Plan a trip to see Old Colony Building

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Arlo Chicago

Downtown Chicago

per person

Oct 2 - Oct 6

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (1,785 reviews)

Many homeless people

Reviewed on Aug. 1, 2025

Trump International Hotel & Tower Chicago

Downtown Chicago

per person

Oct 2 - Oct 6

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,635 reviews)

Great stay :) Mr 47 didn’t disappoint

Reviewed on Aug. 1, 2025

Pendry Chicago

Downtown Chicago

per person

Oct 2 - Oct 6

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,006 reviews)

The stay so far has been great, but we attempted to order in room dining which, according to the menu, is available until 5AM, but were advised by the front desk staff that we would not be able to order food for at least 40 minutes while the kitchen was “cleaned”. No other solutions were provided and we were very disappointed in this interaction.

Reviewed on Jul. 30, 2025

Tours & day trips

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Architecture River Tour

Free cancellation available

Food, drink & nightlife

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Chicago: Architecture Boat Tour with Drinks

Free cancellation available

Private & custom tours

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Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Attractions

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360 CHICAGO Observation Deck

Free cancellation available

Adventure & outdoor

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Chicago White Sox Baseball Game at Guaranteed Rate Field

Popular places to visit

Printer\'s Row featuring a city and heritage architecture

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Harold Washington Library Center is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Discover the entertainment choices and notable monuments in this vibrant area.

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Rookery

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CIBC Theatre

You can get tickets for a performance at CIBC Theatre on your trip to Chicago. Discover the fascinating museums and notable monuments in this vibrant area.

Fisher Building

You can find out about the history of Chicago with a visit to Fisher Building. Discover the acclaimed theater scene and notable monuments in this vibrant area.