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

Arlo Chicago

Downtown Chicago

€476

per person

2 Jan - 6 Jan

found 9 hours ago

Return flight included

Toronto (YYZ) to Chicago (ORD)

9.2/10 Wonderful! (1,852 reviews)

The room was really clean and the staff was very friendly and accommodating

Reviewed on 10 Nov 2025

Pendry Chicago

Downtown Chicago

€564

per person

2 Jan - 6 Jan

found 9 hours ago

Return flight included

Toronto (YYZ) to Chicago (ORD)

9.4/10 Exceptional! (1,110 reviews)

Very nice, service was stellar, the bed was super comfortable, location perfect for our activities. Bar and resturaunt inviting and comfortable. We will definitely return on our next visit to Chicago.

Reviewed on 9 Nov 2025

The Emily Hotel

Downtown Chicago

€580

per person

2 Jan - 6 Jan

found 9 hours ago

Return flight included

Toronto (YYZ) to Chicago (ORD)

9.2/10 Wonderful! (1,248 reviews)

Really cool modern space

Reviewed on 4 Nov 2025

Tours & day trips

See all 159 activities

Architecture River Tour

Free cancellation available

Private & custom tours

See all 50 activities

Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Food, drink & nightlife

See all 25 activities

Odyssey Lake Michigan Premier Dinner Cruise

Attractions

See all 16 activities

360 CHICAGO Observation Deck

Free cancellation available

Adventure & outdoor

See all 11 activities

Chicago: Two Flight Indoor Skydiving Experience

Free cancellation available

Popular places to visit

Printer\'s Row which includes a city and heritage architecture

Harold Washington Library Center

Harold Washington Library Center is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Discover the fascinating museums and notable monuments in this vibrant area.

Auditorium Building and Theatre

4.5/5(2 reviews)

You can make plans for a show at Auditorium Building and Theatre on your trip to Chicago. Discover the fascinating museums and notable monuments in this vibrant area.

Roosevelt University

Explore the campus of Roosevelt University during your visit to Chicago. Experience the fascinating museums and entertainment choices in this vibrant area.

DePaul University-Loop Campus

Explore the campus of DePaul University-Loop Campus during your visit to Chicago. Discover the acclaimed theatre scene and notable monuments in this vibrant area.

Afrocentric Bookstore

Enjoy a stop at Afrocentric Bookstore, an entertaining place to visit in Chicago. Discover the acclaimed theatre scene and notable monuments in this vibrant area.

Jazz Institute of Chicago

You can enjoy some culture when you stop by Jazz Institute of Chicago in Chicago. Amble around this vibrant area's riverfront or experience its acclaimed art galleries.