Top Chicago Walking Tours

Chicago West Loop Sweet Treats Food Tour: Donuts, Cookies, & More

It would take days to visit all of Chicago’s famous sights, but who has that kind of time? Cover the highlights of the Windy City during this private half-day walking tour. From the Magnificent Mile to Millennium Park, you’ll tick off top attractions while your guide fills you in on Chicago’s history. Finally, enjoy panoramic views overlooking the city from Hancock Tower’s Observation Deck—admission tickets included.

Welcome to Chicago: Private Half-Day Tour with 360 Observation Deck

3 hoursFree Cancellation

Explore the architectural extravaganza of Chicago downtown and discover the most amazing and captivating facts about the first high-rises, city planning, and construction history. Get a unique chance to combine touring by foot and by L train, and see the city’s most iconic landmarks like The Rookery Building, Chicago Cultural Center, First Arts Building, and more 19th and early 20th-century masterpieces. Be ready to see the City by the Lake from a new perspective and get to know it even closer as you stroll down its streets and travel by train. Enjoy the small-group experience and don’t miss a thing as you travel Discover the downtown and historical building together with your local knowledgeable guide Marvel at architectural landmarks of the City by the Lake and get to know the stories behind them Combine a walking tour with a train to see more landmarks and iconic sights on one tour.

Chicago Architecture Tour - Skyscrapers, History and Photo Ops

2 Hours Chicago Architecture Tour - Skyscrapers and Photo Ops

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

30 to 40 minutesFree Cancellation

Enjoy a flexible way to explore Chicago—and combine your sightseeing with a fun-filled scavenger hunt game—with this two-in-one smartphone excursion. Upon booking, receive access to the game on your smartphone, and set off at a time that works best for you. In between admiring highlights like the Chicago History Museum, Standing Lincoln Monument, and Lincoln Park Zoo, you’ll solve clues and participate in challenges.

Haunted Chicago: Lincoln Park Ghost Escape Game

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

4 hoursFree Cancellation

Custom Chicago Walking Tours

1 to 3 hoursFree Cancellation

Step into the shadows of Chicago’s past on this adults-only haunted pub crawl, where ghost stories, historic landmarks, and legendary nightlife collide. Beginning near the iconic Palmolive Building, this guided experience takes you through the city’s Gold Coast and beyond, uncovering the eerie aftermath of the Great Chicago Fire and the restless spirits it may have left behind. Along the way, you’ll visit a curated mix of historic sites and local bars, blending chilling storytelling with time to grab a drink and soak in the atmosphere. Adults 21+ only, must have valid I.D.

Burning Spirits Haunted Pub Crawl

Chicago Photo Walk to Bean and Landmarks

1 hourFree Cancellation

Explore over 30 iconic movie and TV locations on this two-hour walking tour of downtown Chicago! Visit sites from Ferris Bueller’s Day Off, The Untouchables, The Dark Knight, The Bear, and more. See the theater from Public Enemies, Harold Washington Library from Ocean’s Eleven, the Chicago Board of Trade and Calder’s Flamingo from Ferris Bueller, iconic Blues Brothers spots, and Bruce Wayne’s penthouse and Harvey Dent’s office from The Dark Knight. Perfect for film buffs and Chicago enthusiasts alike.

Chicago Downtown TV and Movie Sites Private 2-Hour Walking Tour

Private Chicago History Museum Tour

Immerse yourself in Chicago's architectural heritage on an exclusive walking tour, delving into the city's iconic structures and Art Deco gems. Begin your intimate journey by marveling at the grandeur of the Wrigley Building, followed by a step into the opulence of the Palmer House Hilton lobby. Admire the sleek lines of the Carbide and Carbon Building, a testament to Art Deco elegance, before appreciating the historic significance of the Reliance Building. Conclude your architectural odyssey with a visit to the exquisite Chicago Cultural Center, a masterpiece of design and culture. Throughout the tour, your knowledgeable guide illuminates Chicago's rich history and architectural evolution, weaving captivating stories that offer insight into the city's vibrant past and enduring legacy.

Chicago Highlights Private Walking Tour with a Guide

Chicago Highlights Private Walking Tour with a Guide

Discover the heart of Chicago’s architectural legacy on this guided walking tour through the historic Loop District. Step back in time as you explore some of the world’s first skyscrapers and venture inside a collection of the city’s most influential and iconic buildings. Your expert local guide will share captivating stories about the rise of Chicago, the Great Fire, and the visionary architects whose bold designs shaped the skyline we know today. This tour offers the perfect mix of history, design, and city energy—a must for architecture lovers and curious travelers alike. - Explore the birthplace of the modern skyscraper - Step inside landmark buildings like The Rookery and the Palmer House - Learn about the Great Chicago Fire and its lasting impact on the city - Enjoy a relaxed pace through Chicago’s vibrant downtown Loop

Private Chicago Architecture Walking Tour

Private Chicago Architecture Walking Tour

3 hoursFree Cancellation

Lincoln Park Zoo & Nature Museum Private Tour

Private Wicker Park and Bucktown Walking Tour

2 hours 30 minutesFree Cancellation

Chicago City Private Tours

2 to 8 hoursFree Cancellation

The Art Institute of Chicago is home to over 300,000 works of art by local and international artists. With so much to explore, it’s easy to get overwhelmed by all of the options during a visit. Sit back and let an expert guide handle the planning as they take you through the museum’s major pieces. Learn about the history and context behind each piece in this culturally enriching experience.

