Cook County holiday homes

We found 3,979 holiday rentals — enter your dates for availability
Discover a selection of 832 homes, 2585 apartments and other holiday rentals in Cook County that are perfect for your trip. Whether you’re travelling with friends, family or even pets, holiday homes have the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a pool. You'll be able to choose a property to rent for everyone's needs, including places that are non-smoking or accessible.

Popular Cook County destinations on Bookabach

Holiday rentals with weekly discounts – Cook County

Showing deals for:18 Dec - 25 Dec

Living area
Interior
Terrace/patio
Exterior
Exceptional
(39 reviews)

Private Historical Mansion,Luxury Home in Chicago’s Gold Coast, Event-Capable.

Chicago

8% off
NZ$44,818
for 7 nights, 1 home
NZ$6,403 per night
includes taxes & fees
Private Historical Mansion,Luxury Home in Chicago’s Gold Coast, Event-Capable.
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
NZ$13,605
for 7 nights, 1 home
NZ$1,944 per night
includes taxes & fees
Historic luxury townhouse on Chicago's Gold Coast
Dining
Interior
Room
Living area
Exceptional
(40 reviews)

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

Berwyn

8% off
NZ$3,639
for 7 nights, 1 apartment
NZ$520 per night
includes taxes & fees
Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
Interior
Cozy Home
Private kitchen
Living area
Exceptional
(12 reviews)

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

Chicago

7% off
NZ$6,190
for 7 nights, 1 home
NZ$884 per night
includes taxes & fees
Spacious 4BR Near O’Hare & Rosemont Sleeps 8 / 2 Kitchens / Free Parking
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
NZ$14,140
for 7 nights, 1 home
NZ$2,020 per night
includes taxes & fees
Stunning Lincoln Park Single-Family House with Fantastic Game Room
Bedroom 1 (King Size) + 55Inch TV
Living Room
Front Yard View
Kitchen
Exceptional
(23 reviews)

Spacious 5 BR / King Size Beds + Private Parking!

Chicago

7% off
NZ$11,227
for 7 nights, 1 home
NZ$1,604 per night
includes taxes & fees
Spacious 5 BR / King Size Beds + Private Parking!
Private kitchen
Living area
Dining
Room
Exceptional
(22 reviews)

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

Berwyn

8% off
NZ$3,272
for 7 nights, 1 apartment
NZ$467 per night
includes taxes & fees
Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW
Dining
Living area
Exterior
Private kitchen
Exceptional
(111 reviews)

Wrigley Field/Lakeview -Entire Home- Large Groups!

Chicago

11% off
NZ$9,568
for 7 nights, 1 home
NZ$1,367 per night
includes taxes & fees
Wrigley Field/Lakeview -Entire Home- Large Groups!
Living area
Dining
Private kitchen
Interior
Exceptional
(15 reviews)

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

Burr Ridge

8% off
NZ$6,870
for 7 nights, 1 home
NZ$981 per night
includes taxes & fees
Elegant Escape by Downtown Burr Ridge with an easy access to Chicago Landmarks
View of Robey Hotel from back deck
3 bedroom unit is top floor of historic greystone
Dining room area
Living room area opens into dining room & kitchen
Exceptional
(100 reviews)

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

Chicago

7% off
NZ$8,025
for 7 nights, 1 home
NZ$1,146 per night
includes taxes & fees
Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
Dining
Interior
Interior
Room
Exceptional
(38 reviews)

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

Chicago

7% off
NZ$13,368
for 7 nights, 1 home
NZ$1,910 per night
includes taxes & fees
Lincoln Park 3BR Townhome • Rooftop • King Suite • Sleeps 10
Living area
Living area
Dining
Terrace/patio
Exceptional
(57 reviews)

Cozy two bedroom close to Wrigley Field

Chicago

15% off
NZ$5,385
for 7 nights, 1 apartment
NZ$769 per night
includes taxes & fees
Cozy two bedroom close to Wrigley Field
Room
Living area
Dining
Interior detail
Exceptional
(14 reviews)

