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Pendry Chicago

Downtown Chicago

Save 100% on your flight

€468

per person

31 Oct - 2 Nov

found 15 hours ago

Return flight included

New York (NYC) to Chicago (ORD)

9.4/10 Exceptional! (1,085 reviews)

This is an exceptional hotel. The rooms are clean. The service is impeccable, and the products!! The signature scent is to die for. It is now a part of my life. I had to buy a candle on the way out and have already visited the online store for body wash and lotion. Well done. There are a lot of choices in Chicago, but this is now my go to. Will definitely be back!

Reviewed on 12 Sept 2025

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

€635

per person

31 Oct - 2 Nov

found 15 hours ago

Return flight included

New York (NYC) to Chicago (ORD)

9.4/10 Exceptional! (1,716 reviews)

This property is fabulous in every aspect. Huge rooms, modern and fresh. The spa and workout facilities are amazing. I loved everything about this hotel. Location is perfect to explore the river walk, shopping and best dining options. Only small critique is only one person at the front and if they are busy with a guest, can be a long wait to check in or out.

Reviewed on 21 Sept 2025

Park Hyatt Chicago

Downtown Chicago

Save 100% on your flight

€672

per person

31 Oct - 2 Nov

found 15 hours ago

Return flight included

New York (NYC) to Chicago (ORD)

9.6/10 Exceptional! (1,001 reviews)

Got pick pocketed in the elevator. I really like this hotel. Plan to return.

Reviewed on 8 Sept 2025

Tours & day trips

See all 163 activities

Architecture River Tour

Free cancellation available

Food, drink & nightlife

See all 29 activities

Chicago: Architecture Boat Tour with Drinks

Free cancellation available

Private & custom tours

See all 28 activities

Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Attractions

See all 15 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

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.

Illinois Institute of Technology

Explore the campus of Illinois Institute of Technology as part of your travels around Chicago. Experience the fascinating museums and acclaimed art galleries in this vibrant area.

Margaret Burroughs Beach

Why not spend a lazy afternoon at Margaret Burroughs Beach during your trip to Chicago? Wander the area's Chinatown or simply enjoy one of its top-notch restaurants.

Copernicus Statue which includes a statue or sculpture

Lakefront Trail

5/5(1 review)

Lakefront Trail is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Wander the lakeside and beautiful beaches in the area.

Captain Ernest A Griffin Place

You can learn about the history of Chicago with a visit to Captain Ernest A Griffin Place. Wander the area's Chinatown or simply enjoy one of its top-notch restaurants.

Pilgrim Baptist Church

After visiting Pilgrim Baptist Church, make a plan to see the other sights and activities in Chicago. Stroll along the lakeside or visit the notable monuments in this vibrant area.