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
Save 100% on your flight
Price was €1,414, price is now €915 per person
€915
per person
1 Feb - 6 Feb
found 7 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
FOOD WAS GOOD, JUST A LITTLE COLD, BUT NO MAJOR PROBLEMS
Reviewed on 12 Nov 2025
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was €862, price is now €588 per person
€588
per person
1 Feb - 6 Feb
found 7 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (303 reviews)
I love the decor and it was very clean. My only problem is they did not clean the room every day other than that is was very clean facility. Very safe location.
Reviewed on 28 Oct 2025
Pendry Chicago
Downtown Chicago
Price was €847, price is now €581 per person
€581
per person
1 Feb - 6 Feb
found 7 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,110 reviews)
A great location, a fabulous building, and a delightful room. The one mystery was a background thumping noise that persisted throughout the stay. Fortunately, didn't disturb sleep. The reception staff sloughed off any knowledge or interest in the cause, but we couldn't imagine that the source was an unknown to hotel staff, and potentially fixable.
Reviewed on 12 Nov 2025
Level Chicago – Old Town
Downtown Chicago
Price was €989, price is now €679 per person
€679
per person
1 Feb - 6 Feb
found 7 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (367 reviews)
Property was clean, centrally located with wonderful staff. Will definitely stay again.
Reviewed on 9 Nov 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
4 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
Fully refundableReserve now, pay when you stay
The price is €96 per night from 25 Nov to 26 Nov
€96
25 Nov - 26 Nov
includes taxes & fees
8.4/10 Very Good! (5,232 reviews)
Clean room. Super friendly front desk staff. Complimentary drinks were a big plus! Whole property was amazing. Walking distance to everything.
Reviewed on 12 Nov 2025
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €99 per night from 7 Dec to 8 Dec
€99
7 Dec - 8 Dec
includes taxes & fees
8.8/10 Excellent! (3,248 reviews)
Room was fine. Check in was not good. Front desk not helpful
Reviewed on 9 Nov 2025
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €106 per night from 16 Nov to 17 Nov
€106
16 Nov - 17 Nov
includes taxes & fees
8/10 Very Good! (9,538 reviews)
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Reviewed on 8 Nov 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
98% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
€21
per adult
84% 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.
