Plan a trip to see Madison Street Theatre

Price found within the past 48 hours. Click for updated prices.

Level Chicago - River North

Downtown Chicago

CA $788

per person

Sep 25 - Sep 28

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (666 reviews)

The hotel never got cool, hot everywhere, even the community areas. We had to use the TV in the communal area as ours didn't work. We called on day one and the girl laughed and never sent anyone to fix it. Our key cards didn't work multiple times during the stay. The party that happened at the pool on Sunday night of our stay was awful. I couldn't imagine what my kids saw even those this hotel said no parties.

Reviewed on Aug. 25, 2025

Staypineapple, An Iconic Hotel, The Loop

Downtown Chicago

CA $1,070

per person

Oct 6 - Oct 10

found 11 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,014 reviews)

We loved the experience! We shall come back again😊

Reviewed on Aug. 24, 2025

The Langham, Chicago

Downtown Chicago

CA $1,933

per person

Oct 6 - Oct 10

found 11 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.8/10 Exceptional! (1,003 reviews)

Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.

Reviewed on Aug. 12, 2025

Tours & day trips

See all 158 activities

Architecture River Tour

Free cancellation available

Food, drink & nightlife

See all 34 activities

Chicago: Architecture Boat Tour with Drinks

Free cancellation available

Private & custom tours

See all 25 activities

Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Attractions

See all 14 activities

360 CHICAGO Observation Deck

Free cancellation available

Classes & workshops

See all 10 activities

CHICAGo MUSt Do Hidden GEm SPEAKeasy's

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