Uptown Vacation Packages
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Top Holiday Package Deals in Uptown
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,544, price is now CA $1,096 per person
CA $1,096
per person
Aug 3 - Aug 8
found 11 hours ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
8.2/10 Very good! (2,767 reviews)
Would have liked coffeemaker in the room and some glasses or cups for water. The bathroom was nice, but for the price, we felt the room was cramped and the window small. Location was convenient.
Reviewed on Jun 26, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $2,463, price is now CA $1,624 per person
CA $1,624
per person
Aug 26 - Aug 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (504 reviews)
Upscale amazing stay in trendy neighborhood in Chcago. Walking distance to coffee shops, great restaurants. The amenities were beyond what I expected/ great lap pool, hot tubs, sauna steam room and amazing gym with enough equipment to do a full strength training workout. We will stay here again!
Reviewed on Jun 25, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $3,213, price is now CA $2,212 per person
CA $2,212
per person
Aug 26 - Aug 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,557 reviews)
The hotel and location are beautiful but there needs to be much clearer signage as to where the entrance of the hotel is and the main lobby. Extremely confusing to travellers.
Reviewed on Jun 23, 2026
Omni Chicago Hotel
Downtown Chicago
Price was CA $2,026, price is now CA $1,407 per person
CA $1,407
per person
Aug 26 - Aug 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,813 reviews)
Located in a walkable area near many Chicago attractions. We had a delicious breakfast in the hotel restaurant and the bar is nice. Room was large and comfortable
Reviewed on Jun 23, 2026
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 $194 per night from Jun 29 to Jun 30
CA $194
CA $231 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very good! (10,129 reviews)
"Great experience! Close to everywhere we wanted to go!"
Reviewed on Jun 26, 2026
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $227 per night from Jul 6 to Jul 7
CA $227
CA $270 total
Jul 6 - Jul 7
includes taxes & fees
9/10 Wonderful! (4,459 reviews)
"Did a turn and burn stay here (checked in Saturday and checked out Monday) and had a pleasant visit. The front desk customer service was A+. My only 2 feedback are: the valet attendant should be more attentive. I waited 10 mins while the valet attendant was chatting away with a co-worker and then ..."
Reviewed on Jun 26, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $254 per night from Jul 5 to Jul 6
CA $254
CA $342 total
Jul 5 - Jul 6
includes taxes & fees
9.4/10 Exceptional! (4,537 reviews)
"The hotel room cleanliness is of a very high standard. The complementary breakfast is extraordinary with a different majority of food and with a good procedure to take care of guests. The rooftop bar was sophisticated and attracts high class clientele. The room space is big enough to feel comfortable. ..."
Reviewed on Jun 25, 2026
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
Stay near popular Uptown attractions
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
88% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $62
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.