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Chicago villas
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634 Villa rentals in Chicago

A Pleasant Stay In Oak Park - Chicago
10 64 reviews
Chicago
07/05 – 07/07
$228/nighttotal: $456 (2 )

A Pleasant Stay In Oak Park

1 2
house, Oak Park
This Oak Park townhouse is ideally located one block from the Chicago Transit Authority (CTA) Green Line station and two blocks from the Oak Park Arts District, offering easy access to downtown Chicago and Barrie Park.
The two-bedroom, one-bathroom rental accommodates four guests and features a fully equipped kitchen, in-unit laundry, smart TVs, free Wi-Fi, and free off-street parking.
3-story Townhome Free Parking Private Patio Washer-dryer - Chicago
10 1 review
Chicago
10/06 – 10/15
$1220/nighttotal: $10980 (9 )

3-story Townhome Free Parking Private Patio Washer-dryer

2 2
house, Chicago
This three-story townhome is located in Chicago's Lincoln Park neighborhood, a 7-minute walk from Lincoln Park Zoo and 1.2 miles from North Avenue Beach.
This 1400-square-foot house features two bedrooms, two bathrooms, and accommodates up to 13 guests, offering free parking, a private patio, in-unit laundry, and a fully equipped kitchen with a fridge, microwave, and dishwasher.
Apartaestudio Para 2 Personas Máximo, Cómodo Y Limpio, Muy Central Con Múltiples Vías De Acceso, Transporte Urbano Y Cercanía A La Estación Del Tren, Variedad De Restaurantes Y Tiendas. - Chicago
9.7 196 reviews
Chicago
09/25 – 09/27
$151/nighttotal: $302 (2 )

Apartaestudio Para 2 Personas Máximo, Cómodo Y Limpio, Muy Central Con Múltiples Vías De Acceso, Transporte Urbano Y Cercanía A La Estación Del Tren, Variedad De Restaurantes Y Tiendas.

1 2
house, Chicago
This centrally located Chicago house, registration number R21000072720, offers a peaceful stay in a quiet neighborhood with easy access to shops and restaurants.
The one-bedroom, one-bathroom unit sleeps two guests and includes a fully equipped kitchen (fridge, freezer, microwave, dishwasher), air conditioning, free street parking, and a fitness center.
4 Bedroom Home In Best Location Parking Fireplace Back Yard Pets Welcome - Chicago
9.6 685 reviews
Chicago
07/20 – 07/24
$993/nighttotal: $3972 (4 )

4 Bedroom Home In Best Location Parking Fireplace Back Yard Pets Welcome

4 4
house, Chicago
This house is located in Chicago's Old Town district, just a short walk from Oak Street Beach, North Avenue Beach, and Lincoln Park Zoo. The neighborhood is known for its historic charm, art galleries, and lively nightlife. The property has received excellent ratings for location, cleanliness, and overall user experience.
The house has four bedrooms and four bathrooms, providing ample space for families or groups of friends. It features a patio, balcony, garden, spa, fitness center, and a tennis court, along with free parking.
Spacious Oak Park Home, 11 Mi To Downtown Chicago! - Chicago
9.4 65 reviews
Chicago
08/10 – 08/13
$392/nighttotal: $1176 (3 )

Spacious Oak Park Home, 11 Mi To Downtown Chicago!

3 3
house, Oak Park
The Oak Park House is a family-friendly home located in the historic Oak Park district of Chicago, renowned for its Frank Lloyd Wright architecture. It has excellent user, location, and cleanliness ratings.
The house has three bedrooms, two bathrooms, a well-equipped kitchen, air conditioning, a private patio, and free Wi-Fi. It can accommodate up to six guests and has a floor area of 2400 square feet. The house is close to major tourist attractions such as Union Station, Willis Tower, United Center, and Lincoln Park Zoo.
Spacious 3br Urban Getaway W Gym - Chicago
Chicago
07/07 – 07/09
$309/nighttotal: $618 (2 )

Spacious 3br Urban Getaway W Gym

1 2
house, Chicago
This Chicago urban getaway is located 8.1 miles from Midway International Airport and 1.4 miles from Guaranteed Rate Field, with Grant Park 2.4 miles away.
This 1800 sq ft house offers accommodations for up to 12 guests, featuring a fully equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, free WiFi, an on-site fitness center, and an outdoor patio.
Ideal Lakeview Location! Walk To Wrigley, Depaul - Chicago
9.9 57 reviews
Chicago
10/12 – 10/14
$393/nighttotal: $786 (2 )

