-top double-decker bus from downtown to Museum Campus and back, seeing landmarks such as the Bean, Willis Tower, and the Wrigley Building as evening falls. A live English-speaking guide adds city stories along the way. The 90-minute tour is not hop-on hop-off, so you stay on the bus for the full circuit.

“Not very excited, definetely overpriced, the tour guide was not respectful. Also forgot an expensive scarf on the bus, the stuff even did not try to locate me although the guide asked me where I was from, what hotel I was staying in and what conference I have attended.”

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Chicago: Art Institute Skip-the-Line Tour with Guide - Hopper, Picasso, Cassatt, and other familiar names
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Chicago: Art Institute Skip-the-Line Tour with Guide

12.Art Institute Skip-the-Line Tour with Guide

★★★★★★★★★★5.0 · 49 reviews · 2h 30m · from $90

Meet your English-speaking guide by the left lion outside the Art Institute for early entry and a 150-minute tour. Expect a focused route through celebrated works by Hopper, Picasso, Cassatt, Dalí, and others, with time for questions. Groups are capped at eight; guides such as Heath, Mandy, and Joe have been praised for clear explanations and lively stories.

“Our guide was very knowledgeable and did a wonderful job curating a set of important pieces in the time we had. Megan M. delivered great information and with enthusiasm and also allowed time for questions.”

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Chicago: Offbeat Guided Street Art Tour - Reading the walls in Wicker Park
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Chicago: Offbeat Guided Street Art Tour

13.Offbeat Guided Street Art Tour

★★★★★★★★★★4.7 · 38 reviews · 2 hours · from $40

Walk through Wicker Park, Bucktown, and Logan Square with an English-speaking guide who explains the art and artists shaping Chicago’s street scene. The two-hour tour starts near the Damen Blue Line stop and may include the chance to see artists at work. Guides have included Briana and Brian.

“Briana was a very informativ guide. We enjoyed the tour a lot”

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Chicago: Private custom tour with a local guide - Make the guide part of the planning
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Chicago: Private custom tour with a local guide

14.Private custom tour with a local guide

★★★★★★★★★★4.4 · 28 reviews · 2 - 8 hours · from $129

Shape a private Chicago walking tour around the sights and areas you care about, with a local guide, hotel pickup in the city, and options for 2 to 8 hours. Guides speak English, French, Italian, or Spanish. Bart has been praised for explaining Chicago history in French, though guide assignments vary.

“Service sublime notre guide Bart nous a bien expliqué l’histoire de Chicago le tout dans un français parfait :) une visite à faire on aurait du prendre davantage de temps que 2h je recommande vivement cette visite en français de l’histoire de Chicago”

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Starved Rock State Park: Guided Kayaking Tour - From campground check-in to the river
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Starved Rock State Park: Guided Kayaking Tour

15.Starved Rock State Park: Guided Kayaking Tour

★★★★★★★★★★4.9 · 26 reviews · 2 hours · from $74

Launch from Kayak Starved Rock Campground for a guided two-hour paddle along the Illinois River, below Starved Rock’s sandstone bluffs and beside shoreline canyons and lotus plants. Guides such as Rich, Matt, and Dave mix local history with jokes. Kayaks, paddles, and life jackets are included. Bring waterproof shoes; dogs can join in a tandem kayak.

“Rich and Matt were great guides! We had so much fun! Would definitely come again”

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