
West Side Cheap Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Flight and Cheap hotel deals in West Side
Price found within the past 48 hours. Click for updated prices.





5* Cheap holidays in West Side
Price found within the past 48 hours. Click for updated prices.



The Peninsula Chicago
Downtown Chicago
CA $2,117
per person
Nov 9 - Nov 12
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,013 reviews)
The hotel and the team are great. The daytime staff, in particular, are super friendly and helpful. The amenities are good; the pool, Jacuzzi, and gym are nice spaces. However, I did miss having communal areas for socializing. It struck me as a hotel geared toward an older crowd—which I understand helps maintain a more exclusive, private atmosphere—but as someone in my 30s, I was looking for a place to hang out and chat with friends late at night, and there wasn't one, since the pool and terraces close. The few social areas the hotel does have are very formal and business-oriented...
Reviewed on Sep 2, 2026
3 Night Cheap holidays in West Side
Price found within the past 48 hours. Click for updated prices.



4 Night Cheap holidays in West Side
Price found within the past 48 hours. Click for updated prices.



Freehand Chicago
Downtown Chicago
CA $2,050
per person
Oct 9 - Oct 13
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
7.8/10 Good! (3,328 reviews)
Pros - this hotel is conveniently located and its less expensive than some others in the area.
Cons - the first room I was given had water damage in the ceiling and did not smell good. I also checked the AC unit and the filter was completely clogged with dust, this type of washable filter is supposed to be cleaned every month and it looks like it has at least 9+ months of dust on it. I complained about the water damage and they moved me to another room. The next room didn't have soap or shampoo in the bathroom for some reason, and I checked the air filter in this room also and it clearly hasn't been cleaned in forever. In addition to cleaning the air filters, this type of AC unit is supposed to be professionally cleaned once per year. This one has clearly not been cleaned in years.
If you want a well maintained hotel, try somewhere else.
Reviewed on Sep 2, 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, a 24-hour business center, and laundry facilities. Our guests praise the helpful staff ...
7.6/10 Good! (260 reviews)
"Everyone was friendly, welcoming and accommodating. The facility was clean, but do know they were making some repairs. Kitchen had what you needed. I could have used a fuller pillow, but that was no biggie. Close to a grocery store, pharmacy, Ulta (which was so helpful!), and some eateries. Close ..."
Reviewed on Aug 31, 2026

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 ...

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 ...
9.2/10 Wonderful! (1,610 reviews)
"The staffs are very friendly, the rooms are very comfortable"
Reviewed on Sep 1, 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

Wendella's Lake and River Architecture Tour
CA $62
per adult
94% 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.








