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.
The Talbott, Autograph Collection
Downtown Chicago
CA $860
per person
Dec 20 - Dec 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (185 reviews)
It’a a beautiful and charming building with just the right amount of modernity.
My room was a tad bit smalller than I’d expected (queen bed) and the view was nonexistent but cozy and comfortable for for a single person. The room came with a fully stocked mini fridge, a Nespresso
machine and two very plush bath robes.
The staff was very accommodating and friendly. Each day I was there(three), housekeeping was excellent
Shopping, dining and spectacular architecture are in ample supply right outside your door. Will definitely stay here when I’m there city!
Reviewed on Oct 26, 2026
5* Cheap holidays in West Side
Price found within the past 48 hours. Click for updated prices.
3 Night Cheap holidays in West Side
Price found within the past 48 hours. Click for updated prices.
Sheraton Grand Chicago Riverwalk
Downtown Chicago
CA $954
per person
Dec 19 - Dec 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)
Very nice property. However there were loud drunk college age kids who woke us up repeatedly throughout the night at 4 to 5 am by yelling in the hallway and banging on doors over and over. They also left bags of trash in the hallway near our room. Please up your security
Reviewed on Oct 26, 2026
4 Night Cheap holidays in West Side
Price found within the past 48 hours. Click for updated prices.
Sheraton Grand Chicago Riverwalk
Downtown Chicago
CA $1,097
per person
Dec 18 - Dec 22
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)
Very nice property. However there were loud drunk college age kids who woke us up repeatedly throughout the night at 4 to 5 am by yelling in the hallway and banging on doors over and over. They also left bags of trash in the hallway near our room. Please up your security
Reviewed on Oct 26, 2026
Cheap Hotels in West Side
STAY
1415 Ashland Ave Chicago IL
- 5 min drive from United Center
Book a stay at this business-friendly hostel in Chicago. Enjoy free WiFi, parking (surcharge), and a 24-hour business center. Our guests praise the helpful staff ...
7.6/10 Good! (289 reviews)
"while my friend and i were not able to complete our stay (she has cerebral palsy and cannot go up many steps) which i had confirmed before we even arrived to make sure we would have a lower level room and then we were placed on the 3rd floor. i would like to shoutout amelio and syd! they were so ..."
Reviewed on Oct 23, 2026
Hyatt House Chicago Medical/University District
1835 West Harrison Street Chicago IL
- 10 min walk from United Center
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 ...
Chicago Parthenon Hostel
310 S. Halsted Street Chicago IL
- 19 min walk from United Center
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! (603 reviews)
"The absence of an elevator was a major drawback, as guests are expected to carry their own heavy luggage up the stairs. This is quite unacceptable and difficult to comprehend in this day and age. The Wi-Fi was adequate, and the room cleanliness and staff cooperation were satisfactory. Overall, while ..."
Reviewed on Oct 25, 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
Skydeck Chicago at Willis Tower
CA $60
per adult
84% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $64
per adult
94% of travellers recommend
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
