Uptown Vacation Packages
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Top Holiday Package Deals in Uptown
Price found within the past 48 hours. Click for updated prices.
JW Marriott Chicago
Downtown Chicago
Price was CA $1,039, price is now CA $707 per person
CA $707
per person
May 1 - May 3
found 6 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.2/10 Wonderful! (1,000 reviews)
Bottle of waters were not stocked in the refrigerator.
Reviewed on Jan 6, 2026
La Banque Hotel
Price was CA $1,044, price is now CA $743 per person
CA $743
per person
Apr 9 - Apr 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring.
Reviewed on Jan 26, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,155, price is now CA $828 per person
CA $828
per person
Apr 17 - Apr 20
found 1 day ago
Roundtrip flight included
Montreal Metropolitan Airport (YHU) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Everything was amazing, specially the breakfast buffet.
Reviewed on Feb 7, 2026
Level Chicago - River North
Downtown Chicago
Price was CA $949, price is now CA $708 per person
CA $708
per person
Apr 17 - Apr 20
found 1 day ago
Roundtrip flight included
Montreal Metropolitan Airport (YHU) to Chicago (ORD)
9/10 Wonderful! (766 reviews)
Great stay. Would come again.
Reviewed on Jan 19, 2026
Holiday Inn Club Vacations at Lake Geneva Resort by IHG
Price was CA $952, price is now CA $723 per person
CA $723
per person
Apr 21 - Apr 25
found 11 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
8.8/10 Excellent! (1,003 reviews)
My room was very clean, which I appreciated. We booked a suite, but the first one opened directly into the bedroom, and being on the first floor, I didn’t feel comfortable with that layout. I requested a room change, and the staff handled it quickly and professionally, which I really appreciated.
One thing that was a bit confusing was the inconsistency between suites—some had a full kitchen while others only had a range top. It would be helpful to know that in advance when booking.
Overall, the stay was quiet and peaceful during the week, which was exactly what we wanted. When we arrived on Saturday afternoon, the atmosphere was completely different—lots of people, plenty of activity, and a lively environment.
The only real downside was that the room felt drafty. We ended up putting a towel under the door to help block the cold air.
Aside from those small issues, it was a comfortable stay with a good stay.
Reviewed on Jan 16, 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 $122 per night from Feb 12 to Feb 13
CA $122
CA $143 total
Feb 12 - Feb 13
includes taxes & fees
8/10 Very Good! (9,839 reviews)
Great a+++
Reviewed on Feb 1, 2026
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $190 per night from Feb 21 to Feb 22
CA $190
CA $263 total
Feb 21 - Feb 22
includes taxes & fees
8.4/10 Very Good! (2,597 reviews)
Some of the nicest people you'll ever meet! Excellent location for a Bears game stay, walking distance to Soldier Field.
Reviewed on Feb 1, 2026
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $140 per night from Feb 24 to Feb 25
CA $140
CA $165 total
Feb 24 - Feb 25
includes taxes & fees
8.4/10 Very Good! (5,637 reviews)
Yes room was spotless
Reviewed on Feb 4, 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
Discover the most popular places to visit in Uptown
Aragon Ballroom
Catch an event at Aragon Ballroom during your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.
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.
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 art scene.
Things to do
Wendella's 90-min Chicago River Architecture Tour
CA $55
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.