Plan a trip to see Haskell Building

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Pendry Chicago

Downtown Chicago

CA $1,060

per person

Aug 6 - Aug 9

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (1,126 reviews)

Great and very elegant hotel! I absolutely loved it! The only thing is a little bit noisy but it’s the price you have to pay to be in an excellent location, you have everything you need in a walking distance. I would definitely stay here again.

Reviewed on May 30, 2026

Urban Chicago Oasis

Lakeview

CA $1,671

per person

Aug 12 - Aug 16

found 13 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Chicago (ORD)

No reviews

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

CA $1,168

per person

Jul 23 - Jul 26

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (2,511 reviews)

Great experience and beautiful views

Reviewed on Jun 1, 2026

Tours & day trips

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Architecture River Tour

Free cancellation available

Private & custom tours

See all 49 activities

Chamarel 7 Colours and Waterfalls - Exclusive South West Tour

Free cancellation available

Food, drink & nightlife

See all 34 activities

City Cruises Chicago: Lake Michigan Premier Dinner Cruise

Attractions

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360 CHICAGO Observation Deck

Free cancellation available

Classes & workshops

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Chicago: BYOB Spray Paint and Sip Workshop

Free cancellation available

Popular places to visit

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State Street

During your visit to Chicago, you can search for that perfect souvenir at State Street. Experience the acclaimed theater scene and entertainment choices in this vibrant area.

CIBC Theatre

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

Cloud Gate

You can learn about the history of Chicago with a stop at Cloud Gate. Discover the acclaimed art scene and notable monuments in this vibrant area.

Chicago Cultural Center

Enjoy a stop at Chicago Cultural Center, an entertaining place to visit in Chicago. Discover the acclaimed theater scene and notable monuments in this vibrant area.

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Chase Tower

Chase Tower is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Amble around this vibrant area's riverfront or experience its entertainment choices.