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Hilton Chicago O'Hare Airport

O'Hare

€295

per person

31 Oct - 2 Nov

found 1 day ago

Return flight included

New York (NYC) to Chicago (ORD)

8.2/10 Very Good! (2,123 reviews)

We were dead tired from a long flight from Turkey the day before. We slept well most of the night but still did not want to drag our heavy bags to Terminal 5 via the light rail. The hotel graciously transported us directly to the outdoor check in and we were on our way to security an hour ahead of our schedule! Thanks. The only improvement would be to service the slightly noisy air conditioner in our room.

Reviewed on 20 Sept 2025

Park Hyatt Chicago

Downtown Chicago

Save 100% on your flight

€670

per person

31 Oct - 2 Nov

found 1 day ago

Return flight included

New York (NYC) to Chicago (ORD)

9.6/10 Exceptional! (1,002 reviews)

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

Reviewed on 8 Sept 2025

Staypineapple, An Iconic Hotel, The Loop

Downtown Chicago

€401

per person

31 Oct - 2 Nov

found 1 day ago

Return flight included

New York (NYC) to Chicago (ORD)

9.4/10 Exceptional! (1,008 reviews)

Best hotel ever! The staff was incredible. The location was premium-you could be at the “bean” in a couple minutes!! The bed was so cozy. The place was clean and beautiful. There was a snack daily. It really was so fantastic!

Reviewed on 17 Sept 2025

Tours & day trips

See all 164 activities

Architecture River Tour

Free cancellation available

Food, drink & nightlife

See all 30 activities

Chicago: Architecture Boat Tour with Drinks

Free cancellation available

Private & custom tours

See all 29 activities

Eastside Chicago The Heist Exploration Game and Tour

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

Shops at North Bridge

Spend a day exploring the department store, luxury fashion outlets and food court at this mall on the glitzy Magnificent Mile shopping district.

Magnificent Mile - River North showing street scenes, signage and night scenes

Michigan Avenue

4.5/5(14 reviews)

You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Tribune Tower

You can learn about the history of Chicago with a visit to Tribune Tower. Discover the fascinating museums and notable monuments in this vibrant area.

Wrigley Building

4.5/5(3 reviews)

Learn about the local history of Chicago when you take a trip to Wrigley Building. Discover the fascinating museums and notable monuments in this vibrant area.

St. James Cathedral

St. James Cathedral is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Stroll along the riverfront or visit the notable monuments in this vibrant area.

Michigan Avenue Bridge

4.5/5(8 reviews)

Learn about the local history of Chicago when you take a trip to Michigan Avenue Bridge. Amble around this vibrant area's riverfront or experience its acclaimed theatre scene.