Villas and Holiday homes in Chicago, IL

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

Woodlawn Oasis - Chicago, IL
8.9 9 reviews
Chicago, IL
10/08 – 19/08
428 €/nighttotal: 3852 € (9 )

Woodlawn Oasis

3 4
house, Chicago
Woodlawn Oasis, a three-bedroom, three-bathroom house in Chicago's Woodlawn neighbourhood, is located 2.4km from the Museum of Science and Industry and 2.6km from 63rd Street Beach, offering easy access to other attractions such as Guaranteed Rate Field (9km) and the Field Museum (11.5km).
This Chicago dwelling, boasting a 20 square metre floor area, comfortably sleeps 23 guests and includes a fully equipped kitchen, in-unit laundry, a garden, and free on-site parking.
Commuter-friendly Bungalow In Chicagos South Side - Chicago, IL
Chicago, IL
27/06 – 31/07
190 €/nighttotal: 6460 € (34 )

Commuter-friendly Bungalow In Chicagos South Side

3 1
house, Chicago
This bungalow is located on Chicago's South Side, offering convenient access to attractions such as the Museum of Science and Industry (7.7 kilometres) and Grant Park (17.7 kilometres).
This property provides 3 bedrooms, 2 bathrooms, and accommodates up to 9 guests, featuring air conditioning, free WiFi, a kitchen with a fridge and microwave oven, and a garden with an outdoor dining area, with a floor area of 139 square meters.
Portage Park, Jacuzzi, Movie Theater, Games & Arcade - Chicago, IL
Chicago, IL
09/08 – 13/08
786 €/nighttotal: 3144 € (4 )

Portage Park, Jacuzzi, Movie Theater, Games & Arcade

5 2
house, Chicago
This spacious 5-bedroom holiday home is situated in Chicago's Portage Park district, approximately 9.6 kilometres from Wrigley Field and 12.8 kilometres from Lincoln Park Zoo.
This detached property offers 204 square metres of living space, accommodating up to 30 guests with a fully equipped kitchen, private terrace, on-site jacuzzi, dedicated cinema room, games arcade, and free private parking with Wi-Fi.
Coachhouse In Central Op 4 Blk To L - Chicago, IL
9.8 553 reviews
Chicago, IL
11/09 – 13/09
166 €/nighttotal: 332 € (2 )

Coachhouse In Central Op 4 Blk To L

1 2
house, Oak Park
This furnished apartment is located in Oak Park's Frank Lloyd Wright Historic District, just one kilometre from the farmers market and within walking distance of Hemingway and Frank Lloyd Wright attractions. The property has received excellent ratings for cleanliness, location and overall experience.
The two-bedroom, one-bathroom property sleeps four guests and includes a fully equipped kitchen, in-unit laundry facilities, a private garage entrance and free WiFi. Guests can enjoy a range of entertainment options including a TV, Xbox and FireTV.
New Construction Building In River North - Chicago, IL
Chicago, IL
01/09 – 03/09
1819 €/nighttotal: 3638 € (2 )

New Construction Building In River North

1 2
house, Chicago
This new construction flat in River North, Chicago, is a 17-minute walk from the Museum of Contemporary Art and 1.77 kilometres from Shops at Northbridge.
This spacious 11-bedroom, 10-bathroom residence offers a fully equipped kitchen, air conditioning, complimentary Wi-Fi, and parking, with a guest capacity of 31.
Charming Private Coach House - Chicago, IL
9.9 56 reviews
Chicago, IL
27/08 – 30/08
329 €/nighttotal: 987 € (3 )

Charming Private Coach House

1 2
house, Chicago
This restored coach house is located in Chicago's East Village, just a short walk from the shops and restaurants on Chicago Avenue and Damen Avenue. The property has received excellent ratings for cleanliness, location, and user experience.
The house offers a spacious and open layout, perfect for up to four guests. It features a fully equipped kitchen, a dedicated office space, and a shared yard and patio, providing everything you need for a comfortable stay.
Entire House/united Center  /Garage-walk To Train - Chicago, IL
9.7 542 reviews
Chicago, IL
14/08 – 17/08
330 €/nighttotal: 990 € (3 )

