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Apartments in Southwest Side

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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Our top choices for Southwest Side apartments

Interior
Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10

Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10

Brighton Park
10.0 out of 10, Exceptional, (1)
"Family-friendly, quiet, perfect for a family or friends vacationing in Chicago. The apartment is very clean and the host was always available and responded quickly. The next time I come to Chicago, i will definitely stay at the apartment [if available]. "
United States
Fabian H.
Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10
Fridge, microwave, oven, stovetop
Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6

Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6

Brighton Park
8.6 out of 10, Excellent, (20)
"Clean and nice. My son loved the arcade game. Would stay again "
United States
Nichole S.
The price is NZ$351
includes taxes & fees
22 Dec - 23 Dec
Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6
Fridge, microwave, oven, stovetop
W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade

W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade

Brighton Park
9.2 out of 10, Wonderful, (7)
"Great location, spacious, and family friendly. Had cousins over and they had a blast playing the video games. "
United States
Jessica H.
The price is NZ$505
includes taxes & fees
1 Jan - 2 Jan 2026
W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade
Desk, iron/ironing board, WiFi, bed sheets
Relaxing Chicago Studio

Relaxing Chicago Studio

Edgewater
9.8 out of 10, Exceptional, (38)
"Had a great stay. Great location. "
United States
Justin
The price is NZ$288
includes taxes & fees
5 Jan - 6 Jan 2026
Relaxing Chicago Studio
Fridge, microwave, oven, stovetop
Flexhome Ukrainian Village 2BR D1

Flexhome Ukrainian Village 2BR D1

West Town
10.0 out of 10, Exceptional, (4)
"Excellent place and location."
United States
Josh L.
Flexhome Ukrainian Village 2BR D1
Children’s area
Cozy Clean Chicago Apartment Free Street Parking Near Downtown Washer & Dryer

Cozy Clean Chicago Apartment Free Street Parking Near Downtown Washer & Dryer

West Ridge
10.0 out of 10, Exceptional, (5)
"This spot was perfect for our Chicago visit where we mostly needed a place to sleep, not hang out. It seemed to have been refinished recently, so beds were comfy, bathroom lovely, and sitting area big enough for the two of us. "
United States
Deb B.
Cozy Clean Chicago Apartment Free Street Parking Near Downtown Washer & Dryer
Fridge, microwave, oven, stovetop
Cozy Boho Chicago - 10 Minutes to Downtown Chicago

Cozy Boho Chicago - 10 Minutes to Downtown Chicago

Lawndale
10.0 out of 10, Exceptional, (8)
"Very nice apartment close to downtown!"
United States
Dariana
The price is NZ$349
includes taxes & fees
10 Dec - 11 Dec
Cozy Boho Chicago - 10 Minutes to Downtown Chicago
Interior
Twice as Nice: Chic 2BR Stay with Style & Space

Twice as Nice: Chic 2BR Stay with Style & Space

Downtown Chicago
9.6 out of 10, Exceptional, (14)
"The neighborhood was so clean and quiet. Friendly neighbors. Perfect location, not far from everything downtown. "
United States
Shederia P.
The price is NZ$352
includes taxes & fees
11 Dec - 12 Dec
Twice as Nice: Chic 2BR Stay with Style & Space
Fridge, microwave, oven, stovetop
West Loop Living – Bright 1BR

West Loop Living – Bright 1BR

Downtown Chicago
10.0 out of 10, Exceptional, (3)
"Pretty cool place to stay for a short trip ! Everything was close to where we were which made traveling a lot easier. Apartment is a pretty decent size I would recommend just 2-3 people. You can easily contact the host about anything and they’ll respond within a timely manner. The only down side of this place was the shower cleanliness itself. Overall, cool place not bad at all definitely a quick trip kind of thing!"
United States
Majanique M.
The price is NZ$292
includes taxes & fees
7 Jan - 8 Jan 2026
West Loop Living – Bright 1BR
Terrace/patio
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

Uptown
10.0 out of 10, Exceptional, (48)
"Clean room and the host was great with communication "
United States
Heather T.
The price is NZ$406
includes taxes & fees
11 Dec - 12 Dec
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
1 bedroom, iron/ironing board, WiFi, bed sheets
Homey 1BR Space Apartment

