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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Featured Condo Rentals in Southwest Side

Chic Urban Retreat Near Wrigley Field w/Parking
Exterior detail

Chic Urban Retreat Near Wrigley Field w/Parking

10.0 out of 10, Exceptional, (32)
"The property was amazing, clean and well organized. Parking was a breeze and check in was easy. Would recommend this place to anyone looking to stay in the area."
The price is AU$715
includes taxes & fees
24 Aug - 25 Aug
Chic Urban Retreat Near Wrigley Field w/Parking
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
Spacious 4BRCondo near Wrigley/Dtwn +FreeParking
Fridge, microwave, oven, stovetop

Spacious 4BRCondo near Wrigley/Dtwn +FreeParking

9.6 out of 10, Exceptional, (42)
"It was a great place to stay and very spacious!"
The price is AU$1,290
includes taxes & fees
18 Sept - 19 Sept
Spacious 4BRCondo near Wrigley/Dtwn +FreeParking
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, (35)
"3 night stay with a family of 5. Was perfect for us! Clean, quiet, and easy to access. Would stay again! "
The price is AU$1,290
includes taxes & fees
31 Aug - 1 Sept
3BR Modern Condo near Wrigley/Dwtn +Free Parking
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
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
Spacious & Comfortable 3 Bedrooms + Bonus Room
4 bedrooms, desk, iron/ironing board, free WiFi

Spacious & Comfortable 3 Bedrooms + Bonus Room

The price is AU$840
includes taxes & fees
25 Aug - 26 Aug
Spacious & Comfortable 3 Bedrooms + Bonus Room
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
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
MICH AVE #23 2bd/2ba Downtown, Museums w/ Views
Interior

MICH AVE #23 2bd/2ba Downtown, Museums w/ Views

9.8 out of 10, Exceptional, (23)
"It was perfect and everything as promised. "
MICH AVE #23 2bd/2ba Downtown, Museums w/ Views
Comfortable Condo in the Heart of Bronzeville by RedAwning
Fridge, microwave, oven, coffee/tea maker

Comfortable Condo in the Heart of Bronzeville by RedAwning

6.6 out of 10, (4)
"There was confusion with VRBO regarding our arrival date, no fault of the property owner. They made arrangements to clean the unit and provide lunch for our group while we waited and offered a second night free for the inconvenience. Highly recommend. Property owner went above and beyond!"
The price is AU$634
includes taxes & fees
25 Aug - 26 Aug
Comfortable Condo in the Heart of Bronzeville by RedAwning
Gorgeous 3BR River North Condo - Free Parking
Fridge, microwave, oven, stovetop

Gorgeous 3BR River North Condo - Free Parking

10.0 out of 10, Exceptional, (20)
"House was very accommodating and well stocked for a family of 4 including two teenage children. Check in was easy and as described, and location was easy walking distance to restaurants and shopping. Would definitely stay here again when in Chicago!"
Gorgeous 3BR River North Condo - Free Parking
Entire 2 bedroom with Office & Deck!
Property grounds

Entire 2 bedroom with Office & Deck!

8.8 out of 10, Excellent, (13)
"Good stay"
Entire 2 bedroom with Office & Deck!
Bronzeville Manor walking distance to hospitals
Interior

Bronzeville Manor walking distance to hospitals

9.8 out of 10, Exceptional, (17)
"Great location, very clean place. Ample street parking and the owner is very nice. I’ll definitely be booking this location again."
Bronzeville Manor walking distance to hospitals
Beautiful, modern 3 bed 2 bath condo near Hyde Park, Obama Center and Lakefront
Smart TV, computer monitors

Beautiful, modern 3 bed 2 bath condo near Hyde Park, Obama Center and Lakefront

10.0 out of 10, Exceptional, (2)
"Clean, comfortable, and quiet! We enjoyed the condo very much. "
Beautiful, modern 3 bed 2 bath condo near Hyde Park, Obama Center and Lakefront
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
Wrigley Field All Star Suite 3 Bedrooms 2 Bath
Exterior

Wrigley Field All Star Suite 3 Bedrooms 2 Bath

9.4 out of 10, Exceptional, (18)
"Enjoyed a dinner party with friends Place was perfect Management helpful "
The price is AU$1,483
includes taxes & fees
24 Aug - 25 Aug
Wrigley Field All Star Suite 3 Bedrooms 2 Bath
Up to 8 Spacious lovely Chicago-style 3BDR condo. Safe & quiet neighborhood
Fridge, microwave, oven, stovetop

Up to 8 Spacious lovely Chicago-style 3BDR condo. Safe & quiet neighborhood

8.6 out of 10, Excellent, (19)
"This place was clean and host was very nice"
Up to 8 Spacious lovely Chicago-style 3BDR condo. Safe & quiet neighborhood
Parking, Balcony, Near Universities, Ravinia, NAPA & Train to Chicago
Fridge, microwave, oven, stovetop

Parking, Balcony, Near Universities, Ravinia, NAPA & Train to Chicago

9.8 out of 10, Exceptional, (19)
"Everything went well. Will stay again."
Parking, Balcony, Near Universities, Ravinia, NAPA & Train to Chicago
Perfect for Groups! Steps to the Beach and Room for All! Enjoy All Andersonville Has to Offer! by AllSet Turnover
Fridge, microwave, oven, dishwasher

Perfect for Groups! Steps to the Beach and Room for All! Enjoy All Andersonville Has to Offer! by AllSet Turnover

10.0 out of 10, Exceptional, (35)
"Wonderful location and home. Thanks to our hosts!"
Perfect for Groups! Steps to the Beach and Room for All! Enjoy All Andersonville Has to Offer! by AllSet Turnover
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

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

10/10 Excellent
"Very good experience! Thanks "
Michail 5-night trip
Posted 21 hours ago
The Whitehall Hotel, BW Premier Collection