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Arlo Chicago

Downtown Chicago

€565

per person

10 Nov - 16 Nov

found 15 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 15 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 15 hours ago

Return flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (2,765 reviews)

We stayed for a week and have 0 complaints. Great views, smelled good, nice staff and walkable to any bus or train

Reviewed on 8 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 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.

South Wentworth Street

You can find the perfect gifts to bring home at South Wentworth Street during your trip to Chicago. Amble around this family-friendly area's Chinatown and enjoy its top-notch restaurants.

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.

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.

Bubbly Creek

Commune with nature and explore the great outdoors at Bubbly Creek during your travels in Chicago. Stroll along the lakeside or experience the entertainment choices 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.