Search Southwest Side Condo Rentals

    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

Next weekend
18 Jul - 20 Jul
In two weeks
25 Jul - 27 Jul
In one month
8 Aug - 10 Aug
In two months
5 Sept - 7 Sept

Featured Condo Rentals in Southwest Side and around

Huge Projector and Designated Workspace - Near Wrigley!
Restful retreat with a neatly made bed and a bedside lamp.

Huge Projector and Designated Workspace - Near Wrigley!

Huge Projector and Designated Workspace - Near Wrigley!
Experience Chicago living near United Center
Enjoy cooking in this well-equipped kitchen with a central island, white cabinetry, and granite countertop.

Experience Chicago living near United Center

9.0 out of 10, Wonderful, (16)
"The place was amazing. The area is questionable but we didn't experience any problems while we stayed. "
Experience Chicago living near United Center
The Chic Urban Oasis Near the Lake!
Overlooking the sandy beach and rocky shoreline, this property offers stunning views of the surrounding lush greenery and distant buildings.

The Chic Urban Oasis Near the Lake!

7.6 out of 10, Good, (4)
"Everything about the host and stay was amazing this will be my go to spot for my family and me"
The Chic Urban Oasis Near the Lake!
Spacious 4BRCondo near Wrigley/Dtwn +FreeParking
Enjoy cooking in this well-equipped kitchen with a central island, microwave, oven, refrigerator, sink, and dishwasher.

Spacious 4BRCondo near Wrigley/Dtwn +FreeParking

9.8 out of 10, Exceptional, (36)
"Fantastic! Great location, parking spot available, very clean! "
Spacious 4BRCondo near Wrigley/Dtwn +FreeParking
Downtown Mich Ave #7| Park View Penthouse +gym
Relax on the outdoor terrace with a barbecue grill and comfortable seating.

Downtown Mich Ave #7| Park View Penthouse +gym

10.0 out of 10, Exceptional, (5)
"Great location...host quick response..."
Downtown Mich Ave #7| Park View Penthouse +gym
Stunning, Spacious, & Sun-soaked 2BR Uptown Condo by AllSet Turnover
Relax in this inviting room with a large bed, a comfortable armchair, and stunning views of the surrounding landscape.

Stunning, Spacious, & Sun-soaked 2BR Uptown Condo by AllSet Turnover

10.0 out of 10, Exceptional, (28)
"Had a great trip and this place was clean and quiet with plenty of room. Second sleeping area would make a great area to hang out and read for a while with the beautiful windows and natural light. "
Stunning, Spacious, & Sun-soaked 2BR Uptown Condo by AllSet Turnover
Urban Chicago Escape ~ 1 Mi to Local Beaches!
Kitchen features a microwave, gas stove, and oven, along with a granite countertop and stainless steel sink.

Urban Chicago Escape ~ 1 Mi to Local Beaches!

9.4 out of 10, Exceptional, (19)
"The place was clean and fit our needs. Great location near the lake and close to the train stop."
Urban Chicago Escape ~ 1 Mi to Local Beaches!
Walking distance to restaurants, shops and Lake Michigan,
Classic corner building with a central entrance, surrounded by a black iron fence and lush greenery.

Walking distance to restaurants, shops and Lake Michigan,

9.6 out of 10, Exceptional, (182)
"We enjoyed our stay in Rogers Park. The property was nice and a welcome retreat at the end of the day. "
Walking distance to restaurants, shops and Lake Michigan,
Entire 2 bedroom with Office & Deck!
Enjoy panoramic views of the surrounding cityscape from this rooftop terrace.

Entire 2 bedroom with Office & Deck!

8.6 out of 10, Excellent, (12)
"Good stay"
Entire 2 bedroom with Office & Deck!
Elizabeth by Coast to Cactus | Chic Artists Loft
Enjoy a formal dining experience with a beautifully set table, complete with teapot and pitcher, in this stylish space.

Elizabeth by Coast to Cactus | Chic Artists Loft

9.4 out of 10, Exceptional, (18)
"Great place, excellent location and close to the trains!!!!"
Elizabeth by Coast to Cactus | Chic Artists Loft
NEW LUXURY CONDO WITH PATIO DECK
Relax on the covered patio with a wooden deck, wicker table, and chair.

