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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Browse Select Southwest Side Condo Rentals

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 £303
includes taxes & fees
25 Aug - 26 Aug
Comfortable Condo in the Heart of Bronzeville by RedAwning
East Lincoln Park Gem: Spacious 4BR apartment with modern amenities.
Beach

East Lincoln Park Gem: Spacious 4BR apartment with modern amenities.

10.0 out of 10, Exceptional, (6)
"Convenient to areas we visited"
The price is £743
includes taxes & fees
16 Sept - 17 Sept
East Lincoln Park Gem: Spacious 4BR apartment with modern amenities.
Wrigley Field MVP Suite 1 Bedroom Apartment
Private kitchen

Wrigley Field MVP Suite 1 Bedroom Apartment

9.4 out of 10, Exceptional, (12)
"We found a used razer that was left in the shower and also some dishes that didn't look like they were washed. Other than those couple of things it was clean and an extremely nice stay. We went for a concert at the wrigley stadium and were able to listen to them rehearse the day before. The walk was just across the road and we were able to walk and pick up groceries from whole foods."
The price is £509
includes taxes & fees
24 Aug - 25 Aug
Wrigley Field MVP Suite 1 Bedroom Apartment
Wrigley Field Stadium Suite 4 Bedroom 2 Bathroom
Private kitchen

Wrigley Field Stadium Suite 4 Bedroom 2 Bathroom

10.0 out of 10, Exceptional, (21)
"We had a great experience. We would stay here again!"
The price is £824
includes taxes & fees
24 Aug - 25 Aug
Wrigley Field Stadium Suite 4 Bedroom 2 Bathroom
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 £709
includes taxes & fees
18 Aug - 19 Aug
Wrigley Field All Star Suite 3 Bedrooms 2 Bath
Wrigley Field Grand Slam Suite 4 Bedrooms, 2 Bathrooms
Private kitchen

Wrigley Field Grand Slam Suite 4 Bedrooms, 2 Bathrooms

9.0 out of 10, Wonderful, (14)
"We loved the location and the VRBO itself. Clean, stocked with essentials, and easy to communicate with!"
The price is £814
includes taxes & fees
19 Aug - 20 Aug
Wrigley Field Grand Slam Suite 4 Bedrooms, 2 Bathrooms
Wrigley Field Home Run 4 Bedroom, 2 Bathroom
Private kitchen

Wrigley Field Home Run 4 Bedroom, 2 Bathroom

9.6 out of 10, Exceptional, (18)
"Would definitely stay there again "
The price is £814
includes taxes & fees
15 Sept - 16 Sept
Wrigley Field Home Run 4 Bedroom, 2 Bathroom
Wrigley Field Legend Suite 4 Bedrooms, 2 Bathrooms
Private kitchen

Wrigley Field Legend Suite 4 Bedrooms, 2 Bathrooms

9.6 out of 10, Exceptional, (23)
"It was great to be able to walk to Cubs games and back right after. It was a cold three days worth of game so very nice to be able to walk across the street and get warm quick. The place was absolutely great! Very spacious and comfy. The property manager was so very easy to work with when we requested an early check in. Thanks and we look forward to our next stay there. Go Cubs Go!!!"
The price is £824
includes taxes & fees
24 Aug - 25 Aug
Wrigley Field Legend Suite 4 Bedrooms, 2 Bathrooms
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, (34)
"3 night stay with a family of 5. Was perfect for us! Clean, quiet, and easy to access. Would stay again! "
The price is £592
includes taxes & fees
31 Aug - 1 Sept
3BR Modern Condo near Wrigley/Dwtn +Free Parking
Chicago 1BR Condo w Free Gated Parking & Highspeed Internet
Smart TV, video games

Chicago 1BR Condo w Free Gated Parking & Highspeed Internet

9.0 out of 10, Wonderful, (2)
"The space was nice and cozy. The location was great as it was right off the freeway. "
The price is £218
includes taxes & fees
17 Aug - 18 Aug
Chicago 1BR Condo w Free Gated Parking & Highspeed Internet
Cozy Wicker Park Home with Movie Room
Fridge, microwave, oven, stovetop

