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.
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,509, price is now CA $1,013 per person
CA $1,013
per person
May 11 - May 15
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (421 reviews)
10/10 makes you feel at home. One of the best hotels I’ve ever stayed in.
Reviewed on Mar 23, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,939, price is now CA $1,428 per person
CA $1,428
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Just an amazing place to stay. The staff is lovely, the rooms are wonderful and the location is perfect for a day at the waterline.
Reviewed on Mar 27, 2026
Hotel Arista
Price was CA $1,425, price is now CA $1,058 per person
CA $1,058
per person
Jun 3 - Jun 9
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,011 reviews)
Our room was spacious, clean and well appointed. I love a bathroom with good lighting and the tv in the vanity mirror was fantastic to catch the morning news as we got ready!!
The staff was exceptional. From check in, to drinks at the bar, to room service, everyone was incredibly friendly and professional. I highly recommend Hotel Arista.
Reviewed on Mar 24, 2026
The Peninsula Chicago
Downtown Chicago
Price was CA $2,387, price is now CA $1,773 per person
CA $1,773
per person
May 18 - May 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.8/10 Exceptional! (1,010 reviews)
Excellent room and facilities. Helpfull staff and amazing locstion.
Reviewed on Mar 27, 2026
5* Cheap holidays in West Side
Price found within the past 48 hours. Click for updated prices.
The Peninsula Chicago
Downtown Chicago
Price was CA $2,387, price is now CA $1,773 per person
CA $1,773
per person
May 18 - May 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.8/10 Exceptional! (1,010 reviews)
Excellent room and facilities. Helpfull staff and amazing locstion.
Reviewed on Mar 27, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was CA $2,456, price is now CA $1,939 per person
CA $1,939
per person
May 8 - May 12
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,007 reviews)
Great place to stay . The staff was friendly and helpful !!!
Reviewed on Mar 22, 2026
3 Night Cheap holidays in West Side
Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,735, price is now CA $1,277 per person
CA $1,277
per person
Jun 4 - Jun 7
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (421 reviews)
10/10 makes you feel at home. One of the best hotels I’ve ever stayed in.
Reviewed on Mar 23, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,939, price is now CA $1,428 per person
CA $1,428
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Just an amazing place to stay. The staff is lovely, the rooms are wonderful and the location is perfect for a day at the waterline.
Reviewed on Mar 27, 2026
4 Night Cheap holidays in West Side
Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,509, price is now CA $1,013 per person
CA $1,013
per person
May 11 - May 15
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (421 reviews)
10/10 makes you feel at home. One of the best hotels I’ve ever stayed in.
Reviewed on Mar 23, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,455, price is now CA $1,058 per person
CA $1,058
per person
May 23 - May 27
found 3 hours ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Just an amazing place to stay. The staff is lovely, the rooms are wonderful and the location is perfect for a day at the waterline.
Reviewed on Mar 27, 2026
Cheap Hotels in West Side
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! (452 reviews)
Hostel was great. Plenty of space in the rooms and bathrooms. Nice area to eat and plenty of fridge space. Easy access and nice neighborhood. My only complaint would be the matttess. It was very thin and not the most comfortable after a few days.
Reviewed on Mar 15, 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! (1,462 reviews)
Thisis the best hotel to stay for events at thw United Center. Its close enough to the city that you can drive in for other experiences. Breakfast was great, drinks in the afternoon are perfect too.
Reviewed on Mar 27, 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.
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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.
