Plan a trip to see Broadway Playhouse

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Swissotel - Chicago

Downtown Chicago

CA $867

per person

Jul 23 - Jul 26

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (3,332 reviews)

Great location and very convenient to river walk and vicinity.

Reviewed on May 22, 2026

Level Chicago – Old Town

Downtown Chicago

CA $1,411

per person

Aug 2 - Aug 7

found 1 hour ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (474 reviews)

Minimum effort. Pleasant stay. Very quiet. Enjoyed the 8th floor common area. Service at the front desk was really great. Convenient coffee shop / bakery in the lobby.

Reviewed on May 18, 2026

The Talbott, Autograph Collection

Downtown Chicago

CA $1,063

per person

Jun 27 - Jul 1

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (116 reviews)

We thoroughly enjoyed our stay. The location was excellent, conveniently close to everything we needed. The room was spacious and spotless. The breakfast was fantastic, offering a wide variety of options to choose from.

Reviewed on May 17, 2026

Tours & day trips

See all 228 activities

Architecture River Tour

Free cancellation available

Private & custom tours

See all 48 activities

Sip Happens: Chicago Loop Prohibition 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 20 activities

Chicago: BYOB Spray Paint and Sip Workshop

Free cancellation available

Popular places to visit

875 North Michigan Avenue

You can find out about the history of Chicago with a visit to 875 North Michigan Avenue. Amble around this vibrant area's lakeside or experience its acclaimed art scene.

Water Tower Place

Enjoy endless shopping, see exhibits of sporting memorabilia and attend shows at a live theater at this huge shopping mall.

Water Tower view on Michigan Ave in Chicago City

Chicago Water Tower

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.

900 North Michigan Shops

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.

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.

Chicago Gold Coast highrise residential towers with a lakeshore beach in the foreground.

Oak Street Beach

Why not spend a carefree afternoon at Oak Street Beach during your travels in Chicago? Stroll along the riverfront or experience the fascinating museums in this vibrant area.