Top Chicago Walking Tours - page 2

Chicago Architecture Walking Tour: What's New

(80)

Sample some of the Windy City's tastiest donuts—and head to locals-loved dessert destinations that most visitors miss—on this one-of-a-kind walking tour. With your guide in the lead, head to a number of Chicago’s tastiest donut bakeries, all while exploring the city's vibrant downtown Loop neighborhood. All tastings are included in the tour cost, and vegan, gluten-, and nut-free options are also available upon request.

from $35

Delicious Donuts & City Sights: Chicago's Original Donut Tour

(1,409)

from $70

Chicago Murder Mystery Tour

(732)

from $35

Chicago Architecture and True Crime Tour

(349)

1 hour 30 minutes to 1 hour 45 minutesFree Cancellation

from $35

Skip the hassle of planning your Chicago itinerary with this convenient hop-on hop-off tour, covering the city's must-see sights. With multiple strategically located stops, explore the Windy City at your own pace, hopping off to visit top attractions like the iconic Art Institute and famous skyscrapers. Enjoy insightful audio commentary as you cruise through the city, learning about its rich history and vibrant culture. Perfect for first-time visitors or those short on time, this tour offers flexibility and ease, ensuring you don’t miss any of Chicago’s highlights. Book your ticket today and experience the best of Chicago hassle-free!

Hop-On Hop-Off Sightseeing Tour by Open-top Bus

3.9

(2,221)

Discover a side of the Windy City that many visitors overlook—and immerse yourself in its vibrant street art scene—on this urban walking tour. With your art-expert guide in the lead, you can focus on soaking up the city's ambiance, and spotting artworks and murals you may not have discovered on your own. As you go, listen to in-depth commentary about the artists and artworks, and explore some of the city's hippest neighborhoods.

from $44

Offbeat Street Art Tour of Chicago: Urban Graffiti, Art, and Murals

(203)

Wind and Souls an Adults Only Ghost Tour in Chicago

from $40

4.2

(42)

Discover one of Chicago’s top architectural marvels when you explore Frank Lloyd Wright’s UNESCO-listed Frederick C. Robie House, located right on the University of Chicago’s campus. Considered a masterpiece of Prairie School architecture, the building is famed for its cantilevered roof and rich wood details. Save money when you book tickets to the house in advance; call ahead to reserve a space on one of the museum’s frequent, small-group public tours.

from $35

Frank Lloyd Wright Robie House Admission

4.2

(132)

1 hourFree Cancellation

from $27

Get to know the Windy City the easy and comfortable way on a small-group minibus tour. Instead of long walks and navigating public transit, see major landmarks like Museum Campus, Buckingham Fountain, the Magnificent Mile, and Millennium Park from an uncrowded minibus with large picture windows. Your driver and guide knows where to find all the best views, and there are plenty of photo stops along the way.

Chicago City Minibus Tour

(543)

Enjoy the opportunity to go behind-the-scenes at one of the Windy City's most storied venues on this insider tour of the Chicago Theater. Let your guide lead the way, as you hear about the theater's architecture, history, and famous performers throughout the years. Stand on the famed stage and take in the atmosphere, and see artist signatures from notable performers, including Frank Sinatra and Dolly Parton. A great activity for fans of music and live performance.

from $50

The Chicago Theatre Tour Experience

4.0

(54)

1 hour to 1 hour 15 minutes

from $30

Take your architecture spotting off the streets and inside some of the most iconic buildings in Chicago with this unique Art Deco-themed tour. Get up close and personal with the glamorous style of the early 20th century as you delve beyond the downtown facades to explore glorious interior spaces from the 1920s and 1930s, with their ornate brass and marble details, mosaics, stained glass, and other treasures that most architecture tours miss.

Chicago Architecture Walking Tour: Incredible Art Deco Interiors

(92)

Zoom along the shoreline of Lake Michigan, zipping past famous landmarks as you go, during this exhilarating speedboat ride in Chicago. Climb aboard your 2,000-horsepower speed boat at Navy Pier, then hang on for the ride of a lifetime, as you zip past famous attractions like the Willis Tower, Grant Park, and Buckingham Fountain, pausing to learn a little about the history and architecture of the Windy City along the way.

from $35

Lake Michigan 30-Minute Speedboat Ride

4.1

(334)

30 minutesFree Cancellation

from $31

Pilsen Neighborhood Train & Walking Tour in Chicago

Delve into Chicago’s one-of-a-kind cuisine and learn something that you would never expect on this small-group Secret Food Tour. Eat your way through the most prominent neighborhoods of the city and immerse yourself in its tastes and flavors. Stroll through the Loop and Millenium Park, wander down the Riverwalk and discover iconic sights and hidden gems from another perspective. Get inside Chicago’s life through food and connect your heart and soul to the Windy City vibe while tasting classic deep-dish pizza, dipped Italian beef, and Chicago-style hot-dogs. • Benefit from small-group experience and undivided attention from your local guide • Savor the classic Chicago eats and get to know the history of their creation • Witness fascinating art objects, architecture landmarks, and beautiful cityscapes • Get useful recommendation of where to eat and drink from your guide

