Chicago Holidays
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Top Flight + Hotel Deals in Chicago
Price found within the past 48 hours. Click for updated prices.
Springhill Suites by Marriott Chicago Downtown/ River North
Downtown Chicago
Price was €972, price is now €847 per person
€847
per person
28 Dec - 1 Jan
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,007 reviews)
The room was fantastic! The staff is charming! Loved the breakfast options! I was very impressed!
Reviewed on 11 Oct 2025
Pendry Chicago
Downtown Chicago
Price was €1,162, price is now €880 per person
€880
per person
29 Dec - 2 Jan
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,110 reviews)
Ideal area if it’s your first time visiting Chicago. Hotel staff was very friendly.
Reviewed on 16 Oct 2025
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was €1,073, price is now €899 per person
€899
per person
29 Dec - 2 Jan
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (3,374 reviews)
This hotel was nearly perfect! Great staff. Great location. Clean. My only complaint was the ice machine was broken on our floor. We reported it to staff 3 separate occasions and it wasn’t fixed in the 5 days we were there. Hotel is located on a busy street so there is some noise but if that Doesn't bother you… this is perfect. Very walkable location! The staff there are fantastic. From the moment you walk in until the moment you leave. They understand the assignment. Highly recommend.
Reviewed on 21 Oct 2025
Residence Inn by Marriott Chicago Downtown / River North
Downtown Chicago
Price was €979, price is now €848 per person
€848
per person
28 Dec - 1 Jan
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,003 reviews)
Hotel staff was great and hotel was in great location!
Reviewed on 10 Oct 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
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
The price is €172 per night from 2 Nov to 3 Nov
€172
2 Nov - 3 Nov
includes taxes & fees
7.8/10 Good! (9,473 reviews)
"Everything was great."
Reviewed on 19 Oct 2025
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €118 per night from 16 Nov to 17 Nov
€118
16 Nov - 17 Nov
includes taxes & fees
8.8/10 Excellent! (3,133 reviews)
"Every think was wonderful except the heater wasn’t working and the toilet was loose."
Reviewed on 19 Oct 2025
Freehand Chicago
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €96 per night from 10 Nov to 11 Nov
€96
10 Nov - 11 Nov
includes taxes & fees
7.8/10 Good! (2,494 reviews)
"Bathroom recently redone and was fabulous, but room was old and tattered. Bed was nice and comfy. Nice crisp sheets."
Reviewed on 18 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
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
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
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