Chicago Holidays
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Top Flight + Hotel Deals in Chicago
Price found within the past 48 hours. Click for updated prices.
Congress Plaza Hotel
Downtown Chicago
Price was €628, price is now €382 per person
€382
per person
20 Nov - 27 Nov
found 20 hours ago
Return flight included
Boston (BOS) to Chicago (ORD)
8/10 Very Good! (9,398 reviews)
I loved staying here only thing was elevators weren't working Saturday and walking down 11 flights of stairs wasn't fun!
Reviewed on 20 Oct 2025
Pendry Chicago
Downtown Chicago
Price was €1,009, price is now €529 per person
€529
per person
20 Nov - 27 Nov
found 20 hours ago
Return flight included
Boston (BOS) 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
Arlo Chicago
Downtown Chicago
Price was €828, price is now €452 per person
€452
per person
20 Nov - 27 Nov
found 20 hours ago
Return flight included
Boston (BOS) to Chicago (ORD)
9.2/10 Wonderful! (1,852 reviews)
The location so close to Millennium station was perfect. Staff was very helpful & friendly. Room was very comfortable. Only complaint is the sliding frosted glass bathroom door. Not the best for privacy when sharing a room.
Reviewed on 19 Oct 2025
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was €763, price is now €433 per person
€433
per person
20 Nov - 27 Nov
found 20 hours ago
Return flight included
Boston (BOS) to Chicago (ORD)
9/10 Wonderful! (1,011 reviews)
Our guests that are not from Chicago there should be some sort of a quick tips handout that gives an overview of the events that are taking place over the next week popular restaurants things that are within walking distance of the hotel
Reviewed on 20 Oct 2025
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was €776, price is now €463 per person
€463
per person
20 Nov - 27 Nov
found 20 hours ago
Return flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (2,188 reviews)
Rooms were clean with a great view of the lake and the city
Reviewed on 19 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! (9,473 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
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.