Entire House/united Center /Garage-walk To Train

3 4
house, Chicago
This West Loop townhouse, a seven-minute walk from the Blue Line and three miles (4.8km) from Lake Michigan, offers easy access to the United Centre and the trendy West Loop bars and restaurants.
Sleeping eight guests, the property boasts three bedrooms, two bathrooms, a well-equipped kitchen with dishwasher, free street parking (subject to snow restrictions) plus garage parking, a 48-inch Roku TV, and premium mattresses.
Luxurious Home In Chicago Fulton Market Downtown - Chicago, IL
9.9 59 reviews
Chicago, IL
02/08 – 13/08
812 €/nighttotal: 8932 € (11 )

Luxurious Home In Chicago Fulton Market Downtown

4 5
house, Chicago
The Hubbard House is situated in Chicago's Fulton Market District, offering easy access to numerous restaurants and shops, and is within walking distance of Downtown Chicago's attractions.
This four-bedroom, three-and-a-half-bathroom property sleeps up to eleven guests, boasting a fully equipped kitchen, multiple living areas, and a luxurious master suite; the registration number is R22000092686.
Downtown Penthouse - Mich Ave 2bd Gym And Views #12 - Chicago, IL
Chicago, IL
04/08 – 10/08
666 €/nighttotal: 3996 € (6 )

Downtown Penthouse - Mich Ave 2bd Gym And Views #12

2 3
house, Chicago
This downtown Chicago penthouse is situated a mere 11-minute walk from the Art Institute of Chicago, 700 metres from the Chicago Symphony Orchestra, and a 9-minute walk from Grant Park, placing you within 2 kilometres of the city centre.
This penthouse offers 65 square metres of living space with two bedrooms and two bathrooms, accommodating up to seven guests with amenities including a fully equipped kitchen with a dishwasher, air conditioning, and complimentary WiFi, alongside access to an on-site fitness centre.
Stunning 5br Home In Heart Of Chicago With 2 Rooftops - Chicago, IL
10 2 reviews
Chicago, IL
03/07 – 05/07
1743 €/nighttotal: 3486 € (2 )

Stunning 5br Home In Heart Of Chicago With 2 Rooftops

1 2
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.
Beautiful & Spacious Family Friendly Town House - Chicago, IL
9.4 7 reviews
Chicago, IL
22/07 – 27/07
621 €/nighttotal: 3105 € (5 )

Beautiful & Spacious Family Friendly Town House

3 8
house, Chicago
This Lakeview townhouse, a 10-minute walk (1.6km) from the Southport Corridor and Diversey CTA station, offers easy access to Chicago's Wrigleyville and Jewel-Osco supermarket.
The four-bedroom, three-bathroom property sleeps eight guests and features a spacious layout with high ceilings, a well-equipped kitchen, and a family room; nearby attractions include the Southport Corridor's shops and restaurants.
Oak Park Home With Grill - 5 Mi To Garfield Park! - Chicago, IL
9.8 67 reviews
Chicago, IL
19/10 – 26/10
265 €/nighttotal: 1855 € (7 )

Oak Park Home With Grill - 5 Mi To Garfield Park!

3 4
house, Oak Park
This charming Oak Park house is situated just 14 kilometres from the United Center, 16 kilometres from Lincoln Park Zoo, and 18 kilometres from Union Station, offering easy access to Chicago's attractions. It is located in a quiet neighbourhood within the historic village of Oak Park, known for its beautiful architecture and vibrant arts scene. The house has received excellent ratings for cleanliness, location, and user experience.
The property has three bedrooms and one bathroom, spanning 167 square metres and comfortably accommodating up to six guests. Enjoy amenities such as a fully equipped kitchen, free Wi-Fi, a private fire pit, and a peaceful setting, perfect for a relaxing getaway.

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

Sleeps7 • 2br • Coffee Station • Backyard W/ Grill - Chicago, IL
Chicago, IL
17/08 – 22/08
218 €/nighttotal: 1090 € (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.
102 M² House ∙ 3 Bedrooms ∙ 6 Guests - Chicago, IL
Chicago, IL
01/01 – 31/01
287 €/nighttotal: 8610 € (30 )

102 M² House ∙ 3 Bedrooms ∙ 6 Guests

3 6
house, Des Plaines
House listing for 6 guests. You will be based in Des Plaines.
Facilities and services: a freeze, a swimming pool and free parking. Take advantage of the air conditioning in this house in Des Plaines.
Pet Friendly Walk To Uic Campus And Train! - Chicago, IL
Chicago, IL
01/09 – 31/10
367 €/nighttotal: 22020 € (60 )

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.
Forest Park Oasis - Dog Friendly - Parks - The "L" - Chicago, IL
9.9 23 reviews
Chicago, IL
25/06 – 28/06
328 €/nighttotal: 984 € (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.

