Plan a trip to see Theater Wit

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Chicago Marriott Downtown Magnificent Mile

Downtown Chicago

CA $987

per person

Jun 11 - Jun 14

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

8.8/10 Excellent! (1,002 reviews)

Patrick was excellent at check in despite how busy it was. I felt the staff handled the crush of people efficiently and pleasantly. I was pleasantly surprised I received $15 per day towards the bar or snack room. The snack room selections included hot and cold items. My room was a bit hot for my taste and they took care of it immediately.

Reviewed on May 3, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

CA $1,142

per person

Jul 9 - Jul 12

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (2,478 reviews)

My stay was exceptional the staff were very polite and patient, they answered all my questions. I had a very nice view will definitely book again

Reviewed on May 6, 2026

Level Chicago - River North

Downtown Chicago

CA $1,036

per person

Jun 25 - Jun 28

found 18 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (973 reviews)

Everything was clean and great

Reviewed on May 6, 2026

Tours & day trips

See all 215 activities

Architecture River Tour

Free cancellation available

Private & custom tours

See all 53 activities

Sip Happens: Chicago Loop Prohibition Tour

Free cancellation available

Food, drink & nightlife

See all 33 activities

City Cruises Chicago: Lake Michigan Premier Dinner Cruise

Attractions

See all 23 activities

360 CHICAGO Observation Deck

Free cancellation available

Classes & workshops

See all 18 activities

Chicago: BYOB Spray Paint and Sip Workshop

Free cancellation available

Popular places to visit

Wrigley Field

4.5/5(159 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Bailiwick Repertory Theatre

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Vic Theatre

You can get tickets for a performance at Vic Theatre during your trip to Chicago. Amble around this vibrant area's lakeside and enjoy its top-notch restaurants.

Athenaeum Theatre

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Defiant Theatre

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Lucky Strike at Wrigleyville

You can take time to visit Lucky Strike at Wrigleyville during your travels to Chicago. Experience the acclaimed theater scene and entertainment choices in this vibrant area.