Apartments in Southwest Side

Change your mind

Book hotels with free cancellation

Treat yourself

Be picky

Search almost a million properties worldwide

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

Featured Apartments in Southwest Side

Relax in this stylish room with a large bed, flat-screen TV, and seating area.

includes taxes & fees

27 July - 28 July

"Great location, charming building. The photos in the listing are very accurate. Super close to the L and restaurants."

includes taxes & fees

27 July - 28 July

Enjoy cooking in this well-lit kitchen with a stainless steel sink and microwave.

"Great property! Would visit again!"

Relax in this inviting bedroom with a comfortable bed, sofa, and lush greenery.

"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 "

includes taxes & fees

11 Aug - 12 Aug

Relax in this stylish living space with a sofa, armchair, and coffee table, plus a dining area with a table and chairs.

"This place was great! Loved my stay!"

includes taxes & fees

27 July - 28 July

1 bedroom, iron/ironing board, WiFi, bed sheets

"Great area and accommodation was nice. Host was great at communicating with. Ravenswood is a great location with lots of restaurants and little shops."

includes taxes & fees

6 Aug - 7 Aug

Enjoy breathtaking views of the city from this rooftop terrace with a glass door and windows.

"This was convenient and check-in process was easy. We would stay here again."

includes taxes & fees

30 July - 31 July

Stroll through the beautifully maintained garden surrounding this charming two-story building with a covered porch area.

"Easy to find, slept like a baby. "

includes taxes & fees

27 July - 28 July

"It was what I thought it would be "

Relax in a serene space with a large bed, bedside tables, and lamps.

"Nice property, enjoyed the stay."

Relax in a spacious living room with a sofa, coffee table, and TV, and enjoy a fully equipped kitchen with a large bed and modern amenities.

"Good location! Brewery, coffee shop, sandwich shop and nice restaurants all within walking distance! Host was very responsive"

includes taxes & fees

5 Aug - 6 Aug

Relax by the pool surrounded by lush flower beds and a glass wall offering a city view.

"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 "

"We showed up with our two grandchildren. The host does not have a working phone number in the account by the way. He said we didn’t actually have a reservation and would not give us access. We were left to find a hotel. Do not recommend 100%. "

Two single beds with white linens and grey headboards, set against a light-colored backdrop.

"Everything was as described, clean and enjoyable, had everything you might need. Its not the biggest studio, but they did a good job with the space. Its great for the price. "

includes taxes & fees

11 Aug - 12 Aug

Enjoy cooking and dining in this well-equipped kitchen with a refrigerator, microwave, and oven.

"We had a great time and the host was very responsive. Pilsen is a great neighborhood, very safe, and super close to down town."

includes taxes & fees

27 July - 28 July

Guests can enjoy the beach with calm waters and a scenic lighthouse in the distance.

"Beautiful property! Short walk to DePaul. We enjoyed our stay very much!Thank you!"

Enjoy breathtaking views of the city from this rooftop terrace with a metal railing and paved floor.

"Loved the space, nice decor, clean. Perfect for 2 people."

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.

"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"