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Rainy Day Activities in Chicago (Updated November 2026)

Chicago, USA
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 …More

Likely to Sell Out
Likely to Sell Out

Gaze upon the city sights from the pinnacle of Chicago, the Skydeck. Located on the 103rd floor of Willis Tower, formerly Sears Tower -- the...

30 to 90 minutes Free Cancellation
4.5 (1,515)
from
$44
Flyover in Chicago

The Flyover experience takes 30 minutes from beginning to end. First, on-the-ground stories connect you with the spirit of the Windy City. Then, you’ll discover …More

The Flyover experience takes 30 minutes from beginning to end. First, on-the-ground stories connect you with the spirit of the Windy City. Then, you’ll discover...

30 minutes Free Cancellation
4.8 (742)
from
$28
LEGOLAND Discovery Center Chicago Admission Ticket

LEGOLAND® Discovery Center Chicago, located at Schaumburg’s Streets of Woodfield shopping center, is a 30,000-square-foot indoor LEGO playground designed for families with children aged 2 …More

LEGOLAND® Discovery Center Chicago, located at Schaumburg’s Streets of Woodfield shopping center, is a 30,000-square-foot indoor LEGO playground designed for families with children aged 2...

3 hours Free Cancellation
3.2 (92)
from
$23
Chicago's Navy Pier Centennial Wheel Ticket

No visit to Navy Pier is complete without a ride on the Centennial Wheel, Navy Pier's iconic, 200-foot-tall Ferris wheel, promising unparalleled views of Lake …More

No visit to Navy Pier is complete without a ride on the Centennial Wheel, Navy Pier's iconic, 200-foot-tall Ferris wheel, promising unparalleled views of Lake...

15 minutes Free Cancellation
4.4 (88)
from
$24
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