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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Southwest Side apartments

A corner building with a stone facade, multiple windows, and a visible fire hydrant.

1. 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 CA $109
CA $361 total
includes taxes & fees
Nov 9 - Nov 10
Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10
A living room with a sectional sofa, two armchairs, a coffee table, and artwork on the walls.

2. Spacious Apt | 4 Queen Beds | Free Parking

Spacious Apt | 4 Queen Beds | Free Parking
Brighton Park
The price is CA $165
CA $545 total
includes taxes & fees
Nov 2 - Nov 3
Spacious Apt | 4 Queen Beds | Free Parking
A neatly arranged bedroom with a bed, bedside tables, and abstract wall art.

3. Hyde Park Trendy Studio Apartment in Good Spot

Hyde Park Trendy Studio Apartment in Good Spot
Hyde Park
10.0 out of 10, Exceptional, (1 review)
"Such a cozy stay! Definitely recommend!"
United States
Angelina
The price is CA $112
CA $249 total
includes taxes & fees
Nov 15 - Nov 16
Hyde Park Trendy Studio Apartment in Good Spot
A corner room with a green upholstered chair, a small round table with a potted plant, and a framed picture on the wall.

4. Cozy Urban View Retreat Near Downtown - Sleeps 7

Cozy Urban View Retreat Near Downtown - Sleeps 7
Lawndale
10.0 out of 10, Exceptional, (1 review)
The price is CA $86
CA $278 total
includes taxes & fees
Nov 3 - Nov 4
Cozy Urban View Retreat Near Downtown - Sleeps 7
A modern living room with a blue sofa, a patterned rug, and a television.

5. 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 CA $99
CA $290 total
includes taxes & fees
Nov 10 - Nov 11
Great Area Logan Square Apt Games Pets - Sleeps 5
A dining area with a round wooden table, four upholstered chairs, a vase with white flowers, and two wall-mounted light fixtures.

6. Studio Near Wrigley • Sleeps 4 • Games • Fireplace

Studio Near Wrigley • Sleeps 4 • Games • Fireplace
Irving Park
10.0 out of 10, Exceptional, (7 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 CA $58
CA $363 total
includes taxes & fees
Nov 5 - Nov 6
Studio Near Wrigley • Sleeps 4 • Games • Fireplace
A modern hotel room with a large bed, a sitting area with a table and chairs, a kitchenette, and artwork on the wall.

7. Cozy Charm Studio Apt in Chicago

Cozy Charm Studio Apt in Chicago
Hyde Park
The price is CA $92
CA $274 total
includes taxes & fees
Nov 24 - Nov 25
Cozy Charm Studio Apt in Chicago
A rooftop terrace with a brick wall, large windows, and a metal railing.

8. 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 CA $105
CA $363 total
includes taxes & fees
Nov 1 - Nov 2
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
A table with a book titled "MANIFEST & EXECUTE," a cup of coffee, a bowl of raspberries, a small potted plant, and a vase with white flowers.

9. 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 CA $93
CA $406 total
includes taxes & fees
Nov 1 - Nov 2
2BR Fitness Pad • Private Gym • Sleeps 7
A wooden dining table with two chairs, a potted plant, and a painting on the wall.

10. 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, (1 review)
"Great little spot in a fun area of downtown Chicago. Lots of bars & restaurants within walking distance."
United States
Ryan
The price is CA $138
CA $347 total
includes taxes & fees
Nov 30 - Dec 1
Chic Studio in the Heart of the Gold Coast
A rooftop terrace with a brick wall, large windows, and a metal railing.

11. Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake

Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
Uptown
9.4 out of 10, Exceptional, (31 reviews)
"Very nice and clean place in a great location if you are going to Wrigley"
United States
Paul J.
The price is CA $105
CA $365 total
includes taxes & fees
Nov 4 - Nov 5
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
A multi-story building with a brick facade, large windows, and a visible entrance with steps.

12. Flexhome West Town · Spacious 2BR Duplex · Sleeps 8

Flexhome West Town · Spacious 2BR Duplex · Sleeps 8
West Town
10.0 out of 10, Exceptional, (3 reviews)
"Thank you. We had a wonderful stay."
United States
Janice G.
The price is CA $131
CA $252 total
includes taxes & fees
Dec 1 - Dec 2
Flexhome West Town · Spacious 2BR Duplex · Sleeps 8
A modern living room with a grey sofa, a glass coffee table, and a potted plant.

