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

Arlo Chicago

Downtown Chicago

€565

per person

10 Nov - 16 Nov

found 20 hours ago

Return flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (1,826 reviews)

I wish that all the staff was more accommodating! some of them were some were not!

Reviewed on 6 Oct 2025

Pendry Chicago

Downtown Chicago

€678

per person

10 Nov - 16 Nov

found 20 hours ago

Return flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,085 reviews)

The bed was extremly comfortable Staff was very attentive. Highly recommend

Reviewed on 7 Oct 2025

Swissotel - Chicago

Downtown Chicago

€694

per person

10 Nov - 16 Nov

found 20 hours ago

Return flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (2,765 reviews)

The view from the panoramic view was amazing. The gym was comfortable and the credit to amuse was nice

Reviewed on 9 Oct 2025

Tours & day trips

See all 156 activities

Architecture River Tour

Free cancellation available

Private & custom tours

See all 28 activities

Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Food, drink & nightlife

See all 25 activities

Chicago: Architecture Boat Tour with Drinks

Free cancellation available

Attractions

See all 16 activities

360 CHICAGO Observation Deck

Free cancellation available

Adventure & outdoor

See all 13 activities

Chicago: Two Flight Indoor Skydiving Experience

Free cancellation available

Popular places to visit

Illinois Institute of Technology

Explore the campus of Illinois Institute of Technology as part of your travels around Chicago. Experience the acclaimed art galleries and fascinating museums in this vibrant area.

McCormick Tribune Center

You can find out about the history of Chicago with a visit to McCormick Tribune Center. Stroll along the lakeside or visit the notable monuments in this vibrant area.

Stephen A. Douglas Tomb and Memorial

Find out about the history of Chicago when you spend time at Stephen A. Douglas Tomb and Memorial. Experience the entertainment choices and fascinating museums in this vibrant area.

Zhou B Art Center

You can spend time browsing the exhibits at Zhou B Art Center during your trip to Chicago. Experience the entertainment choices and acclaimed art galleries in this vibrant area.

University of Illinois Mile Square Health Center

If University of Illinois Mile Square Health Center is what brings you to town, hopefully you'll have a chance to explore more of Chicago.

Bridgeport Art Center

You can spend time browsing the exhibits at Bridgeport Art Center during your travels in Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices.