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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 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

Chopin Theatre-Death and Harry Houdini

You can get tickets for a performance at Chopin Theatre-Death and Harry Houdini during your trip to Chicago. Experience the acclaimed theatre scene and fascinating museums in this vibrant area.

House Theatre

You can get tickets for a performance at House Theatre during your stay in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.

Flat Iron Building

You can learn about the history of Chicago with a visit to Flat Iron Building. Stroll along the lakeside or experience the acclaimed theatre scene in this vibrant area.

Monique Meloche Gallery

You can spend time browsing the exhibits at Monique Meloche Gallery during your travels in Chicago. Stroll along the lakeside or experience the entertainment choices in this vibrant area.

Holy Trinity Russian Orthodox Cathedral

After visiting Holy Trinity Russian Orthodox Cathedral, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art galleries.

St. Stanislaus Kostka Church

After visiting St. Stanislaus Kostka Church, make a plan to see the other sights and activities in Chicago. Stroll along the lakeside or experience the entertainment choices in this vibrant area.