Plan a trip to see Old Colony Building

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theWit Chicago, a Hilton Hotel

Downtown Chicago

CA $543

per person

Nov 6 - Nov 9

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (1,007 reviews)

This was by far the BEST Hotel!!!

Reviewed on Sep. 1, 2025

Park Hyatt Chicago

Downtown Chicago

CA $2,089

per person

Nov 17 - Nov 23

found 18 hours ago

Roundtrip flight included

Vancouver (YVR) to Chicago (ORD)

9.6/10 Exceptional! (1,000 reviews)

Excellent service with great top notch amenities and a room that has everything you can need away from home. Highly recommend!

Reviewed on Aug. 31, 2025

Art Villa

West Town

CA $2,538

per person

Nov 17 - Nov 23

found 18 hours ago

Roundtrip flight included

Vancouver (YVR) to Chicago (ORD)

10/10 Exceptional! (2 reviews)

Tours & day trips

See all 169 activities

Architecture River Tour

Free cancellation available

Food, drink & nightlife

See all 34 activities

Chicago: Architecture Boat Tour with Drinks

Free cancellation available

Private & custom tours

See all 31 activities

Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Attractions

See all 15 activities

360 CHICAGO Observation Deck

Free cancellation available

Adventure & outdoor

See all 13 activities

Chicago: Two Flight Indoor Skydiving Experience

Free cancellation available

Popular places to visit

Printer\'s Row featuring a city and heritage architecture

Harold Washington Library Center

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 fascinating museums and notable monuments in this vibrant area.

Chicago Board of Trade Building

You can learn about the history of Chicago when you stop by Chicago Board of Trade Building. Experience the entertainment choices and acclaimed theater scene in this vibrant area.

Rookery

Built by famed 19th-century architects and renovated in 1907 by Frank Lloyd Wright, this early skyscraper is a great stop on a Chicago architecture tour.

Auditorium Building and Theatre

You can make plans for a show at Auditorium Building and Theatre during your trip to Chicago. Discover the acclaimed theater scene and notable monuments in this vibrant area.

CIBC Theatre

You can get tickets for a performance at CIBC Theatre on your trip to Chicago. Discover the acclaimed art scene 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.