Cook County holiday rentals

We found 4,048 holiday rentals — enter your dates for availability
Discover a selection of 825 homes, 2667 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 Stayz

Holiday rentals with weekly discounts – Cook County

Showing deals for:1 Jan - 8 Jan

Dining
Our downtown Townhouse is in an amazing location
Interior
It is huge! With lots of areas for relaxing and entertaining
Exceptional
(92 reviews)

Historic luxury townhouse on Chicago's Gold Coast

Chicago

5% off
AU$10,243
for 7 nights, 1 home
AU$1,463 per night
includes taxes & fees
Historic luxury townhouse on Chicago's Gold Coast
The building
River North Luxury Living
French Bistro and Wine Bar - right downstairs
Outdoors at night
Exceptional
(106 reviews)

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

Chicago

7% off
AU$5,294
for 7 nights, 1 apartment
AU$756 per night
includes taxes & fees
River North's Rock N' Roll - In The Heart of the City
Private kitchen
Dining
Interior
Living area
Exceptional
(17 reviews)

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

Burr Ridge

8% off
AU$5,546
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
Room
Private kitchen
Interior
Living area
Exceptional
(13 reviews)

Stylish 4BR near ORD: games, yard, firepit, desk

Schaumburg

9% off
AU$6,078
for 7 nights, 1 home
AU$868 per night
includes taxes & fees
Stylish 4BR near ORD: games, yard, firepit, desk
Terrace/patio
Exterior
Interior
Interior
Exceptional
(14 reviews)

Spacious 6BR South Loop Luxury Suite Near McCormick Place & Soldier Field for 12

Chicago

7% off
AU$7,609
for 7 nights, 1 apartment
AU$1,087 per night
includes taxes & fees
Spacious 6BR South Loop Luxury Suite Near McCormick Place & Soldier Field for 12
Living area
Interior
Room
Living area
Exceptional
(25 reviews)

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

Berwyn

8% off
AU$2,421
for 7 nights, 1 apartment
AU$346 per night
includes taxes & fees
Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT
Open Concept Living Room
Polk Street
Sunny Bay Window
Room 2  Queen bed  black out curtains vintage snd Original art and a TV
Exceptional
(315 reviews)

3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place

Chicago

7% off
AU$2,834
for 7 nights, 1 apartment
AU$405 per night
includes taxes & fees
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
Fun Mirror Wall Upstairs
Downstairs living area
Downstairs living room
Upstairs queen bedroom 2
Exceptional
(100 reviews)

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

Chicago

7% off
AU$14,463
for 7 nights, 1 apartment
AU$2,066 per night
includes taxes & fees
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Kitchen
Living Room
Patio Deck 2
Bedroom 1 (King Size) + 55Inch TV
Exceptional
(23 reviews)

Spacious 5 BR / King Size Beds + Private Parking!

Chicago

8% off
AU$7,172
for 7 nights, 1 home
AU$1,025 per night
includes taxes & fees
Spacious 5 BR / King Size Beds + Private Parking!
Private kitchen
Interior
Room
Living area
Wonderful
(41 reviews)

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

Berwyn

8% off
AU$2,861
for 7 nights, 1 apartment
AU$409 per night
includes taxes & fees
Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
Private kitchen
Living area
Interior
Exterior detail
Exceptional
(8 reviews)

Cozy 3BR Near Obama Presidential Center, Hyde Park & UChicago

Chicago

10% off
AU$3,318
for 7 nights, 1 apartment
AU$474 per night
includes taxes & fees
Cozy 3BR Near Obama Presidential Center, Hyde Park & UChicago
Dining
Private kitchen
Living area
Room
Exceptional
(69 reviews)

Steps from the “L” train to Wrigley & Downtown

Chicago

7% off
AU$4,720
for 7 nights, 1 apartment
AU$674 per night
includes taxes & fees
Steps from the “L” train to Wrigley & Downtown
Enjoy your stay in the well appointed living room with a 55" Roku Smart TV
5 minutes drive to McCormick Place (0.9 miles)
Upscale kitchen with an equally spacious dining room
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$3,414
for 7 nights, 1 apartment
AU$488 per night
includes taxes & fees
23rd St - Modern 2 Bedroom with Parking - near McCormick Place, Chinatown
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$9,476
for 7 nights, 1 home
AU$1,354 per night
includes taxes & fees
Stunning Lincoln Park Single-Family House with Fantastic Game Room
Living area
Dining
Private kitchen
Living area
Wonderful
(21 reviews)

