West Side Cheap Vacations
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Flight and Cheap hotel deals in West Side
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $960, price is now CA $667 per person
CA $667
per person
Sep 2 - Sep 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,767 reviews)
Clean rooms and comfortable beds but the windows were a little thin that you could hear everything outside.
Reviewed on Jun 27, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $3,635, price is now CA $2,437 per person
CA $2,437
per person
Sep 12 - Sep 18
found 16 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (495 reviews)
Front desk people was very helpful Eric was amazing was on top of everything and helped with everything as well
Reviewed on Jun 26, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $2,991, price is now CA $2,125 per person
CA $2,125
per person
Aug 3 - Aug 8
found 18 hours ago
Roundtrip flight included
Hamilton (YHM) 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
Level Chicago - River North
Downtown Chicago
Price was CA $1,181, price is now CA $887 per person
CA $887
per person
Sep 5 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,034 reviews)
Really plan ahead when it comes to parking. You’ll get ticketed for just trying to put your things in your vehicle.
Reviewed on Jun 19, 2026
5* Cheap holidays in West Side
Price found within the past 48 hours. Click for updated prices.
Nobu Hotel Chicago
Downtown Chicago
Price was CA $1,523, price is now CA $1,314 per person
CA $1,314
per person
Aug 1 - Aug 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (869 reviews)
The staff was amazing. My suite was beautiful. I will definitely come back here and to other Nobu hotels
Reviewed on Jun 27, 2026
The Langham, Chicago
Downtown Chicago
Price was CA $2,469, price is now CA $1,893 per person
CA $1,893
per person
Sep 3 - Sep 6
found 15 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,007 reviews)
Love this hotel! Staff is extremely welcoming, knowledgeable about the area, rooms are nice and cozy, it's quiet, and you can't beat the location!! We will be back - without doubt!
Reviewed on Jun 26, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $2,034, price is now CA $1,618 per person
CA $1,618
per person
Aug 16 - Aug 19
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
Great location, wonderful staff.
Reviewed on Jun 26, 2026
3 Night Cheap holidays in West Side
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $960, price is now CA $667 per person
CA $667
per person
Sep 2 - Sep 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,767 reviews)
Clean rooms and comfortable beds but the windows were a little thin that you could hear everything outside.
Reviewed on Jun 27, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,678, price is now CA $1,241 per person
CA $1,241
per person
Aug 15 - Aug 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (495 reviews)
Front desk people was very helpful Eric was amazing was on top of everything and helped with everything as well
Reviewed on Jun 26, 2026
4 Night Cheap holidays in West Side
Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection
Downtown Chicago
Price was CA $1,296, price is now CA $919 per person
CA $919
per person
Aug 30 - Sep 3
found 18 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (126 reviews)
Always a pleasure and a great location
Reviewed on Jun 24, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $2,431, price is now CA $1,747 per person
CA $1,747
per person
Aug 7 - Aug 11
found 17 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (495 reviews)
Front desk people was very helpful Eric was amazing was on top of everything and helped with everything as well
Reviewed on Jun 26, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $2,354, price is now CA $1,743 per person
CA $1,743
per person
Aug 11 - Aug 15
found 1 day ago
Roundtrip flight included
Montreal (YUL) 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
Cheap Hotels in West Side
STAY
1415 Ashland Ave Chicago IL
Book a stay at this business-friendly hostel in Chicago. Enjoy free WiFi, a 24-hour business center, and laundry facilities. Our guests praise the helpful staff ...
7.6/10 Good! (233 reviews)
"Room was dirty, shower grout featured black mold, the first room they tried to put me in smelled horrible they had to put me in another room which was really dirty. Just spend the extra dollars and stay at an actual hotel. When approached about the cleanliness they tried to gaslight me that "they ..."
Reviewed on Jun 20, 2026
Chicago Parthenon Hostel
310 S. Halsted Street Chicago IL
Stay at this hostel in Chicago. Enjoy free WiFi, concierge services, and rainfall showerheads. Our guests praise the helpful staff in our reviews. Popular attractions ...
8.2/10 Very good! (478 reviews)
"Great stay! First time in a hostel, would stay again!"
Reviewed on Jun 26, 2026
Hyatt House Chicago Medical/University District
1835 West Harrison Street Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the helpful staff and ...
9/10 Wonderful! (1,550 reviews)
"The staff were all very friendly, the breakfast was good, room was clean."
Reviewed on Jun 24, 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.
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
88% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
CA $56
per adult
94% of travellers recommend
More vacations you might like
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
