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Check prices for these dates

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1 Aug - 3 Aug
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22 Aug - 24 Aug
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19 Sept - 21 Sept

Featured Apartments in Far Southwest Side and around

Clean & Equipped 1BR Apt
A small dining table with two chairs sits against a wall, accompanied by a potted plant.

Clean & Equipped 1BR Apt

8.0 out of 10, Very good, (6)
The price is €166
includes taxes & fees
28 Jul - 29 Jul
Clean & Equipped 1BR Apt
Lakeview 2BR Apartment
Fridge, microwave, oven, stovetop

Lakeview 2BR Apartment

8.8 out of 10, Excellent, (3)
"Great location, charming building. The photos in the listing are very accurate. Super close to the L and restaurants."
The price is €166
includes taxes & fees
27 Jul - 28 Jul
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, (14)
"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 €149
includes taxes & fees
28 Jul - 29 Jul
Cozy studio in Andersonville Chicago
Charming 2BR in Vibrant Lakeview
Modern kitchen with stainless steel stove, white cabinetry, and wooden flooring.

Charming 2BR in Vibrant Lakeview

9.6 out of 10, Exceptional, (4)
"This place was great! Loved my stay!"
The price is €168
includes taxes & fees
27 Jul - 28 Jul
Charming 2BR in Vibrant Lakeview
Nice 1BR Spot, Unwind & Relax
Fridge, microwave, oven, stovetop

Nice 1BR Spot, Unwind & Relax

10.0 out of 10, Exceptional, (2)
"Great area and accommodation was nice. Host was great at communicating with. Ravenswood is a great location with lots of restaurants and little shops."
The price is €157
includes taxes & fees
30 Jul - 31 Jul
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, (35)
"This was convenient and check-in process was easy. We would stay here again."
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
9.6 out of 10, Exceptional, (31)
"Easy to find, slept like a baby. "
The price is €282
includes taxes & fees
27 Jul - 28 Jul
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!

9.0 out of 10, Wonderful, (32)
"It was what I thought it would be "
Wrigley/Lakeview Gem- Walk to Wrigley Field/ Parking available!
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, (96)
"Nice property, enjoyed the stay."
Walk to Wrigley/ Boystown -Chicago 3BR/2Ba Duplex-paid parking available!
Spacious 3BR | 2BA Family-Friendly Home
Relax in this stylish living room with a plush sofa, round coffee table, and geometric art piece.

Spacious 3BR | 2BA Family-Friendly Home

10.0 out of 10, Exceptional, (1)
"Good location! Brewery, coffee shop, sandwich shop and nice restaurants all within walking distance! Host was very responsive"
The price is €180
includes taxes & fees
29 Jul - 30 Jul
Spacious 3BR | 2BA Family-Friendly Home
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

9.6 out of 10, Exceptional, (11)
"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

2.0 out of 10, (1)
"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%. "
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, (2)
"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. "
The price is €164
includes taxes & fees
18 Aug - 19 Aug
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

9.6 out of 10, Exceptional, (4)
"We had a great time and the host was very responsive. Pilsen is a great neighborhood, very safe, and super close to down town."
The price is €216
includes taxes & fees
28 Jul - 29 Jul
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, (151)
"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, (15)
"Loved the space, nice decor, clean. Perfect for 2 people."
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

6.6 out of 10, (4)
"Very nice place and nice host "
Central Haven Escape: Stylish 3BR With Free Parking
1F Chicago's Little italy Graystone nearDowntown
Stately entrance with a black door, flanked by white columns and a potted plant with vibrant flowers.

1F Chicago's Little italy Graystone nearDowntown

10.0 out of 10, Exceptional, (147)
"This is an awesome place to stay in Chicago."
1F Chicago's Little italy Graystone nearDowntown
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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Top Far Southwest Side Hotel Reviews

citizenM Chicago Downtown

citizenM Chicago Downtown

10/10 Excellent
"What a great hotel -selected from many close to my conference at the Hyatt. It was also walking distance (1.2 miles) from Union Station (Amtrak). Hotel check-in and check-out is seamless -all done at central kiosk. Hotel staff ever-present to assist. Rooms are exceptionally clean and comfortable. Every room control (blinds-curtains-climate-TV) accessed by room iPad or cell phone app. Eco friendly -no single use disposables. Hotel nearby to so many dining options and entertainment. Loved the friendly and helpful staff -I would stay here again! "
John 4-night trip
Posted 17 hours ago
citizenM Chicago Downtown