Chicago Holidays
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Top Flight + Hotel Deals in Chicago
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
Price was €830, price is now €674 per person
€674
per person
19 Dec - 22 Dec
found 8 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (2,765 reviews)
The view from the panoramic view was amazing. The gym was comfortable and the credit to amuse was nice
Reviewed on 9 Oct 2025
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was €950, price is now €740 per person
€740
per person
19 Dec - 22 Dec
found 8 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (291 reviews)
Food price was high but everything was fine
Reviewed on 4 Oct 2025
Pendry Chicago
Downtown Chicago
Price was €915, price is now €726 per person
€726
per person
19 Dec - 22 Dec
found 8 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
Level Chicago - River North
Downtown Chicago
Price was €887, price is now €740 per person
€740
per person
19 Dec - 22 Dec
found 8 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (698 reviews)
This is one of the nicest hotels I have stayed in (and I travel almost weekly).
Floor to ceiling windows with incredible views of the city and the water.
It is within walking distance of my favorite Chicago restaurants.
I will be back!
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
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
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €154 per night from 9 Nov to 10 Nov
€154
9 Nov - 10 Nov
includes taxes & fees
8.4/10 Very Good! (5,052 reviews)
"good"
Reviewed on 7 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! (2,426 reviews)
"Excellent location, clean and good room partners"
Reviewed on 6 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 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
