Plan a trip to see Pontiac Building

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Chicago Athletic Association, a Hyatt Hotel

Downtown Chicago

CA $1,276

per person

Oct 25 - Oct 29

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (1,002 reviews)

A beautiful step back in time with modern amenities. Amazing staff and easy access to anything you want to do in the city.

Reviewed on Aug. 21, 2025

Park Hyatt Chicago

Downtown Chicago

CA $2,089

per person

Nov 17 - Nov 23

found 9 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 9 hours ago

Roundtrip flight included

Vancouver (YVR) to Chicago (ORD)

10/10 Exceptional! (2 reviews)

Tours & day trips

See all 170 activities

Architecture River Tour

Free cancellation available

Food, drink & nightlife

See all 35 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.

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.

Chicago Board of Trade Building

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Roosevelt University

Explore the campus of Roosevelt University during your stay in Chicago. Experience the acclaimed art scene and entertainment choices in this vibrant area.

Mergenthaler Lofts

Learn about the local history of Chicago when you take a trip to Mergenthaler Lofts. Discover the fascinating museums and notable monuments in this vibrant area.

Second Franklin Building

Learn about the local history of Chicago when you spend time at Second Franklin Building. Discover the entertainment choices and notable monuments in this vibrant area.