Walking tours in Chicago
211 bookable experiences
A good walking tour is the cheapest way to make sense of Chicago on your first morning — history, neighbourhoods and where to come back for dinner.
Hostbnb earns a commission when you book through the links on this page. It never changes what you pay, and we only list what Viator can actually sell you today — prices and availability come straight from their catalogue.
Chicago River 90-Minute Architecture Tour
Be inspired by the captivating, visual art that is Chicago’s legendary architecture, and the exceptional architects who created this ever-changing, dynamic legacy for all to enjoy and admire. This comprehensive 90…
Chicago Architecture River Cruise
Experience the stunning beauty of Chicago on a captivating cruise along the historic Chicago River. This architectural tour takes you down the main branch of the river, up the north branch to the East Bank Club, and…
Chicago River 45-Minute Architecture Tour from Magnificent Mile
Experience Chicago's legendary architecture and the exceptional architects who created this ever-changing legacy for all to admire. This family-friendly introduction to the Windy City's rich history and architectural…
Chicago Architecture Center River Cruise aboard First Lady
The Chicago Architecture Center River Cruise aboard Chicago's First Lady has long been the gold standard among all Chicago tour experiences, and is the only Chicago architecture boat tour led by highly trained expert…
Chicago Sightseeing River and Lake Cruise
Our popular 90-minute daytime river and lake sightseeing tour delights family members of all ages with incredible views of Chicago's world-renowned buildings and stunning skyline. Lively, knowledgeable tour guides bring…
Chicago By Night River and Lake Cruise
Glide along the Chicago River and Lakefront as you're dazzled by the sparkle of the city at night! Enjoy breathtaking views of the dramatic skyscrapers and Buckingham Fountain's spectacular light display. Hear lively…
Chicago Skyline Snap Tour Helicopter Flight Over Chicago
Witness Chicago’s stunning skyline from above on this exhilarating helicopter tour. Departing from the Vertiport, the flight offers breathtaking views of the city’s iconic architecture, including Soldier Field and the…
Lake Michigan Skyline Cruise in Chicago
Embark on an unforgettable journey along Lake Michigan and marvel at Chicago's iconic lakefront sights and attractions. Cruise along Lake Michigan and enjoy stunning views of Chicago's renowned skyscrapers from a unique…
Chicago Lake and River Architecture Tour
An authentic Chicago tradition since 1935, this is the tour that started it all. This unique excursion tells the story of more than 200 years of fascinating social, cultural and political history, and explores more than…
Lake Michigan Sunset Cruise in Chicago
The Lake Michigan Sunset Cruise departs near the DuSable (Michigan Avenue) Bridge on Wendella's world class tour boats. The Cruise will navigate from the Chicago River, through the Chicago Lock and out onto Lake…
Chicago Hop-on Hop-off Sightseeing Tour by Open-top Bus
Discover Chicago at your own pace with Big Bus. Travel aboard an open-top, double-decker bus and enjoy panoramic views of the city's most famous landmarks, including the Magnificent Mile, Millennium Park, Willis Tower,…
Skydeck - Willis Tower Admission
Gaze upon the city sights from the pinnacle of Chicago, the Skydeck. Located on the 103rd floor of Willis Tower, formerly Sears Tower -- the third-tallest building in the world -- the Skydeck offers spectacular sweeping…
Chicago River 90-Minute Architecture Boat Tour
Marvel at the magnificent architecture on the Chicago River with expert tour guides! All ages welcome. Each architecture river tour is narrated by a professional guide which leads passengers down the Chicago River to…
360 CHICAGO Observation Deck Admission
The best views of Chicago can be yours at 360 Chicago Observation Deck! Perched 94 stories above the Windy City in the former John Hancock Building, 360 Chicago provides commanding views of Lake Michigan and Chicago’s…
Chicago CityPASS®
Experience 5 top attractions and save up to 50% with Chicago CityPASS® tickets. One simple purchase removes the stress of planning, so you can relax and enjoy your memories in the making. With 9 days to use your…
Chicago Architectural River Cruise
Take in the views on this award-winning 90-minute Architectural Tour, a jaw-dropping excursion through a city that defies all expectations!
Chicago's Chinatown Food and Walking Tour
Chicago's Chinatown: Few neighborhoods in America combine such delicious cuisine with fascinating history. Join Bobby’s Bike Hike & Food Tours, whose food tours have ranked Top 10 in America by USA Today & Top 20 in the…
Historical and Architectural Chicago Fireboat River & Lake Cruise
Travel on a piece of history, learning Chicago fire history as well as Architecture! We travel on Lake Michigan and through the Chicago River seeing the sights. Perfect for Fire enthusiasts, families and everyone in…
City Cruises Chicago: Signature Lunch Cruise on Lake Michigan
Join us for an unforgettable afternoon on Lake Michigan with a Signature Chicago Lunch Cruise. Whether it’s a family outing or a meal with friends, upgrade your lunch with a chef-prepared buffet and sweeping views of…
City Cruises Chicago: Premier Plus Brunch Cruise on Chicago River
Sail along the magnificent skyline on our Premier Plus Chicago Brunch Cruise. A chef-curated menu of plated brunch specials will delight your palate while unparalleled panoramas of the city’s iconic architecture are…
360 Chicago Observation Deck Sip and View Ticket
The best views of Chicago can be yours at 360 Chicago Observation Deck! Perched 94 stories above the Windy City in the former John Hancock Building, 360 Chicago provides commanding views of Lake Michigan and Chicago’s…
Chicago City Minibus Tour
Enjoy Chicago’s famous sights and fabulous skyline views on this award-winning small-group sightseeing tour of the city. Travel through Chicago with an expert guide on a comfortable minibus, stopping at iconic locations…
Chicago Explorer Pass: 35+ Things To Do - Includes 360 CHICAGO
Access top Chicago attractions, tours and activities with Go City's Explorer Pass. Save on entry to your choice of up to seven top things to do. Hop-on a Big Bus tour for an introduction to the city, check out the…
Lake Michigan 30 Minute Speedboat Ride
Enjoy Chicago’s iconic skyline with an exciting speedboat Tour on Lake Michigan. Departing from Navy Pier, the Lakefront Speedboat Tour is the best way to view Chicago from the water. Seadog offers fun for the whole…
Prices and availability last checked 2026-09-13. Both are confirmed on Viator before you pay.