Plan a trip to see Dearborn St Station

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

Chicago Athletic Association, a Hyatt Hotel

Downtown Chicago

CA $837

per person

Oct 19 - Oct 22

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (1,002 reviews)

A beautiful step back in time with modern amenities. Amazing staff and easy access to anything you want to do in the city.

Reviewed on Aug. 21, 2025

Park Hyatt Chicago

Downtown Chicago

CA $1,334

per person

Nov 5 - Nov 8

found 8 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.6/10 Exceptional! (1,000 reviews)

Excellent service with great top notch amenities and a room that has everything you can need away from home. Highly recommend!

Reviewed on Aug. 31, 2025

Arlo Chicago

Downtown Chicago

CA $905

per person

Oct 6 - Oct 10

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (1,844 reviews)

Good spot, convenient to everything. Staff was helpful. Very urban so some issues with people begging for money etc.

Reviewed on Sep. 3, 2025

Tours & day trips

See all 168 activities

Architecture River Tour

Free cancellation available

Food, drink & nightlife

See all 31 activities

Chicago: Architecture Boat Tour with Drinks

Free cancellation available

Private & custom tours

See all 31 activities

Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Attractions

See all 15 activities

360 CHICAGO Observation Deck

Free cancellation available

Adventure & outdoor

See all 13 activities

Chicago: Two Flight Indoor Skydiving Experience

Free cancellation available

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