Top Chicago Walking Tours - page 4

Chicago Haunted Ghost Tour GPS Self-Guided Walking Tour

4.7

(3)

1 hour to 1 hour 15 minutesFree Cancellation

from $10

From deep-dish to hot dogs, taste Chicago Classic Dishes on our Chicago Food & Bike Tour. Ride by Bicycle, learn the stories, and savor every stop on the best Food & Bike Tour in Chicago.

Chicago dogs, deep-dish pizza, brownies, and craft beer are all sampled on this half-day bike tour through the Windy City. Cover about 13 miles (21 km), following your guide at a moderate pace through Chicago neighborhoods. On the day tour, ride through Wrigleyville, Old Town, Lincoln Park, and Gold Coast. On the night tour, visit Chicago’s Riverwalk, Millennium Park, Buckingham Fountain and the Lakefront Trail. As you go, stop for generous food and beer tasters.

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

4.9

(734)

4 hours 30 minutesFree Cancellation

from $89

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

Stop off the bus at Chicago Landmark Building with Prohibition Era History

4.8

(483)

Chicago Night Crimes Tour by Bus

2 hours to 2 hours 30 minutesFree Cancellation

from $55

On this small-group Windy City bike tour, you won't just pedal past the lakefront neighborhoods of Chicago's North Side—you'll see more of the city than you could if exploring on your own. Follow a local guide along quiet streets, city parks, and scenic beaches, starting at Lake Shore Drive and continuing along Rush Street and the Magnificent Mile. As you go, glimpse offbeat attractions like the Playboy Mansion, Oprah’s penthouse, and the Victorian houses of Old Town.

Smiles ear to ear as you ride our Chicago Bike Tour through scenic Lakefront Neighborhoods. Fresh air, open paths, and lake views make this the ultimate Bicycle Tour in Chicago.

Bike Tour of Chicago's Lakefront Neighborhoods

4.9

(241)

3 hoursFree Cancellation

from $59

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

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

Explore the new Old Post Office Building, whose early 20th-century design has been adaptively reused into a beautiful, modern Class A Office building. It once seemed as though the stunning architectural details of Chicago's Old Post Office would be lost to time while the building sat vacant for almost two decades. But the 2.8 million square foot building, completed in 1934, recently went through a monumental renovation and now serves as a modern multi-use event and office space that meets today's need for large, light-filled workspaces. See how historic artifacts and building details have been creatively incorporated into the Old Post Office's design including the conversion of the roof to a 3.5-acre urban rooftop park. Old places can become new spaces when a developer with vision collaborates with an award-winning architectural team.

Explore the Historic Old Post Office in Chicago

4.9

(20)

1 hour 30 minutesFree Cancellation

from $15

Chicago is renowned for its dynamic dining scene—and this private walking tour offers a personalized introduction to its must-eats. Pick a time that works best for you, and head to Gino’s East: one of the city’s classic deep-dish pizzerias. From there, set off on a tour of the Loop, where you’ll taste sweet and savory treats—and learn about the city’s architecture, history, and culture as you go.

Private Chicago Food Tour with Deep Dish and Beef Sandwich

(64)

3 hoursFree Cancellation

from $225

Price varies by group size

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)

Downtown Chicago TV and Movie Sites Guided Walking Tour

2 hoursFree Cancellation

from $44

Take in sweeping views of Chicago from the air during a scenic helicopter flight that offers a premier experience of the Windy City. This private 45-minute flight provides an aerial look at landmarks such as Millennium Park, Navy Park, and Wrigley Field. Ideal for a special occasion, this helicopter tour accommodates up to three people and includes the use of noise-cancelling headsets to hear the pilot clearly.

Private 45-Minute Chicago Skyline Helicopter Tour

4.8

(127)

45 minutesFree Cancellation

from $849

Per group

Discover one of Chicago’s most picturesque, historic neighborhoods—and learn all about the buildings that make it an architectural standout—on this small-group walking tour of Wicker Park. Meet your guide in the morning, and set off on foot: you’ll discover the 19th-century workers’ cottages that fill the neighborhood, will admire local landmarks like mansions and historic baths, and will learn all about the city’s architectural history.

Historic Homes and Cottages of Wicker Park Walking Tour

(44)

1 hour 30 minutes

from $45

Chicago West Loop Pizza Crawl

(7)

3 hours

from $79

Discover the architectural splendor of downtown Chicago—and learn all about the city’s early skyscrapers, urban planning, and modern history—on this small-group tour. Meet your guide in the morning on Michigan Avenue and set off by foot and by L train. You’ll see world-renowned landmarks like the Rookery Building, will visit the Chicago Cultural Center to admire the world’s largest Tiffany dome, will explore the Fine Arts Building, and much more.

Walking Tour: Chicago's Loop - Home of the Modern Skyscraper

(36)

3 hours 30 minutesFree Cancellation

from $65

Embark on an interactive adventure through Chicago’s Chinatown with the Dragon Kings Quest, a mobile escape game blending urban exploration, riddles, and local legends. Use your phone and the Questo app to follow clever clues, unlock stories, and discover must-see landmarks from Chinatown Square and colorful murals to hidden gems and Ping Tom Memorial Park. Go at your own pace, play solo or with friends, and experience the city in a totally new way. Fun for all ages—perfect for families, date nights, or teams seeking a unique outdoor challenge!

Chinatown Chicago: Dragon Kings Quest Outdoor Escape Game

4.1

(9)

48 minutes to 1 hour 18 minutesFree Cancellation

from $7

Price varies by group size

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)

Custom Chicago Walking Tours

1 to 3 hoursFree Cancellation

from $20

Per group

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

Leave behind Chicago’s buzz and see the Windy City as it used to be, some 150 years ago. The Oldtown Triangle—one of the most beloved ‘hoods in the city—survived the Great Chicago Fire of 1871, and it still stands today as a beacon to history. With your guide at the helm, you’ll witness fantastic architecture, national landmarks, and hear stories of the city’s often wild past.

Workers Cottages of Oldtown Triangle Walking Tour

(49)

1 hour 45 minutes

from $45

Visit Cloud Gate on our Chicago Walking Tour—a Walking Tour of Chicago featuring Top Attractions, iconic art, and unforgettable Highlights at the city’s most photographed landmark.

This tour is ideal for first-time visitors or anyone eager to discover the city’s most iconic Top Attractions and Highlights on a guided Chicago Walking Tour. During this 2-hour Walking Tour of Chicago, stroll through downtown’s beautiful streets as expert local guides share rich history, colorful characters, and insider tips to enhance your list of Things to do in Chicago. Your experience includes a FREE 2-hour bike or kayak rental—bike the Lakefront Trail or kayak on Lake Michigan for unforgettable skyline views. Bobby’s Bike Hike tours are nationally recognized by National Geographic, USA Today, and Condé Nast Traveler for excellence in storytelling and urban exploration. You’ll see the landmarks that define Chicago: Millennium Park, the Chicago Riverwalk, the Wrigley Building, the Chicago Theatre, and the famed Magnificent Mile. Covering 1.5 miles (2.25 km) of easy, flat terrain, this tour offers a complete and memorable introduction to the city.

Chicago Walking Tour of Highlights with Free Bike or Kayak Rental

(5)

2 hoursFree Cancellation

from $45

Discover the Art Institute in a unique way that blends art, storytelling, and photography. After a warm welcome, we'll head inside with tickets included & begin an immersive journey through the galleries. Together, we'll explore the museum's most celebrated highlights, featuring masterpieces by Monet, Picasso, Van Gogh, Dalí, Warhol, Hopper, and more. I'll share fascinating stories that bring the art and its creators to life, revealing the hidden meanings and personal histories behind. Along the way, I'll capture beautiful, candid photographs at the best photo spots. Using your phone or my iPhone 14 Pro, I'll guide you with simple posing tips and angles to ensure you receive stunning, professional-quality images perfect for memories or social media. Anyone looking for more than just a museum visit, you'll leave with gallery-worthy images plus knowledge that transforms how you experience art—an unforgettable blend of photography, storytelling, & culture. Looking forward to hosting you!

