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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 159 activities

Architecture River Tour

Free cancellation available

Private & custom tours

See all 29 activities

Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Food, drink & nightlife

See all 26 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

Intuit: The Center for Intuitive and Outsider Art

You can spend time browsing the exhibits at Intuit: The Center for Intuitive and Outsider Art in Chicago. Stroll along the riverfront or experience the acclaimed theatre scene in this vibrant area.

Chicago Center for the Performing Arts

You can get tickets for a performance at Chicago Center for the Performing Arts during your trip to Chicago. Stroll along the riverfront or experience the acclaimed theatre scene in this vibrant area.

Kendall College

Explore the campus of Kendall College as part of your travels around Chicago. Experience the acclaimed art galleries and entertainment choices in this vibrant area.

Polish Museum of America

You can spend time exploring the galleries in Polish Museum of America during your travels in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art galleries.

Touch of Jane Addams

You can find out about the history of Chicago with a visit to Touch of Jane Addams. Experience the acclaimed art galleries and fascinating museums in this vibrant area.

Holy Innocents Church

After visiting Holy Innocents Church, make a plan to see the other sights and activities in Chicago. Experience the entertainment choices and fascinating museums in this vibrant area.