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Apartments in Southwest Side for Rent

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Southwest Side apartments

A living room with a flat-screen TV, a sofa, a coffee table, and a staircase leading to another room.

1. 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)
"Excellent location and go anywhere so close."
United States
Yiu S.
The price is ￥12,823
￥37,668 total
includes taxes & fees
Oct 13 - Oct 14
Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6
Private kitchen

2. Large Chicago Apt 3 BR - King Bed - 12 Min Downtown w/ Arcade

Large Chicago Apt 3 BR - King Bed - 12 Min Downtown w/ Arcade
Brighton Park
9.4 out of 10, Exceptional, (13 reviews)
"It was great it had the basic amenities for a family to enjoy the stay"
United States
Damary T.
The price is ￥11,826
￥44,352 total
includes taxes & fees
Oct 13 - Oct 14
Large Chicago Apt 3 BR - King Bed - 12 Min Downtown w/ Arcade
A compact kitchen with a dining table, a refrigerator, and a trash can.

3. Spacious Apt | 4 Queen Beds | Free Parking

Spacious Apt | 4 Queen Beds | Free Parking
Brighton Park
The price is ￥20,346
￥64,003 total
includes taxes & fees
Oct 22 - Oct 23
Spacious Apt | 4 Queen Beds | Free Parking
A hotel room with a bed, two bedside lamps, a wall-mounted artwork, and a small table with a lamp.

4. 2BR Apt with 2 Baths & Laundry

2BR Apt with 2 Baths & Laundry
Near West Side
10.0 out of 10, Exceptional, (1 review)
"The property was very clean and perfect for our overnight stay. Thank you"
United States
michele
The price is ￥15,198
￥36,936 total
includes taxes & fees
Nov 2 - Nov 3
2BR Apt with 2 Baths & Laundry
Private kitchen

5. Cozy Boho - 10 Minutes to Downtown Chicago + Arcades

Cozy Boho - 10 Minutes to Downtown Chicago + Arcades
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 ￥11,683
￥34,068 total
includes taxes & fees
Oct 20 - Oct 21
Cozy Boho - 10 Minutes to Downtown Chicago + Arcades
A modern living room with a blue sofa, a patterned rug, and a television.

6. Great Area Logan Square Apt Games Pets - Sleeps 5

Great Area Logan Square Apt Games Pets - Sleeps 5
Avondale
10.0 out of 10, Exceptional, (2 reviews)
"Place was nice and clean. Great communication from the host! Would stay here again!"
United States
Deborah J.
The price is ￥11,240
￥34,648 total
includes taxes & fees
Oct 13 - Oct 14
Great Area Logan Square Apt Games Pets - Sleeps 5
A hotel room with a geometric-patterned wall, a bed with white bedding and a beige throw, two bedside lamps, and a window with blinds.

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

Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6
West Town
9.0 out of 10, Wonderful, (16 reviews)
"Great location! Comfortable and quiet. "
United States
Jonalyn B.
The price is ￥10,448
￥26,567 total
includes taxes & fees
Nov 2 - Nov 3
Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6
A living room with a gray sofa, a coffee table, a TV mounted on the wall, and a wooden door.

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

Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW
Berwyn
9.8 out of 10, Exceptional, (23 reviews)
"Parking was free and right out front. Great apartment and the host was great with accommodations."
United States
Travis C.
The price is ￥10,716
￥28,401 total
includes taxes & fees
Oct 13 - Oct 14
Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW
A modern living room with a grey sofa, a coffee table, and a view of the outside through large windows.

9. Conveniently Situated 1BR Apartment

Conveniently Situated 1BR Apartment
Hyde Park
The price is ￥14,565
￥41,918 total
includes taxes & fees
Nov 1 - Nov 2
Conveniently Situated 1BR Apartment
A modern living room with a sofa, a round coffee table, a TV mounted on the wall, and a bed with a headboard.

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

Studio Near Wrigley • Sleeps 4 • Games + Fireplace
Irving Park
10.0 out of 10, Exceptional, (7 reviews)
"We had a great time at this property! After our previous rental cancelled at the last minute, we found this gem and couldn’t have been happier. Communication was clear, check-in was easy, and the property was clean and comfortable. Thanks for a great stay!"
United States
Emily G.
The price is ￥7,941
￥44,941 total
includes taxes & fees
Oct 14 - Oct 15
Studio Near Wrigley • Sleeps 4 • Games + Fireplace
Game room

11. Logan Square Boho Getaway - Sleeps 6 - Remodeled

Logan Square Boho Getaway - Sleeps 6 - Remodeled
Avondale
10.0 out of 10, Exceptional, (1 review)
"The host was very communicative. We had an issue with our AC when we arrived but he was on it immediately & had a tech over the next morning. As stated the parking is tight, and it being in Chicago it is understood. We were able to park our car on the same street where the house was on but had to wake up at 7am to move it daily as there’s only permit parking under certain hours but the park right up the street has good spaces available on the side of it. Space itself was extremely clean & all...
United States
Mayra R.
The price is ￥10,385
￥41,681 total
includes taxes & fees
Oct 27 - Oct 28
Logan Square Boho Getaway - Sleeps 6 - Remodeled
A living room with a brick fireplace, a flat-screen TV mounted above it, and a large potted plant.

12. Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP

Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
Berwyn
9.2 out of 10, Wonderful, (41 reviews)
"Beautiful clean and comfy loved my stay"
United States
Tania W.
The price is ￥12,114
￥31,252 total
includes taxes & fees
Oct 12 - Oct 13
Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
A modern building with large glass windows, surrounded by a grassy area with trees and a pathway.

13. The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
9.4 out of 10, Exceptional, (8 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is ￥17,224
￥37,298 total
includes taxes & fees
Oct 28 - Oct 29
The Oak Park Loft
A rooftop terrace with a brick wall, large windows, and a metal railing.

14. 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, (60 reviews)
"Clean, efficient, and conveniently located to plenty of transportation and culture."
United States
Michael S.
The price is ￥14,248
￥46,510 total
includes taxes & fees
Oct 12 - Oct 13
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
A modern kitchen with white cabinets, a central island with stools, a microwave, and a refrigerator.

15. 3BR Complete and Spacious Apartment in Ideal Spot

3BR Complete and Spacious Apartment in Ideal Spot
West Town
8.2 out of 10, Very good, (22 reviews)
"absolutely would stay here again. Great property and great communcation"
United States
Daniel J.
The price is ￥16,306
￥40,401 total
includes taxes & fees
Oct 20 - Oct 21
3BR Complete and Spacious Apartment in Ideal Spot
A dining area with a table set for two, a black leather sofa, and a ceiling fan.

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

Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
Berwyn
9.8 out of 10, Exceptional, (34 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 ￥10,871
￥28,736 total
includes taxes & fees
Oct 14 - Oct 15
Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
A rooftop terrace with a fire pit, seating area, and a city skyline view.

17. Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6

Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6
West Town
9.8 out of 10, Exceptional, (6 reviews)
"Very happy with our stay. Loved the rooftop views! The host was very friendly and welcoming."
United States
Jessica C.
The price is ￥17,414
￥36,706 total
includes taxes & fees
Nov 4 - Nov 5
Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6
A hotel room with a bed, a view of a cityscape, and a window with curtains.

18. Elegant Style Loft Montrose|13 mins DT|4 mins Lake

Elegant Style Loft Montrose|13 mins DT|4 mins Lake
Uptown
8.6 out of 10, Excellent, (11 reviews)
"Great location and great place! "
United States
Ryinne P.
The price is ￥12,728
￥37,986 total
includes taxes & fees
Oct 12 - Oct 13
Elegant Style Loft Montrose|13 mins DT|4 mins Lake
A modern living room with a white coffee table, a vase with flowers, a bottle of wine, and a cheese board with snacks.

19. 2BR Fitness Pad • Private Gym • Sleeps 7

2BR Fitness Pad • Private Gym • Sleeps 7
Irving Park
9.4 out of 10, Exceptional, (8 reviews)
"Great property in a central location. Neighborhood was quiet and safe with good parks nearby. Apartment had good amenities and perfect for our stay. Communication with host was excellent"
United States
Carey M.
The price is ￥10,170
￥47,756 total
includes taxes & fees
Oct 12 - Oct 13
2BR Fitness Pad • Private Gym • Sleeps 7
A modern bedroom with a bed, a sofa, and a hanging plant.

20. Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (102 reviews)
"Great location and amazing space! Perfect for visiting the city to apartment search for an upcoming move."
United States
Audrey A.
The price is ￥9,974
￥22,075 total
includes taxes & fees
Nov 2 - Nov 3
Cozy studio in Andersonville 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.
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Top Southwest Side Hotel Reviews

Congress Plaza Hotel

Congress Plaza Hotel

8/10 Good
"The Congress is a historic hotel right at the Southern end of Michigan Avenue. Clearly, it's seen better days. Now, they are restoring it floor by floor. But, the main entry to the hotel is pretty rough. Some of the floors haven't been rehabbed, the bar is possibly the poorest bar in terms of quality of any of the historic hotels I've stayed in during my Chicago trips. The check in process is largely like going to the DMV. There's not a lot of customer service or friendly welcoming banter. No valet parking, there isn't daily maid service, either. The room I had was pretty nice, as it had been on the rehabbed side of the South tower. There was only one working elevator on this tower, so the rides up and down were long and packed. The bed was comfortable, the pillows were fluffy, and the bathroom was really good. The Congress is typically less expensive than the more upgraded spots such as the Blackstone, Hilton, or Palmer House."
Timothy 1-night trip
Posted 1 hour ago
Congress Plaza Hotel

Find out more about Southwest Side

Southwest Side Apartments information

Number of reviews
229
Accommodation
646 Apartments
Lowest Price
￥22,075
Highest Price
￥64,003

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