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Apartments in Southwest Side for Rent

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Our top choices for Southwest Side apartments

1. 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, (11 reviews)
"It was great it had the basic amenities for a family to enjoy the stay"
United States
Damary T.
The price is ¥13,101
¥44,192 total
includes taxes & fees
Aug 25 - Aug 26
W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade

2. 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, (2 reviews)
"The rooms were spotless. The apartment was spacious. I enjoyed my stay. "
United States
Rachel
The price is ¥13,386
¥44,508 total
includes taxes & fees
Aug 25 - Aug 26
Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10

3. Spacious Apt | 4 Queen Beds | Free Parking

Spacious Apt | 4 Queen Beds | Free Parking
Brighton Park
The price is ¥22,382
¥56,094 total
includes taxes & fees
Aug 25 - Aug 26
Spacious Apt | 4 Queen Beds | Free Parking

4. Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP

Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
Berwyn
10.0 out of 10, Exceptional, (31 reviews)
"Relaxing stay and safe location. Host JD provided great communication throughout the stay. Stores are nearby in case you need items for your trip. Food options are abundant in the area. 30 min drive to downtown Chicago."
United States
Cynthia M.
The price is ¥10,958
¥28,967 total
includes taxes & fees
Aug 23 - Aug 24
Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP

5. 3BR | Complete & Well-Located Apt in Hyde Park

3BR | Complete & Well-Located Apt in Hyde Park
Hyde Park
7.6 out of 10, Good, (5 reviews)
"Enjoyed our stay. Thank you"
United States
Nicolle C.
The price is ¥15,001
¥38,060 total
includes taxes & fees
Aug 24 - Aug 25
3BR | Complete & Well-Located Apt in Hyde Park

6. 5 Mins to Downtown CHI Sleeps 10 - Parking + Games

5 Mins to Downtown CHI Sleeps 10 - Parking + Games
Lower West Side
9.0 out of 10, Wonderful, (4 reviews)
"We loved the location, the area is awesome! Great stay, highly recommend. "
United States
Db D.
The price is ¥22,111
¥58,937 total
includes taxes & fees
Sep 8 - Sep 9
5 Mins to Downtown CHI Sleeps 10 - Parking + Games

7. Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW

Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW
Berwyn
9.6 out of 10, Exceptional, (19 reviews)
"Great place to stay "
United States
Harquesha S.
The price is ¥10,711
¥28,387 total
includes taxes & fees
Aug 24 - Aug 25
Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW

8. Smart Simple and Spacious 4BR Apt

Smart Simple and Spacious 4BR Apt
Near South Side
8.0 out of 10, Very Good, (11 reviews)
"Some issues checking in, but otherwise a fantastic stay!"
United States
James B.
The price is ¥21,045
¥65,671 total
includes taxes & fees
Aug 31 - Sep 1
Smart Simple and Spacious 4BR Apt

9. Group-Friendly 4BR Hyde Park Retreat Near UChicago

Group-Friendly 4BR Hyde Park Retreat Near UChicago
Hyde Park
6.0 out of 10, (5 reviews)
"Pretty standard for a VRBO property. No frills but excellent location and great that it had 4 bedrooms for our group. "
United States
Cuoghi E.
The price is ¥15,665
¥58,392 total
includes taxes & fees
Aug 31 - Sep 1
Group-Friendly 4BR Hyde Park Retreat Near UChicago

10. Stylish 2BR Near Hyde Park, UChicago & Lake

Stylish 2BR Near Hyde Park, UChicago & Lake
Woodlawn
10.0 out of 10, Exceptional, (5 reviews)
"Definitely would rent again "
United States
Brittney J.
The price is ¥26,583
¥65,416 total
includes taxes & fees
Sep 8 - Sep 9
Stylish 2BR Near Hyde Park, UChicago & Lake