NEW LUXURY CONDO WITH PATIO DECK

10.0 out of 10, Exceptional, (169)
"This is the perfect place for you to stay when you’re in Chicago. We have stayed here at least four or five times already the place is immaculate. If you need any help someone is there for you ASAP. "
NEW LUXURY CONDO WITH PATIO DECK
Chicago Chic: Cozy 1BR with Stylish Workspace
Enjoy cooking in this well-equipped kitchen with a microwave, gas stove, toaster oven, and coffee maker.

Chicago Chic: Cozy 1BR with Stylish Workspace

10.0 out of 10, Exceptional, (1)
"We enjoyed our stay here"
Chicago Chic: Cozy 1BR with Stylish Workspace
Bright 2 Bed/2 Bath Condo With Patio Less Than 10 Mins From Major Attractions
Classic residential building with a brick and stone facade, featuring a prominent entrance and large windows.

Bright 2 Bed/2 Bath Condo With Patio Less Than 10 Mins From Major Attractions

8.0 out of 10, Very good, (8)
"We enjoyed our stay, and the condo was perfect for my daughter and me. Great location, prompt responses to all communication with owner, super clean and very comfy beds! Main building corridor could use some sprucing up, but nothing major. Overall, very satisfied! Thanks, Khoy!"
Bright 2 Bed/2 Bath Condo With Patio Less Than 10 Mins From Major Attractions
Walk to Train: Convenient Skokie Condo!
Enjoy cooking in this fully equipped kitchen with a dining area and convenient washing machine.

Walk to Train: Convenient Skokie Condo!

2.0 star property
10.0 out of 10, Exceptional, (2)
"property manager was friendly & accommodating... all info was accurate... no problems at all..."
Walk to Train: Convenient Skokie Condo!
Experience Chicago living near United Center
Enjoy cooking in this well-lit kitchen with a dishwasher, microwave, and oven.

Experience Chicago living near United Center

9.2 out of 10, Wonderful, (25)
"overall place is good, the only bad thing is the location!"
Experience Chicago living near United Center
NEW LUXURY PENTHOUSE CONDO
Relax in a stylish seating area with a wicker sofa, armchair, and coffee table, surrounded by lush greenery and a brick wall.

NEW LUXURY PENTHOUSE CONDO

10.0 out of 10, Exceptional, (184)
"A perfect place to stay. The rooftop bar has the BEST views of the city, especially around sunset. I would definitely stay here again! "
NEW LUXURY PENTHOUSE CONDO
Just remodeled apartment close to airport and mall
Enjoy cooking in this well-equipped kitchen with a stainless steel refrigerator and ample counter space.

Just remodeled apartment close to airport and mall

10.0 out of 10, Exceptional, (11)
"The location was great for my purposes, nice apartment, great neighborhood and close to the airport."
The price is €205
includes taxes & fees
14 Jul - 15 Jul
Just remodeled apartment close to airport and mall
Stunning 3 BR in prime Chicago location
Enjoy cooking in this well-equipped kitchen with a refrigerator, microwave, oven, and dishwasher.

Stunning 3 BR in prime Chicago location

9.8 out of 10, Exceptional, (106)
"Very clean, good location. "
Stunning 3 BR in prime Chicago location
New Modern 3BR, Gym, Workspace, Quiet Location
Relax in this inviting living room with a sofa, coffee table, and comfortable seating area.

New Modern 3BR, Gym, Workspace, Quiet Location

2.0 star property
10.0 out of 10, Exceptional, (1)
"Great time, clean and lovely place in a quiet area!"
New Modern 3BR, Gym, Workspace, Quiet Location
Downtown Penthouse - Mich Ave 2bd | +gym & VIEWS
Enjoy al fresco dining and take in the city views from this rooftop terrace with a seating area, barbecue grill, and lush greenery.

Downtown Penthouse - Mich Ave 2bd | +gym & VIEWS

9.6 out of 10, Exceptional, (27)
"Everything was good and it was in a great location. Renters were kind and frequently checked in. "
Downtown Penthouse - Mich Ave 2bd | +gym & VIEWS
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