Homey 1BR Space Apartment

Lincoln Square
9.8 out of 10, Exceptional, (12)
"Great location. Very walkable to restaurants and bars. Awesome park nearby. Host was easy to communicate with. "
United States
Kayla K.
The price is NZ$296
includes taxes & fees
15 Dec - 16 Dec
Homey 1BR Space Apartment
1 bedroom, iron/ironing board, free WiFi, bed sheets
Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago

Edgewater
9.4 out of 10, Exceptional, (50)
"Small, but perfect for an overnight stay"
United States
Meagen E.
The price is NZ$246
includes taxes & fees
15 Dec - 16 Dec
Cozy studio in Andersonville Chicago
TV
Nice 1BR Spot, Unwind & Relax

Nice 1BR Spot, Unwind & Relax

Lincoln Square
9.6 out of 10, Exceptional, (25)
"Great stay"
United States
Kayla K.
The price is NZ$292
includes taxes & fees
1 Jan - 2 Jan 2026
Nice 1BR Spot, Unwind & Relax
TV, offices
Modern West Loop Gem-City Views & Prime Location 4

Modern West Loop Gem-City Views & Prime Location 4

2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (2)
"Amazing accommodation"
United States
Jiri N.
The price is NZ$621
includes taxes & fees
22 Dec - 23 Dec
Modern West Loop Gem-City Views & Prime Location 4
Fridge, microwave, oven, stovetop
Special Skevanston Space 2mi to Northwestern University & beach

Special Skevanston Space 2mi to Northwestern University & beach

Evanston
9.0 out of 10, Wonderful, (22)
"Very nice stay. Host was super nice and accommodating. "
United States
Melissa K.
The price is NZ$369
includes taxes & fees
4 Jan - 5 Jan 2026
Special Skevanston Space 2mi to Northwestern University & beach
Property grounds
Stylish Luxe King bed w/Free Parkng near DT Oak Pk

Stylish Luxe King bed w/Free Parkng near DT Oak Pk

Oak Park
9.6 out of 10, Exceptional, (96)
"Great central and safe location. Home is quaint and cozy. Some minor updates are needed but it worked well for our visit. Really appreciated the close reserved parking so we always had a spot to park. Host was always in contact and easily accessible if needed."
United States
JoLiz B.
The price is NZ$414
includes taxes & fees
16 Dec - 17 Dec
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
2 bedrooms, iron/ironing board, WiFi, bed sheets
Warm & Inviting 2BR Apt

Warm & Inviting 2BR Apt

Hermosa
10.0 out of 10, Exceptional, (4)
"Comfortable beds, great location"
United States
Jason
The price is NZ$336
includes taxes & fees
10 Dec - 11 Dec
Warm & Inviting 2BR Apt
Interior
Gold Coast Living: Modern Studio Unit

Gold Coast Living: Modern Studio Unit

Downtown Chicago
10.0 out of 10, Exceptional, (4)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
United States
Seynabou
The price is NZ$287
includes taxes & fees
1 Jan - 2 Jan 2026
Gold Coast Living: Modern Studio Unit
2 bedrooms, iron/ironing board, WiFi, bed sheets
Comfortable 2BR Chicago Apt

Comfortable 2BR Chicago Apt

Albany Park
9.6 out of 10, Exceptional, (4)
"Perfect location for our trip. Very functional and comfortable. "
United States
Michael
The price is NZ$336
includes taxes & fees
11 Dec - 12 Dec
Comfortable 2BR Chicago Apt
Exterior detail
2-bedroom apartment just 2 minutes drive to Wrigley Field

2-bedroom apartment just 2 minutes drive to Wrigley Field

2.0 star property
North Center
9.6 out of 10, Exceptional, (52)
"Nice property, great location, super helpful host!"
United States
Carin O.
The price is NZ$455
includes taxes & fees
10 Dec - 11 Dec
2-bedroom apartment just 2 minutes drive to Wrigley Field
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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Top Southwest Side Hotel Reviews

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

10/10 Excellent
"Was a very nice hotel and in a great location"
Ben 2-night trip
Posted 16 hours ago
The Allegro Royal Sonesta Hotel Chicago Loop

Find out more about Southwest Side

Southwest Side Apartments information

Number of reviews
407
Accommodation
703 Apartments
Lowest Price
NZ$246
Highest Price
NZ$621

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