Ideal Lakeview Location! Walk To Wrigley, Depaul

1 4
house, Chicago
This Lakeview East rowhouse offers a prime Chicago location near Wrigley Field, Lake Michigan, and Boystown, providing easy access to public transportation and DePaul University.
The two-bedroom, one-and-a-half-bathroom unit includes a full kitchen, dining room, laundry facilities, high-speed Wi-Fi, and accommodates up to six guests, with nearby parking available.
Downtown Penthouse - Mich Ave 2bd Gym And Views #12 - Chicago
Chicago
08/04 – 08/10
$770/nighttotal: $4620 (6 )

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

2 3
house, Chicago
This downtown Chicago penthouse is located an 11-minute walk from the Art Institute of Chicago and 0.7 miles from the Chicago Symphony Orchestra, placing it within a 9-minute walk of Grant Park and 1.2 miles of the city center.
This 700 sq ft, 2-bedroom vacation home accommodates up to 7 guests and features air conditioning, free WiFi, a fully equipped kitchen with a dishwasher, and access to a fitness center.
Sleeps 18 • 8br • Game Room • Gym • Theater - Chicago
Chicago
12/15 – 01/15
$1217/nighttotal: $37727 (31 )

Sleeps 18 • 8br • Game Room • Gym • Theater

8 5
house, Chicago
This 8-bedroom house in Chicago is located 6 miles from Wrigley Field and 8.8 miles from Lincoln Park Zoo, offering convenient access to attractions.
This 10,760 square foot residence accommodates up to 35 guests with a fully equipped kitchen, on-site gym, game room, and theater.
West Loop 3bd/2ba Th | 2 Jacuzzis | Garage Parking - Chicago
9.7 95 reviews
Chicago
09/18 – 09/21
$1014/nighttotal: $3042 (3 )

West Loop 3bd/2ba Th | 2 Jacuzzis | Garage Parking

1 8
house, Chicago
This stylish three-bedroom Chicago townhouse, perfect for large groups, is located on a main street; the exact neighborhood is unspecified, but its proximity to major attractions isn't detailed in the listing.
The 3-bedroom, 2-bathroom property boasts a game room, private one-car garage, fully equipped kitchen with granite island, patio, and comfortably sleeps 12 guests with a mix of King, Queen, and double beds plus roll-away beds.
Coach House With Garage Parking & Ev Charging - Chicago
10 89 reviews
Chicago
10/29 – 11/01
$258/nighttotal: $774 (3 )

Coach House With Garage Parking & Ev Charging

1 2
house, Chicago
This Wicker Park coach house boasts a prime location, a five-minute walk from both the Damen Blue Line and the 606 Trail.
The one-bedroom, one-bathroom unit sleeps two guests and features a spacious loft-like living area, private patio, enclosed garage with EV charging, and access to a shared garage bar with wine fridge; solar power adds a sustainable touch.
Coachhouse In Central Op 4 Blk To L - Chicago
9.8 553 reviews
Chicago
09/11 – 09/13
$192/nighttotal: $384 (2 )

Coachhouse In Central Op 4 Blk To L

1 2
house, Oak Park
This charming house is located in the Frank Lloyd Wright Historic District, just a block from the farmers market and within walking distance of Hemingway and Frank Lloyd Wright attractions. It has excellent user, location, and cleanliness ratings.
The house has two bedrooms and one bathroom, comfortably accommodating up to four guests. It features a fully equipped kitchen, laundry facilities, and amenities like TV/Xbox/FireTV, free parking, and WiFi.

Our Favorite Vacation Homes with a Pool in Chicago

Enjoy a proper swim in the heart of the city. These vacation homes in Chicago include pool access for your daily routine.

