Plan a trip to see Second City

Price found within the past 48 hours. Click for updated prices.

Hotel Riu Plaza Chicago

Downtown Chicago

￥217,344

per person

Mar 17 - Mar 19

found 1 day ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

9.4/10 Exceptional! (2,790 reviews)

Room was clean, comfortable and quiet.

Reviewed on Jan 30, 2026

Pendry Chicago

Downtown Chicago

￥225,989

per person

Mar 17 - Mar 19

found 1 day ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

9.4/10 Exceptional! (1,130 reviews)

Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium.

Reviewed on Jan 31, 2026

Fairmont Chicago at Millennium Park

Downtown Chicago

￥219,954

per person

Mar 17 - Mar 19

found 1 day ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

8.6/10 Excellent! (2,008 reviews)

Friendly staff and great service, very accommodating! Very clean lobby and great decorations put out for Christmas. Overall great stay!

Reviewed on Jan 31, 2026

Browse tours and tickets to explore Second City

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Flyover in Chicago

Free cancellation available

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Chicago Cocktail Adventure Part 1

Free cancellation available

Food, drink & nightlife

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Chicago's Chinatown Food and Walking Tour

Free cancellation available

Attractions

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360 CHICAGO Observation Deck

Free cancellation available

Classes & workshops

See all 16 activities

BYOB Spray Paint and Sip at Studio W.I.P.

Free cancellation available

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