Art Institute of Chicago Private Expert Guided Tour

This tour is special because it combines a personalized street and night tour experience with expert photography guidance in Chicago. You’ll explore both iconic landmarks and hidden streets, capturing the city’s character from golden hour through to its dazzling night lights. As skyscrapers glow and trains blur past, your professional guide helps you master techniques like composition, long exposure, and low-light shooting. Designed around your skill level, this private tour ensures one-on-one coaching, creative development, and unique photo opportunities. It’s more than sightseeing—it’s a hands-on journey through Chicago’s streets after dark, where every corner becomes a chance to create striking images. Creative composition, using lines, repetition, camera angles Training your eye: finding subjects, lighting, composition Taking control of your camera: f-stop, shutter speed, ISO and focusing Reviewing your photography

Chicago Photography Masterclass Private Photography Lesson

Chicago Photography Masterclass Private Photography Lesson

3 hoursFree Cancellation

Private Magnificent Mile Architecture Tour and 360 Chicago Ticket

Private Vacation Photoshoot with Photographer in Chicago

1 hourFree Cancellation

Explore the surprising beauty and history of the Windy City with this combo tour of Chicago’s Millennium Park and Riverwalk! Snap a picture by the famous Cloud Gate sculpture and get away from the hustle and bustle in the city’s most iconic park. Then, stroll along the picturesque riverside, admire Chicago’s totally unique architecture, and learn the fascinating stories behind the city’s skyline. This combo is the easiest, best way to get to know this complex city! After booking, check your email/text to download the separate Audio Tour Guide App by Action while connected to WiFi or mobile data. Enter the password, download the tour, and enjoy it offline. Follow the audio instructions and route from the designated starting point. New, Lifetime access, no expiry. Use it anytime, on any trip, as many times as you want. This isn't an entrance ticket. Check opening hours before your visit.

Special Offer

Chicago Riverwalk & Millennium Park Self-Guided Audio Tour Bundle

Chicago Riverwalk & Millennium Park Self-Guided Audio Tour Bundle

1 to 2 hoursFree Cancellation

With this AI app, you're no longer restricted to crowded group tours or rigid scripts. Explore iconic Chicago sites like Millennium Park and the Magnificent Mile—or dive deep into 1920s mobster hangouts and hidden Prairie Style masterpieces. Ask about literally anything that catches your eye—from a Gilded Age historic district to a secret jazz club or a towering steel-and-glass skyscraper. The Windy City's deepest secrets are entirely yours to uncover. Point & Discover: Snap a photo of any monument or museum masterpiece to instantly receive a captivating and accurate story. It’s like having a historian in your pocket! Ultimate Freedom: Navigate seamlessly with interactive map-based audio tours. Your schedule, your pace, your rules. Choose Your Vibe: Select a narrator persona that matches your style—from a deep-diving scholar to a fun companion for the kids. Get Started: 7 Days of Premium Access available instantly for iPhone and Android.

Chicago and All MidWest Self Guided AI Audio Tours for 7 Days

7 daysFree Cancellation

Chicago Haunts and Hooligans Tour

1 hour 30 minutesFree Cancellation

Learn from a local as you discover Chicago’s top spots for food, drinks, architecture, and culture. On this tour, you'll explore downtown uncovering their history, iconic landmarks, hidden gems, and must-see photo opportunities. From legendary deep-dish pizza and historic jazz venues to world-famous architecture and vibrant local districts, the local guides provide personalized recommendations for every type of traveler. No need to spend hours planning your trip—this tour is designed to give you the insights, stories, and local knowledge needed to make your Chicago experience unforgettable. * Learn about the essentials of Chicago * Get tailored recommendations from local guides * Take amazing photos at iconic and hidden-gem locations * Get familiar with the city's history, culture, and neighborhoods

Welcome to Chicago: The Essential City Tour with photo stops

1 hour 30 minutesFree Cancellation

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Must-Dos in Chicago

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What are people saying about Chicago

Haunted Chicago: Crime, Ghosts, and Capone Walking Tour

Todd_M, Nov 2026

Excellent Experience!

Sydney, an incredibly knowledgeable and friendly guide, led us on a fantastic walking tour of The Loop. The tour delves into the city’s rich history, infamous criminals, and even shares a few chilling ghost stories. It’s a great way to get some exercise while immersing yourself in Chicago’s past.