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

Cozy Downtown Mich Ave Gym And Rooftop #7 - Chicago, IL
Chicago, IL
01/07 – 06/07
427 €/nighttotal: 2135 € (5 )

Cozy Downtown Mich Ave Gym And Rooftop #7

2 3
house, Chicago
This apartment is located in central Chicago, 966 metres from Grant Park and the Art Institute of Chicago, and within a 30-minute walk of the CIBC Theatre and Millennium Park.
This holiday home offers 64 square metres of living space with 2 bedrooms, 2 bathrooms, and can accommodate up to 7 guests, featuring a fully equipped kitchen, WiFi, and a fitness centre.
House In The Park 5 Min From O'hare - Chicago, IL
9.2 5 reviews
Chicago, IL
24/07 – 26/07
640 €/nighttotal: 1280 € (2 )

House In The Park 5 Min From O'hare

4 10
house, Des Plaines
This Des Plaines house, ideally located 2 km from O'Hare International Airport and 24 km from Wrigley Field and Loyola University Chicago, offers easy access to major attractions.
This spacious 167-square-metre property boasts four bedrooms, two bathrooms, two living rooms, and can comfortably accommodate up to 19 guests, featuring amenities such as a terrace, garden, free Wi-Fi, and on-site parking, plus a casino and water park.
Spacious 4br Townhouse In West Loop/fulton Market - Chicago, IL
10 280 reviews
Chicago, IL
16/09 – 23/09
945 €/nighttotal: 6615 € (7 )

Spacious 4br Townhouse In West Loop/fulton Market

1 14
house, Chicago
This spacious four-bedroom townhouse is situated in Chicago's West Loop/Fulton Market district, offering easy access to Restaurant Row and major attractions such as Navy Pier and the Loop, all within a convenient distance.
The 91-metre-squared, four-storey property comfortably sleeps up to 15 guests, boasting a fully equipped kitchen, private parking, two outdoor spaces including a rooftop terrace, and high-speed internet access; nearby activities include exploring the culinary delights of Fulton Market and utilising excellent public transport links to O'Hare Airport.
Hidden Gem - 3 Story House & Pet Friendly! - Chicago, IL
9.9 120 reviews
Chicago, IL
30/10 – 01/11
488 €/nighttotal: 976 € (2 )

Hidden Gem - 3 Story House & Pet Friendly!

3 3
house, Chicago
This Chicago triplex is located in Lincoln Park, offering easy access to local parks and attractions.
The spacious three-floor property sleeps six guests, boasting a fully equipped kitchen, multiple entertainment areas including a games room and bar, a private patio, and in-unit laundry facilities.

Frequently asked questions about villa rentals in Chicago, IL

Destinations nearby

Best Chicago, IL villas and holiday homes with parking

Spacious Row Home Next Transit Near Downtown W Parking - Chicago, IL
8.2 21 reviews
Chicago, IL
13/09 – 16/09
471 €/nighttotal: 1413 € (3 )

Spacious Row Home Next Transit Near Downtown W Parking

4 2
house, Chicago
This spacious Chicago townhouse is situated near the city centre, approximately 3.2km from the United Centre and 6.4km from Union Station, offering easy access to public transport and major attractions.
The 260 square metre property boasts four bedrooms, three living rooms, and three bathrooms, comfortably accommodating up to 31 guests, and includes a fully equipped kitchen, private parking, and outdoor space with a balcony and picnic area.
Spacious Retreat Near Convention Centers Home - Chicago, IL
Chicago, IL
03/07 – 12/07
445 €/nighttotal: 4005 € (9 )

