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Southwest Side holiday rentals

We found 2,852 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Southwest Side

Showing deals for:13 Nov - 20 Nov

Outdoors at night
River North Luxury Living
French Bistro and Wine Bar - right downstairs
Interior
Exceptional
(104 reviews)

River North's Rock N' Roll - In The Heart of the City

Chicago

7% off
AU$4,585
for 7 nights, 1 apartment
AU$655 per night
includes taxes & fees
River North's Rock N' Roll - In The Heart of the City
Living area
Interior
Dining
Living area
Exceptional
(35 reviews)

Lux Home in Chicago 7mins Downtown

Chicago

7% off
AU$6,608
for 7 nights, 1 home
AU$944 per night
includes taxes & fees
Lux Home in Chicago 7mins Downtown
Room
Private kitchen
Living area
Property grounds
Exceptional
(74 reviews)

Private Historic Coach House Wicker Park

Chicago

7% off
AU$3,373
for 7 nights, 1 home
AU$482 per night
includes taxes & fees
Private Historic Coach House Wicker Park
Private kitchen
Interior
Interior
6 steps to enter the unit.
Exceptional
(19 reviews)

Lofty Garden Retreat Artist-Music Friendly 2BR in Humboldt Park

Chicago

7% off
AU$2,977
for 7 nights, 1 home
AU$425 per night
includes taxes & fees
Lofty Garden Retreat Artist-Music Friendly 2BR in Humboldt Park
Dining
Private kitchen
Bedroom 1
Living area
Wonderful
(22 reviews)

Renovated 6 Bedroom 5 Bathroom Home 10 Minutes from Downtown Chicago

Chicago

7% off
AU$6,707
for 7 nights, 1 home
AU$958 per night
includes taxes & fees
Renovated 6 Bedroom 5 Bathroom Home 10 Minutes from Downtown Chicago
Private kitchen
Interior
Dining
Living area
Exceptional
(39 reviews)

Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP

Berwyn

8% off
AU$1,837
for 7 nights, 1 apartment
AU$262 per night
includes taxes & fees
Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
Front Yard View
Living Room
Bedroom 1 (King Size) + 55Inch TV
Kitchen
Exceptional
(21 reviews)

Spacious 5 BR / King Size Beds + Private Parking!

Chicago

8% off
AU$6,638
for 7 nights, 1 home
AU$948 per night
includes taxes & fees
Spacious 5 BR / King Size Beds + Private Parking!
Private kitchen
Dining
Interior
Living area
Exceptional
(15 reviews)

Elegant Escape by Downtown Burr Ridge with an easy access to Chicago Landmarks

Burr Ridge

8% off
AU$5,541
for 7 nights, 1 home
AU$792 per night
includes taxes & fees
Elegant Escape by Downtown Burr Ridge with an easy access to Chicago Landmarks
Living room area
3 bedroom unit is top floor of historic greystone
View of Robey Hotel from back deck
Dining room area
Exceptional
(96 reviews)

Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.

Chicago

7% off
AU$6,352
for 7 nights, 1 home
AU$907 per night
includes taxes & fees
Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
Private kitchen
Spacious Living Room with Roku TV, sofa bed, smart thermostat, etc
7 minutes drive to downtown and Millenium Park
Convenient on-premis laundry room with coin operated washer and dryer
Wonderful
(20 reviews)

1 #12 - 2 Bedroom / 1 Bath Condo near McCormick Place, Wintrust Arena, Chinatown

Chicago

7% off
AU$2,700
for 7 nights, 1 apartment
AU$386 per night
includes taxes & fees
1 #12 - 2 Bedroom / 1 Bath Condo near McCormick Place, Wintrust Arena, Chinatown
Private kitchen
Living area
Terrace/patio
Dining
Exceptional
(55 reviews)

Cozy two bedroom close to Wrigley Field

Chicago

15% off
AU$3,698
for 7 nights, 1 apartment
AU$528 per night
includes taxes & fees
Cozy two bedroom close to Wrigley Field
Point of interest
Living area
Miscellaneous
Private kitchen
Exceptional
(12 reviews)

1 #23 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown

Chicago

11% off
AU$4,876
for 7 nights, 1 home
AU$697 per night
includes taxes & fees
1 #23 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown
Room
Interior
Living area
Private kitchen
Exceptional
(10 reviews)

Peaceful Living-2Bdrm/2Bath w/Private Parking, WiFi-Work Station-Wicker Park!

Chicago

7% off
AU$2,988
for 7 nights, 1 apartment
AU$427 per night
includes taxes & fees
Peaceful Living-2Bdrm/2Bath w/Private Parking, WiFi-Work Station-Wicker Park!
Interior
Living area
Room
Private kitchen
Exceptional
(6 reviews)

The En Bronze ~ 7mins To Dining & Downtown Chicago

Chicago

7% off
AU$4,466
for 7 nights, 1 apartment
AU$638 per night
includes taxes & fees
The En Bronze ~ 7mins To Dining & Downtown Chicago
Dining
Interior
Interior
Private kitchen
Exceptional
(13 reviews)

Modern + Cozy Chicago stay w/garage parking & 20min to downtown

Chicago

7% off
AU$1,772
for 7 nights, 1 apartment
AU$253 per night
includes taxes & fees
Modern + Cozy Chicago stay w/garage parking & 20min to downtown
Room
Living area
Private kitchen
Interior
Exceptional
(19 reviews)

Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW

Berwyn

8% off
AU$1,566
for 7 nights, 1 apartment
AU$224 per night
includes taxes & fees
Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW
Downstairs living room
Downstairs living area
Upstairs queen bedroom 2
Kitchen (upstairs)
Exceptional
(97 reviews)

Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!

