
Uptown Vacation Packages
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Top Holiday Package Deals in Uptown
Price found within the past 48 hours. Click for updated prices.

Trump International Hotel & Tower Chicago
Downtown Chicago
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,659 reviews)
Bad room service, bad dinner/breakfast service at the restaurants and no house keeping - had to ask for it - and when they finally did they didn’t restock the bar or towels.
Reviewed on Aug. 4, 2025



Eurostars Magnificent Mile
Downtown Chicago
per person
Oct 10 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (3,055 reviews)
Had a lovely stay during the weekend and would likely stay here again in the near future. Staff always greeted me when leaving or entering the building every day and wished me well.
Reviewed on Aug. 4, 2025

Hotel Felix River North/Magnificent Mile
Downtown Chicago
per person
Oct 10 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very Good! (1,961 reviews)
I liked that this was easy walking distance to most things. I didn’t like that it didn’t have a mini fridge and when you wanted to call the front desk they barely answered.
Reviewed on Aug. 5, 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.
Uptown Hotel Deals

Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $185 per night from Aug 6 to Aug 7
CA $185
CA $217 total
Aug 6 - Aug 7
includes taxes & fees
7.8/10 Good! (8,974 reviews)
"Great location! Rooms are newly renovated and nice."
Reviewed on Aug. 5, 2025

Palmer House a Hilton Hotel
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $239 per night from Aug 21 to Aug 22
CA $239
CA $315 total
Aug 21 - Aug 22
includes taxes & fees
8.2/10 Very Good! (1,830 reviews)
"Love the gym!"
Reviewed on Aug. 5, 2025

Crowne Plaza Chicago West Loop by IHG
25 South Halsted Street, Chicago, IL
Fully refundable
The price is CA $201 per night from Aug 24 to Aug 25
CA $201
CA $236 total
Aug 24 - Aug 25
includes taxes & fees
8.8/10 Excellent! (1,335 reviews)
"Thanks beautiful place"
Reviewed on Aug. 3, 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
Discover the most popular places to visit in Uptown

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.
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.
Riviera Theatre
You can enjoy a show at Riviera Theatre during your stay in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.
Things to do

Chicago Sightseeing River and Lake Cruise
CA $62
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.