102 M² House ∙ 3 Bedrooms ∙ 6 Guests - Chicago
Chicago
01/01 – 01/31
$332/nighttotal: $9960 (30 )

102 M² House ∙ 3 Bedrooms ∙ 6 Guests

3 6
house, Des Plaines
House rental for up to 6 guests. This accommodation is located in Des Plaines.
Facilities and services include a kitchen, air conditioning and a garden.
Sleeps7 • 2br • Coffee Station • Backyard W/ Grill - Chicago
Chicago
08/28 – 08/31
$465/nighttotal: $1395 (3 )

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

2 2
apartment, Chicago
This 2-bedroom house in Chicago is located 7.4 miles from the United Center, 7.6 miles from Lincoln Park Zoo, and 9 miles from Union Station and 360 Chicago.
This spacious 10,760 square foot residence accommodates up to 7 guests, featuring a fully equipped kitchen, a private backyard with a grill, a garden, and free WiFi.
Forest Park Oasis - Dog Friendly - Parks - The "L" - Chicago
9.9 23 reviews
Chicago
06/25 – 06/28
$379/nighttotal: $1137 (3 )

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

1 4
house, Forest Park
This Forest Park townhouse is located directly across from Forest Park, Roos Recreation Center, a pool, and tennis courts, and a five-minute walk from the Harlem Blue Line station.
This pet-friendly rental boasts two bedrooms, one bathroom, and sleeps four, featuring a fully equipped kitchen with a bean-to-cup coffee machine, smart TVs, a fenced yard, and on-site parking plus free street parking.
Extended Stay: Walk To Uic Campus & Train! - Chicago
Chicago
09/01 – 10/31
$424/nighttotal: $25440 (60 )

Extended Stay: Walk To Uic Campus & Train!

2 2
house, Chicago
This 1250 sq ft, 2-bedroom, 2-bathroom condo in Chicago is located near the UIC campus and DePaul University, with Union Station 2 miles away, Willis Tower 2.1 miles away, and the United Center 2.3 miles away.
This pet-friendly rental offers Wi-Fi, a full kitchen, air conditioning, a swimming pool, and parking, accommodating up to 7 guests with a 10:00 AM check-out.

Best family friendly Chicago villas and beach houses

Among the 634 accommodations in Chicago, here are the 4 best family friendly villas and beach houses

House In The Park 5 Min From O'hare - Chicago
9.2 5 reviews
Chicago
08/09 – 08/11
$503/nighttotal: $1006 (2 )

House In The Park 5 Min From O'hare

4 4
house, Des Plaines
This house is located in Des Plaines, just 5 minutes from O'Hare International Airport and a short drive from Wrigley Field and Loyola University Chicago. It's a convenient location for exploring the city, with easy access to public transportation and attractions.
This 4-bedroom house can comfortably accommodate up to 19 guests, offering ample space for families or groups of friends. The property features a range of amenities, including a fully equipped kitchen, a private patio, a garden, and a water park, ensuring a comfortable and enjoyable stay.
Huge! 3br Private Home+garage+360° Roof Deck+hot Tub+ev+sleeps 12 - Chicago
9.8 19 reviews
Chicago
08/09 – 08/13
$728/nighttotal: $2912 (4 )

Huge! 3br Private Home+garage+360° Roof Deck+hot Tub+ev+sleeps 12

3 2
house, Chicago
This spacious Chicago West Loop apartment, two minutes from Fulton Market and the United Center, offers easy access to Grant Park, Michigan Avenue, and Lake Michigan.
The 1700-square-foot residence boasts three bedrooms, three bathrooms, sleeps twelve guests, and includes a private garage with an EV charger, a roof deck with Willis Tower views, and a fenced backyard.
5 Bedroom Huge House In Best Location Parking Fireplace Back Yard - Chicago
9.6 271 reviews
Chicago
10/12 – 10/14
$766/nighttotal: $1532 (2 )

5 Bedroom Huge House In Best Location Parking Fireplace Back Yard

5 4
house, Chicago
This 5-bedroom home is located in Chicago's Old Town neighborhood, a short walk from North Avenue Beach, Oak Street Beach, and Lincoln Park Zoo. The property has excellent ratings for cleanliness, location, and user experience.
This spacious house offers 3,000 square feet of living space. Enjoy amenities like a fully equipped kitchen, private patio and balcony, a backyard with a barbecue and outdoor play equipment, a spa, a restaurant, a fitness center, and free parking.
Lincoln Park 3br Townhome  Rooftop  King Suite  Sleeps 10 - Chicago
9.9 175 reviews
Chicago
12/22 – 12/26
$1643/nighttotal: $6572 (4 )

Lincoln Park 3br Townhome Rooftop King Suite Sleeps 10

3 3
apartment, Chicago
This Chicago townhouse is located in Lincoln Park, a vibrant neighborhood with easy access to the lakefront, Lincoln Park Zoo, farmers markets, and numerous shops and restaurants. This home has excellent user ratings, location ratings, and cleanliness ratings.
The three-bedroom, two-bathroom house can accommodate up to nine guests. Enjoy a fully equipped kitchen, a rooftop bar with a mini-fridge, smart TVs, a private rooftop patio, and a secondary outdoor space with a bistro table and BBQ.

