Apartments in Southwest Side for Rent

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Sep 5 - Sep 7
In two months
Oct 17 - Oct 19
In three months
Nov 14 - Nov 16
In four months
Dec 12 - Dec 14

Apartments in Southwest Side

Our top choices for Southwest Side apartments

Clean & Equipped 1BR Apt
1 bedroom, iron/ironing board, WiFi, bed sheets

Clean & Equipped 1BR Apt

8.4 out of 10, Very Good, (15)
"Good experience. Would stay there again "
The price is ￥13,560
￥30,386 total
includes taxes & fees
Sep 3 - Sep 4
Clean & Equipped 1BR Apt
Charming 2BR in Vibrant Lakeview
2 bedrooms, iron/ironing board, travel crib, WiFi

Charming 2BR in Vibrant Lakeview

8.8 out of 10, Excellent, (10)
The price is ￥13,855
￥33,306 total
includes taxes & fees
Sep 3 - Sep 4
Charming 2BR in Vibrant Lakeview
Stylish 1BR in Lakeview Chicago
Fridge, microwave, oven, stovetop

Stylish 1BR in Lakeview Chicago

8.4 out of 10, Very Good, (11)
"This is a great apartment. It was very clean, well equipped kitchen and comfortable bed. Close to restaurants, grocery store, Starbucks and Wrigley Field. We could not find any parking on the street where the apartment is. I do recommend that you get in touch with the property owners couple of days prior to your visit because there is a vetting process prior to getting the keys to the apartment. "
The price is ￥15,329
￥32,638 total
includes taxes & fees
Sep 3 - Sep 4
Stylish 1BR in Lakeview Chicago
Relaxing Chicago Studio
Desk, iron/ironing board, WiFi, bed sheets

Relaxing Chicago Studio

10.0 out of 10, Exceptional, (6)
"Had a great stay. Great location. "
The price is ￥14,833
￥30,201 total
includes taxes & fees
Sep 16 - Sep 17
Relaxing Chicago Studio
Cozy, Fully Set-Up 1BR Space
Fridge, microwave, oven, stovetop

Cozy, Fully Set-Up 1BR Space

8.8 out of 10, Excellent, (15)
"Great place! 15 min walk to Wrigley "
The price is ￥13,560
￥30,386 total
includes taxes & fees
Sep 3 - Sep 4
Cozy, Fully Set-Up 1BR Space
Cozy Studio in Hyde Park-Walk to Lake & University
Microwave, oven, stovetop, coffee/tea maker

Cozy Studio in Hyde Park-Walk to Lake & University

10.0 out of 10, Exceptional, (2)
"This place was nice and clean and close to what I needed to do. I appreciated that it was affordable. "
The price is ￥13,560
￥28,550 total
includes taxes & fees
Sep 3 - Sep 4
Cozy Studio in Hyde Park-Walk to Lake & University
BOUTIQUE DESIGNER FLAT IN LINCOLN PARK
Interior

BOUTIQUE DESIGNER FLAT IN LINCOLN PARK

BOUTIQUE DESIGNER FLAT IN LINCOLN PARK
Homey 1BR Space Apartment
1 bedroom, iron/ironing board, WiFi, bed sheets

Homey 1BR Space Apartment

9.0 out of 10, Wonderful, (4)
"Great location. Very walkable to restaurants and bars. Awesome park nearby. Host was easy to communicate with. "
The price is ￥12,528
￥28,994 total
includes taxes & fees
Sep 3 - Sep 4
Homey 1BR Space Apartment
Cozy studio in Andersonville Chicago
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cozy studio in Andersonville Chicago

9.2 out of 10, Wonderful, (21)
"It was a great location, internet was a little spotty on streaming services but we were in walking distance to so much it was worth it "
The price is ￥13,265
￥25,462 total
includes taxes & fees
Sep 3 - Sep 4
Cozy studio in Andersonville Chicago
Nice 1BR Spot, Unwind & Relax
TV

Nice 1BR Spot, Unwind & Relax

10.0 out of 10, Exceptional, (13)
"Super clean. Cozy. SAFE. Short drive to nearly every big attraction! Host was very communicative and kind!!"
The price is ￥12,528
￥28,994 total
includes taxes & fees
Sep 3 - Sep 4
Nice 1BR Spot, Unwind & Relax
Uptown Studio Gem Sum
TV

