
Downtown Chicago Holidays
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Price found within the past 48 hours. Click for updated prices.

theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was €1,169, price is now €779 per person
€779
per person
2 Nov - 7 Nov
found 21 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
The service was excellent, they made my birthday very special!
Reviewed on 19 Aug 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was €1,927, price is now €1,160 per person
€1,160
per person
2 Nov - 7 Nov
found 21 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.
Reviewed on 19 Aug 2025

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was €1,807, price is now €1,195 per person
€1,195
per person
10 Oct - 14 Oct
found 4 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very Good! (2,061 reviews)
Great spot, good location, nice rooms.
Reviewed on 20 Aug 2025

The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Save 100% on your flight
Price was €1,713, price is now €1,140 per person
€1,140
per person
10 Oct - 14 Oct
found 4 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,962 reviews)
Staff were excellent, I needed to mail some parcels for a business event which they held for over a week (arrived earlier than expected!) breakfast was also excellent. Rooms were noisy, not from outside but from the other rooms. Walls must be thin and could hear conversation and the TV from both sides.
Reviewed on 20 Aug 2025

The Langham, Chicago
Downtown Chicago
Price was €1,782, price is now €1,218 per person
€1,218
per person
2 Nov - 7 Nov
found 21 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.
Reviewed on 12 Aug 2025
Where to stay in Downtown Chicago
Find the best Downtown Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Downtown Chicago

Magnificent Mile
Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.
Top hotels in Downtown Chicago

The Wade
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €152 per night from 1 Sept to 2 Sept
€152
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (1,205 reviews)
"The pool could have been a bit better"
Reviewed on 19 Aug 2025

Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €190 per night from 14 Sept to 15 Sept
€190
14 Sept - 15 Sept
includes taxes & fees
7.8/10 Good! (9,006 reviews)
"Great history . Staff was excellent"
Reviewed on 19 Aug 2025

Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
The price is €162 per night from 3 Sept to 4 Sept
€162
3 Sept - 4 Sept
includes taxes & fees
8.4/10 Very Good! (4,729 reviews)
"The hotel was wonderfully nestled downtown and an easy walk to sites and restaurants."
Reviewed on 18 Aug 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.
Frequently asked questions
Popular places to visit

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.

Millennium Park
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
Things to do

Chicago By Night River & Lake Cruise
€39
per adult
96% of travellers recommend

Wendella's 90-min Chicago River Architecture Tour
€35
per adult
94% of travellers recommend
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