Plan a trip to see Chicago Women's Park

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Pendry Chicago

Downtown Chicago

CA $801

per person

Oct 30 - Nov 2

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,059 reviews)

Slow elevators. Solid hotel but nothing spectacular. Would choose other properties in this price point next time.

Reviewed on Aug. 26, 2025

Trump International Hotel & Tower Chicago

Downtown Chicago

CA $1,234

per person

Oct 30 - Nov 2

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,690 reviews)

It is a beautiful, well maintained property. The staff is the true gem of the property. They elevate the visitors experience to a new level of excellence.

Reviewed on Aug. 25, 2025

Level Chicago – Old Town

Downtown Chicago

CA $1,128

per person

Oct 13 - Oct 17

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

9/10 Wonderful! (339 reviews)

It was fine but nit as good as I had expected. Staff were un friendly and un helpful fur an expensive stay.

Reviewed on Aug. 27, 2025

Tours & day trips

See all 173 activities

Architecture River Tour

Free cancellation available

Food, drink & nightlife

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Chicago: Architecture Boat Tour with Drinks

Free cancellation available

Private & custom tours

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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

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Chicago: Two Flight Indoor Skydiving Experience

Free cancellation available

Popular places to visit

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.

Soldier Field

Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.

McCormick Place

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

Burnham Park

After visiting Burnham Park, make a plan to see the other sights and activities in Chicago. Stroll along the area's lakeside, or simply savor its top-notch restaurants.

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.