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Southwest Side holiday rentals

We found 2,951 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Southwest Side

Showing deals for:1 Jan - 8 Jan

Interior
Our downtown Townhouse is in an amazing location
Dining
Room
Exceptional
(92 reviews)

Historic luxury townhouse on Chicago's Gold Coast

Chicago

5% off
AU$10,068
for 7 nights, 1 home
AU$1,438 per night
includes taxes & fees
Historic luxury townhouse on Chicago's Gold Coast
Outdoors at night
River North Luxury Living
French Bistro and Wine Bar - right downstairs
The building
Exceptional
(106 reviews)

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

Chicago

7% off
AU$5,265
for 7 nights, 1 apartment
AU$752 per night
includes taxes & fees
River North's Rock N' Roll - In The Heart of the City
Living area
Interior
Room
Private kitchen
Wonderful
(41 reviews)

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

Berwyn

8% off
AU$2,846
for 7 nights, 1 apartment
AU$407 per night
includes taxes & fees
Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
Interior
Living area
Room
Kitchen
Exceptional
(30 reviews)

Sunny 2-Bedroom Logan Square Apartment – Your Perfect Chicago Base

Chicago

6% off
AU$2,295
for 7 nights, 1 apartment
AU$328 per night
includes taxes & fees
Sunny 2-Bedroom Logan Square Apartment – Your Perfect Chicago Base
Living area
Dining
Living area
Private kitchen
Wonderful
(21 reviews)

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

Berwyn

8% off
AU$2,589
for 7 nights, 1 apartment
AU$370 per night
includes taxes & fees
Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI
Dining
Living area
Room
Private kitchen
Exceptional
(23 reviews)

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

Berwyn

8% off
AU$2,336
for 7 nights, 1 apartment
AU$334 per night
includes taxes & fees
Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW
Patio Deck 2
Living Room
Bedroom 1 (King Size) + 55Inch TV
Front Yard View
Exceptional
(23 reviews)

Spacious 5 BR / King Size Beds + Private Parking!

Chicago

8% off
AU$7,206
for 7 nights, 1 home
AU$1,029 per night
includes taxes & fees
Spacious 5 BR / King Size Beds + Private Parking!
View of Robey Hotel from back deck
3 bedroom unit is top floor of historic greystone
Living room area
Living room area opens into dining room & kitchen
Exceptional
(101 reviews)

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

Chicago

7% off
AU$8,313
for 7 nights, 1 home
AU$1,188 per night
includes taxes & fees
Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
Property grounds
Room
Interior
Terrace/patio
Exceptional
(75 reviews)

Private Historic Coach House Wicker Park

Chicago

6% off
AU$3,426
for 7 nights, 1 home
AU$489 per night
includes taxes & fees
Private Historic Coach House Wicker Park
Living Room with 60 in Smart TV
Chef kitchen with Sub-Zero refrigerator, Wolf stove, Bosch dishwasher.
Living Room with 60 in Smart TV
Living Room with 60 in Smart TV
Exceptional
(92 reviews)

Stunning Lincoln Park Single-Family House with Fantastic Game Room

Chicago

11% off
AU$9,455
for 7 nights, 1 home
AU$1,351 per night
includes taxes & fees
Stunning Lincoln Park Single-Family House with Fantastic Game Room
Room
Living area
Dining
Exterior
Exceptional
(114 reviews)

Wrigley Field/Lakeview -Entire Home- Large Groups!

Chicago

11% off
AU$7,840
for 7 nights, 1 home
AU$1,120 per night
includes taxes & fees
Wrigley Field/Lakeview -Entire Home- Large Groups!
Room
Private kitchen
Exterior detail
Living area
Exceptional
(69 reviews)

Steps from the “L” train to Wrigley & Downtown

Chicago

7% off
AU$4,695
for 7 nights, 1 apartment
AU$671 per night
includes taxes & fees
Steps from the “L” train to Wrigley & Downtown
Room
Interior
Living area
Dining
Exceptional
(24 reviews)

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

Berwyn

8% off
AU$2,404
for 7 nights, 1 apartment
AU$343 per night
includes taxes & fees
Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT
Bedroom 1
Private kitchen
Exterior
Living area
Wonderful
(22 reviews)

