Photo by throwingsofas

West Side holiday rentals

We found 3,268 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – West Side

Showing deals for:25 Dec - 1 Jan

Living area
Terrace/patio
Private kitchen
Living area
Exceptional
(13 reviews)

6BD/5BTH + Roofdeck - Downtown Chicago!

Chicago

8% off
AU$20,520
for 7 nights, 1 apartment
AU$2,931 per night
includes taxes & fees
6BD/5BTH + Roofdeck - Downtown Chicago!
Room
Our downtown Townhouse is in an amazing location
Interior
It is huge! With lots of areas for relaxing and entertaining
Exceptional
(91 reviews)

Historic luxury townhouse on Chicago's Gold Coast

Chicago

5% off
AU$18,660
for 7 nights, 1 home
AU$2,666 per night
includes taxes & fees
Historic luxury townhouse on Chicago's Gold Coast
Living area
Dining
Room
Private kitchen
Wonderful
(21 reviews)

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

Berwyn

8% off
AU$2,982
for 7 nights, 1 apartment
AU$426 per night
includes taxes & fees
Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI
Private kitchen
Interior
Dining
Living area
Exceptional
(40 reviews)

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

Berwyn

8% off
AU$3,341
for 7 nights, 1 apartment
AU$477 per night
includes taxes & fees
Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
Private kitchen
Cozy Home
Interior
Living area
Exceptional
(12 reviews)

Spacious 4BR Near O’Hare & Rosemont Sleeps 8 / 2 Kitchens / Free Parking

Chicago

7% off
AU$4,864
for 7 nights, 1 home
AU$695 per night
includes taxes & fees
Spacious 4BR Near O’Hare & Rosemont Sleeps 8 / 2 Kitchens / Free Parking
2 spots come with the unit- occupied by the van and SUV in this photo.
Top floor kitchen and dining area
Kitchen on Top Floor
Bedroom 3 w/ Queen Bed
Exceptional
(34 reviews)

The Exclusive- 7 Bed, 6 Bath Retreat

Chicago

5% off
AU$10,400
for 7 nights, 1 apartment
AU$1,486 per night
includes taxes & fees
The Exclusive- 7 Bed, 6 Bath Retreat
Interior
Exterior
Outdoor dining
Dining
Exceptional
(25 reviews)

Beautiful Berwyn Bungalow Close to Downtown Chicago

Berwyn

8% off
AU$3,905
for 7 nights, 1 home
AU$558 per night
includes taxes & fees
Beautiful Berwyn Bungalow Close to Downtown Chicago
Private kitchen
Living area
Interior
Room
Exceptional
(22 reviews)

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

Berwyn

8% off
AU$3,053
for 7 nights, 1 apartment
AU$436 per night
includes taxes & fees
Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW
Bedroom 1 - King Bed
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$10,283
for 7 nights, 1 home
AU$1,469 per night
includes taxes & fees
Stunning Lincoln Park Single-Family House with Fantastic Game Room
Bedroom 1 (King Size) + 55Inch TV
Living Room
Kitchen
Patio Deck 2
Exceptional
(23 reviews)

Spacious 5 BR / King Size Beds + Private Parking!

Chicago

8% off
AU$9,223
for 7 nights, 1 home
AU$1,318 per night
includes taxes & fees
Spacious 5 BR / King Size Beds + Private Parking!
Exterior
Living area
Private kitchen
Dining
Exceptional
(113 reviews)

Wrigley Field/Lakeview -Entire Home- Large Groups!