Chicago

7% off
AU$12,379
for 7 nights, 1 apartment
AU$1,768 per night
includes taxes & fees
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Dining
Interior
Room
Living area
Exceptional
(24 reviews)

Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT

Berwyn

8% off
AU$1,527
for 7 nights, 1 apartment
AU$218 per night
includes taxes & fees
Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT
Private kitchen
Patio
Queen Bedroom
Enjoy a meal in the dining room
Exceptional
(9 reviews)

Modern 2BR with Free Parking in Avondale

Chicago

7% off
AU$2,440
for 7 nights, 1 apartment
AU$349 per night
includes taxes & fees
Modern 2BR with Free Parking in Avondale
Property grounds
Exterior
Games room
Private kitchen
Very good
(30 reviews)

Peaceful place Great location food markets transportation downtown lake Michigan

Chicago

7% off
AU$1,223
for 7 nights, 1 apartment
AU$175 per night
includes taxes & fees
Peaceful place Great location food markets transportation downtown lake Michigan
Living area
Dining
Living area
Room
Wonderful
(18 reviews)

Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI

Berwyn

8% off
AU$1,541
for 7 nights, 1 apartment
AU$220 per night
includes taxes & fees
Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI
Private kitchen
Living area
Dining
Room
Exceptional
(11 reviews)

Ridgeland Retreat/ Street level Apt easy access

Berwyn

8% off
AU$2,106
for 7 nights, 1 apartment
AU$301 per night
includes taxes & fees
Ridgeland Retreat/ Street level Apt easy access
Interior
Interior
Private kitchen
Living area
Wonderful
(84 reviews)

Chic, Cozy home, by Blue Line Train Stop + Free parking

Chicago

5% off
AU$1,272
for 7 nights, 1 apartment
AU$182 per night
includes taxes & fees
Chic, Cozy home, by Blue Line Train Stop + Free parking
Interior
Exterior
Dining
Private kitchen
Exceptional
(34 reviews)

Lincoln Park Charm Near Everything + On site Parking Spot Included

Chicago

7% off
AU$8,691
for 7 nights, 1 apartment
AU$1,242 per night
includes taxes & fees
Lincoln Park Charm Near Everything + On site Parking Spot Included
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Book a holiday rental for your Southwest Side getaway

Learn about the unique charm of Southwest Side with a stay in a holiday home rental. This city has something for everyone. McCormick Place and United Center are just a couple of the must-see attractions in the area. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Sightseeing in and around Southwest Side

Are you looking for things to do while you're in town? Venture out of your cosy holiday rental and experience everything that makes Southwest Side a fun spot to go on holiday. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Lincoln Park Zoo (9.6 mi / 15.4 km)
  • Oak Brook Golf Course (12.2 mi / 19.6 km)
  • Cog Hill Golf & Country Club (15.3 mi / 24.7 km)
  • The Dome at the Parkway Bank Sports Complex (15.8 mi / 25.4 km)
  • Ravisloe Country Club (16 mi / 25.8 km)
  • Orland Park Sportsplex (16.6 mi / 26.7 km)

Exploring the natural landscape of Southwest Side

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Southwest Side is a great place to spend some time outside. Here are a few of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Millennium Park (7.5 mi / 12 km)
  • Grant Park (7 mi / 11.3 km)
  • Marquette Park (1.7 mi / 2.7 km)
  • Canalport Riverwalk Park (4 mi / 6.5 km)
  • Washington Park (4.7 mi / 7.5 km)
  • Anna and Frederick Douglass Park (4.9 mi / 7.9 km)

How to get to and around Southwest Side

The nearest airport is in Chicago Midway Airport (MDW), located 2 mi (3.3 km) from the city centre.

You can see more of Southwest Side by jumping on the metro at Kedzie Station (Orange Line), Western Station (Orange Line) or Pulaski Station (Orange Line).

Frequently asked questions

How much does it cost to rent a holiday home in Southwest Side?
A number of factors influence how much you'll pay for a holiday home in Southwest Side, like the season, length of stay and type of property. But, all our holiday homes have something in common — unbeatable value. Just enter your travel dates to find your perfect match.
How much does it cost to rent a beach house in Southwest Side?
The average price for a holiday home near the beach in Southwest Side depends on when you're going and the type and size of property you want. You can easily and quickly find prices on Stayz by entering your destination and travel dates. Then use the handy filter tool to choose the number of bedrooms and amenities important to you, such as air conditioning, WiFi and a hot tub.
How old do you have to be to rent a holiday home in Southwest Side?
Age restrictions can vary across properties on Stayz, so double-check the rules of the holiday home in Southwest Side you're considering. But typically, it's 16, 18 or 21.
How long can I rent a holiday home in Southwest Side for?
The amount of time you can rent a Southwest Side holiday home for varies depending on the property. Just tap in your travel dates to find options offering extended stays. They feature all the things you need to make your extended getaway more convenient and enjoyable, like air conditioning and laundries. Some Stayz holiday homes may also offer discounted weekly or monthly prices, so you can stick around for longer for less.

More holiday ideas