Plan a trip to see Jazz Institute of Chicago

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Trump International Hotel & Tower Chicago

Downtown Chicago

CA $1,066

per person

Oct 28 - Oct 31

found 1 day ago

Roundtrip non-stop flight included

Québec (YQB) to Chicago (ORD)

9.4/10 Exceptional! (1,694 reviews)

Place is great, staff, location. So many great restaurants, river boats, shopping. Loved our stay at Trump International

Reviewed on Aug. 31, 2025

The Langham, Chicago

Downtown Chicago

CA $1,091

per person

Nov 11 - Nov 14

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.8/10 Exceptional! (1,003 reviews)

Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.

Reviewed on Aug. 12, 2025

Hyatt Centric Chicago Magnificent Mile

Downtown Chicago

CA $1,198

per person

Oct 25 - Oct 29

found 3 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (1,028 reviews)

Overall is good but 1 concern we encountered is there is a clicking sound in our room or near our room, that distracts my husband while sleeping.

Reviewed on Aug. 24, 2025

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

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