11. 10 Minutes to Downtown Chicago - Sleeps 12 - King Beds - Games and Arcades

10 Minutes to Downtown Chicago - Sleeps 12 - King Beds - Games and Arcades
Lawndale
8.0 out of 10, Very Good, (4 reviews)
"Great stay, perfect for our group of 6, everyone had there own room! Necessities right around the corner if needed Cermack rd a few feet away, gets you about everywhere! We wanted a real life Chicago experience, and it was great. Owner very responsive! Permit on street parking pretty accessible most times. Definitely will stay again!"
United States
Beth
The price is ¥22,785
¥55,398 total
includes taxes & fees
Sep 14 - Sep 15
10 Minutes to Downtown Chicago - Sleeps 12 - King Beds - Games and Arcades

12. Flexhome East Village • Modern 2BR • Quiet Street

Flexhome East Village • Modern 2BR • Quiet Street
West Town
9.6 out of 10, Exceptional, (22 reviews)
"Great location! "
United States
Andrea B.
The price is ¥18,607
¥37,532 total
includes taxes & fees
Aug 30 - Aug 31
Flexhome East Village • Modern 2BR • Quiet Street

13. Sleeps 12 - Games - 10 Min to Downtown - Arcades - Walking Distance to Train

Sleeps 12 - Games - 10 Min to Downtown - Arcades - Walking Distance to Train
Lawndale
10.0 out of 10, Exceptional, (1 review)
The price is ¥25,633
¥60,209 total
includes taxes & fees
Aug 25 - Aug 26
Sleeps 12 - Games - 10 Min to Downtown - Arcades - Walking Distance to Train

14. Flexhome Ukrainian Village • 2BR • Convenient Walkability · Sleeps 6

Flexhome Ukrainian Village • 2BR • Convenient Walkability · Sleeps 6
West Town
8.0 out of 10, Very Good, (1 review)
"On busy street so was a little noisy."
United States
Diane M.
The price is ¥14,043
¥31,113 total
includes taxes & fees
Aug 31 - Sep 1
Flexhome Ukrainian Village • 2BR • Convenient Walkability · Sleeps 6

15. Studio Near Wrigley • Sleeps 4 • Games + Fireplace

Studio Near Wrigley • Sleeps 4 • Games + Fireplace
Irving Park
10.0 out of 10, Exceptional, (4 reviews)
"Clean, comfortable bed, plenty of amenities. Steps and entry were a little awkward. Street parking only unless you paid extra for their garage which was a very tight fit for my sedan. Note older building so could hear neighbors but it wasn’t intrusive. Also note 3.6 miles to Wrigley was a 25 minute drive. Overall great place and would stay again."
United States
Meagan C.
The price is ¥5,918
¥40,145 total
includes taxes & fees
Aug 31 - Sep 1
Studio Near Wrigley • Sleeps 4 • Games + Fireplace

16. 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, (58 reviews)
"So hospitable "
United States
Adrian
The price is ¥11,393
¥42,091 total
includes taxes & fees
Aug 24 - Aug 25
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

17. Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (89 reviews)
"It was small and cozy and perfect for a weekend trip in Chicago"
United States
Lilly L.
The price is ¥10,681
¥22,944 total
includes taxes & fees
Sep 8 - Sep 9
Cozy studio in Andersonville Chicago

18. Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6

Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6
West Town
8.8 out of 10, Excellent, (14 reviews)
"Great location! Comfortable and quiet. "
United States
Jonalyn B.
The price is ¥14,098
¥31,065 total
includes taxes & fees
Sep 1 - Sep 2
Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6

19. Stylish friendly 3BR Suite near McCormick

Stylish friendly 3BR Suite near McCormick
Near South Side
The price is ¥27,711
¥88,273 total
includes taxes & fees
Sep 7 - Sep 8
Stylish friendly 3BR Suite near McCormick

20. LIVN Millennium Park Downtown Chicago 1 BR

LIVN Millennium Park Downtown Chicago 1 BR
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Great location to sights, shops, and food."
United States
Adrianna W.
The price is ¥26,650
¥35,818 total
includes taxes & fees
Aug 23 - Aug 24
LIVN Millennium Park Downtown Chicago 1 BR
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
255
Accommodation
646 Apartments
Lowest Price
¥22,944
Highest Price
¥88,273

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