Apartments in Southwest Side for Rent

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Our top choices for Southwest Side apartments

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, (21 reviews)
"Clean and nice. My son loved the arcade game. Would stay again "
United States
Nichole S.
The price is ¥8,760
¥33,606 total
includes taxes & fees
Apr 14 - Apr 15
Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6

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

W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade
Brighton Park
9.4 out of 10, Exceptional, (9 reviews)
"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 ¥12,742
¥42,615 total
includes taxes & fees
Apr 22 - Apr 23
W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade

Sunlit 1BR Apartment | Warm & Welcoming Space

Sunlit 1BR Apartment | Warm & Welcoming Space
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
United States
Tyler B.
The price is ¥17,998
¥36,362 total
includes taxes & fees
Apr 13 - Apr 14
Sunlit 1BR Apartment | Warm & Welcoming Space

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.6 out of 10, Exceptional, (5 reviews)
"We had a very comfortable stay here. The hosts are exceptionally communicative and helpful. Loved having a place to park my car, and the hosts set it up so my license plate was recognized at the gate so that parking was free. The unit was very clean and spacious. Note, the kitchen does not have pots or pans to cook, so plan on eating out!"
United States
Jennifer M.
The price is ¥25,483
¥72,734 total
includes taxes & fees
Apr 14 - Apr 15
River North Rooftop With In and Out Parking 3

Chic Studio in the Heart of the Gold Coast

Chic Studio in the Heart of the Gold Coast
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"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 ¥17,042
¥34,041 total
includes taxes & fees
Apr 29 - Apr 30
Chic Studio in the Heart of the Gold Coast

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (9 reviews)
"Great spot next to the green line train a few restaurants and a Starbucks right up the street I will book again for sure "
United States
2k G.
The price is ¥15,608
¥33,363 total
includes taxes & fees
Apr 13 - Apr 14
West Loop Living – Bright 1BR

Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry
Downtown Chicago
9.0 out of 10, Wonderful, (17 reviews)
"Great location, apt well equipped and host very responsive. Wonderful stay. "
United States
Gina G.
The price is ¥11,467
¥28,512 total
includes taxes & fees
Apr 19 - Apr 20
Modern Comfort: 1BR Unit w/ Laundry

Plymouth Collection: 2BD with Lobby, Gym, Rooftop

Plymouth Collection: 2BD with Lobby, Gym, Rooftop
Chicago
Plymouth Collection: 2BD with Lobby, Gym, Rooftop

Modern West Loop Gem-City Views & Prime Location 3

Modern West Loop Gem-City Views & Prime Location 3
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"Loved the place 4 bedroom & 4 bathrooms was ideal for our stayGreat locationLoved the well stocked convenience store a block away "
United States
Tina Y.
Modern West Loop Gem-City Views & Prime Location 3

LIVN West Loop Chicago King Studio

LIVN West Loop Chicago King Studio
Downtown Chicago
The price is ¥21,501
¥29,175 total
includes taxes & fees
Apr 26 - Apr 27
LIVN West Loop Chicago King Studio

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
8.0 out of 10, Very Good, (2 reviews)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is ¥17,998
¥36,362 total
includes taxes & fees
Apr 13 - Apr 14
1BR Modern Luxe Apt with In-Unit Laundry

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (13 reviews)
"Great location, comfortable room, welcoming host."
United States
Treseanne A.
The price is ¥22,776
¥71,345 total
includes taxes & fees
Apr 26 - Apr 27
Spacious 4BR Central Apartment w/ Skyline Views

Downtown Chicago Stay with Free In & Out Parking 5

Downtown Chicago Stay with Free In & Out Parking 5
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"This VRBO was perfect for our family as we visited our college student in downtown Chicago. Plenty of space, sparkling clean, comfy beds. Only two things that I think could be improved/better communicated: only one key card is provided, and the beds are full size not queen (but they were SUPER comfortable!!!)"
United States
Gina C.
The price is ¥35,039
¥86,297 total
includes taxes & fees
Apr 26 - Apr 27
Downtown Chicago Stay with Free In & Out Parking 5

Cozy Boho Chicago - 10 Minutes to Downtown Chicago

Cozy Boho Chicago - 10 Minutes to Downtown Chicago
Lawndale
9.8 out of 10, Exceptional, (10 reviews)
"Wonderful space and convenient location. Really responsive host and super quiet neighborhood! "
United States
Jess S.
The price is ¥8,887
¥28,748 total
includes taxes & fees
Apr 20 - Apr 21
Cozy Boho Chicago - 10 Minutes to Downtown Chicago

Uptown Studio Gem Sum

Uptown Studio Gem Sum
Uptown
7.4 out of 10, Good, (6 reviews)
"This studio is very clean and is located in a neighborhood with access to anything you would want to do or see. The stairway and halls are not pristine, but studio is good. Neighbors were quiet and seldom seen during my stay. Excellent restaurant right across the street and grocery nearby. Wrigley Field is easy walk. Check in was confusing for me, but it worked out. "
United States
Leah W.
The price is ¥10,830
¥26,174 total
includes taxes & fees
Apr 13 - Apr 14
Uptown Studio Gem Sum

NEW Private West Loop 1br with Backyard near Green Line and CTA

NEW Private West Loop 1br with Backyard near Green Line and CTA
East Garfield Park
9.6 out of 10, Exceptional, (5 reviews)
"Clean, and was exactly how described in the booking. Host was quick to respond to any questions we had. "
United States
Cyril M.
The price is ¥10,722
¥38,777 total
includes taxes & fees
Apr 13 - Apr 14
NEW Private West Loop 1br with Backyard near Green Line and CTA

Cozy & Furnished 2BR Unit

Cozy & Furnished 2BR Unit
Lincoln Square
9.2 out of 10, Wonderful, (18 reviews)
"Very cozy, amenities in great condition."
United States
Kaitlin T.
The price is ¥14,971
¥35,006 total
includes taxes & fees
Apr 16 - Apr 17
Cozy & Furnished 2BR Unit

2-bedroom apartment just 2 minutes drive to Wrigley Field

2-bedroom apartment just 2 minutes drive to Wrigley Field
North Center
9.6 out of 10, Exceptional, (66 reviews)
"Nice property, great location, super helpful host!"
United States
Carin O.
The price is ¥18,491
¥48,360 total
includes taxes & fees
Apr 13 - Apr 14
2-bedroom apartment just 2 minutes drive to Wrigley Field

Stylish and Roomy 2BR in Chicago

Stylish and Roomy 2BR in Chicago
Edgewater
9.0 out of 10, Wonderful, (14 reviews)
"Clean room, easy, check-in, great location"
United States
brent w.
The price is ¥14,971
¥35,006 total
includes taxes & fees
Apr 13 - Apr 14
Stylish and Roomy 2BR in Chicago

Nice 1BR Spot, Unwind & Relax

Nice 1BR Spot, Unwind & Relax
Lincoln Square
9.8 out of 10, Exceptional, (33 reviews)
"This was a great apartment in the heart of Lincoln Square. The kitchen is fully equipped, the bed was comfortable and there are a lot of amenities and public transportation close by. I will definitely be staying hear again! "
United States
Lisa
The price is ¥14,016
¥31,497 total
includes taxes & fees
Apr 13 - Apr 14
Nice 1BR Spot, Unwind & Relax
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

Find out more about Southwest Side

Southwest Side Apartments information

Number of reviews
214
Accommodation
623 Apartments
Lowest Price
¥26,174
Highest Price
¥86,297

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