Top Chicago Walking Tours - page 3

River North Food Walking Tour

4.7

(88)

3 hoursFree Cancellation

from $89

Enjoy an immersive way to discover Chicago's more recent architectural heritage with this small-group walking tour. Led by your architectural expert guide, you'll discover many of the Windy City's modern, postmodern, and other newer structures, including works by architects like Mies van der Rohe, Bertrand Goldberg, and beyond. As you go, your guide will point out the buildings many visitors overlook, and share stories from their history you wouldn't otherwise hear.

Chicago Walking Tour: Modern Architecture

4.8

(61)

1 hour 30 minutesFree Cancellation

from $35

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.

Frank Lloyd Wright Robie House Admission

4.2

(132)

1 hourFree Cancellation

from $27

Leave behind the stuffy, slow-moving tour groups and explore Chicago’s Millennium Park on your own with a private, self-guided app tour. Using just your smartphone, pausing as you like, you’ll learn all about “The Bean,” Lurie Garden, Crown Fountain, and more. With your GPS cuing your audio experience, this tour lets you go at your pace, style, and time, with lifetime access and no expiry.

Chicago Millennium Park Self-Guided Walking Tour

4.6

(5)

1 to 2 hoursFree Cancellation

from $15

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.

The Chicago Theatre Tour Experience

4.0

(54)

1 hour to 1 hour 15 minutes

from $30

Explore the sights and skyscrapers of Chicago’s spectacular Riverwalk—and enjoy the most budget-friendly and flexible sightseeing experience around—on this self-led, smartphone walking tour. Upon booking, download the app and receive a password to access your tour; once it’s on your phone, it is valid for an entire year. Set off at a time that works best for you: see highlights like the Merchandise Mart, Wrigley Building, Vietnam Veterans Memorial, and much more.

Chicago Riverwalk Self-Guided Walking Tour

4.2

(6)

1 to 2 hoursFree Cancellation

from $15

See Chicago's magnificent skyline at night!

4.2

(231)

Chicago 3D Fireworks Cruise

from $52

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

In the beloved 1980s teen comedy “Ferris Bueller’s Day Off,” the Art Institute of Chicago plays a starring role—and on this immersive, small-group tour, you’ll follow in the footsteps of Ferris and his friends all while visiting the museum’s best-known masterpieces. Meet your guide inside of the museum in the Modern Wing (tickets own expense). You can look forward to seeing masterworks by Chagall, Seurat, Cassatt, and more, all while hearing behind-the-scenes stories.

Ferris Bueller Movie Tour at the Art Institute of Chicago

(26)

1 hour 30 minutes

from $50

On this cheerful tour you’ll see Chicago’s most famous Christmas trees, as well as several under-the-radar ones you may not know about. Your guide will lead you around downtown, stopping at the Christkindlmarkt and the old Marshall Field’s, as well as hidden-gem spots with some of the city’s most impressive holiday decor. All the while, you’ll learn about some beloved Christmas stories and traditions from across the globe, and even get to stop for some holiday sweets.

The Christmas Tree Crawl Experience Chicago at the Holidays

4.9

(44)

Magnificent Mile Tour With Optional 360 Chicago Upgrade

from $35

4.9

(80)

Lincoln Park Hauntings Ghost Investigation Tour

from $39

4.9

(45)

2 hours 15 minutesFree Cancellation

from $40

4.3

(23)

Downtown Chicago TV and Movie Sites Guided Walking Tour

The Art Institute of Chicago houses one of the finest American and Impressionist painting collections in the world, but it can be overwhelming to explore on your own. Remove the guesswork and maximize your time inside the museum on a private tour that covers major highlights by Picasso, Chagall, Warhol, Hopper, and others. Plus, there's no waiting to get inside, as the tour includes a skip-the-line ticket.

from $44

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

(282)

2 hours 30 minutesFree Cancellation

from $90

Price varies by group size

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

(904)

30 to 45 minutesFree Cancellation

from $33

4.8

(483)

Chicago Night Crimes Tour by Bus

2 hours to 2 hours 30 minutesFree Cancellation

from $55

Discover Chicago like never before with complete freedom to explore at your own rhythm, lingering at fascinating locations or moving swiftly through others as your interests guide you. Our expertly crafted audio experience unveils exclusive historical insights and hidden stories that even longtime residents don't know, transforming you from tourist to insider as you uncover the authentic soul of the Windy City. Unlike rigid group tours that rush you past remarkable details, you'll have the flexibility to choose which attractions captivate you most, creating a personalized journey that matches your curiosity and schedule perfectly. You'll experience the city as locals do – unhurried, authentic, and deeply connected to the stories that shaped this magnificent metropolis, all while enjoying a superior experience that combines the convenience of independence with the depth of expert knowledge.

Chicago Self-Guided Audio Tour

3.9

(9)

3 to 9 hours

from $6

Let’s take photos at one of Chicago’s most famous spots - the bright red CHICAGO sign at the Chicago Theatre! During this 30-40 minute photo walk, I’ll help you pose and feel comfortable while taking high-quality photos using iPhone, optimized for social media. You’ll receive about 50 digital photos, including 5 professionally color-edited images, delivered via a private online gallery. Please download your photos within 14 days after receiving access, as the gallery link will expire.

