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

The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
per person
30 Oct - 3 Nov
just found
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.8/10 Excellent! (1,925 reviews)
Helpful and friendly staff that i interacted with including front desk, concierge, bar, door, and bell. Housekeeping kept the room nice and neat
Reviewed on 10 Aug 2025

Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
per person
30 Oct - 3 Nov
just found
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (2,270 reviews)
This was my first time staying. The staff was very friendly and helpful. Our room was very nice and perfectly located downtown. Also, the breakfast buffet was amazing and a nice surprise.
Reviewed on 9 Aug 2025


Where to stay in Uptown
Find the best Uptown areas and neighborhoods for the activities you enjoy most. Learn more about Uptown

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 Uptown

Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €253 per night from 7 Sept to 8 Sept
€253
7 Sept - 8 Sept
includes taxes & fees
7.8/10 Good! (8,917 reviews)
Great stay.
"Hotel has old charm, which is a great change. a/c worked well to keep our room cool and great water pressure in the shower. Beds were comfortable and room was spacious. Location was top priority."
Reviewed on 7 Aug 2025

Palmer House a Hilton Hotel
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €196 per night from 22 Aug to 23 Aug
€196
22 Aug - 23 Aug
includes taxes & fees
8.2/10 Very Good! (1,836 reviews)
"The property if beautiful and historic. The main room is incredible. The rooms are well taken care of, you can just tell they are a little dated with a slight smell. I would definitely stay here again."
Reviewed on 8 Aug 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
10 E Grand Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €155 per night from 24 Aug to 25 Aug
€155
24 Aug - 25 Aug
includes taxes & fees
8.4/10 Very Good! (3,632 reviews)
"Very Nice Staff"
Reviewed on 7 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

Montrose Beach
Soak up the sun with views of Lincoln Park and Lake Michigan at this city beach known for its fun sports and extensive amenities.

Montrose Harbor
With trails, a beach and a bird sanctuary, this spacious city harbor is a good place to sail from and a great place to hang out.
Aragon Ballroom
Catch an event at Aragon Ballroom during your trip to Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices.
Things to do

BYOB Spray Paint 'n' Sip at Studio W.I.P. Chicago
€39
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.