Uptown Studio Gem Sum

8.8 out of 10, Excellent, (3)
"This studio is very clean and is located in a neighborhood with access to anything you would want to do or see. The stairway and halls are not pristine, but studio is good. Neighbors were quiet and seldom seen during my stay. Excellent restaurant right across the street and grocery nearby. Wrigley Field is easy walk. Check in was confusing for me, but it worked out. "
The price is ￥13,560
￥28,550 total
includes taxes & fees
Sep 3 - Sep 4
Uptown Studio Gem Sum
Sleek Style 3BR Haven - Free Parking
3 bedrooms, iron/ironing board, travel crib, WiFi

Sleek Style 3BR Haven - Free Parking

9.6 out of 10, Exceptional, (7)
The price is ￥16,213
￥38,643 total
includes taxes & fees
Aug 25 - Aug 26
Sleek Style 3BR Haven - Free Parking
Luxurious 3 Bedroom Apartment in Chicago
Microwave, oven, stovetop, dishwasher

Luxurious 3 Bedroom Apartment in Chicago

9.2 out of 10, Wonderful, (21)
"Great property! Would visit again!"
Luxurious 3 Bedroom Apartment in Chicago
Central Haven Escape: Stylish 3BR With Free Parking
Smart TV

Central Haven Escape: Stylish 3BR With Free Parking

6.6 out of 10, (4)
"Very nice place and nice host "
Central Haven Escape: Stylish 3BR With Free Parking
Lakeview 2BR Apartment
Fridge, microwave, oven, stovetop

Lakeview 2BR Apartment

9.2 out of 10, Wonderful, (12)
"Great experience overall. Check-in was easy and the unit was very well kept. Very happy that we were so close to so much public transportation. It is a little noisy for those who aren’t used to hearing the L train nearby. Parking is hard to find, but there is paid parking nearby and easy to access public transit. If you plan on parking your car for the full time you’re there."
The price is ￥13,560
￥32,961 total
includes taxes & fees
Sep 3 - Sep 4
Lakeview 2BR Apartment
Wicker Park 2Bdrm Near Downtown & Salt Shed Weekend Special 149.00 August 22-24
Exterior detail

Wicker Park 2Bdrm Near Downtown & Salt Shed Weekend Special 149.00 August 22-24

9.8 out of 10, Exceptional, (40)
"Loved the location of the place. Great place to walk to bars and places to eat. Communication with Cheryl was great, parking was no problem at all. "
Wicker Park 2Bdrm Near Downtown & Salt Shed Weekend Special 149.00 August 22-24
Cozy & Furnished 2BR Unit
Interior

Cozy & Furnished 2BR Unit

9.8 out of 10, Exceptional, (6)
The price is ￥12,970
￥32,085 total
includes taxes & fees
Sep 3 - Sep 4
Cozy & Furnished 2BR Unit
New Garden Studio near Wrigley/DePaul/Dwtn
Desk, iron/ironing board, travel crib, WiFi

New Garden Studio near Wrigley/DePaul/Dwtn

9.4 out of 10, Exceptional, (18)
"Loved our stay! Everything was exactly as described online. Great communication with host the entire time, everything was clean and tidy. Location was great and had close access to everything we needed. "
New Garden Studio near Wrigley/DePaul/Dwtn
1F Chicago's Little italy Graystone nearDowntown
Exterior

1F Chicago's Little italy Graystone nearDowntown

10.0 out of 10, Exceptional, (151)
"This is an awesome place to stay in Chicago."
1F Chicago's Little italy Graystone nearDowntown
Bright & Roomy 3BR in Pilsen
Interior

Bright & Roomy 3BR in Pilsen

7.8 out of 10, Good, (7)
The price is ￥17,982
￥44,755 total
includes taxes & fees
Aug 25 - Aug 26
Bright & Roomy 3BR in Pilsen
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Southwest Side Hotel Reviews

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

10/10 Excellent
"Parking"
Terri 4-night trip
Posted 16 hours ago
The Allegro Royal Sonesta Hotel Chicago Loop