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Our top choices for Southwest Side apartments

1. 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
9.6 out of 10, Exceptional, (14 reviews)
"Excellent communication from The Host on a beautiful property located close to everything you could want to do in Chicago. The check-in process was smooth and the host kept in constant communication to ensure that everything was Flawless from check in to check out"
United States
AJ B.
The price is CA $113
CA $386 total
includes taxes & fees
Nov 15 - Nov 16
Large Chicago Apt 3 BR - King Bed - 12 Min Downtown w/ Arcade

2. Spacious Apt | 4 Queen Beds | Free Parking

Spacious Apt | 4 Queen Beds | Free Parking
Brighton Park
The price is CA $181
CA $546 total
includes taxes & fees
Nov 16 - Nov 17
Spacious Apt | 4 Queen Beds | Free Parking

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, (2 reviews)
"Location could not be beat of looking to be near University of Chicago. Within walking distance to several restaurants, coffee, shops, and stores. Perfect for our trip!"
United States
rebecca
The price is CA $100
CA $224 total
includes taxes & fees
Nov 15 - Nov 16
Hyde Park Trendy Studio Apartment in Good Spot

4. 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 $86
CA $274 total
includes taxes & fees
Nov 16 - Nov 17
Great Area Logan Square Apt Games Pets - Sleeps 5

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

Flexhome East Village • Modern 2BR • Quiet Street
West Town
9.6 out of 10, Exceptional, (29 reviews)
"Great location! "
United States
Andrea B.
The price is CA $109
CA $244 total
includes taxes & fees
Dec 9 - Dec 10
Flexhome East Village • Modern 2BR • Quiet Street

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 $72
CA $387 total
includes taxes & fees
Nov 17 - Nov 18
Studio Near Wrigley • Sleeps 4 • Games • Fireplace

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, (25 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 $124
CA $313 total
includes taxes & fees
Nov 18 - Nov 19
3BR Complete and Spacious Apartment in Ideal Spot

8. Sleek & Functional 2-Bedroom Apt

Sleek & Functional 2-Bedroom Apt
Hyde Park
10.0 out of 10, Exceptional, (1 review)
"Great place, great location!"
United States
Lisa T.
The price is CA $130
CA $295 total
includes taxes & fees
Nov 15 - Nov 16
Sleek & Functional 2-Bedroom Apt

9. 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 CA $109
CA $244 total
includes taxes & fees
Nov 15 - Nov 16
Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6

10. Logan Square Boho Getaway - Sleeps 6 - Remodeled

Logan Square Boho Getaway - Sleeps 6 - Remodeled
Avondale
10.0 out of 10, Exceptional, (2 reviews)
"Good location, super communicative host. Was not able to check in until 20 minutes late because housekeeping was still doing laundry. The coffee maker (keurig) didn't work. Everything else was perfect and our host was awesome. Thank you!"
United States
Telea D.
The price is CA $108
CA $390 total
includes taxes & fees
Nov 16 - Nov 17
Logan Square Boho Getaway - Sleeps 6 - Remodeled

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

Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
Uptown
9.2 out of 10, Wonderful, (32 reviews)
"Very nice and clean place in a great location if you are going to Wrigley"
United States
Paul J.
The price is CA $107
CA $372 total
includes taxes & fees
Nov 17 - Nov 18
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake

12. Cozy King bed,Nsmk|Kitchen|Studio 6 Chicago

Cozy King bed,Nsmk|Kitchen|Studio 6 Chicago
Chicago
9.8 out of 10, Exceptional, (28 reviews)
"Great staff clean rooms"
United States
Anonymous traveller
The price is CA $100
CA $110 total
includes taxes & fees
Dec 13 - Dec 14
Cozy King bed,Nsmk|Kitchen|Studio 6 Chicago

13. 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 $88
CA $520 total
includes taxes & fees
Nov 15 - Nov 16
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill

14. 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 $231
CA $490 total
includes taxes & fees
Dec 3 - Dec 4
Skyline View Apt - 5 minutes to Downtown - Games + Arcades - Free Parking

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
The price is CA $123
CA $325 total
includes taxes & fees
Dec 7 - Dec 8
Chic Studio in the Heart of the Gold Coast

16. Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake

Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake
Uptown
8.8 out of 10, Excellent, (20 reviews)
"READ THE FULL LISTING BEFORE YOU BOOK!! I've never had to jump through so many hoops to book a room before! Then they reached out multiple times via Vrbo messaging, texting and now a phone call requesting a 5 star review. What a pain just for a room to sleep in after a concert at Wrigley!With that said, the space was great! Clean, comfy and looked to have all of the essentials should you need to use the apartment more than we did."
United States
Heather B.
The price is CA $107
CA $372 total
includes taxes & fees
Nov 17 - Nov 18
Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake

17. 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 $149
CA $340 total
includes taxes & fees
Nov 17 - Nov 18
Stylish Luxe King bed w/Free Parkng near DT Oak Pk

18. King Bed Non-Smoking

King Bed Non-Smoking
Chicago
10.0 out of 10, Exceptional, (289 reviews)
"Clean room and friendly staff made it a good stay."
United States
Anonymous traveller
The price is CA $88
CA $106 total
includes taxes & fees
Dec 1 - Dec 2
King Bed Non-Smoking

19. 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.
The price is CA $102
CA $241 total
includes taxes & fees
Nov 22 - Nov 23
Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP

20. 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 CA $103
CA $187 total
includes taxes & fees
Dec 10 - Dec 11
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.

Learn more about Southwest Side

Explore attractions like Balzekas Museum of Lithuanian Culture and Ephraim Bajar Cultural Center as you discover things to see and do in Southwest Side.

An airport with multiple runways, parked airplanes, and a large terminal building.
Photo by by Midway Intl Airport
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