Frequently Asked Questions about villa rentals in Chicago

  • What are the must-see attractions in Chicago, IL?

    You can't miss the iconic Willis Tower (formerly Sears Tower) for panoramic views of the city. The Art Institute of Chicago is a must-see for art lovers, and Millennium Park with Cloud Gate (the Bean) is a great place to take pictures.
  • What are the best villa rentals in Chicago?

  • What's the best district to book a villa in Chicago?

    Chicago doesn't have traditional villas, but for a luxurious stay, the Gold Coast neighborhood offers upscale apartments and condos with top-notch amenities.
  • What indoor activities for families are available in Chicago, IL on rainy days?

    The Field Museum is a great place to spend a rainy day, especially if you have kids. The Shedd Aquarium is another popular choice, and the Museum of Science and Industry is always a hit with families.
  • What are the best villa rentals with a pool in Chicago?

  • Which high-end restaurants in Chicago offer the finest local cuisine?

    High-end restaurants in Chicago that offer the finest local cuisine include Alinea, Spiaggia, and Oriole.
  • What are the best activities in Chicago, IL?

    Chicago is known for its food scene, so be sure to try some deep-dish pizza. You can take a boat tour on the Chicago River, visit Wrigley Field for a Cubs game, or catch a show in the theater district.
  • What are the best villa rentals with a jacuzzi in Chicago?

  • What cultural experiences in Chicago can families enjoy together?

    Families can enjoy cultural experiences at the Art Institute of Chicago and Navy Pier.
  • What are the advantages of renting a house or a villa in Chicago, IL

    You won't find many villas in Chicago, but renting a house can give you more space and privacy, especially if you're traveling with a large group. You'll also have a kitchen to cook in, which can save money on dining out.
  • What are the best villa rentals for families and kids in Chicago?

  • Are VIP passes available to Chicago's popular attractions, events or behind-the-scenes experiences?

    VIP passes are available for popular attractions and events, offering behind-the-scenes access and skip-the-line privileges.
  • What food festivals or culinary events take place in and around Chicago, IL?

    Chicago has tons of food festivals throughout the year. The Taste of Chicago is a huge event in the summer, and the Chicago Gourmet festival is a popular event for foodies.
  • What are the best pet friendly villa rentals in Chicago?

  • Are there any nearby UNESCO sites of profound cultural or natural significance in Chicago?

    While there are no nearby UNESCO sites in Chicago, the city is rich in cultural significance with its diverse neighborhoods and iconic architecture.
  • What exclusive experiences are available when visiting Chicago, IL?

    You can take a private tour of the Art Institute of Chicago, go on a behind-the-scenes tour of Wrigley Field, or have a private chef prepare a meal in your rented house.
  • What are the best villa rentals with parking in Chicago?

  • Which restaurants are suitable for vegetarian, vegan, gluten-free or other dietary requirements in Chicago?

    Chicago offers a variety of restaurants catering to different dietary requirements. For vegetarian and vegan options, try The Chicago Diner or Handlebar. For gluten-free options, check out Beatrix or Wildfire.
  • Which part of Chicago, IL would be ideal for a villa rental?

    If you want a more residential feel, Lincoln Park or Lakeview are good options. If you want to be closer to the action, you could try River North or the Gold Coast.

Destinations nearby

Best Chicago houses with parking

Lincoln Park Living - Suite 1 - Chicago
8.2 39 reviews
Chicago
12/22 – 12/30
$378/nighttotal: $3024 (8 )

Lincoln Park Living - Suite 1

2 2
house, Chicago
This Lincoln Park vacation home offers convenient access to Lincoln Park Zoo (1.6 miles), Wrigley Field (1.2 miles), and nearby beaches (1.5-1.9 miles).
This 1190-square-foot rental boasts two bedrooms, two bathrooms, and can comfortably accommodate up to four guests, featuring a fully equipped kitchen, in-unit laundry, and free Wi-Fi.
Historic Estate 10 Br, Sleeps 16, Game Room - Chicago
Chicago
10/30 – 11/01
$4420/nighttotal: $8840 (2 )

