Plan a trip to see South Wentworth Street

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Pendry Chicago

Downtown Chicago

CA $655

per person

Nov 6 - Nov 9

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,064 reviews)

This hotel was lovely. The room was large and smelled divine. Everything was spotless, beds were comfy, location was excellent, staff were friendly and accommodating. Would definitely stay here again. :)

Reviewed on Sep. 4, 2025

Park Hyatt Chicago

Downtown Chicago

CA $1,693

per person

Nov 17 - Nov 22

found 1 day 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

Trump International Hotel & Tower Chicago

Downtown Chicago

CA $1,008

per person

Nov 6 - Nov 9

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,694 reviews)

Best, very clean, best view, really enjoyed the stay!

Reviewed on Sep. 2, 2025

Tours & day trips

See all 168 activities

Architecture River Tour

Free cancellation available

Food, drink & nightlife

See all 31 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

Ping Tom Memorial Park

After visiting Ping Tom Memorial Park, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices.

Clarke House Museum

You can spend an afternoon exploring the galleries in Clarke House Museum during your travels in Chicago. Experience the fascinating museums and acclaimed art scene in this vibrant area.

Glessner House Museum

You can spend time exploring the galleries in Glessner House Museum during your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.

On Leong Building

You can learn about the history of Chicago with a trip to On Leong Building. Stroll along the lakeside or experience the acclaimed theater scene in this vibrant area.

Chinatown Gateway

Learn about the local history of Chicago when you spend time at Chinatown Gateway. Amble around this family-friendly area's Chinatown and enjoy its top-notch restaurants.

Chinese American Museum of Chicago

You can spend an afternoon exploring the galleries in Chinese American Museum of Chicago in Chicago. Amble around this family-friendly area's Chinatown and enjoy its top-notch restaurants.