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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Southwest Side apartments

A living room with a grey sofa, two chairs, a coffee table, and a small side table.

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 AED 228
AED 874 total
includes taxes & fees
10 Nov - 11 Nov
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 AED 467
AED 1,406 total
includes taxes & fees
4 Nov - 5 Nov
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 AED 301
AED 632 total
includes taxes & fees
16 Nov - 17 Nov
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)
Cozy Urban View Retreat Near Downtown - Sleeps 7
A modern living room with a grey sofa, a dining table with chairs, and a kitchen area with a kettle.

5. Perfect 1BR Spot near Attractions

Perfect 1BR Spot near Attractions
Hyde Park
The price is AED 338
AED 923 total
includes taxes & fees
16 Nov - 17 Nov
Perfect 1BR Spot near Attractions
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.
Great Area Logan Square Apt Games Pets - Sleeps 5
A modern living room with a sofa, a TV, and a dining area with stools.

7. 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, (24 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 AED 738
AED 1,327 total
includes taxes & fees
29 Nov - 30 Nov
3BR Complete and Spacious Apartment in Ideal Spot
A dining area with a round wooden table, four upholstered chairs, a vase with white flowers, and two wall-mounted light fixtures.

8. 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 AED 154
AED 914 total
includes taxes & fees
5 Nov - 6 Nov
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.

9. Cozy Charm Studio Apt in Chicago

Cozy Charm Studio Apt in Chicago
Hyde Park
The price is AED 301
AED 834 total
includes taxes & fees
16 Nov - 17 Nov
Cozy Charm Studio Apt in Chicago
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.

10. 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 AED 227
AED 1,335 total
includes taxes & fees
4 Nov - 5 Nov
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
A rooftop terrace with a brick wall, large windows, and a metal railing.

11. 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 AED 275
AED 954 total
includes taxes & fees
4 Nov - 5 Nov
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
A modern living room with a grey sofa, a glass coffee table, and a potted plant.

12. Conveniently Situated 1BR Apartment

Conveniently Situated 1BR Apartment
Hyde Park
10.0 out of 10, Exceptional, (1 review)
"Cute, cozy place in walking distance to UChicago. Would stay here again."
United States
Jane L.
The price is AED 246
AED 797 total
includes taxes & fees
4 Nov - 5 Nov
Conveniently Situated 1BR Apartment
A neatly made bed with a black headboard, two fluffy pillows, and a stack of towels.

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

Bright & Spacious 2BR– Prime Hyde Park Location
Hyde Park
Bright & Spacious 2BR– Prime Hyde Park Location
A hotel room with a large bed, a desk, a chair, a lamp, and artwork on the wall.

14. 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 AED 297
AED 647 total
includes taxes & fees
10 Nov - 11 Nov
Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6
A wooden dining table with two chairs, a potted plant, and a painting on the wall.

15. 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
Chic Studio in the Heart of the Gold Coast
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.
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
A modern bedroom with a bed, a sofa, and a hanging plant.

17. Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (110 reviews)
"Great location for us near the Edgewood neighborhood. Property was very clean, bed comfy, and owner responsive. We’d stay here again!"
United States
Sherry M.
The price is AED 241
AED 488 total
includes taxes & fees
23 Nov - 24 Nov
Cozy studio in Andersonville Chicago
A dining area with a table set for two, a black leather sofa, and a ceiling fan.

18. 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, (35 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.
Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
A modern kitchen with a large island, coffee maker, and a view of the city.

19. 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
Skyline View Apt - 5 minutes to Downtown - Games + Arcades - Free Parking
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
10.0 out of 10, Exceptional, (3 reviews)
"Wouldn’t change a thing. Great location to downtown and all the things that we wanted to do."
United States
beth m.
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

Arlo Chicago

Arlo Chicago

8/10 Good
"Excellent location. Very comfortable beds and extremely healthy and friendly staff."
Guillermo 1-night trip
Posted less than an hour ago
Arlo Chicago

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