Express Chicago Photo Tour of Landmarks

(4)

30 to 40 minutesFree Cancellation

from $99

Embark on a captivating walking tour that delves into the intriguing legacy of the Midwest's most notorious mobsters and gangs. Immerse yourself in the rich history of the Windy City as you stroll through its vibrant streets, where the echoes of a century of Mob activity intertwine with the modern cityscape. Traverse the iconic Michigan Avenue, once a hub of illicit operations masterminded by the infamous Al Capone, and uncover the hidden secrets of the past that now lie beneath the surface of changing demographics and contemporary establishments. Brace yourself for chilling tales of mob hits and ongoing underworld dealings, as you unravel a dark and compelling narrative that still resonates through the streets today.

Gangs and Mobsters Crime Tour at Chicago

(1)

1 hourFree Cancellation

from $26

See the Second City from the water with a sightseeing cruise along the Chicago River and the Lake Michigan shoreline, offering a unique perspective of towering skyscrapers and historic architecture. This tour offers stories about the city’s history and culture as you pass by Chicago's landmarks, museums, and buildings. Capture unforgettable images of the city skyline from Lake Michigan, ensuring a unique look at Chicago, perfect for all ages.

Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

4.7

(560)

1 hour 30 minutesFree Cancellation

from $46

Delve into the rich history and notable architecture of one of Chicago’s most luxurious neighborhoods—and learn insider stories as you go—with this self-led smartphone audio walking tour. Upon booking, download the app and set off at a time and pace that work best for you. You’ll discover Gold Coast landmarks from historic piano bars to the original Playboy Mansion, and can stop and start the tour whenever you like.

Chicago's Gold Coast Hidden History: A Self-Guided Audio Walk

4.3

(7)

50 minutes

from $8

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

(711)

2 to 4 hoursFree Cancellation

from $50

Explore one of the country’s great art museums—and discover many of its collection highlights—on this small-group Art Institute of Chicago tour. Meet your guide right out front, and see works from artists the likes of Picasso, Chagall, Seurat, O’Keeffe, and many more. As you go, your guide will share the stories behind the masterpieces, and will help bring the history of the museum and its collection to life.

Skip the Line Art Institute of Chicago Tour Semi-Private 8ppl Max

(168)

2 hours 30 minutesFree Cancellation

from $90

Price varies by group size

Best Chinatown Food and Walking Tour in town! The Chicago’s Chinatown Food and Walking Tour is a 3-hour immersive culinary and cultural experience designed to highlight the unique tastes, rich history, and vibrant culture of Chicago’s Chinatown. This comprehensive tour combines a curated food-tasting journey with an exploration of iconic landmarks, making it the most enriching and flavorful Chinatown experience available in such a short duration. All of the restaurants and shops we pick for you are our member businesses of Chicago Chinatown Chamber of Commerce with guaranteed food quality and hospitality! You get the most of your money and time! A minimum of 4 participants is required for this experience. If the minimum is not met, the tour may be canceled, and you will receive a full refund.

Taste of Chicago's Chinatown Food Tours

(2)

3 hoursFree Cancellation

from $85

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What are people saying about Chicago

Chicago's Chinatown Food and Walking Tour

Jasmine_C, Apr 2026

Here’s a polished, warm,...

We need had an amazing time on our Chinatown food tour. We visited five different restaurants, each with its own unique flavors, and our tour guide Greg made the entire experience unforgettable. He was incredibly knowledgeable, engaging, and clearly passionate about the history and culture of the neighborhood. As we were entering one of the restaurants, there was a car accident right outside. Nothing on our end was affected, but Greg immediately shifted into action he checked to make sure everyone in our group was safe, called 911 to help with the situation, and still managed to keep the tour running smoothly and on schedule. His professionalism and calmness really stood out. We ended the tour with the most incredible egg tarts, which were the perfect final touch. It also happened to be my boyfriend’s birthday, and this was such a great way to kick off his day. He loved every moment. Highly recommend this tour and especially Greg. Truly a memorable experience.

Chicago Mobs and Haunts Walking Tour

Lynn_H, Apr 2026

Lark's Knowledgeable and Entertaining Tour

Lark was a fantastic tour guide- knowledgeable, enthusiastic, and genuinely engaging. Our group was small, which made the experience feel personal and easy to connect with. We were able to ask plenty of questions, and Lark handled each one with ease and insight. His depth of knowledge about Chicago's history was especially impressive. He shared fascinating stories and facts that we never would have discovered on our own. The places we visited were rich with historical significance, and his storytelling made each stop come alive. We absolutely recommend Lark to anyone looking for a fun and informative tour of the city.

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 Architecture and True Crime Tour

Markie_B, Mar 2026

David was the best!

We needed something to do for a couple hours until we had to head to the airport. We looked into one of the boat architecture tours, but sadly, they were all booked. This ended up being an amazing thing, because we REALLY enjoyed our tour and time with David. David is clearly passionate about the information he presents and it was lovely spending time with him. The buildings we viewed were beautiful and it was great to place factual information into how things came to be. I would recommend to anyone and the true crime information was a really fun addition to the tour!

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.