
Northwest Side Cheap Vacations
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Top Cheap vacation packages in Northwest Side
Price found within the past 48 hours. Click for updated prices.

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ₩1,147,684, price is now ₩776,348 per person
₩776,348
per person
Sep 2 - Sep 5
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
8.2/10 Very Good! (2,797 reviews)
Rooms were small, but for the price it was good. The valet was expensive and took a while to get our car, but I don't think they are associated with the hotel, just use their lobby.
Reviewed on Jul 3, 2026

Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was ₩1,812,060, price is now ₩1,101,252 per person
₩1,101,252
per person
Sep 2 - Sep 5
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (1,128 reviews)
Wonderful hotel with attentive staff. Should bring back ice machines.
Reviewed on Jul 3, 2026

Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was ₩1,540,960, price is now ₩988,158 per person
₩988,158
per person
Sep 2 - Sep 5
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (4,518 reviews)
Excellent hotel, service, amenities, and location. The included breakfast was a wonderful option.
Reviewed on Jul 3, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was ₩1,676,603, price is now ₩1,175,544 per person
₩1,175,544
per person
Sep 2 - Sep 5
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (2,554 reviews)
stay away, no one told us it had been damage and under repair, staff could not even help get me bording pass, room service sub par. We got a notice from Expedia after we checked in saying we could cancil, a bit to late.
Reviewed on Jul 3, 2026

Omni Chicago Hotel
Downtown Chicago
Price was ₩1,261,054, price is now ₩884,314 per person
₩884,314
per person
Sep 2 - Sep 5
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (1,821 reviews)
The room was very clean and spacious. Very helpful staff. We were able to get into our room early and get a later checkout due to our flights. The Doorman were also very courteous and helpful. Great location!
Reviewed on Jul 3, 2026
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View all trips5* Cheap vacations in Northwest Side
Price found within the past 48 hours. Click for updated prices.

Nobu Hotel Chicago
Downtown Chicago
Save 100% on your flight
Price was ₩2,132,728, price is now ₩1,612,792 per person
₩1,612,792
per person
Sep 2 - Sep 5
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (873 reviews)
The staff was friendly and helpful. They let us check in early, and I got an upgraded room. Very nice property, I would stay here again.
Reviewed on Jul 2, 2026


The Langham, Chicago
Downtown Chicago
Save 100% on your flight
Price was ₩2,268,322, price is now ₩1,696,016 per person
₩1,696,016
per person
Sep 2 - Sep 5
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.8/10 Exceptional! (1,007 reviews)
Everything was mostly great. Except it was a bit overpriced (especially the spa) and minibar person kept adding stuff I didn't use to my bill. Also they don't tell you what perks you have depending on your reservation. You have to ask. Also I stayed in a junior suite for 8 days and they wouldn't give me a late check out. Finally, they begrudgingly have me an hour after I reminded them I spent almost $9,000 dollars there. Gee, thanks. Front desk guy at check in was mostly unhelpful although he was friendly and polite. Tons of great stuff.
Reviewed on Jul 2, 2026
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View all trips3 Night Cheap vacations in Northwest Side
Price found within the past 48 hours. Click for updated prices.

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ₩1,147,684, price is now ₩776,348 per person
₩776,348
per person
Sep 2 - Sep 5
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
8.2/10 Very Good! (2,797 reviews)
Rooms were small, but for the price it was good. The valet was expensive and took a while to get our car, but I don't think they are associated with the hotel, just use their lobby.
Reviewed on Jul 3, 2026

Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was ₩1,812,060, price is now ₩1,101,252 per person
₩1,101,252
per person
Sep 2 - Sep 5
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (1,128 reviews)
Wonderful hotel with attentive staff. Should bring back ice machines.
Reviewed on Jul 3, 2026

Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was ₩1,540,960, price is now ₩988,158 per person
₩988,158
per person
Sep 2 - Sep 5
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (4,518 reviews)
Excellent hotel, service, amenities, and location. The included breakfast was a wonderful option.
Reviewed on Jul 3, 2026
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See all available trips from Toronto to Northwest Side
View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
