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

Chicago, USA
Chicago Exotic Auto Experience

This tour offers a personalized and stress-free way to experience Chicago, combining comfortable transportation with local insights and flexible stops. Guests enjoy a private ride …More

Likely to Sell Out
Likely to Sell Out

This tour offers a personalized and stress-free way to experience Chicago, combining comfortable transportation with local insights and flexible stops. Guests enjoy a private ride...

3 to 7 hours
from
$1,800
Private and All-Inclusive Tour of Chicago

Experience the best of Chicago on this private full-day city tour designed for a fun, stress-free day of exploring. Enjoy comfortable hotel pickup, ride in …More

Experience the best of Chicago on this private full-day city tour designed for a fun, stress-free day of exploring. Enjoy comfortable hotel pickup, ride in...

6 hours Hotel pickup offered Free Cancellation
from
$750
4 Hours of Chicago City Tour Sedan

Luxury vehicles Professional chauffeurs Updated fleet Licensed chauffeurs Knowledge about navigating in the city …More

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

4 hours Hotel pickup offered Free Cancellation
from
$640
Chicago’s Ragtime & Jazz Eras: A Self-Guided Audio Tour

See Chicago through the eyes of Al Capone and the Everleigh Sisters at your own pace with this affordable walking tour. • Walk in the …More

See Chicago through the eyes of Al Capone and the Everleigh Sisters at your own pace with this affordable walking tour. • Walk in the...

45 to 60 minutes
from
$7
Great Smoky Mountains,Gatlinburg 4-Day Tour from Chicago

1. Explore Motorsports Hall of Fame. 2. Be in the National Park with most visitors in US -- Great Smoky Mountains. 3. Southern dinner show …More

1. Explore Motorsports Hall of Fame. 2. Be in the National Park with most visitors in US -- Great Smoky Mountains. 3. Southern dinner show...

4 days Free Cancellation
from
$1,030
Private Tour Art Institute of Chicago Guided Museum

Experience our Private Excursion tailored exclusively for you! Embark on a serene journey through the picturesque landscapes of USA as you make your way to …More

Experience our Private Excursion tailored exclusively for you! Embark on a serene journey through the picturesque landscapes of USA as you make your way to...

5 hours Hotel pickup offered
from
$443
Chicago Private Tour to Lake Geneva and Anderson Japanese Gardens

Discover the natural beauty of Lake Geneva and the tranquil Anderson Japanese Gardens on this private 10‑hour getaway from Chicago. Begin your day with convenient …More

Discover the natural beauty of Lake Geneva and the tranquil Anderson Japanese Gardens on this private 10‑hour getaway from Chicago. Begin your day with convenient...

9 to 10 hours Hotel pickup offered Free Cancellation
from
$1,200
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 …More

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...

30 minutes Free Cancellation
4.5 (317)
from
$39
Chicago Seadog River & Lake Architectural Tour

Soak in unobstructed views of Chicago’s world-famous architecture from the water with an exciting ride on our Seadog River and Lake Architectural Tour! Sail through …More

Soak in unobstructed views of Chicago’s world-famous architecture from the water with an exciting ride on our Seadog River and Lake Architectural Tour! Sail through...

1 hour 15 minutes Free Cancellation
4.6 (301)
from
$42
Chicago Shoreline Adventure Boat Tour

This tour is the perfect way to experience the shoreline of Chicago in a new and exciting way! Our tour vessel is a former military …More

This tour is the perfect way to experience the shoreline of Chicago in a new and exciting way! Our tour vessel is a former military...

1 hour 30 minutes Free Cancellation
5.0 (39)
from
$90
Golden Hour Motorized Paddleboard Tours w/ Mobile DJ

One of a kind experience you can only find in Chicago. Motorized paddle boards take the stress out of paddling. LED-lights make the boards illuminate …More

One of a kind experience you can only find in Chicago. Motorized paddle boards take the stress out of paddling. LED-lights make the boards illuminate...

1 hour Free Cancellation
5.0 (2)
from
$105
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