Historic Estate 10 Br, Sleeps 16, Game Room

1 3
house, Chicago
This historic estate is located in Chicago, 2.4 miles from the United Center and 3.8 miles from Water Tower Chicago.
This 3700 square foot house features 10 bedrooms, 7 bathrooms, a fully equipped kitchen, a game room, and can accommodate up to 16 guests with free Wifi and a private entrance.
Classic Forest Park Foursquare < 1 Mi To Blue Line - Chicago
Chicago
10/29 – 11/04
$295/nighttotal: $1770 (6 )

Classic Forest Park Foursquare < 1 Mi To Blue Line

1 2
cottage, Forest Park
This Forest Park cottage offers a prime location, situated 1.1 miles from the Frank Lloyd Wright Historic District and within 3 miles of the Ernest Hemingway Museum and House and Loyola University Medical Center.
This pet-friendly rental features air conditioning, a full kitchen with a microwave and dishwasher, a garden, and complimentary WiFi and parking, making it ideal for exploring the area.
Spacious Retreat Near Convention Centers Home - Chicago
Chicago
08/09 – 08/11
$493/nighttotal: $986 (2 )

Spacious Retreat Near Convention Centers Home

4 4
house, Des Plaines
This Des Plaines vacation home is conveniently located just 13 miles from Loyola University Chicago and 15 miles from Wrigley Field, offering easy access to popular attractions. The surrounding area provides a peaceful and suburban ambiance, perfect for a relaxing getaway.
This 4-bedroom house offers ample space for families and groups, accommodating up to 19 guests. The 1,600 square foot home features a fully equipped kitchen, a balcony, free parking, and free Wi-Fi, along with a washing machine, a satellite flat-screen TV, and yoga classes.

Neighborhoods and points of interest in Chicago

Best Chicago houses with a garden

Polk Street Coach House Apartment, Little Italy/medical Dist - Chicago
10 934 reviews
Chicago
09/01 – 09/03
$197/nighttotal: $394 (2 )

Polk Street Coach House Apartment, Little Italy/medical Dist

1 2
house, Chicago
This private 2-bedroom carriage house is located in Chicago's Little Italy neighborhood, just a block south of Taylor Street and within walking distance of the Medical District. The house has excellent user, location, and cleanliness ratings.
The apartment is perfect for groups of up to 6 guests and features a well-equipped kitchen, comfortable amenities, and access to a courtyard with a Weber grill. Guests can enjoy the mid-century modern design, free parking, and convenient access to public transportation.
Logan Square Duplex Smart Home W/garage By 606 Trl - Chicago
9.7 69 reviews
Chicago
09/05 – 09/07
$642/nighttotal: $1284 (2 )

Logan Square Duplex Smart Home W/garage By 606 Trl

1 6
house, Chicago
This three-bedroom townhome enjoys a prime location in Chicago, a convenient 20-minute drive from both downtown Chicago and O'Hare International Airport.
The 3-bedroom house offers sleeping for up to 8 guests, a full kitchen with fridge, freezer, and microwave, in-unit laundry (washer and dryer), a private garage, and a safety deposit box.
Whispering Oaks Retreat - Chicago
Chicago
08/27 – 08/30
$682/nighttotal: $2046 (3 )

Whispering Oaks Retreat

5 1
house, Forest Park
Whispering Oaks Retreat, a Forest Park house rental, is conveniently located 10 miles from Union Station and DePaul University, offering easy access to major Chicago attractions.
This 1910-square-foot home features one bedroom, two bathrooms, and sleeps up to 14 guests, boasting a fully equipped kitchen, air conditioning, Wi-Fi, a fireplace, and a TV.
Location! 5 Beds House With Parking And Patio! - Chicago
9.6 114 reviews
Chicago
07/01 – 08/31
$514/nighttotal: $31354 (61 )

Location! 5 Beds House With Parking And Patio!

4 3
house, Chicago
This Lincoln Park townhouse, steps from popular Chicago attractions and two supermarkets, offers a prime location for exploring the city.
The 4-bedroom, 2-bathroom home sleeps 9 guests comfortably, boasting a high-end kitchen, large patio with BBQ, and private parking—perfect for families or groups visiting Chicago.
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