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

Park Hyatt Chicago

Downtown Chicago

CA $1,118

per person

Nov 21 - Nov 24

found 2 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.6/10 Exceptional! (1,000 reviews)

Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on Aug. 10, 2025

Staypineapple, An Iconic Hotel, The Loop

Downtown Chicago

CA $1,070

per person

Oct 6 - Oct 10

found 21 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

Tours & day trips

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Architecture River Tour

Free cancellation available

Food, drink & nightlife

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Chicago: Architecture Boat Tour with Drinks

Free cancellation available

Private & custom tours

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Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Attractions

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360 CHICAGO Observation Deck

Free cancellation available

Classes & workshops

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CHICAGo MUSt Do Hidden GEm SPEAKeasy's

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