Chicago Foods Tour with The Loop, Skyline, Millennium Park

(4)

3 hoursFree Cancellation

from $145

Tower above the Windy City’s world-famous skyline with pre-booked admission to 360 Chicago—a great way to avoid long ticket lines. Ascend one of the tallest buildings in North America aboard its lightning-fast elevator, and be rewarded with bird’s-eye views of Chicago and Lake Michigan. You can also upgrade to the Sip and View ticket, which includes one drink at the newly renovated CloudBar. Once onsite, you can purchase tickets to TILT, 360 Chicago's top attraction.

360 CHICAGO Observation Deck Admission

3.9

(1,231)

1 to 4 hoursFree Cancellation

from $30

Drink in a one-of-a-kind perspective on the Windy City when you go for an evening cruise, perfectly timed to coincide with the sunset. Hop aboard your open-top vessel (with an enclosed and climate-controlled lounge) in the heart of the Magnificent Mile, and cruise along the Chicago River. Then, see the skyline from a distance, and watch the skyscrapers light up, when you continue to Lake Michigan for a sunset viewing.

Lake Michigan Sunset Cruise in Chicago

4.5

(1,518)

Discover some of the Windy City’s spookiest ghost stories—and step back in time to the era of gangsters, bootleggers, jazz performers, and more—on this small-group walking tour. Meet your guide in Chicago’s Lincoln Park neighborhood, and set off after dark. You’ll visit supposedly haunted former burial grounds, pubs, theaters, and more—and will hear about macabre legends and unexplained happenings as you go.

from $45

Feel the presence of the unseen as we wander through haunted history under the moon's glow.

Embers of the Windy City: Chilling Chicago Ghost Tours

4.4

(121)

1 hourFree Cancellation

from $26

Get a front row perspective on the exquisite buildings that line the Chicago River during a 45-minute architecture cruise. Hear live commentary about the history and architectural heritage of Chicago on this family-friendly tour, which highlights landmarks such as the Chicago Riverwalk, Michigan Avenue Bridge, Wrigley Building, and Willis Tower. Sit on the open-air top deck or the sheltered bottom deck for the ultimate view of Chicago.

Join us in the daytime or evening for City lights and breathtaking views

Chicago River 45-Minute Architecture Tour from Magnificent Mile

4.7

(3,098)

45 minutesFree Cancellation

from $28

Get to know the foodie Chicago neighborhood made famous by "The Bear"—and taste your way through some of the Windy City's best bites—on this small-group walking tour of River North. Visit locals-loved hotspots that represent the best of the city's dining scene, and Be sure to come hungry: You'll try everything from tacos and Italian beef sandwiches to deep-dish pizza, all while learning about the neighborhood's history and food culture.

River North Food Walking Tour

4.7

(88)

3 hoursFree Cancellation

from $89

Skip navigating around the city with a map and guidebook and explore Chicago's iconic landmarks in just a few hours on this sightseeing tour led by an expert guide. Board a comfortable, large-windowed minibus and explore Downtown and North Side neighborhoods, stopping to visit several locations and hear about the historical and cultural factors that make Chicago unique. Upgrade your tour with a popular open-top boat tour on the Chicago River that focuses on the city's renowned architecture.

Chicago City Tour with Architecture River Cruise Option

4.8

(713)

2 to 4 hoursFree Cancellation

from $50

It isn’t a trip to Chicago without tasting deep-dish pizza—and this private tour for food lovers will introduce you to true Chicago-style pizza, plus other Windy City specialties. Meet your guide downtown, and be sure to come hungry: You’ll eat hot dogs, Italian beef sandwiches, pizza, donuts, and more. Along the way, see highlights like the Wrigley Building and Magnificent Mile, and learn more about the city’s history and culture.

Private Chicago Foodie Tour

(6)

4 hoursFree Cancellation

from $288

Special Offer

Tourgoers in front of the Marshall Field Mansion

Considered Chicago’s original “Millionaire’s Row,” Prairie Avenue in the Near South Side is renowned for its Gilded Age mansions—and this tour makes exploring easy (and delightfully spooky). In the evening, meet your guide in front of the Glessner House, and set off with ghost-hunting gear to accompany you. In between spotting highlights including the Marshall Field Jr. Mansion and the Henry B. Clarke House, you’ll hunt for specters and hear ghost stories.

