Northwest Side holiday homes

We found 3,061 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Northwest Side

Showing deals for:13 Nov - 20 Nov

Interior
River North Luxury Living
French Bistro and Wine Bar - right downstairs
The building
Exceptional
(104 reviews)

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

Chicago

7% off
NZ$5,629
for 7 nights, 1 apartment
NZ$804 per night
includes taxes & fees
River North's Rock N' Roll - In The Heart of the City
Dining
Interior
Living area
Living area
Exceptional
(34 reviews)

Lux Home in Chicago 7mins Downtown

Chicago

7% off
NZ$8,035
for 7 nights, 1 home
NZ$1,148 per night
includes taxes & fees
Lux Home in Chicago 7mins Downtown
Room
Interior
Exterior
Living area
Exceptional
(11 reviews)

NEW! Large/Beautiful Home with 6BDS/4BTH + Garage!

Chicago

7% off
NZ$9,284
for 7 nights, 1 home
NZ$1,326 per night
includes taxes & fees
NEW! Large/Beautiful Home with 6BDS/4BTH + Garage!
Private kitchen
Exterior
Exterior
Interior
Wonderful
(9 reviews)

Luxe Home 20 min from Downtown Chicago ,heated indoor pool, Spa bath, tree house

Skokie

7% off
NZ$12,711
for 7 nights, 1 home
NZ$1,816 per night
includes taxes & fees
Luxe Home 20 min from Downtown Chicago ,heated indoor pool, Spa bath, tree house
Room
Interior
Interior
Private kitchen
Very good
(11 reviews)

Charming Home in Portage Park

Chicago

13% off
NZ$2,368
for 7 nights, 1 home
NZ$338 per night
includes taxes & fees
Charming Home in Portage Park
Interior
Private kitchen
Room
Property grounds
Exceptional
(74 reviews)

Private Historic Coach House Wicker Park

Chicago

6% off
NZ$4,062
for 7 nights, 1 home
NZ$580 per night
includes taxes & fees
Private Historic Coach House Wicker Park
Dining
Private kitchen
Bedroom 1
Exterior
Wonderful
(22 reviews)

Renovated 6 Bedroom 5 Bathroom Home 10 Minutes from Downtown Chicago

Chicago

7% off
NZ$8,426
for 7 nights, 1 home
NZ$1,204 per night
includes taxes & fees
Renovated 6 Bedroom 5 Bathroom Home 10 Minutes from Downtown Chicago
Lobby
Interior
Interior
Private kitchen
Exceptional
(19 reviews)

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

Chicago

7% off
NZ$3,558
for 7 nights, 1 home
NZ$508 per night
includes taxes & fees
Lofty Garden Retreat Artist-Music Friendly 2BR in Humboldt Park
Kitchen
Living Room
Bedroom 1 (King Size) + 55Inch TV
Front Yard View
Exceptional
(21 reviews)

Spacious 5 BR / King Size Beds + Private Parking!

Chicago

8% off
NZ$8,402
for 7 nights, 1 home
NZ$1,200 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
Dining room area
Exceptional
(95 reviews)

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

Chicago

7% off
NZ$7,731
for 7 nights, 1 home
NZ$1,104 per night
includes taxes & fees
Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
Living area
Interior
Dining
Room
Exceptional
(39 reviews)

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

Berwyn

8% off
NZ$2,157
for 7 nights, 1 apartment
NZ$308 per night
includes taxes & fees
Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
Convenient on-premis laundry room with coin operated washer and dryer
Spacious Living Room with Roku TV, sofa bed, smart thermostat, etc
Private kitchen
Bedroom #1 w 2 full size beds plus a desk
Wonderful
(20 reviews)

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

Chicago

7% off
NZ$3,224
for 7 nights, 1 apartment
NZ$461 per night
includes taxes & fees
1 #12 - 2 Bedroom / 1 Bath Condo near McCormick Place, Wintrust Arena, Chinatown
Dining
Living area
Terrace/patio
Private kitchen
Exceptional
(55 reviews)

Cozy two bedroom close to Wrigley Field

Chicago

15% off
NZ$4,453
for 7 nights, 1 apartment
NZ$636 per night
includes taxes & fees
Cozy two bedroom close to Wrigley Field
Private kitchen
Living area
Miscellaneous
Room
Exceptional
(12 reviews)

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

Chicago

11% off
NZ$5,987
for 7 nights, 1 home
NZ$855 per night
includes taxes & fees
1 #23 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown
Interior
Living area
Interior
Private kitchen
Exceptional
(6 reviews)

The En Bronze ~ 7mins To Dining & Downtown Chicago

Chicago

7% off
NZ$5,484
for 7 nights, 1 apartment
NZ$783 per night
includes taxes & fees
The En Bronze ~ 7mins To Dining & Downtown Chicago
Living area
Interior
Private kitchen
Room
Exceptional
(10 reviews)

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

Chicago

7% off
NZ$3,571
for 7 nights, 1 apartment
NZ$510 per night
includes taxes & fees
Peaceful Living-2Bdrm/2Bath w/Private Parking, WiFi-Work Station-Wicker Park!
Interior
Interior
Dining
Private kitchen
Exceptional
(13 reviews)

