Chicago Holidays
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Top Flight + Hotel Deals in Chicago
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was €1,973, price is now €1,222 per person
€1,222
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
Beautiful hotel centrally located
Reviewed on 16 Sept 2025
Park Hyatt Chicago
Downtown Chicago
Price was €2,266, price is now €1,437 per person
€1,437
per person
2 Nov - 7 Nov
found 20 hours ago
Return direct flight included
Dublin (DUB) 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
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was €1,219, price is now €828 per person
€828
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,014 reviews)
First time but won’t be the last. Very nice place with lots to do right around there.
Reviewed on 9 Sept 2025
Where to stay in Chicago
Find the best Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Chicago
Downtown Chicago
5 out of top 10 points of interest in this area
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Top hotels in Chicago
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
The price is €182 per night from 24 Sept to 25 Sept
€182
24 Sept - 25 Sept
includes taxes & fees
8.4/10 Very Good! (4,927 reviews)
First time exploring
"To start this hotel is extraordinary, the location is key if you want to explore Chicago. There is a Starbucks conveniently located outside and the grocery store across the street as well as multiple restaurants down the block. I would definitely rebook and consider this hotel as my first pick any ..."
Reviewed on 15 Sept 2025
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €148 per night from 22 Sept to 23 Sept
€148
22 Sept - 23 Sept
includes taxes & fees
7.8/10 Good! (9,188 reviews)
"Clean room, Confortable bed"
Reviewed on 16 Sept 2025
Hilton Garden Inn Chicago Downtown/Magnificent Mile
10 E Grand Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €183 per night from 22 Sept to 23 Sept
€183
22 Sept - 23 Sept
includes taxes & fees
8.4/10 Very Good! (3,898 reviews)
"There were fees that were not disclosed on the website until you got to the hotel to check in."
Reviewed on 16 Sept 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
4.5/5(40 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
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.
Navy Pier
4/5(125 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Chicago
Wendella's 90-min Chicago River Architecture Tour
€38
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
€38
per adult
96% of travellers recommend
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