Chicago

11% off
AU$7,619
for 7 nights, 1 home
AU$1,088 per night
includes taxes & fees
Wrigley Field/Lakeview -Entire Home- Large Groups!
View of Robey Hotel from back deck
3 bedroom unit is top floor of historic greystone
Living room area
Dining room area
Exceptional
(100 reviews)

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

Chicago

7% off
AU$6,363
for 7 nights, 1 home
AU$909 per night
includes taxes & fees
Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
Bedroom #1 w 2 full size beds plus a desk
Spacious Living Room with Roku TV, sofa bed, smart thermostat, etc
Private kitchen
7 minutes drive to downtown and Millenium Park
Wonderful
(26 reviews)

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

Chicago

7% off
AU$2,704
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
Room
Interior
Living area
Interior
Exceptional
(38 reviews)

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

Chicago

7% off
AU$11,100
for 7 nights, 1 home
AU$1,586 per night
includes taxes & fees
Lincoln Park 3BR Townhome • Rooftop • King Suite • Sleeps 10
Private kitchen
Living area
Room
Dining
Exceptional
(14 reviews)

Ridgeland Retreat/ Street level Apt easy access

Berwyn

8% off
AU$4,908
for 7 nights, 1 apartment
AU$701 per night
includes taxes & fees
Ridgeland Retreat/ Street level Apt easy access
Dining
Living area
Terrace/patio
Living area
Exceptional
(57 reviews)

Cozy two bedroom close to Wrigley Field

Chicago

15% off
AU$4,833
for 7 nights, 1 apartment
AU$690 per night
includes taxes & fees
Cozy two bedroom close to Wrigley Field
Dining
Interior
Living area
Room
Exceptional
(24 reviews)

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

Berwyn

8% off
AU$2,965
for 7 nights, 1 apartment
AU$424 per night
includes taxes & fees
Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT
Private kitchen
Living area
Point of interest
Room
Exceptional
(16 reviews)

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

Chicago

11% off
AU$4,884
for 7 nights, 1 home
AU$698 per night
includes taxes & fees
1 #23 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown
Living area
Interior
Interior
Private kitchen
Wonderful
(91 reviews)

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

Chicago

5% off
AU$1,901
for 7 nights, 1 apartment
AU$272 per night
includes taxes & fees
Chic, Cozy home, by Blue Line Train Stop + Free parking
Downstairs living room
Downstairs living area
Fun Mirror Wall Upstairs
Upstairs queen bedroom 2
Exceptional
(99 reviews)

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

Chicago

7% off
AU$13,213
for 7 nights, 1 apartment
AU$1,888 per night
includes taxes & fees
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Fully fenced yard - perfect for fur babies
Breakfast bar seating also available
Interior
Master bedroom w/king size memory foam bed
Exceptional
(23 reviews)

Wonderful in Wood Dale, right by O’Hare airport!

Wood Dale

13% off
AU$5,108
for 7 nights, 1 home
AU$730 per night
includes taxes & fees
Wonderful in Wood Dale, right by O’Hare airport!
Room
Interior
Private kitchen
Dining
Exceptional
(18 reviews)

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

Chicago

7% off
AU$2,707
for 7 nights, 1 apartment
AU$387 per night
includes taxes & fees
Modern + Cozy Chicago stay w/garage parking & 20min to downtown
Private kitchen
Interior
Interior
Room
Exceptional
(12 reviews)

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

Chicago

7% off
AU$2,994
for 7 nights, 1 apartment
AU$428 per night
includes taxes & fees
Peaceful Living-2Bdrm/2Bath w/Private Parking, WiFi-Work Station-Wicker Park!
Upscale kitchen with an equally spacious dining room
5 minutes drive to McCormick Place (0.9 miles)
Enjoy your stay in the well appointed living room with a 55" Roku Smart TV
Upscale kitchen with an equally spacious dining room
Wonderful
(9 reviews)

23rd St - Modern 2 Bedroom with Parking - near McCormick Place, Chinatown

Chicago

7% off
AU$3,349
for 7 nights, 1 apartment
AU$478 per night
includes taxes & fees
23rd St - Modern 2 Bedroom with Parking - near McCormick Place, Chinatown
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    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Find the perfect holiday rental for your West Side getaway