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

Berwyn

8% off
AU$2,608
for 7 nights, 1 apartment
AU$373 per night
includes taxes & fees
Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI
Exterior
Private kitchen
Full size bed, smart tv closet
Dining
Exceptional
(29 reviews)

Peaceful and Lovely 3-bedroom house near MDW. Furry friends welcomed

Chicago

7% off
AU$2,235
for 7 nights, 1 home
AU$319 per night
includes taxes & fees
Peaceful and Lovely 3-bedroom house near MDW. Furry friends welcomed
Private kitchen
Belmont Harbor
Living area
Exterior
Exceptional
(193 reviews)

Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

Chicago

8% off
AU$5,729
for 7 nights, 1 home
AU$818 per night
includes taxes & fees
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Dining
Exterior detail
Property grounds
Interior
Exceptional
(12 reviews)

Historic feel, Modern comfort Walk to parks and food in beautiful Chicago

Chicago

6% off
AU$2,006
for 7 nights, 1 apartment
AU$287 per night
includes taxes & fees
Historic feel, Modern comfort Walk to parks and food in beautiful Chicago
Interior
Living area
Bedroom #4 with a double and single bed
Close to the beautiful Ping Tom Park and a short water taxi ride to downtown
Exceptional
(22 reviews)

1 #33 - 4 Bedroom / 2 Bath Condo near McCormick Place, Wintrust Arena, Chinatown

Chicago

7% off
AU$5,128
for 7 nights, 1 apartment
AU$733 per night
includes taxes & fees
1 #33 - 4 Bedroom / 2 Bath Condo near McCormick Place, Wintrust Arena, Chinatown
Exterior
Living area
Private kitchen
Room
Excellent
(10 reviews)

High-end 2Bdrm Garden Apt. Where Comfort Meets Style

Chicago

7% off
AU$2,623
for 7 nights, 1 apartment
AU$375 per night
includes taxes & fees
High-end 2Bdrm Garden Apt. Where Comfort Meets Style
Room
Living area
Private kitchen
Dining
Exceptional
(23 reviews)

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

Berwyn

8% off
AU$2,487
for 7 nights, 1 apartment
AU$355 per night
includes taxes & fees
Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW
Dining
Living area
Private kitchen
Interior
Exceptional
(7 reviews)

Stylish 2BR Near Hyde Park, UChicago & Lake

Chicago

7% off
AU$3,227
for 7 nights, 1 apartment
AU$461 per night
includes taxes & fees
Stylish 2BR Near Hyde Park, UChicago & Lake
Living area
Dining
Terrace/patio
Room
Exceptional
(7 reviews)

The Dakin Estate: A refined 4BR Art Deco speakeasy duplex in Wrigleyville. Featuring curated interiors, elevated finishes, and a private entertainment lounge just minutes from Wrigley Field, dining, nightlife, and Chicago’s iconic attractions.

Chicago

7% off
AU$10,547
for 7 nights, 1 apartment
AU$1,507 per night
includes taxes & fees
The Dakin Estate: A refined 4BR Art Deco speakeasy duplex in Wrigleyville. Featuring curated interiors, elevated finishes, and a private entertainment lounge just minutes from Wrigley Field, dining, nightlife, and Chicago’s iconic attractions.
Private kitchen
Living area
Interior detail
Room
Exceptional
(14 reviews)

Ridgeland Retreat/ Street level Apt easy access

Berwyn

8% off
AU$3,743
for 7 nights, 1 apartment
AU$535 per night
includes taxes & fees
Ridgeland Retreat/ Street level Apt easy access

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)
  • Canalport Riverwalk Park (7.6 mi / 12.2 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. Stayz 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 Stayz 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, Stayz 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 Stayz 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 Stayz, 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 Stayz'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