Crestwood Holidays
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Top Flight + Hotel Deals in Crestwood
Price found within the past 48 hours. Click for updated prices.
The Emily Hotel
Downtown Chicago
Price was €1,179, price is now €823 per person
€823
per person
20 Nov - 24 Nov
found 11 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,222 reviews)
I stayed here for one night for business travel. The room was huge. Great mini bar options. I had a nice breakfast at the restaurant.
Reviewed on 10 Oct 2025
Pendry Chicago
Downtown Chicago
Price was €957, price is now €672 per person
€672
per person
20 Nov - 24 Nov
found 11 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
I loved the hotel, however I would request an inside room next time. It was extremely noisy outside.
Reviewed on 11 Oct 2025
Top hotels in Crestwood
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
7.8/10 Good! (9,366 reviews)
"Shockingly updated interior of the rooms based on the historic feel of the common areas- I was so pleasantly surprised!"
Reviewed on 10 Oct 2025
Freehand Chicago
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €97 per night from 10 Nov to 11 Nov
€97
10 Nov - 11 Nov
includes taxes & fees
7.8/10 Good! (2,461 reviews)
"Wonderful hotel. First time staying at a place like this. Ended up having the quad room to myself for both nights I was there. Will definitely try to book there again if traveling solo."
Reviewed on 13 Oct 2025
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €146 per night from 9 Nov to 10 Nov
€146
9 Nov - 10 Nov
includes taxes & fees
8.8/10 Excellent! (3,088 reviews)
"Clean rooms, great service."
Reviewed on 13 Oct 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Popular places to visit
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Michigan Avenue
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.
Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Crestwood
Skydeck - Willis Tower Admission
€38
per adult
100% of travellers recommend
Chicago By Night River & Lake Cruise
€38
per adult
96% of travellers recommend
Chicago Sightseeing River and Lake Cruise
€38
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
