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Arlo Chicago

Downtown Chicago

€565

per person

10 Nov - 16 Nov

found 7 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 7 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 7 hours ago

Return flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (2,765 reviews)

Great views. Really helpful staff.

Reviewed on 7 Oct 2025

Tours & day trips

See all 22 activities

Frank Lloyd Wright's Home & Studio Tour Ticket

Free cancellation available

Private & custom tours

See all 6 activities

Chicago Lincoln Square Quest Experience

Free cancellation available

Food, drink & nightlife

See all 5 activities

Vito's Vault Chicago finest dinner theatre speakeasy

Free cancellation available

Adventure & outdoor

See all 3 activities

Rosemont: Two Flight Indoor Skydiving Experience

Free cancellation available

Popular places to visit

Milwaukee Avenue

You can search for that perfect souvenir at Milwaukee Avenue during your trip to Chicago. Experience the live music and theatre scene in this vibrant area.

Resurrection Medical Center

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Presence Resurrection Medical Center

If Presence Resurrection Medical Center is what brings you to town, hopefully you'll have a chance to explore more of Chicago.

North Suburban Family Medicine

If North Suburban Family Medicine is what brings you to town, hopefully you'll have a chance to explore more of Chicago.

AMITA Health Resurrection Medical Center Chicago

If AMITA Health Resurrection Medical Center Chicago is what brings you to town, hopefully you'll have a chance to explore more of Chicago.

Monument Park

After visiting Monument Park, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside or attend a sporting event.