Spacious Retreat Near Convention Centers Home

4 7
house, Des Plaines
This Des Plaines property is situated 4km from O'Hare International Airport, providing easy access to Chicago attractions such as Loyola University and Wrigley Field, both within a 24km radius.
The 149 square metre house offers a spacious four-bedroom layout sleeping up to 19 guests, boasting a fully equipped kitchen, free Wi-Fi, on-site yoga classes, and private parking.
Designer Themed 4 Bedroom In Best Location With Patio And Fireplace - Chicago, IL
9.6 685 reviews
Chicago, IL
04/12 – 10/12
507 €/nighttotal: 3042 € (6 )

Designer Themed 4 Bedroom In Best Location With Patio And Fireplace

4 2
house, Chicago
This four-bedroom holiday home is located in Chicago's Old Town district, just a short walk from Oak Street Beach and Lincoln Park Zoo, offering easy access to the city's attractions and restaurants. The property consistently receives excellent ratings for its location, cleanliness, and overall experience.
The house is spacious and comfortable, accommodating larger groups with ease. Guests can enjoy a range of amenities, including a fully equipped kitchen, a patio, a garden, a spa, a fitness centre, and a tennis court.
Lincoln Park 3br Townhome  Rooftop  King Suite  Sleeps 10 - Chicago, IL
9.9 175 reviews
Chicago, IL
22/12 – 26/12
1421 €/nighttotal: 5684 € (4 )

Lincoln Park 3br Townhome Rooftop King Suite Sleeps 10

3 3
apartment, Chicago
This three-storey townhome is ideally situated in Chicago's Lincoln Park neighbourhood, a short walk (less than 1.6 km) from Lake Michigan, Lincoln Park Zoo, and numerous shops and restaurants.
The property offers three bedrooms sleeping up to nine guests, a fully equipped kitchen with William Sonoma appliances, a private rooftop terrace with a bar and BBQ, plus guest parking passes and boutique amenities; enjoy nearby farmers' markets and easy access to public transport.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL villas and holiday homes with a garden

New 10-min To Downtown - Chicago, IL
Chicago, IL
10/08 – 13/08
394 €/nighttotal: 1182 € (3 )

New 10-min To Downtown

1 3
house, Oak Park
This Oak Park detached house offers convenient access to Chicago landmarks, situated 9.2 kilometres from the United Centre and 11.9 kilometres from Union Station.
This spacious property provides accommodation for up to 12 guests across 4 bedrooms and 2 bathrooms, featuring a fully equipped kitchen with a dishwasher and oven, complimentary on-site parking, and free Wi-Fi, with a garden for guest relaxation.
Modern Home Near Rosemont Allstate Arena O'hare Home - Chicago, IL
Chicago, IL
04/08 – 08/08
374 €/nighttotal: 1496 € (4 )

Modern Home Near Rosemont Allstate Arena O'hare Home

3 2
house, Des Plaines
This modern three-bedroom holiday home in Des Plaines is situated just 966 metres from Chicago O'Hare International Airport, offering convenient access to Chicago city centre attractions including Loyola University Chicago (19 kilometres) and Wrigley Field (21 kilometres).
This spacious 102 square metre property comfortably accommodates up to 11 guests, boasting a fully equipped kitchen with a dishwasher, complimentary WiFi, air conditioning, a garden, and on-site yoga classes.
Luxury Home Away From Your Home - Chicago, IL
Chicago, IL
13/09 – 16/09
219 €/nighttotal: 657 € (3 )

Luxury Home Away From Your Home

1 2
house, Chicago
This recently refurbished dwelling in Chicago offers excellent access, situated approximately 800 metres from the United Centre and 2.4 kilometres from the city centre.
This accommodation sleeps up to eight guests in three bedrooms and features two bathrooms, internet access, and a garden, making it ideal for family holidays with public transport just a short walk away.
The Avondale Guesthouse - Chicago, IL
9.7 393 reviews
Chicago, IL
30/10 – 01/11
231 €/nighttotal: 462 € (2 )

The Avondale Guesthouse

3 3
house, Chicago
The Avondale Guesthouse is situated in the Avondale neighbourhood of Chicago, just a short distance from Wrigley Field and Lincoln Park Zoo, making it a great base for exploring the city. The guesthouse consistently receives excellent ratings for its cleanliness, location, and overall user experience.
The property has three bedrooms, accommodating up to six guests, and is ideal for families or groups of friends. You can enjoy modern amenities like free Wi-Fi, a fully equipped kitchen, and a private patio, as well as explore the neighbourhood by bike or relax in the garden.
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