Roscoe Village Vacation Packages
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Top Holiday Package Deals in Roscoe Village
Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,367, price is now CA $1,530 per person
CA $1,530
per person
Jun 1 - Jun 5
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Great hotel had a great time..planning to stay again real soon…home away from home
Reviewed on Apr 16, 2026
Sports Illustrated Resorts Chicago
Downtown Chicago
Price was CA $2,032, price is now CA $1,384 per person
CA $1,384
per person
Jun 1 - Jun 5
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (1,409 reviews)
Great location and converted old Virgin Hotel. Room was fine and hotel basics were fine. There wasn’t any room service daily or for my 3 night stay. There was a strike for housekeepers and they were LOUD out front everyday. Not sure what the hotel fee was for on top of Expedia hotel charge was for, they gave me 2 waters the first day and that was it. They also upsell their vacation club/time share a lot, kinda odd.
Reviewed on Apr 14, 2026
DoubleTree by Hilton Chicago - Alsip
Price was CA $1,526, price is now CA $1,082 per person
CA $1,082
per person
Jun 25 - Jun 30
found 18 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (MDW)
8.4/10 Very Good! (1,015 reviews)
Didn't eat breakfast..parking was fine.
Reviewed on Apr 12, 2026
The Langham, Chicago
Downtown Chicago
Price was CA $2,434, price is now CA $1,746 per person
CA $1,746
per person
Jul 6 - Jul 10
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.8/10 Exceptional! (1,010 reviews)
We loved everything about the Langham. Our room was beautiful, the staff was so kind and helpful and great location! Willa absolutley stay again!
Reviewed on Apr 16, 2026
Where to stay in Roscoe Village
Find the best Roscoe Village areas and neighborhoods for the activities you enjoy most. Learn more about Roscoe Village
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.
Roscoe Village Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $158 per night from Apr 26 to Apr 27
CA $158
CA $186 total
Apr 26 - Apr 27
includes taxes & fees
8/10 Very Good! (10,121 reviews)
Clean room, uncomfortable bathtub, cheap amenities- heater was broken in room. Light in bathroom dim. Maintenance staff was nice and things are very clean, but won’t be staying here again.
Reviewed on Apr 16, 2026
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $188 per night from Apr 26 to Apr 27
CA $188
CA $221 total
Apr 26 - Apr 27
includes taxes & fees
9/10 Wonderful! (4,133 reviews)
Great location. Clean room. Friendly staff. Pool was kinda chilly. But that’s the only little criticism
Reviewed on Apr 16, 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 $214 per night from Apr 26 to Apr 27
CA $214
CA $251 total
Apr 26 - Apr 27
includes taxes & fees
8.6/10 Excellent! (5,848 reviews)
They didn’t clean our room even when I requested to be cleaned and we had to go and request towels and paper, breakfast is not good at all.
Reviewed on Apr 16, 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 Roscoe Village
Wrigley Field
4.5/5(159 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Naval Base Great Lakes
4.5/5(3 reviews)
After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.
Navy Pier
4.5/5(460 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Things to do
Skydeck - Willis Tower Admission
CA $60
per adult
98% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.