Category Guided

Chicago · GUIDED

Top 15 Guided Tours in Chicago

39 tours

Chicago River: 1.5-Hour Guided Architecture Cruise

Chicago River: 1.5-Hour Guided Architecture Cruise - Getting to the dock near 400 N Michigan Avenue and choosing your deck

1.Chicago River: 1.5-Hour Guided Architecture Cruise

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

A 90-minute Chicago River architecture cruise with expert guides, indoor climate comfort, and iconic skyline views for about $44.

“We really appreciate the service—our tour was both enjoyable and meaningful. We loved getting a historical view of the city and listening to such a professional and friendly guide. We actually wanted to leave a tip but didn’t have any cash with us. Having a barcode or QR code option for tipping would be really helpful. We also noticed how friendly the people around us were—they waved and interacted with us, which made the experience even better. Overall, it really changed the way I thought about Chicago.”

Check availability →Read our full review

Chicago: Gangsters and Ghosts Guided Walking Tour

Chicago: Gangsters and Ghosts Guided Walking Tour - Entering the Story at Hoyt’s Tavern, Then Heading to the Riverwalk

2.Gangsters and Ghosts Guided Walking Tour

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

A 2-hour Chicago South Loop walk mixing Al Capone era stories and ghost legends, with stops at iconic landmarks and hotel interiors.

“Sophia was a delight! This was my favorite tour of this trip. So much knowledge and lore crammed into 2 hours. A must for true crime, history, and ghost story fans.”

Check availability →Read our full review

Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting

Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting - The main stop: exploring the 6000 sq ft exhibition

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

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

Chicago’s Medieval Torture Museum includes an audio guide and ghost-hunting app, with hands-on displays for a spooky 1.5-hour visit.

“There is a lot to see and interact with. Be mindful that lighting is very dim when you enter. However, this is unlike any traditional museum I have been to--aquarium, history, etc. I definitely recommend it.”

Check availability →Read our full review

2-Hour Guided Segway Tour of Chicago

2-Hour Guided Segway Tour of Chicago - Getting oriented at the meeting point on E 8th St

4.2-Hour Guided Segway Tour of Chicago

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

2-hour small-group Segway tour in downtown Chicago, covering Millennium Park, Buckingham Fountain, lakefront views, and more with training.

“Fantastic tour and Mike is a fantastic guide. I felt safe and secure. Mike chose the absolute best Chicago locations to tour. I will go again many more times.”

Check availability →Read our full review

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

Skip-the-line: Art Institute of Chicago Guided Tour - Skip-the-Line Entry and the Semi-Private Advantage for Real Questions

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

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

Skip-the-line, small-group Art Institute tour with admission included. See key works from Van Gogh to Warhol in 2.5 hours.

“Really enjoyed our guide Joel's enthusiasm and love for the museum and Chicago. Learning the milestones of the museum's collecting its most famous collections and pieces, and the stories behind them was fascinating. Well worth the 2.5 hour tour!!”

Check availability →Read our full review

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

Private Art Institute of Chicago Skip-the-Line Guided Tour - Getting to 111 S Michigan Ave and what to expect inside

Chicago River: Guided Sunset Cocktail & Architecture Tour

Chicago River: Guided Sunset Cocktail & Architecture Tour - Getting On Board: What the First 15 Minutes Feel Like

7.Chicago River: Guided Sunset Cocktail & Architecture Tour

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

Sip a cocktail while an award-winning guide explains Chicago River architecture, from historic towers to lit skyline at dusk.

“I had a great experience, the staff was friendly and the tour guide was very informative, I learned a lot of interesting facts about the buildings and had a good time sightseeing with a drink in my hand. 5 out of 5 stars”

Check availability →Read our full review

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

Big Bus Chicago: Sunset Tour by Open-Top Bus with Live Guide - The 90-Minute Night Loop: What You’ll See as the City Lights Up

Chicago River: 1.5-Hour Guided Architecture Riverboat Tour

Chicago River: 1.5-Hour Guided Architecture Riverboat Tour - Getting Onboard: Boat Comfort, Snacks, and the Onboard Bar

Art Institute of Chicago Private Expert Guided Tour

Art Institute of Chicago Private Expert Guided Tour - Customization That Actually Changes What You See

Chicago: Sunset Tour by Open-top Bus with Live Guide

Chicago: Sunset Tour by Open-top Bus with Live Guide - From downtown to Museum Campus: the Lake Michigan skyline moment

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

★★★★★★★★★★4.3 · 69 reviews · from $50

90-minute Chicago sunset skyline tour on an open-top double-decker bus with a live guide, Lake Michigan views, Millennium Park, and Art on the Mart.

“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.”

Check availability →Read our full review

Chicago: Art Institute Skip-the-Line Tour with Guide

Chicago: Art Institute Skip-the-Line Tour with Guide - Early entry and the skip-the-line effect at a 1.79 million visitor museum

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

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

Skip Art Institute lines with an expert, early entry 30 minutes before opening, and a small-group 150-minute Picasso to Hopper tour.

“We had a very informative guide, Marlin. He told interesting stories and guided us through in a timely way…almost an impossible task! He was willing to adjust his tour based on our interests.”

Check availability →Read our full review

Chicago: Private custom tour with a local guide

Chicago: Private custom tour with a local guide - Hotel pickup and the start of your day in Chicago

14.Private custom tour with a local guide

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

A private, customizable Chicago walking tour with a local guide, museum-exterior focus, and insider tips, from $129 per person.

“Visite agréable avec guide parlant bien le français… aurions aimé un peu plus d’explications culturelles.”

Check availability →Read our full review