Cozy Wicker Park Home with Movie Room

9.8 out of 10, Exceptional, (9)
"Great stay!! I think the 7 bed is a little misleading but overall was a great space with 5 beds for a group. Great location and vibe."
The price is £1,010
includes taxes & fees
9 Sept - 10 Sept
Cozy Wicker Park Home with Movie Room
MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking
Fridge, microwave, oven, stovetop

MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking

9.6 out of 10, Exceptional, (24)
"Great location near Northwestern University. Plenty of on street parking for our group. Good communication with owner."
The price is £388
includes taxes & fees
19 Aug - 20 Aug
MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking
Chicago 1BR: Stylish Stay with Workspace
Fridge, microwave, oven, stovetop

Chicago 1BR: Stylish Stay with Workspace

9.4 out of 10, Exceptional, (3)
"Overall very nice and parking was easy to find"
The price is £210
includes taxes & fees
21 Aug - 22 Aug
Chicago 1BR: Stylish Stay with Workspace
Huge Projector and Designated Workspace - Near Wrigley!
2 bedrooms, desk, iron/ironing board, free WiFi

Huge Projector and Designated Workspace - Near Wrigley!

The price is £213
includes taxes & fees
18 Aug - 19 Aug
Huge Projector and Designated Workspace - Near Wrigley!
Fitness Pad: Stylish 2BR with Gym in Chicago
Fridge, microwave, oven, stovetop

Fitness Pad: Stylish 2BR with Gym in Chicago

8.0 out of 10, Very good, (1)
The price is £216
includes taxes & fees
20 Aug - 21 Aug
Fitness Pad: Stylish 2BR with Gym in Chicago
Chic Suite/Mins to L Train /Laundry/Free Parking
Fridge, microwave, oven, stovetop

Chic Suite/Mins to L Train /Laundry/Free Parking

9.6 out of 10, Exceptional, (51)
"I stood here for 1 week with my family, including a 6 and 13 yr old. Let’s start with what’s important, The cleanliness, this was 20/10, it exceeded my expectations. I’m a very picky person when it comes to cleaning, and I’m glad everything was spotless. The communication was GREAT, the location was perfect. The apartment is very spacious. I have NO complaints. Everything was great!!! For sure I will stay here again."
The price is £156
includes taxes & fees
18 Aug - 19 Aug
Chic Suite/Mins to L Train /Laundry/Free Parking
Spacious & Comfortable 3 Bedrooms + Bonus Room
4 bedrooms, desk, iron/ironing board, free WiFi

Spacious & Comfortable 3 Bedrooms + Bonus Room

The price is £400
includes taxes & fees
19 Aug - 20 Aug
Spacious & Comfortable 3 Bedrooms + Bonus Room
Cozy Forest Park Condo!
Living area

Cozy Forest Park Condo!

8.0 out of 10, Very good, (1)
"Convenient location. Property as described is accurate. Fabulous, firm king beds. Host communication is superb. "
The price is £313
includes taxes & fees
19 Aug - 20 Aug
Cozy Forest Park Condo!
Just remodeled apartment close to airport and mall
Paper towels

Just remodeled apartment close to airport and mall

10.0 out of 10, Exceptional, (12)
"The location was great for my purposes, nice apartment, great neighborhood and close to the airport."
The price is £194
includes taxes & fees
21 Aug - 22 Aug
Just remodeled apartment close to airport and mall
Cozy One Bedroom, Washer Dryer, Central Location, Fireplace, Monthly Discounts
Fridge, microwave, oven, stovetop

Cozy One Bedroom, Washer Dryer, Central Location, Fireplace, Monthly Discounts

9.2 out of 10, Wonderful, (22)
"Good location, clean, and very well kept"
The price is £286
includes taxes & fees
1 Sept - 2 Sept
Cozy One Bedroom, Washer Dryer, Central Location, Fireplace, Monthly Discounts
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

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

10/10 Excellent
"Nice and very clean. Friendly and helpful staff. Very close to bus stop (bus 20) takes you to Magnificent Mile, The Bean…and bus 8 took us right to Rate field for a White Sox game. Just blocks down from Randolph Ave… lots of fun outdoor eateries!! Only recommendation- don’t take a room next to elevator because you’ll hear it go up and down ALL night long."
Betty 3-night trip
Posted 10 hours ago
Crowne Plaza Chicago West Loop by IHG