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

Chicago

7% off
NZ$2,193
for 7 nights, 1 apartment
NZ$313 per night
includes taxes & fees
Modern + Cozy Chicago stay w/garage parking & 20min to downtown
Downstairs living room
Downstairs living area
Upstairs queen bedroom 2
Fun Mirror Wall Upstairs
Exceptional
(97 reviews)

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

Chicago

7% off
NZ$15,481
for 7 nights, 1 apartment
NZ$2,212 per night
includes taxes & fees
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Interior
Living area
Room
Private kitchen
Exceptional
(19 reviews)

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

Berwyn

8% off
NZ$1,901
for 7 nights, 1 apartment
NZ$272 per night
includes taxes & fees
Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW
Dining
Interior
Room
Living area
Exceptional
(22 reviews)

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

Berwyn

8% off
NZ$1,850
for 7 nights, 1 apartment
NZ$264 per night
includes taxes & fees
Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT
Enjoy a meal in the dining room
Patio
Queen Bedroom
Private kitchen
Exceptional
(9 reviews)

Modern 2BR with Free Parking in Avondale

Chicago

7% off
NZ$2,872
for 7 nights, 1 apartment
NZ$410 per night
includes taxes & fees
Modern 2BR with Free Parking in Avondale
Private kitchen
Dining
Living area
Living area
Wonderful
(18 reviews)

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

Berwyn

8% off
NZ$1,893
for 7 nights, 1 apartment
NZ$270 per night
includes taxes & fees
Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI
Private kitchen
Interior
Room
Living area
Wonderful
(84 reviews)

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

Chicago

5% off
NZ$1,574
for 7 nights, 1 apartment
NZ$225 per night
includes taxes & fees
Chic, Cozy home, by Blue Line Train Stop + Free parking
Private kitchen
Living area
Dining
Room
Exceptional
(11 reviews)

Ridgeland Retreat/ Street level Apt easy access

Berwyn

8% off
NZ$2,314
for 7 nights, 1 apartment
NZ$331 per night
includes taxes & fees
Ridgeland Retreat/ Street level Apt easy access
  • 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

Find the perfect holiday rental for your Northwest Side getaway

Learn about the unique charm of Northwest Side with a stay in a holiday home rental. This city has something for everyone. Wrigley Field and United Center are just a couple of the must-see attractions in the area. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Activities and attractions in and around Northwest Side

Are you looking for attractions to visit in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that Northwest Side has to offer. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • The Dome at the Parkway Bank Sports Complex (6.2 mi / 9.9 km)
  • Lincoln Park Zoo (7 mi / 11.2 km)
  • Galloping Ghost (9.8 mi / 15.8 km)
  • The Glen Club (10.7 mi / 17.2 km)
  • Oak Brook Golf Course (11 mi / 17.7 km)
  • Rainbow Falls Waterpark (12.7 mi / 20.4 km)

Exploring the natural features in Northwest Side

Whether you're looking for adventure or just want to appreciate the scenery, Northwest Side is a great place to get outside. Here are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Millennium Park (8.4 mi / 13.6 km)
  • Grant Park (8.9 mi / 14.3 km)
  • Portage Park (0.9 mi / 1.4 km)
  • Humboldt Park (4.2 mi / 6.7 km)
  • Garfield Park Conservatory (4.6 mi / 7.5 km)
  • Garfield Park (4.8 mi / 7.7 km)

Transport to and around Northwest Side

If you prefer to travel by train, Chicago Grayland Station, Chicago Mayfair Station and Chicago Hanson Park Station are the main stations in the city. You can see more of Northwest Side by catching a ride on the metro at Montrose Station (Blue Line), Irving Park Station (Blue Line) or Addison Station (Blue Line).

Frequently asked questions

How much does it cost to rent a holiday home in Northwest Side?
The average price for a holiday home in Northwest Side depends on several factors, including season, property type and length of stay. Whether you're searching for a sprawling villa with space for extended family or a cosy cabin perfect for just you and the kids, just enter your travel dates to discover stays with unbeatable value.
How much does it cost to rent a beach house in Northwest Side?
When you travel and the style and size of the property will influence the cost of your beachside escape. Enter your Northwest Side travel dates to view your available options on Bookabach. Did someone just say "private pool"? Use the filters to pick the amenities and features you want in your holiday home.
How old do you have to be to rent a holiday home in Northwest Side?
The minimum required age is normally 16, 18 or 21. It can change from one property to another on Bookabach, so check the rules of your chosen Northwest Side holiday home before booking your escape.
How long can I rent a holiday home in Northwest Side for?
The amount of time you can stay in a Northwest Side holiday home for depends on each property. Simply put in your preferred travel dates to browse options that offer long-term stays. They feature everything you need to make your extended trip more convenient and comfortable, like air conditioning and kitchens. Some Bookabach holiday homes may also offer weekly or monthly discounted prices, so you can hang around longer for less.

More holiday ideas