Villas and Holiday homes in Chicago, IL

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Chicago, IL villas
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772 Villa rentals in Chicago, IL

Best Chicago, IL villas and holiday homes with a pool

Among the 772 accommodations in Chicago, IL, here are the 4 best villas and holiday homes with a pool

Jeffjack Heated Pool Penthouse In Chicago's West Loop - Chicago, IL
9.6 147 reviews

Jeffjack Heated Pool Penthouse In Chicago's West Loop

apartment, Chicago
This penthouse apartment is conveniently located in the centre of Chicago, within easy walking distance of Union Station, Willis Tower, and CIBC Theatre. The apartment consistently receives excellent ratings for its location, cleanliness, and overall experience, making it a popular choice for travellers.
The apartment has two bedrooms, comfortably accommodating up to six guests. Enjoy a range of amenities including a rooftop pool, fitness centre, and private parking, as well as a fully equipped kitchen and balcony with stunning city views.
102 M² House ∙ 3 Bedrooms ∙ 6 Guests - Chicago, IL
No reviews

102 M² House ∙ 3 Bedrooms ∙ 6 Guests

house, Des Plaines
Vacation house for 6 people. This accommodation is located in Des Plaines.
Services and facilities include a garden, an iron and a freeze. Take advantage of the air conditioning in this house in Des Plaines.
Sleeps7 • 2br • Coffee Station • Backyard W/ Grill - Chicago, IL
No reviews

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

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.
Extended Stay: Walk To Uic Campus & Train! - Chicago, IL
No reviews

Extended Stay: Walk To Uic Campus & Train!

house, 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 772 accommodations in Chicago, IL, here are the 4 best family friendly villas and holiday homes

Lovely Central Oak Park Th W/parking & On Green El - Chicago, IL
9.9 236 reviews

Lovely Central Oak Park Th W/parking & On Green El

house, Oak Park
This charming house is located in a central Oak Park neighbourhood, just a short walk from the Green Line, Metra, and the Oak Park Farmers Market. It has received excellent ratings for location, cleanliness and user experience.
The property has two bedrooms and two bathrooms, making it ideal for families or groups of up to five people. It comes equipped with a kitchen, a garden, parking, and laundry facilities, as well as air conditioning and internet access.
Live Logan Square The Globally Loved Neighborhood - Chicago, IL
9.7 301 reviews

Live Logan Square The Globally Loved Neighborhood

house, Chicago
This Logan Square flat is situated two blocks from Milwaukee Avenue's restaurants and bars, a 1.1 km walk from the Blue Line 'L' train station providing easy access to Chicago's city centre and O'Hare International Airport.
The spacious four-bedroom, two-bathroom apartment sleeps up to ten guests, offering a fully equipped kitchen, in-unit laundry, a private enclosed yard, Netflix, Amazon Prime, and self check-in; free on-street parking is available.
Beautiful Spacious Riverwest Townhome 4-bed/4-bath - Chicago, IL
10 175 reviews

Beautiful Spacious Riverwest Townhome 4-bed/4-bath

house, Chicago
This modern house is located in the RiverWest neighbourhood, just a minute's walk from the Blue Line, offering easy access to downtown Chicago and its vibrant nightlife. The property has received excellent ratings for location, cleanliness and user experience.
The four-bedroom property spans 251 square metres and includes a gourmet kitchen, Jacuzzi tub, multiple decks with city views, and a natural gas grill. Guests can enjoy high-speed Wi-Fi, flat-screen TVs in every bedroom, and a built-in espresso machine, perfect for a relaxing stay.
House To Relax - Chicago, IL
9.7 108 reviews

House To Relax

house, Berwyn
This Berwyn apartment is conveniently located near local restaurants and gambling establishments, with easy access (within 16km) to Oak Park, Brookfield Zoo, and major hospitals.
The two-bedroom, one-bathroom flat sleeps four guests and offers free street parking (one permit per night), a fully equipped kitchen including a dishwasher, a 50" smart TV, and air conditioning.

