Search Condo Rentals in Southwest Side

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15 Aug - 17 Aug
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22 Aug - 24 Aug
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5 Sept - 7 Sept
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3 Oct - 5 Oct
Spacious 4BRCondo near Wrigley/Dtwn +FreeParking
Fridge, microwave, oven, stovetop

Spacious 4BRCondo near Wrigley/Dtwn +FreeParking

9.8 out of 10, Exceptional, (39)
"Fantastic! Great location, parking spot available, very clean! "
Spacious 4BRCondo near Wrigley/Dtwn +FreeParking
Experience Chicago living near United Center
Fridge, microwave, oven, stovetop

Experience Chicago living near United Center

9.0 out of 10, Wonderful, (17)
"Clean and cozy . Great communication . Not the best neighborhood but felt secure with passcode locks ! Would stay again "
Experience Chicago living near United Center
3BR Modern Condo near Wrigley/Dwtn +Free Parking
Fridge, microwave, oven, stovetop

3BR Modern Condo near Wrigley/Dwtn +Free Parking

9.4 out of 10, Exceptional, (33)
"3 night stay with a family of 5. Was perfect for us! Clean, quiet, and easy to access. Would stay again! "
The price is HK$3,321
HK$6,445 total
includes taxes & fees
31 Aug - 1 Sept
3BR Modern Condo near Wrigley/Dwtn +Free Parking
1-bedroom condo next to Chicago Midway International Airport
Fridge, microwave, oven, stovetop

1-bedroom condo next to Chicago Midway International Airport

10.0 out of 10, Exceptional, (6)
"super nice place!"
1-bedroom condo next to Chicago Midway International Airport
The Suite Spot • Eclectic • Modern • Central • Sleeps 6
Outdoor dining

The Suite Spot • Eclectic • Modern • Central • Sleeps 6

10.0 out of 10, Exceptional, (18)
"Great Place, would stay there again!"
The Suite Spot • Eclectic • Modern • Central • Sleeps 6
Downtown Mich Ave #7| Park View Penthouse +gym
Property grounds

Downtown Mich Ave #7| Park View Penthouse +gym

9.8 out of 10, Exceptional, (6)
"Great location...host quick response..."
Downtown Mich Ave #7| Park View Penthouse +gym
Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field
Smart TV, fireplace, printers

Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field

10.0 out of 10, Exceptional, (103)
"The property is half a block from Wrigley, the owners are easy to communicate with and extremely accommodating. One of the best places I've stayed, would recommend to anyone."
Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field
NEW LUXURY PENTHOUSE CONDO
Terrace/patio

NEW LUXURY PENTHOUSE CONDO

10.0 out of 10, Exceptional, (185)
"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
Chic Urban Retreat Near Wrigley Field w/Parking
Exterior detail

Chic Urban Retreat Near Wrigley Field w/Parking

10.0 out of 10, Exceptional, (27)
"The property was nice. It had everything we needed, close to a store, restaurants and the train. "
The price is HK$1,178
HK$3,574 total
includes taxes & fees
11 Aug - 12 Aug
Chic Urban Retreat Near Wrigley Field w/Parking
Entire 2 bedroom with Office & Deck!
Property grounds

Entire 2 bedroom with Office & Deck!

9.0 out of 10, Wonderful, (12)
"Good stay"
Entire 2 bedroom with Office & Deck!
Spacious, Clean and Steps from Wrigley Field!
Private kitchen

Spacious, Clean and Steps from Wrigley Field!

9.8 out of 10, Exceptional, (15)
"Great stay in Wrigleyville. Steps to the park and all the entertainment. Would definitely stay again. "
Spacious, Clean and Steps from Wrigley Field!
Stunning 3 BR in prime Chicago location
Fridge, microwave, oven, stovetop

Stunning 3 BR in prime Chicago location

9.8 out of 10, Exceptional, (109)
"This property had all the comforts we needed and is in a great location. Would absolutely love to stay there again!"
Stunning 3 BR in prime Chicago location
NEW LUXURY CONDO WITH PATIO DECK
Property grounds

NEW LUXURY CONDO WITH PATIO DECK

10.0 out of 10, Exceptional, (175)
"Throughly enjoyed our weekend in Chicago. The property was as advertised and very comfortable. The host was very communicative and helpful in answering our many questions. "
NEW LUXURY CONDO WITH PATIO DECK
Lincoln Park/depaul 8 Bed 1 Parking Spot Sleeps 18 by AllSet Turnover
Dining

Lincoln Park/depaul 8 Bed 1 Parking Spot Sleeps 18 by AllSet Turnover

9.6 out of 10, Exceptional, (15)
"We had an absolutely lovely stay here!"
Lincoln Park/depaul 8 Bed 1 Parking Spot Sleeps 18 by AllSet Turnover
Bright 2 Bed/2 Bath Condo With Patio Less Than 10 Mins From Major Attractions
Exterior

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
Bright 2BR Apt w/ Private Entrance & Laundry by AllSet Turnover
Interior

Bright 2BR Apt w/ Private Entrance & Laundry by AllSet Turnover

2.0 star property
8.4 out of 10, Very good, (5)
"Stayed 3 nights visiting my son. Good location, large apt., nicely decorated. I wish the tub/shower had a grab bar. The jacuzzi tub has a high profile and is difficult for older adults to step in and out. It was quiet inside--even the nearby train was hard to hear. I did trip several times on the drain cover right outside the entry door. Be careful!"
Bright 2BR Apt w/ Private Entrance & Laundry by AllSet Turnover
NEW! Vintage 3 Bed Condo in Chicagolands Trendy Berwyn by AllSet Turnover
Fridge, microwave, oven, dishwasher

NEW! Vintage 3 Bed Condo in Chicagolands Trendy Berwyn by AllSet Turnover

6.0 out of 10, (1)
"Location is great, but there are few issues:1- house was not very clean (e.g., floor was dirty)2- the front door windows don't have blinds, and given the shared entrance with the other unit, there was not privacy, anyone can peak inside my apartment.The same applies to the window by the stairs in the back."
NEW! Vintage 3 Bed Condo in Chicagolands Trendy Berwyn by AllSet Turnover
Elizabeth by Coast to Cactus | Chic Artists Loft
Interior

Elizabeth by Coast to Cactus | Chic Artists Loft

9.2 out of 10, Wonderful, (20)
"Great place, excellent location and close to the trains!!!!"
Elizabeth by Coast to Cactus | Chic Artists Loft
Experience Chicago living near United Center
Fridge, microwave, oven, stovetop

Experience Chicago living near United Center

9.2 out of 10, Wonderful, (26)
"overall place is good, the only bad thing is the location!"
Experience Chicago living near United Center
Walking distance to restaurants, shops and Lake Michigan,
Exterior

Walking distance to restaurants, shops and Lake Michigan,

9.6 out of 10, Exceptional, (183)
"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,
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 Southwest Side Hotel Reviews

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

10/10 Excellent
"Front desk was extremely helpful, room was a great size and comfortable. The area felt very safe, walkable to quite a few things. Absolutely would stay here again! "
Andrea 2-night trip
Posted 7 hours ago
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical