Southwest Side Hotels from S$75

  • Plan, book, stay with confidence
    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check Southwest Side hotel prices

Tonight
27 Nov - 28 Nov
Tomorrow night
28 Nov - 29 Nov
This weekend
29 Nov - 1 Dec
Next weekend
6 Dec - 8 Dec

Filter by

Guest rating
Guest rating
Property class

Top 10 trending Southwest Side hotels

River Hotel
View from property

River Hotel

4.0 star property
8.8 out of 10, Excellent, (3693)
"Great location! Front desk was very helpful in giving some local recommendations. "
The price is S$171
includes taxes & fees
8 Dec - 9 Dec
River Hotel
Eurostars Magnificent Mile
Lobby lounge

Eurostars Magnificent Mile

4.0 star property
8.6 out of 10, Excellent, (2853)
"Great rooms and best service "
The price is S$185
includes taxes & fees
26 Dec - 27 Dec
Eurostars Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent Mile
Lobby

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (2077)
"Front desk clerk was not the happiest. Tried to check in early. Room was ready but was told there was a 50 early check in fee. Never had that happen before. Last time got water and cookies not this time. Parking went up also."
The price is S$150
includes taxes & fees
24 Dec - 25 Dec
DoubleTree by Hilton Chicago - Magnificent Mile
Hyatt Centric The Loop Chicago
Rooftop terrace

Hyatt Centric The Loop Chicago

4.0 star property
8.8 out of 10, Excellent, (1505)
"Very nice place highly recommended"
The price is S$183
includes taxes & fees
1 Dec - 2 Dec
Hyatt Centric The Loop Chicago
Congress Plaza Hotel
Lobby

Congress Plaza Hotel

3.5 star property
7.8 out of 10, Good, (8590)
"Overall we liked the room we stayed at the only complaint was that the hallway leading to the room had an awful smell like lake dead fish or something when we arrived on 11/23 this morning the smell was less but it still smelled "
The price is S$158
includes taxes & fees
8 Dec - 9 Dec
Congress Plaza Hotel
L7 Chicago by LOTTE
Exterior

L7 Chicago by LOTTE

4.5 star property
9.6 out of 10, Exceptional, (1112)
"very good would stay here again "
The price is S$240
includes taxes & fees
22 Dec - 23 Dec
L7 Chicago by LOTTE
citizenM Chicago Downtown
Terrace/patio

citizenM Chicago Downtown

4.0 star property
9.2 out of 10, Wonderful, (2277)
"Awesome staff they are the sweetest & very helpful. Room was nice and spacious and property was very cozy. My complaints are mainly for the bathroom. We took cold showers our entire stay because the water would not get hot. Also the shower and sink counter space is very small. Also our toilet somewhat would leak every time you flushed it which was kind of gross & unsanitary. Aside from that the stay was cool, most of my stars are for the staff!!"
The price is S$205
includes taxes & fees
10 Dec - 11 Dec
citizenM Chicago Downtown
Hotel Riu Plaza Chicago
Front of property

Hotel Riu Plaza Chicago

4.0 star property
9.2 out of 10, Wonderful, (1026)
"Great stay. "
The price is S$235
includes taxes & fees
22 Dec - 23 Dec
Hotel Riu Plaza Chicago
Freehand Chicago
Cocktail bar

Freehand Chicago

4.0 star property
7.8 out of 10, Good, (1561)
"Great location and amenities! "
The price is S$99
includes taxes & fees
17 Dec - 18 Dec
Freehand Chicago
Hotel Felix River North/Magnificent Mile
Lobby sitting area

Hotel Felix River North/Magnificent Mile

4.0 star property
8.0 out of 10, Very good, (1379)
"Lovely!"
The price is S$171
includes taxes & fees
9 Dec - 10 Dec
Hotel Felix River North/Magnificent Mile
Club Quarters Hotel, Central Loop, Chicago
Premium bedding, in-room safe, desk, laptop workspace

Club Quarters Hotel, Central Loop, Chicago

4.0 star property
8.6 out of 10, Excellent, (3520)
"It was a great experience "
The price is S$162
includes taxes & fees
28 Nov - 29 Nov
Club Quarters Hotel, Central Loop, Chicago
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Exterior

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3.0 star property
8.2 out of 10, Very good, (2707)
"All great "
The price is S$158
includes taxes & fees
9 Dec - 10 Dec
Hilton Garden Inn Chicago Downtown/Magnificent Mile
The Royal Sonesta Chicago Downtown
Exterior

The Royal Sonesta Chicago Downtown

4.0 star property
9.2 out of 10, Wonderful, (2329)
"Great location and a standard room is huge by comparison with other hotels. Highly recommend "
The price is S$255
includes taxes & fees
8 Dec - 9 Dec
The Royal Sonesta Chicago Downtown
voco Chicago Downtown, an IHG Hotel
City view from property

voco Chicago Downtown, an IHG Hotel

3.5 star property
8.8 out of 10, Excellent, (2006)
"Very nice inside very clean a little hard to find but over all super good friendly staff "
The price is S$195
includes taxes & fees
17 Dec - 18 Dec
voco Chicago Downtown, an IHG Hotel
Embassy Suites by Hilton Chicago Downtown River North
Lobby

Embassy Suites by Hilton Chicago Downtown River North

4.0 star property
8.2 out of 10, Very good, (3343)
"Excellent crevice! "
The price is S$186
includes taxes & fees
10 Dec - 11 Dec
Embassy Suites by Hilton Chicago Downtown River North
Aloft Chicago Mag Mile
Exterior

Aloft Chicago Mag Mile

3.0 star property
8.6 out of 10, Excellent, (2526)
"Aloft amazing staff , clean hotel , relaxed vibe. Overall great"
The price is S$146
includes taxes & fees
8 Dec - 9 Dec
Aloft Chicago Mag Mile
Swissotel - Chicago
Front of property – evening/night

Swissotel - Chicago

4.5 star property
8.8 out of 10, Excellent, (2158)
"Excellent"
The price is S$240
includes taxes & fees
16 Dec - 17 Dec
Swissotel - Chicago
The Whitehall Hotel, BW Premier Collection
Egyptian cotton sheets, premium bedding, pillow-top beds, in-room safe

The Whitehall Hotel, BW Premier Collection

3.5 star property
8.2 out of 10, Very good, (3674)
"Convenient "
The price is S$148
includes taxes & fees
28 Nov - 29 Nov
The Whitehall Hotel, BW Premier Collection
Trump International Hotel & Tower Chicago
Terrace/patio

Trump International Hotel & Tower Chicago

5.0 star property
9.4 out of 10, Exceptional, (1522)
"I had to pay fomy upgrade "
The price is S$622
includes taxes & fees
15 Dec - 16 Dec
Trump International Hotel & Tower Chicago
Hilton Chicago
Exterior

Hilton Chicago

4.0 star property
8.4 out of 10, Very good, (1517)
"Overall great. I rated cleanliness a 4 as there was hair in our bathroom behind the door and under sink where it had not been swept. Otherwise everything else was great. Would like to have had a microwave available in the room for leftovers. Every one was friendly "
The price is S$228
includes taxes & fees
22 Dec - 23 Dec
Hilton Chicago
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.
Don't see what you're looking for?
See all available properties in Southwest Side
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals