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Chicago, IL holiday homes
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634 Villa rentals in Chicago, IL

Best Chicago, IL villas and holiday homes with a pool

Among the 634 accommodations in Chicago, IL, here are the 4 best villas and holiday homes with a pool

102 M² House ∙ 3 Bedrooms ∙ 6 Guests - Chicago, IL
Chicago, IL
01/01 – 31/01
NZ$571/nighttotal: NZ$17130 (30 )

102 M² House ∙ 3 Bedrooms ∙ 6 Guests

3 6
house , Des Plaines
Holiday house to rent for 6 people. You will be in Des Plaines.
Facilities and services: a garden, a terrace and free parking. This house in Des Plaines also has air conditioning!
Forest Park Oasis - Dog Friendly - Parks - The "L" - Chicago, IL
9.9 23 reviews
Chicago, IL
25/06 – 28/06
NZ$651/nighttotal: NZ$1953 (3 )

Forest Park Oasis - Dog Friendly - Parks - The "L"

1 4
house , Forest Park
This newly renovated Forest Park townhouse is situated directly opposite Forest Park, Roos Recreation Centre, tennis courts and a swimming pool, and a 0.8 km walk from the Harlem Blue Line station, offering easy access to downtown Chicago and O'Hare Airport.
The two-bedroom, one-bathroom property sleeps four, features a fully equipped kitchen with a bean-to-cup coffee machine, smart TVs, a dedicated workspace, a fenced yard with a pet door, and includes board games; free on-street parking supplements the designated parking space.
Sleeps7 • 2br • Coffee Station • Backyard W/ Grill - Chicago, IL
Chicago, IL
17/08 – 22/08
NZ$434/nighttotal: NZ$2170 (5 )

Sleeps7 • 2br • Coffee Station • Backyard W/ Grill

2 3
apartment , Chicago
This Chicago detached house is located approximately 12 kilometres from the United Centre and 12.2 kilometres from Lincoln Park Zoo, offering straightforward access to several key city attractions.
This detached house provides accommodation for up to 7 guests across 2 bedrooms, featuring a fully equipped kitchen with an oven and microwave, complimentary WiFi, and a backyard with a grill, all within a 1000 square metre floor area.
Pet Friendly Walk To Uic Campus And Train! - Chicago, IL
Chicago, IL
10/08 – 10/10
NZ$730/nighttotal: NZ$44530 (61 )

Pet Friendly Walk To Uic Campus And Train!

2 2
apartment , Chicago
This Chicago flat is located near the University of Illinois Chicago (UIC) campus, offering convenient access within 3.4 kilometres of Willis Tower and 4 kilometres of Union Station.
This 116 square metre apartment accommodates up to seven guests with two bedrooms and two bathrooms, featuring air conditioning, a fully equipped kitchen, complimentary Wi-Fi, and an outdoor swimming pool.

Best family friendly Chicago, IL villas and holiday home

Among the 634 accommodations in Chicago, IL, here are the 4 best family friendly villas and holiday homes

Chicago Bungalow Near Wrigley Field W/ King Suite - Chicago, IL
9.6 265 reviews
Chicago, IL
19/07 – 25/07
NZ$662/nighttotal: NZ$3972 (6 )

Chicago Bungalow Near Wrigley Field W/ King Suite

1 8
bungalow , Chicago
This Chicago bungalow is situated just a short distance from Wrigley Field, in a safe and friendly neighbourhood with plenty of pubs and restaurants nearby. The property has received excellent ratings for its location, cleanliness and overall experience.
The three-bedroom house comfortably sleeps up to nine guests and offers a fully equipped kitchen, a private garden with access until 9pm, and super-fast internet. You’ll also find a separate entrance, a smart lock for easy access, and air conditioning for your comfort.
Wicker Park Crash Pad + 7 Beds - Chicago, IL
9.8 111 reviews
Chicago, IL
13/07 – 15/07
NZ$479/nighttotal: NZ$958 (2 )

Wicker Park Crash Pad + 7 Beds

1 6
house , Chicago
This spacious two-level apartment is located in Chicago's Wicker Park neighbourhood, less than 1.6km from Downtown, Lincoln Park, and Wrigleyville.
The 7-bed dwelling, sleeping up to 8 guests, boasts two bathrooms, two living areas, a fully equipped kitchen with complimentary food items, a shared patio, Wi-Fi, DISH network TV with DVR, and Sirius Satellite Radio.
Walk To The Beach And Golf From Our 3 Story Home. - Chicago, IL
9.4 63 reviews
Chicago, IL
27/06 – 04/07
NZ$657/nighttotal: NZ$4599 (7 )

Walk To The Beach And Golf From Our 3 Story Home.

1 8
house , Chicago
This spacious Chicago house, ideal for groups, offers four bedrooms and two bathrooms sleeping up to twelve guests, and boasts a 251-square-metre floor area across three floors.
The property includes a fully equipped kitchen, rooftop deck with city views, and convenient access to Chicago's attractions, though precise distances to landmarks are not specified.
Hello Again, Chicago! - Chicago, IL
Chicago, IL
09/09 – 12/09
NZ$1740/nighttotal: NZ$5220 (3 )

Hello Again, Chicago!

1 2
house , Chicago
This Chicago residence is situated approximately 1.8 kilometres from the United Centre and 4.3 kilometres from Union Station, with the Chicago Museum of Contemporary Art and Shops at Northbridge also around 4.8 kilometres away.
This spacious holiday home, spanning 418 square metres, accommodates up to 31 guests and offers four bathrooms, complimentary private parking, and free WiFi, alongside a fully equipped kitchen and a balcony.

Frequently asked questions about villa rentals in Chicago, IL

Destinations nearby

Best Chicago, IL villas and holiday homes with parking

Pearly Gates | 3 Bed | Sleeps 5 | W/ 2-car Garage - Chicago, IL
9.5 253 reviews
Chicago, IL
05/07 – 06/07
NZ$910/nightfor 1 night

Pearly Gates | 3 Bed | Sleeps 5 | W/ 2-car Garage

3 6
apartment , Forest Park
This charming house is located in Forest Park, just 1.6km from Madison Street, a bustling area with shops, restaurants, and bars, and a 3-block walk from the CTA Blue Line "L" station, providing easy access to downtown Chicago. The property has received excellent ratings for its location, cleanliness, and overall user experience.
The house features three bedrooms and one bathroom. Amenities include a fully equipped kitchen, air conditioning, parking, a fenced backyard, a washer and dryer, and flexible check-in/check-out options.
Stunning 5br Home In Heart Of Chicago With 2 Rooftops - Chicago, IL
10 2 reviews
Chicago, IL
30/07 – 02/08
NZ$5544/nighttotal: NZ$16632 (3 )

Stunning 5br Home In Heart Of Chicago With 2 Rooftops

1 3
house , Chicago
This five-bedroom Chicago house, located centrally and approximately 5-6 km from Lincoln Park Zoo, the Water Tower, and the United Centre, offers convenient access to major attractions.
The 340 square metre property boasts a fully equipped kitchen, four bathrooms, a private garden, two rooftop terraces, and comfortably accommodates up to 26 guests.
3-story Townhome, Free Parking, Private Patio, Was - Chicago, IL
9.7 54 reviews
Chicago, IL
25/06 – 28/06
NZ$1331/nighttotal: NZ$3993 (3 )

3-story Townhome, Free Parking, Private Patio, Was

1 4
house , Chicago
This southeast Lincoln Park townhouse, a short walk from Lincoln Park Zoo and approximately 1.6 km from downtown Chicago and Wrigley Field, offers convenient access to Chicago's key attractions.
The three-storey property sleeps eight guests in two bedrooms and one bathroom, boasting a fully equipped kitchen, private patio with barbecue and smoker, in-unit laundry, and additional amenities including bicycles and beach equipment.
Beautiful Home In Bridgeview! - Chicago, IL
10 2 reviews
Chicago, IL
15/08 – 17/08
NZ$915/nighttotal: NZ$1830 (2 )

Beautiful Home In Bridgeview!

1 2
house , Bridgeview
This Bridgeview dwelling is situated 9 kilometres from Midway International Airport and 22.5 kilometres from Guaranteed Rate Field, offering convenient access to Chicago's landmarks.
This one-bedroom property accommodates up to 15 guests, featuring air conditioning, complimentary WiFi, and a fully equipped kitchen, with private on-site parking available.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL villas and holiday homes with a garden

Downtown Mich Ave - 6 Penthouses, Sleep 25 - Chicago, IL
Chicago, IL
11/09 – 16/09
NZ$8642/nighttotal: NZ$43210 (5 )

Downtown Mich Ave - 6 Penthouses, Sleep 25

10 4
house , Chicago
This expansive penthouse is located in Downtown Chicago, offering a 9-minute walk to Grant Park and a 17-minute walk to Cloud Gate, placing it near the Art Institute of Chicago and the Chicago Symphony Orchestra.
This property boasts a 310 square meter floor area, with 10 bedrooms and 9 bathrooms suitable for up to 36 guests, and includes a fitness centre and lake views.
Beautifully Renovated House 10 Mins From Downtown - Chicago, IL
8.2 13 reviews
Chicago, IL
21/09 – 24/09
NZ$1354/nighttotal: NZ$4062 (3 )

Beautifully Renovated House 10 Mins From Downtown

6 2
house , Chicago
This renovated house is situated in Chicago, just 1.6km from Oakwood Beach and 3.2km from Guaranteed Rate Field, offering easy access to the city's attractions and a peaceful neighbourhood setting. The property has received excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
This spacious home spans 297 square metres and comfortably accommodates up to 29 guests, making it ideal for large families or groups. The house offers a fully equipped kitchen, a terrace, a garden, a dedicated kids' pool, an indoor play area, and outdoor play equipment, ensuring a relaxing and entertaining stay for everyone.
Charming Andersonville Coach House 3br 2,5ba - Chicago, IL
Chicago, IL
10/08 – 10/10
NZ$332/nighttotal: NZ$20252 (61 )

Charming Andersonville Coach House 3br 2,5ba

3 2
house , Chicago
This private, two-storey coach house in Chicago is located on a quiet, tree-lined street, less than 300 metres from the dining, shopping, and café options on North Clark.
This dwelling offers three bedrooms, two and a half bathrooms, and accommodates up to five guests, with internet, air conditioning, and a kitchen equipped with a fridge, microwave, and dishwasher, plus it allows pets for an additional fee.
Classic Forest Park Foursquare Less Than 1 Mi To Blue Line - Chicago, IL
Chicago, IL
25/11 – 29/11
NZ$682/nighttotal: NZ$2728 (4 )

Classic Forest Park Foursquare Less Than 1 Mi To Blue Line

3 2
house , Forest Park
This Foursquare property in Forest Park offers convenient access to the Blue Line, situated less than 1 kilometre away, providing straightforward journeys to downtown Chicago landmarks such as Union Station and the Willis Tower, both 16 kilometres distant, and the United Centre, 12.7 kilometres away.
This 104 square metre holiday home accommodates up to 13 guests with three bedrooms and two living rooms, featuring a fully equipped kitchen with a dishwasher and coffee machine, air conditioning, free WiFi, a private patio, and an outdoor dining area, with Midway International Airport 13.9 kilometres distant.
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