Frequently asked questions about villa rentals in Chicago, IL

Popular destinations

Best Chicago, IL villas and holiday homes with parking

Historic Estate 10 Br, Sleeps 16, Game Room - Chicago, IL
No reviews

Historic Estate 10 Br, Sleeps 16, Game Room

house, Chicago
This substantial 10-bedroom historic estate in Chicago offers expansive accommodation for up to 16 guests, situated approximately 3.9 kilometres from the United Centre and 6.1 kilometres from the Water Tower Chicago.
Boasting 344 square metres of floor area, this detached house features seven bathrooms, a fully equipped kitchen with a dishwasher, complimentary WiFi, and a dedicated games room, alongside a patio and private entrance.
Spacious 5-br House Near Transit W Parking - Chicago, IL
9.6 155 reviews

Spacious 5-br House Near Transit W Parking

house, Chicago
This spacious house is located in Chicago, just 5.6 kilometres from the United Center and 8.7 kilometres from Union Station, making it ideal for exploring the city. The property has consistently received excellent ratings for cleanliness, location, and overall user experience.
The house is spread over 260 square metres and includes five bedrooms, two living rooms, and three bathrooms, providing ample space for families or groups. Guests can enjoy a fully equipped kitchen, a private garden, a terrace, and free parking, ensuring a comfortable and convenient stay.
Sleeps 10 + Coffee Bar + Game Room + Train To Chgo - Chicago, IL
10 4 reviews

Sleeps 10 + Coffee Bar + Game Room + Train To Chgo

house, Brookfield
This Brookfield holiday home is located 20.9 to 24.1 kilometres from downtown Chicago's Union Station and Willis Tower, with Chicago Midway International Airport 10.9 kilometres away.
This 171 square metre residence offers four bedrooms, three bathrooms, and can accommodate up to ten guests, featuring a dedicated games room, a fully equipped kitchen with a dishwasher, an outdoor fireplace, and both indoor and outdoor play areas, all with free WiFi and private parking.
Windy City Getaway - 3br 2ba Chicago Townhouse Home - Chicago, IL
9.5 2 reviews

Windy City Getaway - 3br 2ba Chicago Townhouse Home

house, Chicago
This Chicago townhouse, situated approximately 8-13 kilometres from Wrigley Field, Lincoln Park Zoo, and the United Centre, offers convenient access to major attractions.
Sleeping up to 17 guests, this three-bedroom, three-bathroom property boasts a fully equipped kitchen, in-unit laundry, free Wi-Fi, private parking, a fireplace, and a terrace/balcony; nearby activities include exploring Lincoln Park Zoo and catching a Cubs game at Wrigley Field.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL villas and holiday homes with a garden

Luxury Villa 10 Mins To Downtown - Chicago, IL
9.3 42 reviews

Luxury Villa 10 Mins To Downtown

house, Chicago
This two-bedroom, one-bathroom apartment is situated in Chicago's La Villita neighbourhood, approximately 24km from The Loop and other major attractions such as Soldier Field and McCormick Place.
The 6-guest property boasts a modern interior, a garden, parking, and a fully equipped kitchen including a fridge, freezer, microwave, and dishwasher; it offers easy access to public transport and is close to diverse dining and cultural experiences.
Addison Art Deco Manor Garage - Chicago, IL
No reviews

Addison Art Deco Manor Garage

house, Chicago
This Chicago lodging is situated a mere 2-minute walk from Wrigley Field, placing guests within 6.8 kilometres of Lincoln Park Zoo and Water Tower Chicago.
This nine-bedroom property offers accommodation for up to 39 guests, featuring a fully equipped kitchen, three living areas, complimentary WiFi, and on-site private parking.
Pearly Gates L 3 Bed L Sleeps 5 L W 2-car Garage - Chicago, IL
9.7 13 reviews

Pearly Gates L 3 Bed L Sleeps 5 L W 2-car Garage

house, Forest Park
Pearly Gates, a three-bedroom holiday home in Forest Park, Illinois, is situated 12 kilometres from Midway International Airport and approximately 16 kilometres from Chicago landmarks such as the Willis Tower and Union Station.
This 93-square-metre property sleeps up to thirteen guests, offering three bedrooms, one bathroom, a fully equipped kitchen with dishwasher and microwave, free Wi-Fi, parking for two cars, a garden, and air conditioning.
Chicago West Town Row House - Chicago, IL
9.7 35 reviews

Chicago West Town Row House

house, Chicago
This Chicago three-bedroom house, perfect for families or groups of up to eight, boasts a central location, though precise neighbourhood and distances to landmarks remain unspecified in the listing (R24000120337).
The four-storey property offers a spacious open-plan kitchen, dining, and living area, plus private and rooftop decks, alongside amenities including Wi-Fi, parking, and a full kitchen with dishwasher.
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