Learn about the unique charm of West Side with a stay in a holiday home rental. This city has something for everyone. Soldier Field and McCormick Place are just a couple of the must-see attractions in the area. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in and around West Side

Are you looking for things to do while you're in the area? Venture out of your cosy holiday rental and experience everything that makes West Side a fun place to get away to. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Lincoln Park Zoo (4.9 mi / 7.9 km)
  • Galloping Ghost (8.6 mi / 13.9 km)
  • Harborside International Golf Center (13.9 mi / 22.4 km)
  • The Glen Club (16 mi / 25.7 km)
  • Northbrook Sports Complex (18.4 mi / 29.6 km)
  • Cog Hill Golf & Country Club (18.9 mi / 30.4 km)

Exploring the natural landscape of West Side

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

  • Millennium Park (4.4 mi / 7.1 km)
  • Grant Park (4.5 mi / 7.3 km)
  • Garfield Park (0.6 mi / 1 km)
  • Garfield Park Conservatory (0.8 mi / 1.3 km)
  • Anna and Frederick Douglass Park (1.1 mi / 1.7 km)
  • Humboldt Park (2 mi / 3.2 km)

How to get to and around West Side

If you prefer to travel by train, Chicago Kedzie Station, Chicago Western Avenue Station (Milwaukee District-West) and Chicago Western Avenue Station (BNSF) are the main stations that serve the city. You can get around West Side by jumping on the metro at Kedzie-Homan Station, Kedzie Station (Green Line) or Conservatory-Central Park Drive Station.

Frequently asked questions

What is the most popular type of holiday home accommodation in West Side?
Based on our research, apartments are the most popular type of holiday property in West Side. But having said that, everyone's idea of an awesome trip differs. Stayz has holiday homes of all sizes and shapes, and we'll help you discover the best fit for your needs.
How much does it cost to rent a holiday home in West Side?
Season, length of stay and property type are some of the conditions that can determine the price of a holiday home. Simply add your travel dates to find your ideal fit. From comfy cabins to expansive luxury villas, all Stayz holiday homes provide unbeatable value.
How much does it cost to rent a beach house in West Side?
When you travel and the style and size of the property will help determine the cost of your beachside escape. Put in your West Side travel dates to see your options on Stayz. Did someone just say "hot tub"? Use our filters to select the amenities and features you want in your beach house.
What are popular home amenities in West Side?
The most popular home amenities people are searching for in West Side are an oven, a fridge and a microwave oven. Whether you're holidaying with family, friends or even pets, Stayz holiday homes come with the best amenities for hanging out with the people closest to you.
Are there large group holiday homes in West Side?
With 26 properties that can sleep 10 or more people in West Side, you won't have to limit the invite list. From fun family holidays to special events like birthday parties and weddings, Stayz will help you find a large group home to suit the occasion.
What are the top attractions for families in West Side?
Keep the kids happy at these top family-friendly attractions in West Side:
  • Anna and Frederick Douglass Park
  • United Centre
  • Humboldt Park
Can I find two-bedroom holiday homes in West Side?
Take off with your loved ones and experience complete comfort and privacy in one of the 84 two-bedroom holiday homes West Side has to offer.
Are there holiday homes with WiFi in West Side?
Whether you want to keep up with the latest headlines, look over emails or update your social media, there are 103 holiday homes with WiFi in West Side. Check the "WiFi" box when searching on Stayz and stay connected on your holiday.
How old do you have to be to rent a holiday home in West Side?
You'll need to check with the West Side holiday property you'd like on Stayz as age restrictions vary. However, it's typically 16, 18 or 21.
How long can I rent a holiday home in West Side for?
The amount of time you can book a West Side holiday home for varies depending on the property. Simply put in your dates of travel to find available options offering extended stays. They have all the things you need to make your extended trip more comfortable and enjoyable, like kitchens and air conditioning. Some Stayz holiday properties may also offer weekly or monthly discounts, so you can hang around longer for less.

More holiday ideas