13. Conveniently Situated 1BR Apartment

Conveniently Situated 1BR Apartment
Hyde Park
The price is CA $106
CA $339 total
includes taxes & fees
Nov 9 - Nov 10
Conveniently Situated 1BR Apartment
A neatly made bed with a black headboard, two fluffy pillows, and a stack of towels.

14. Bright & Spacious 2BR– Prime Hyde Park Location

Bright & Spacious 2BR– Prime Hyde Park Location
Hyde Park
The price is CA $144
CA $318 total
includes taxes & fees
Nov 5 - Nov 6
Bright & Spacious 2BR– Prime Hyde Park Location
A modern dining area with a white table, chairs, and a chandelier. There is a painting on the wall and a plant on the sideboard.

15. Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill

Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
Belmont Cragin
9.6 out of 10, Exceptional, (7 reviews)
"Room was nice and in a safe location."
United States
Jacob
The price is CA $86
CA $510 total
includes taxes & fees
Nov 1 - Nov 2
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
A modern building with a brick facade, large windows, and a central entrance area.

16. 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, (115 reviews)
"Excellent communication from the host, we also appreciated their modern, organized and clean home."
United States
Robin D.
The price is CA $160
CA $372 total
includes taxes & fees
Nov 3 - Nov 4
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
A modern living room with a sofa, a TV, and a dining area with stools.

17. 3BR Complete and Spacious Apartment in Ideal Spot

3BR Complete and Spacious Apartment in Ideal Spot
West Town
8.4 out of 10, Very good, (23 reviews)
"My wife and I stayed here when we came to town for a concert at the united center. We actually walked to the venue and it was about 45 mins, a lovely walk. It was a very convenient location, lovely apartment, and the host communicated very well. Check in and out was easy. Great neighborhood. Would definitely stay here again."
United States
Francis
The price is CA $131
CA $316 total
includes taxes & fees
Nov 1 - Nov 2
3BR Complete and Spacious Apartment in Ideal Spot
A modern kitchen with a large island, coffee maker, and a view of the city.

18. Skyline View Apt - 5 minutes to Downtown - Games + Arcades - Free Parking

Skyline View Apt - 5 minutes to Downtown - Games + Arcades - Free Parking
Lower West Side
8.8 out of 10, Excellent, (6 reviews)
"Incredible place. Awesome neighborhood. Easy access to the freeways. Great neighborhood with tons of great local dining."
United States
Chad
The price is CA $167
CA $405 total
includes taxes & fees
Nov 4 - Nov 5
Skyline View Apt - 5 minutes to Downtown - Games + Arcades - Free Parking
Private kitchen

19. Convenient 2BR Apt w/ In-Unit Laundry

Convenient 2BR Apt w/ In-Unit Laundry
West Town
The price is CA $148
CA $337 total
includes taxes & fees
Nov 23 - Nov 24
Convenient 2BR Apt w/ In-Unit Laundry
A bedroom with a bed, a desk, a chair, a TV, and a window with blinds.

20. Flexhome Wicker Park • Stylish 2BR • Sleeps 6

Flexhome Wicker Park • Stylish 2BR • Sleeps 6
West Town
9.8 out of 10, Exceptional, (10 reviews)
"We liked the location near lots of nice restaurants and nightlife."
United States
Scott F.
The price is CA $113
CA $246 total
includes taxes & fees
Nov 15 - Nov 16
Flexhome Wicker Park • Stylish 2BR • Sleeps 6
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 Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

8/10 Good
"My tv would not connect all 3 days. At my checkout the front desk guy said they have special instructions to turn on the TV. Nobody ever mentioned it to me ."
Sam 3-night trip
Posted less than an hour ago
The Chicago Hotel Collection - Magnificent Mile

Find out more about Southwest Side

Southwest Side Apartments information

Number of reviews
264
Accommodation
648 Apartments
Lowest Price
CA $246
Highest Price
CA $545

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