Ridgeland Retreat/ Street level Apt easy access

Berwyn

8% off
NZ$5,168
for 7 nights, 1 apartment
NZ$738 per night
includes taxes & fees
Ridgeland Retreat/ Street level Apt easy access
Dining
Interior
Living area
Living area
Exceptional
(24 reviews)

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

Berwyn

8% off
NZ$3,187
for 7 nights, 1 apartment
NZ$455 per night
includes taxes & fees
Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT
Room
Living area
Point of interest
Private kitchen
Exceptional
(15 reviews)

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

Chicago

11% off
NZ$6,216
for 7 nights, 1 home
NZ$888 per night
includes taxes & fees
1 #23 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown
Living area
Interior
Room
Interior
Wonderful
(90 reviews)

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

Chicago

5% off
NZ$2,202
for 7 nights, 1 apartment
NZ$315 per night
includes taxes & fees
Chic, Cozy home, by Blue Line Train Stop + Free parking
Living area
Dining
Room
Living area
Wonderful
(21 reviews)

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

Berwyn

8% off
NZ$3,100
for 7 nights, 1 apartment
NZ$443 per night
includes taxes & fees
Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI
Fun Mirror Wall Upstairs
Downstairs living area
Upstairs queen bedroom 2
Kitchen (upstairs)
Exceptional
(99 reviews)

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

Chicago

7% off
NZ$16,068
for 7 nights, 1 apartment
NZ$2,295 per night
includes taxes & fees
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Interior
Interior
Room
Private kitchen
Exceptional
(18 reviews)

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

Chicago

7% off
NZ$3,169
for 7 nights, 1 apartment
NZ$453 per night
includes taxes & fees
Modern + Cozy Chicago stay w/garage parking & 20min to downtown
Interior
Interior
Room
Private kitchen
Exceptional
(12 reviews)

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

Chicago

7% off
NZ$3,709
for 7 nights, 1 apartment
NZ$530 per night
includes taxes & fees
Peaceful Living-2Bdrm/2Bath w/Private Parking, WiFi-Work Station-Wicker Park!
Interior
Living area
Interior
Private kitchen
Exceptional
(7 reviews)

The En Bronze ~ 7mins To Dining & Downtown Chicago

Chicago

7% off
NZ$7,393
for 7 nights, 1 apartment
NZ$1,056 per night
includes taxes & fees
The En Bronze ~ 7mins To Dining & Downtown Chicago
Bedroom #1 with 2 double beds and an in-suite bathroom
5 minutes drive to McCormick Place (0.9 miles)
Upscale kitchen with an equally spacious dining room
Enjoy your stay in the well appointed living room with a 55" Roku Smart TV
Wonderful
(9 reviews)

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

Chicago

7% off
NZ$4,183
for 7 nights, 1 apartment
NZ$598 per night
includes taxes & fees
23rd St - Modern 2 Bedroom with Parking - near McCormick Place, Chinatown
Room
Living area
Games room
Lobby
Exceptional
(8 reviews)

Elite 4BR Art Deco suite. Garage included.

Chicago

7% off
NZ$13,905
for 7 nights, 1 apartment
NZ$1,986 per night
includes taxes & fees
Elite 4BR Art Deco suite. Garage included.
Room
Exterior
Living area
Living area
Exceptional
(110 reviews)

Lg Studio Apt. No cleaning fee. Obama Center 10 mins.

Chicago

7% off
NZ$1,877
for 7 nights, 1 apartment
NZ$268 per night
includes taxes & fees
Lg Studio Apt. No cleaning fee. Obama Center 10 mins.

Find the perfect holiday rental for your Cook County getaway

Learn about the unique charm of Cook County with a stay in a holiday home rental. This city has something for everyone. Navy Pier and Michigan Avenue are a couple of places to search for that perfect souvenir. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in Cook County

Are you looking for attractions to see while you're in town? Venture out of your cosy holiday rental and experience everything that makes Cook County a fun spot to go on holiday. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Harborside International Golf Center (6 mi / 9.7 km)
  • Galloping Ghost (9.8 mi / 15.8 km)
  • Ravisloe Country Club (12.3 mi / 19.7 km)
  • Lincoln Park Zoo (13.1 mi / 21.1 km)
  • Cog Hill Golf & Country Club (13.9 mi / 22.3 km)
  • Oak Brook Golf Course (13.9 mi / 22.3 km)

Exploring the natural features in Cook County

Whether you're an active traveller or just want to take in the scenery, Cook County is a great place to get out in nature. These are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Millennium Park (10.8 mi / 17.3 km)
  • Grant Park (10.2 mi / 16.4 km)
  • Abbott Park (4.1 mi / 6.6 km)
  • Washington Park (6 mi / 9.6 km)
  • Jackson Park (6.7 mi / 10.8 km)
  • Lake Katherine Nature Center (7 mi / 11.2 km)

How to get to and around Cook County

The nearest airport is in Chicago Midway Airport (MDW), located 4.2 mi (6.7 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could also fly into Chicago O'Hare International Airport (ORD), which is 19.7 mi (31.7 km) away.

If you prefer to travel by train, Chicago Ashburn Station, Chicago Wrightwood Station and Chicago 91st Street Station (Beverly Hills) are the main stations in the city. You can get around Cook County by catching a ride on the metro at 95th Street - Longwood Station, 103rd Street Washington Heights Station or Ashland-63rd Station.

Frequently asked questions

What is the best area to stay in Cook County when booking a holiday home?
If you're planning a getaway to Cook County, Steger is one of the most desired places to stay. Whether you're looking for a condo, cabin or other property type, you'll always have the entire place to yourself.
What is the most popular type of holiday home accommodation in Cook County?
Based on our research, apartments are the most in-demand property type in Cook County. But as you know, everyone's idea of the perfect trip can differ. Bookabach has holiday homes in a variety of sizes and shapes, so you're sure to find your ideal match.
How much does it cost to rent a holiday home in Cook County?
A number of factors affect how much you'll pay for a holiday home in Cook County, including the type of property, length of stay and season. Still, all our holiday homes have something in common — excellent value. Just enter your travel dates to find your ideal fit.
How much does it cost to rent a beach house in Cook County?
The average price for a holiday home close to the beach in Cook County depends on when you're travelling and the style and size of property you want. You can find prices quickly and easily on Bookabach by entering your travel dates. Then use our filter tool to select the number of bedrooms and amenities that you prefer, like a pool, WiFi and air conditioning.
What are popular home amenities in Cook County?
A microwave oven, a stovetop and a fridge top the list of most popular home amenities in Cook County. Whether you're planning to travel on your own, with your spouse or as a family, Bookabach can help you find a holiday home that suits your tastes with all the features you need.
Are there large group holiday homes in Cook County?
Choose from 172 holiday homes in Cook County that can host 10 or more guests. Whether you're planning a holiday with extended family or an event like a party, there's enough space to get your group together under one roof.
What are the top attractions for families in Cook County?
Keeping the kids entertained during your Cook County holiday is a breeze with these fabulous family-friendly attractions:
  • Orland Square
  • Odyssey Fun World
  • Hollywood Casino Amphitheatre
Can I find two-bedroom holiday homes in Cook County?
Take off with your besties and enjoy total privacy and comfort in one of the 562 two-bedroom holiday properties Cook County has to offer.
Are there holiday homes with WiFi in Cook County?
Cook County has 639 holiday homes with WiFi, so you'll be able to stay connected while travelling. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming Hollywood blockbusters to scrolling social media, these Bookabach homes will keep you online.
How old do you have to be to rent a holiday home in Cook County?
The minimum required age is typically 16, 18 or 21. It can change across properties on Bookabach, so check the rules of your chosen Cook County holiday home before making a booking.
How long can I rent a holiday home in Cook County for?
It's really down to the Cook County property. To see a list of options offering extended stays, just type your dates and guest number into Bookabach's search page. You can enjoy having the whole place to yourself, along with comforts such as air conditioning, a kitchen and a backyard where the little ones can play. Keep your eyes peeled for long-term stays that offer weekly or monthly discounts.

More holiday ideas