Renovated 6 Bedroom 5 Bathroom Home 10 Minutes from Downtown Chicago

Chicago

7% off
AU$6,475
for 7 nights, 1 home
AU$925 per night
includes taxes & fees
Renovated 6 Bedroom 5 Bathroom Home 10 Minutes from Downtown Chicago
Room
Living area
Interior detail
Dining
Exceptional
(14 reviews)

Ridgeland Retreat/ Street level Apt easy access

Berwyn

8% off
AU$3,702
for 7 nights, 1 apartment
AU$529 per night
includes taxes & fees
Ridgeland Retreat/ Street level Apt easy access
Terrace/patio
Living area
Dining
Private kitchen
Exceptional
(57 reviews)

Cozy two bedroom close to Wrigley Field

Chicago

15% off
AU$4,217
for 7 nights, 1 apartment
AU$602 per night
includes taxes & fees
Cozy two bedroom close to Wrigley Field
Dining
Exterior
Interior
Private kitchen
Exceptional
(26 reviews)

Beautiful Berwyn Bungalow Close to Downtown Chicago

Berwyn

8% off
AU$3,512
for 7 nights, 1 home
AU$502 per night
includes taxes & fees
Beautiful Berwyn Bungalow Close to Downtown Chicago
Living area
Dining
Living area
Private kitchen
Exceptional
(17 reviews)

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

Burr Ridge

8% off
AU$5,516
for 7 nights, 1 home
AU$788 per night
includes taxes & fees
Elegant Escape by Downtown Burr Ridge with an easy access to Chicago Landmarks
Interior
Interior
Dining
Living area
Exceptional
(38 reviews)

Lincoln Park 3BR Townhome • Rooftop • King Suite • Sleeps 10

Chicago

7% off
AU$8,410
for 7 nights, 1 home
AU$1,201 per night
includes taxes & fees
Lincoln Park 3BR Townhome • Rooftop • King Suite • Sleeps 10
Downstairs living room
Downstairs living area
Upstairs queen bedroom 2
Fun Mirror Wall Upstairs
Exceptional
(99 reviews)

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

Chicago

7% off
AU$14,385
for 7 nights, 1 apartment
AU$2,055 per night
includes taxes & fees
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Room
Dining
Living area
Private kitchen
Exceptional
(7 reviews)

Modern 4-bedroom house in peaceful Westmont area

Westmont

8% off
AU$4,508
for 7 nights, 1 home
AU$644 per night
includes taxes & fees
Modern 4-bedroom house in peaceful Westmont area
Interior
Private kitchen
Dining
Interior
Wonderful
(50 reviews)

Gorgeous 5 BDR/ 4BA in Logan Square w/Parking!

Chicago

7% off
AU$5,450
for 7 nights, 1 home
AU$779 per night
includes taxes & fees
Gorgeous 5 BDR/ 4BA in Logan Square w/Parking!
Private kitchen
Interior
Interior
Living area
Exceptional
(12 reviews)

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

Chicago

7% off
AU$3,035
for 7 nights, 1 apartment
AU$434 per night
includes taxes & fees
Peaceful Living-2Bdrm/2Bath w/Private Parking, WiFi-Work Station-Wicker Park!
Private kitchen
Exterior
Games room
Living area
Very good
(33 reviews)

Peaceful place Great location food markets transportation downtown lake Michigan

Chicago

7% off
AU$1,503
for 7 nights, 1 apartment
AU$215 per night
includes taxes & fees
Peaceful place Great location food markets transportation downtown lake Michigan
  • 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 Soldier Field 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:

  • Harborside International Golf Center (8.7 mi / 14 km)
  • Lincoln Park Zoo (9.6 mi / 15.4 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)
  • Seven Bridges Golf Club (19.2 mi / 30.9 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)
  • Washington Park (4.7 mi / 7.5 km)
  • Anna and Frederick Douglass Park (4.9 mi / 7.9 km)
  • Garfield Park (6.3 mi / 10.2 km)
  • Jackson Park (6.4 mi / 10.3 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