Plan a trip to see Washington Square

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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 12 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

See all 231 activities

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 35 activities

City Cruises Chicago: Lake Michigan Premier Dinner Cruise

Attractions

See all 24 activities

360 CHICAGO Observation Deck

Free cancellation available

Classes & workshops

See all 21 activities

Chicago: BYOB Spray Paint and Sip Workshop

Free cancellation available

Popular places to visit

Oak Street

During your trip to Chicago, you can do some window-shopping at Oak Street. Experience the entertainment choices and acclaimed theater scene in this vibrant area.

Holy Name Cathedral

3.5/5(6 reviews)

After visiting Holy Name Cathedral, make a plan to see the other sights and activities in Chicago. Stroll along the riverfront or experience the fascinating museums in this vibrant area.

900 North Michigan Shops

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You can browse for the perfect souvenirs at 900 North Michigan Shops during your visit to Chicago. Stroll along the riverfront or experience the acclaimed theater scene in this vibrant area.

Water Tower view on Michigan Ave in Chicago City

Chicago Water Tower

4/5(83 reviews)

You can learn about the history of Chicago with a visit to Chicago Water Tower. Amble around this vibrant area's lakeside or experience its acclaimed art scene.

Newberry Library

5/5(1 review)

After visiting Newberry Library, make a plan to see the other sights and activities in Chicago. Experience the acclaimed art scene and fascinating museums in this vibrant area.