Top things to do in Chicago in Summer (Updated November 2026)

Don’t miss Chicago’s famous sights and fabulous views on this award-winning private sightseeing tour of the city. Travel through Chicago with an expert guide on...
$999

Explore Chicago’s iconic landmarks and scenic lakefront on a private, fully personalized city tour. Travel in comfort with your English-speaking driver, who shares local stories,...
$57

Discover the vibrant neighborhoods and cultural districts of Chicago on a private, fully personalized tour. Travel in comfort with your English-speaking driver, who shares local...
$77

Discover the rich history and dynamic transformation of Hyde Park on this engaging walking tour. Delve into the neighborhood's evolution from a lakeside retreat for...
$5

Luxury vehicles Professional chauffeurs Updated fleet Licensed chauffeurs Knowledge about navigating in the city...
$960

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...
$89

Take an adventurous half-day journey through the most interesting Chicago neighborhoods with a friendly private guide and see the city from a new perspective riding...
$179

Our knowledgeable and licensed guide will drive you between each location in an open air motorized pedicab! Also a great option for anyone with mobility...
$90

Embark on an engaging scavenger hunt through the historic streets of Chicago! Explore the beautiful Magnificent Mile. Stroll the happening riverwalk See the historic sights...
$8

Take your shot at completing this Chicago Scavenger Hunt around the Loop and River North neighborhoods including the Riverwalk. Complete this solo or build a...
$8

Discover the elegance and beauty of Hanfu, the traditional clothing of ancient China, in this one-of-a-kind cultural experience here at our Chinatown Visitor Center! Step...
$20

Chicago Small Group City Tour
Experience Chicago like never before on your all-inclusive small group city tour, led by an expert guide. Discover iconic landmarks, hidden gems, and vibrant neighborhoods...
$340

Chinatown Food Tour
Experience the authentic flavors of Chinatown on a 3-hour guided food tour curated by Chicago Tribune Good Eating Award winner Z.J. Tong. As you explore...
$98

Discover Chicago's iconic sights on this guided walking tour that highlights five scenic photo spots. With a local guide, enjoy stunning skyline views and learn...
$49

Chicago Crime and Mob Bus Tour
Escape into Chicago's underworld on a crime and mob tour with stops on-and-off the luxury, climate-controlled bus. Explore historic crime scenes with great photo opportunities....
$49

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...
$45

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...
$30

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...
$50

Chicago's Original Gangster Tour by Bus
Our guides present an accurate account of the activities in Chicago during the 1920's and 1930's (Prohibition Era). You will hear about the exploits of...
$48

Lakefront Segway Tour in Chicago
Segways are amazingly fun, and Chicago's lakefront, parks, and skyline are absolutely gorgeous! Add our smart, entertaining tour guides to the mix, and you have...
$70

No city embraces summer quite like Chicago. Join in the celebration with friends and family on this epic fireworks cruise. Get up-close and personal every...
$60

