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Check prices for these dates

Next weekend
Jul 25 - Jul 27
In two weeks
Aug 1 - Aug 3
In one month
Aug 15 - Aug 17
In two months
Sep 12 - Sep 14

Browse Select Southwest Side Apartments

Clean & Equipped 1BR Apt
Relax in this stylish room with a large bed, flat-screen TV, and seating area.

Clean & Equipped 1BR Apt

10.0 out of 10, Exceptional, (1)
"Was very clean and comfortable simply furnished but nice close to the things we were looking for. "
The price is CA $129
CA $255 total
includes taxes & fees
Jul 20 - Jul 21
Clean & Equipped 1BR Apt
Lakeview 2BR Apartment
Fridge, microwave, oven, stovetop

Lakeview 2BR Apartment

10.0 out of 10, Exceptional, (1)
"Great location, charming building. The photos in the listing are very accurate. Super close to the L and restaurants."
The price is CA $134
CA $289 total
includes taxes & fees
Jul 28 - Jul 29
Lakeview 2BR Apartment
Luxurious 3 Bedroom Apartment in Chicago
Enjoy cooking in this well-lit kitchen with a stainless steel sink and microwave.

Luxurious 3 Bedroom Apartment in Chicago

9.6 out of 10, Exceptional, (12)
"Great property! Would visit again!"
Luxurious 3 Bedroom Apartment in Chicago
Cozy studio in Andersonville Chicago
Relax in this inviting bedroom with a comfortable bed, sofa, and lush greenery.

Cozy studio in Andersonville Chicago

9.2 out of 10, Wonderful, (10)
"I thought I was in a $300 night hotel, private, and serene surrounding"
The price is CA $130
CA $242 total
includes taxes & fees
Aug 11 - Aug 12
Cozy studio in Andersonville Chicago
Charming 2BR in Vibrant Lakeview
Relax in this stylish living space with a sofa, armchair, and coffee table, plus a dining area with a table and chairs.

Charming 2BR in Vibrant Lakeview

9.0 out of 10, Wonderful, (2)
"The host was very communicative, the location was in a safe clean neighborhood. Great location for exploring north Chicago. Home was super cute and clean, perfect for our mother/daughter trip. "
The price is CA $133
CA $259 total
includes taxes & fees
Jul 20 - Jul 21
Charming 2BR in Vibrant Lakeview
Nice 1BR Spot, Unwind & Relax
1 bedroom, iron/ironing board, WiFi, bed sheets

Nice 1BR Spot, Unwind & Relax

10.0 out of 10, Exceptional, (2)
"Very nice property. Just what I was looking for. Loved the location. Very clean, very cozy, very comfortable bed. Easy check-in process. "
The price is CA $121
CA $247 total
includes taxes & fees
Jul 21 - Jul 22
Nice 1BR Spot, Unwind & Relax
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Enjoy breathtaking views of the city from this rooftop terrace with a glass door and windows.

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

10.0 out of 10, Exceptional, (34)
"This was convenient and check-in process was easy. We would stay here again."
The price is CA $96
CA $327 total
includes taxes & fees
Jul 21 - Jul 22
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
2-bedroom apartment just 2 minutes drive to Wrigley Field
Stroll through the beautifully maintained garden surrounding this charming two-story building with a covered porch area.

2-bedroom apartment just 2 minutes drive to Wrigley Field

2.0 star property
9.4 out of 10, Exceptional, (29)
"Easy to find, slept like a baby. "
The price is CA $184
CA $445 total
includes taxes & fees
Jul 24 - Jul 25
2-bedroom apartment just 2 minutes drive to Wrigley Field
Wrigley/Lakeview Gem- Walk to Wrigley Field/ Parking available!
Fridge, microwave, oven, stovetop

Wrigley/Lakeview Gem- Walk to Wrigley Field/ Parking available!

8.8 out of 10, Excellent, (29)
"It was what I thought it would be "
Wrigley/Lakeview Gem- Walk to Wrigley Field/ Parking available!
2BR Apt Beautifully Furnished - Grace 11-1
Experience a spacious living area with a dining space, cozy seating, and a well-equipped kitchen.

2BR Apt Beautifully Furnished - Grace 11-1

10.0 out of 10, Exceptional, (1)
The price is CA $201
CA $367 total
includes taxes & fees
Aug 12 - Aug 13
2BR Apt Beautifully Furnished - Grace 11-1
Walk to Wrigley/ Boystown -Chicago 3BR/2Ba Duplex-paid parking available!
Relax in a serene space with a large bed, bedside tables, and lamps.