Photo Shoot and Art Walk at The Art Institute in Chicago

(2)

1 hour 15 minutesFree Cancellation

from $101

We'll explore five (5) of our favorite, Handcrafted Local Micro Breweries in two special locations of the historic, Chicago landmark district, Fulton Market; which used to be the meatpacking district, now becoming the Chicago Brewery District. Here you'll experience the fabulous, intricate world of the art of beer creation. We will all meet at the first one, introduce ourselves and try some delicious appetizers; where Carla will make a special Homemade Guacamole and Homemade Tortilla chips, and here, the first 3 handcrafted beers (3-5oz beers) are on us. Then we'll walk to the other breweries where you'll have a chance to order other beers and serve your own. Here you can stay as long as you want after the tour. During our expedition, we can all share our opinion about the flavors, the creation, etc... All the breweries are within walking distance.

Chicago Local Brewery Expedition with Homemade Guacamole

(4)

1 hour 30 minutesFree Cancellation

from $63

Price varies by group size

Join Chicago Movie Tours on the Midway, and discover the city's film history in an entirely new way! On this leisurely 75-minute walking tour led by a Ph.D. in film, you'll visit 5 spots on the historic Midway Plaisance, once the heart of the 1893 Chicago World's Fair. As you walk the now-grassy strip (0.5 mi.), you'll discover its many connections to early and modern cinema. Guests must digitally sign a general waiver of liability either before or when they arrive. Guardians must sign waivers for children under the age of 18. Note: This limited Chicago movie tour is available on Sunday mornings to give you the most accurate and unobstructed view of the Midway's monumental sculpture Fountain of Time.

Chicago's Midway, Movies, and the 1893 World's Fair Walking Tour

(5)

1 hour 30 minutes

from $50

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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

Linda_P, Apr 2026

Tour guide David gives a very educational, enjoyable, and entertaining walking tour!

Tour guide David confirmed my tour the day of my tour--which I found comforting and professional. This young man is a walking encyclopedia! He shared extensive fascinating history and information about Chicago's architecture and crime background. I was absolutely amazed with his enthusiasm, energy, and expertise! David truly loves what he does! I learned so such in such a short time. Our 1 hours and 45 minutes walking tour flew. The next time I visit Chicago I will take David's tour again. He is an absolute delight--and such a gifted teacher!

Chicago's Chinatown Food and Walking Tour

Elizabeth_W, Apr 2026

A "hidden" gem in Chicago

Greg was a fantastic host/guide. Food was terrific and there were substitutions available for us that don't eat pork/beef/lamb. Walking distance was several blocks - easy even in windy/rainy Chicago weather. Really liked the insights into the history and culture of Chinatown.

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!?!?

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 Walking Tour: Historic Treasures of Chicago

Krista_G, Nov 2025

Pleasant walking tour to see 10 historic Chicago buildings.

Very pleasant walking tour led by our knowledgeable guide, Burt, who showed us 10 historic buildings in downtown Chicago, starting with the Wrigley building on down to the Palmer Hotel. The weather was great, so the streets were crowded and very noisy, but hey, this is Chicago! We saw lots of historic interiors as well. Well worth the time and cost of the ticket.

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.

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

DJ_O, Oct 2025

Great tour every time

This is my favorite tour! I’ve booked it 3 times in the past year and brought new people. It’s always a hit and everyone’s favorite. Aside from the amazing Chicago doughnuts, you get a history of the shops and some of the local building’s you pass on the way. I particularly like that history is more personal and includes nuanced stories that you don’t hear on other tours. I’ve had the same guide all 3 times, Nick, and he is GREAT. He’s funny, personable and makes a point to talk with everyone in the group as we walk around. I highly recommend this tour.

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.