Chicago Gangsters and Ghosts Walking Tour

Avery_W, Oct 2026

Do iiiiiit

This experience was probably one of the best parts of our trip. We were so surprised. Tanner was really engaging with his story telling, he made you want to keep listening and learn about the history of Chicago. I would highly recommend this to anyone that loves history and/or Chicago. We really loved our experience. Give Tanner a raise!!!!!!

Chicago's Chinatown Food and Walking Tour

Lucy_G, Oct 2026

Best food tour in Chicago

Great way to learn about Chinese food, meet people, and have a great, delicious meal. We had Cantonise dumplings and noodles, Szechuan chicken and rice, lamb sandwich from Xian, and we finish with a custard pastry. All the food was delicious. Highly recommended.

Chicago's Delicious Downtown Donut Tour with 8 Amazing Tastings

Nancy_J, Oct 2026

What a wonderful way to...

What a wonderful way to start the day. A nice walk around town. Fun donut shops, with unique donuts. So yummy. Love support small businesses. The best part of the tour was...Jackson, our tour guide. A fountain of knowledge, fun stories and all around great guys.

Original Chicago Architecture Interiors Tour: Dazzling Interiors

Zandra_R, Oct 2026

Book this! You won’t regret

Heath is an excellent guide The tour is expertly delivered and there was structure, flow, intentionality We really really enjoyed the tour and was glad we went ahead with booking as we would have never gone to this places and understood the history and significance of these structures! Thank You Heath ! Anyone coming to Chicago should do your tour It’s a must to have an enjoyable organised tour

Lake Michigan Sunset Cruise in Chicago

michelle_m, Oct 2026

Solo Vacation Week -KCMO Visitor

I have always wanted to have a fun adventure. My bucket list of my things to do includes riding the Subway Train, Boat Ride on Lake Michigan as the Sun sets and be Solo. It's been a challenging year for me. I lost a family member, a personal friend and a professional colleague of mine. This is my way of honoring my friends and family and celebrating them.

Chicago Architecture Tour: Underground Pedway and the Loop

baldy44, Oct 2026

Even though I worked in...

Even though I worked in the Loop for 10 yrs, I hadn't used the pedway. Guide Colleen was fun, knowledgeable, personable, and taught us interesting bits of Chicago history never heard before. She also created a nice connection among our small 6-person tour (people who didn't know each other before the tour).

Bike Tour of Chicago's Lakefront Neighborhoods

Willem_B, Sep 2026

Great afternoon!!!

We had a great bike ride with Kevin our guide. He showed and told a lot about Chicago. His enthusiasm was contagious. With our club of European diversity, he made a connecting group. We really enjoyed this afternoon. This is really recommended!!! And nice bikes!!! Kevin, thanks again 🚴🚴‍♀️🚴‍♂️🚴🚴‍♀️🚴‍♂️ warm regards, from Willem and Roos, the Netherlands

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

Jan_B, Sep 2026

Great intro to the food and history of Chicago

This was an easy biking 3 1/2 hour tour for the evening tour. Just a note the tour does go rain or shine, and we definitely got caught in the rain towards the end! Our guide, Nora, was a native of Chicago and gave us lots of fascinating history of both food and the city.

Chicago Architecture and True Crime: Halloween Edition

Arite_M, Sep 2026

Entertaining, easy to follow – highly recommended!

David made our Chicago Crime & Architecture Tour a real highlight. You can tell he has comedy genes: he presents even complex topics in an incredibly entertaining, engaging, and easy-to-follow way. Although we’re not native English speakers, we could understand him perfectly and truly enjoy the tour. His mix of humor, knowledge, and storytelling turns this into much more than a standard guided tour. Highly recommended for anyone who wants to experience Chicago in a unique and memorable way!

Chicago Food Tour: 6 Dishes with Deep Dish Pizza & Beef Sandwich

Candace_W, Aug 2026

Just do it!

My family and I did this tour while we were in Chicago this past weekend and we were very happy with our experience. Sue was our guide and she was a wealth of knowledge. You could really tell that she enjoys her job. Before we got started, she made sure that everyone in our group was accounted for and even went out of her way to ensure that a few unintentional latecomers were able to jump in without disruption. She was well-prepared with anything we would've needed like wet wipes, hand sanitizer and even a Tide pen! All of the food options were amazing, with the Lou Malnati's pizza being my favorite dish. I would 100% recommend this tour to anyone visiting Chicago! You'll feel like a local for a few hours. :)

Chicago Night Crimes Tour by Bus

Nicolette_R, Jun 2026

Best use of time, No Regrets!

The tour was amazing! I was happy to be driven around downtown area and learn of the various neighborhoods, in addition to the crime history. The tour guide and driver were wonderful! No comments or recommendations, very happy tourist! Can’t wait to come back and bring more riders! See you soon Chicago Crime Tours!