Plan a trip to see Briar Street Theatre

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Viceroy Chicago

Downtown Chicago

CA $835

per person

Apr 8 - Apr 11

found 16 hours ago

Roundtrip flight included

Montreal (YMQ) to Chicago (ORD)

9.4/10 Exceptional! (1,129 reviews)

We stayed at the Viceroy Chicago last night and had a wonderful experience. The hotel is stylish, comfortable, and feels thoughtfully designed in every detail. The staff was warm and welcoming from the moment we arrived, and the service throughout our stay was excellent. Our room was spotless with a great layout, and the overall atmosphere of the hotel made it easy to relax and enjoy the night. A really lovely stay—highly recommend.

Reviewed on Feb 15, 2026

Waldorf Astoria Chicago

Downtown Chicago

CA $1,348

per person

Apr 1 - Apr 4

found 1 day ago

Roundtrip flight included

Montreal (YMQ) to Chicago (ORD)

9.4/10 Exceptional! (1,000 reviews)

Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.

Reviewed on Jan 26, 2026

Level Chicago – Old Town

Downtown Chicago

CA $912

per person

Apr 20 - Apr 24

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Chicago (ORD)

9/10 Wonderful! (380 reviews)

My girlfriend and I had an awesome time enjoying the space for a fun girls night out. Would recommend to anyone!

Reviewed on Feb 2, 2026

Tours & day trips

See all 156 activities

Flyover in Chicago

Free cancellation available

Private & custom tours

See all 59 activities

Chicago Cocktail Adventure Part 1

Free cancellation available

Food, drink & nightlife

See all 23 activities

Chicago's Chinatown Food and Walking Tour

Free cancellation available

Attractions

See all 19 activities

360 CHICAGO Observation Deck

Free cancellation available

Classes & workshops

See all 15 activities

BYOB Spray Paint and Sip at Studio W.I.P.

Free cancellation available

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Wrigley Field

4.5/5(158 reviews)

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

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