Walk to Wrigley/ Boystown -Chicago 3BR/2Ba Duplex-paid parking available!

9.0 out of 10, Wonderful, (93)
"Nice property, enjoyed the stay."
Walk to Wrigley/ Boystown -Chicago 3BR/2Ba Duplex-paid parking available!
Michigan Ave 2BR: Balcony, Exclusive Access
Relax by the pool surrounded by lush flower beds and a glass wall offering a city view.

Michigan Ave 2BR: Balcony, Exclusive Access

10.0 out of 10, Exceptional, (10)
"Roomy 2 bedroom with great hideaway beds.Excellent location easy to get everywhere. Super responsive hosts Nice building with gym and parking option for visitors "
Michigan Ave 2BR: Balcony, Exclusive Access
Spacious 3-bedroom apartment in gorgeous Chicago with WiFi, AC
Interior

Spacious 3-bedroom apartment in gorgeous Chicago with WiFi, AC

Spacious 3-bedroom apartment in gorgeous Chicago with WiFi, AC
Relaxing Chicago Studio
Two single beds with white linens and grey headboards, set against a light-colored backdrop.

Relaxing Chicago Studio

10.0 out of 10, Exceptional, (1)
"The location was perfect. It was clean and just as pictured. For a studio, it had plenty of room. "
The price is CA $123
CA $259 total
includes taxes & fees
Jul 21 - Jul 22
Relaxing Chicago Studio
Bright & Roomy 4BR in Pilsen
Enjoy cooking and dining in this well-equipped kitchen with a refrigerator, microwave, and oven.

Bright & Roomy 4BR in Pilsen

10.0 out of 10, Exceptional, (2)
"We enjoyed our time at this apartment. It was as promised with even more. We had a blast, slept well and we were close to most of the activities in the city. Would highly recommend. "
The price is CA $191
CA $325 total
includes taxes & fees
Jul 21 - Jul 22
Bright & Roomy 4BR in Pilsen
Lakeview/LincolnPark 2BR/1BA Updated Vintage Apartment in walkable neighborhood
Guests can enjoy the beach with calm waters and a scenic lighthouse in the distance.

Lakeview/LincolnPark 2BR/1BA Updated Vintage Apartment in walkable neighborhood

10.0 out of 10, Exceptional, (149)
"Beautiful property! Short walk to DePaul. We enjoyed our stay very much!Thank you!"
Lakeview/LincolnPark 2BR/1BA Updated Vintage Apartment in walkable neighborhood
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
Enjoy breathtaking views of the city from this rooftop terrace with a metal railing and paved floor.

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

8.6 out of 10, Excellent, (14)
"Loved the space, nice decor, clean. Perfect for 2 people."
The price is CA $118
CA $353 total
includes taxes & fees
Jul 20 - Jul 21
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
BIG Downtown Penthouse|Vintage 3bd (GYM+Balcony)
Relax in this open-plan living area with a comfortable sofa and dining table for four, featuring a well-equipped kitchen and a cozy side table.

BIG Downtown Penthouse|Vintage 3bd (GYM+Balcony)

9.4 out of 10, Exceptional, (16)
"Large and spacious shared space and living room, lots of amenities like blankets, pillows, and towels. Comfortable beds and many beds and couches. AC in every room. Fantastic place to stay"
BIG Downtown Penthouse|Vintage 3bd (GYM+Balcony)
Central Haven Escape: Stylish 3BR With Free Parking
Relax in a comfortable seating area with a sofa and two chairs, surrounded by large windows and a wooden door.

Central Haven Escape: Stylish 3BR With Free Parking

7.4 out of 10, Good, (3)
"Very nice place and nice host "
Central Haven Escape: Stylish 3BR With Free Parking
Cozy Studio in Hyde Park-Walk to Lake & University
Compact kitchen with a stainless steel sink, gas stove, and ample countertop space.

Cozy Studio in Hyde Park-Walk to Lake & University

10.0 out of 10, Exceptional, (1)
"The building in itself is very beautiful and serene and the apartment is very well kept, clean and has all the amenities one needs. The hosts are also incredible and just a txt away."
The price is CA $129
CA $255 total
includes taxes & fees
Jul 16 - Jul 17
Cozy Studio in Hyde Park-Walk to Lake & University
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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