Prairie Avenue Haunted History Tour and Ghost Hunt

(12)

Take in views of the Chicago skyline and its landmarks during this Lake Michigan sightseeing boat cruise. Enjoy a laidback ride, soaking up panoramic views from this unique perspective. Listen to audio commentary to give you fresh insight into the landmarks you see, like Navy Pier and the Willis Tower, and feel free to bring your own lunch or grab a drink at the onboard bar (own expense).

Lake Michigan Skyline Cruise in Chicago

4.4

(905)

30 to 45 minutesFree Cancellation

from $33

Discover the architectural gems of the Windy City from an ideal vantage point—and learn insider facts and stories about the city's top attractions—on this Chicago River cruise. Travel in comfort aboard a boat equipped with both indoor and outdoor seating areas. Covering more than 130 years of architectural history, this tour is the perfect opportunity to see a huge area of the city without the hassle of taxis and public transit.

Chicago River 90-Minute Architecture Tour

4.7

(9,815)

from $45

Lincoln Park Hauntings Ghost Investigation Tour

(45)

2 hours 15 minutesFree Cancellation

from $40

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Top Attractions in Chicago

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Attractions

What are people saying about Chicago

Chicago Architecture and True Crime Tour

Kimberly_C, Apr 2026

Fantastic tour with David!

This was such a fun and delightful tour with David! He is a great storyteller. His insight and passion for Chicago architecture and crime lore stayed with us long after the tour was over. The 90 minutes flew by though we were fortunate to have good weather. There were many stops along the way that brought us inside some remarkable spaces. Overall, we highly recommend David and this tour experience! 10 out of 10!

Chicago's Chinatown Food and Walking Tour

Tessa_S, Apr 2026

Great food tour

Lots of delicious food and history about Chinatown in between to give our stomachs some time to settle. It's the perfect amount of food where you don't feel like you're wasting a ton but definitely won't leave hungry. Loved it, thank you for having us!

Chicago Architecture Tour: Underground Pedway and the Loop

Maria_M, Mar 2026

The city under the city...who knew!?!?

We booked the The Underground Pedway & Secrets of the Loop tour on a whim and couldn't have been more impressed! Heath was a knowledgeable, energetic and enthusiastic guide! His passion for the city is beyond evident. We both learned and saw places we had no idea even existed, even having lived in the city for over a decade! Don't miss this tour to learn about the city under the city! Who knew!?!?

Chicago in a Day: Food, History & Architecture Walking Tour

Ashleigh_G, Mar 2026

Best tour ever

Rich was an amazing tour guide. This was my first solo trip and I was nervous. I learned a lot about the cool history of Chicago. He kept the entire tour entertaining even though I was the only tourist. He made my solo stay 10x more comfortable. Thank you so much!

Original Chicago Architecture Interiors Tour: Dazzling Interiors

Andrea_S, Mar 2026

Surprises inside every door

We absolutely loved this tour with Spencer. He has a great way of story telling and helping you to open your eyes all the way up to get the full feeling of the building and spaces we were in. The location choices were terrific and lots of the buildings I would have walked by without a second glance but I appreciated his passion and knowledge. We got several amazing recommendations from him as well as we walked and chatted along like old friends. Great tour, absolutely recommend.

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

Nichole_R, Feb 2026

Best art tour! A must if your in town!

Bernie our tour guide was excellent! We loved to hear the history of the generous donors of Chicago and all the incredible students that came from this institute. We were amazed by all the beautiful collections that are in house and absolutely had a wonderful time! A must see when your in the city!

Chicago Loop District Food Tour with Deep Dish & Beef Sandwich

Sabrina_C, Oct 2025

Excellent

Michael was our tour guide and he was excellent. He even helped us find parking on the street .The tour starts with a short visit inside the library which was the meeting spot. He had lots of stories to tell, and he was very entertaining. He was also very knowledgeable about Chicago. I expected sample servings of all the food, but we actually had an entire slice of pizza, a half of a beef sandwich, an entire hotdog, an entire churro, an entire brownie, and a small sample bag of popcorn. The tour took exactly 3 hours as advertised. I recommend this tour and hopefully you have Michael as your tour guide.

Chicago Sightseeing River and Lake Cruise

Erica_S, Sep 2025

Great experience but hard to find

The tour was great with a very knowledgeable narrator. I enjoyed it. However, we missed out scheduled tour because. Of the difficulty in finding the location. We had to call and a wonderful agent stayed on the phone with us gave us directions and told us where to park. Patrons should be given more information on the location.

Chicago Bike & Classic Food Tour: Bikes, Bites & Views - Adults

Alison_P, Sep 2025

Bike tour around Chicago

I had an afternoon to myself and live the outdoors so I booked the 4 hr bike, bites, and brews tour. I had a great time and was completely comfortable doing this tour by self as the guide was great and others in the group very friendly. Not overly strenuous at all, just a decent ride with plenty of stops to learn about Chicago.