Northwest Side Cheap Vacations
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Flight and Cheap hotel deals in Northwest Side
Price found within the past 48 hours. Click for updated prices.
The Emily Hotel
Downtown Chicago
Price was CA $1,734, price is now CA $1,158 per person
CA $1,158
per person
Dec 19 - Dec 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,358 reviews)
Great location in the West Loop. The rooms are big and the beds are comfy. We’ve stayed there three times. The outdoor theatre shows great films and has an outdoor bar. Coffee shop is in the lobby. There’s not really a fun bar, but lots of places to have cocktails in the neighborhood. A lobby fireplace would be a nice addition in the lobby for cold Chicago nights.
Reviewed on Nov 13, 2026
Park Hyatt Chicago
Downtown Chicago
Price was CA $3,057, price is now CA $2,112 per person
CA $2,112
per person
Dec 28 - Jan 2
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
This place was amazing and the hotel staff was extremely helpful
Reviewed on Nov 10, 2026
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View all trips5* Cheap holidays in Northwest Side
Price found within the past 48 hours. Click for updated prices.
The Ritz-Carlton, Chicago
Downtown Chicago
Price was CA $1,110, price is now CA $1,022 per person
CA $1,022
per person
Dec 28 - Dec 30
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,003 reviews)
Our first time staying at this hotel was a great experience. Staff was very polite, the room/view was amazing. We will be staying at The Ritz again in the future.
Reviewed on Nov 14, 2026
Park Hyatt Chicago
Downtown Chicago
Price was CA $3,057, price is now CA $2,112 per person
CA $2,112
per person
Dec 28 - Jan 2
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
This place was amazing and the hotel staff was extremely helpful
Reviewed on Nov 10, 2026
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View all trips3 Night Cheap holidays in Northwest Side
Price found within the past 48 hours. Click for updated prices.
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View all trips4 Night Cheap holidays in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Le Méridien Essex Chicago
Downtown Chicago
Price was CA $1,126, price is now CA $868 per person
CA $868
per person
Feb 4 - Feb 8
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)
Wonderful staff!! Welcoming, friendly, and very helpful. We ended up arriving 2 hours before check-in, but staff had no problem helping us out and letting us get our room early. Valet staff hepful when we needed to get an item from the car, James was so awesome helping with luggage and to our room. Housekeeping checked in to see if we were happy with the room, which was very clean!! Each contact we had with staff was a positive one. Lobby was small but cute and eclectic. Wish there was a microwave in the room, but not a deal killer..! Stayed on a Thursday night, seemed like a lot of people checking in and busy, but it was quiet and we slept well. location isn’t overly close to shops, but if you cross Michigan Ave, Grant Park area is right there. You could walk to Art Institute, but I would say wear some good shoes! All in all, would stay again!
Reviewed on Nov 14, 2026
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View all tripsThings to do
Skydeck Chicago at Willis Tower
CA $60
per adult
84% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
CA $57
per adult
94% of travellers recommend
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