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634 Villa rentals in Chicago
9.9 174 reviews
Chicago
08/30 – 09/06
$1331/nighttotal: $9317 (7 )
Lincoln Park 3br Townhome Rooftop King Suite Sleeps 10
3 2
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.
Chicago
09/09 – 09/14
$817/nighttotal: $4085 (5 )
Mich Ave Downtown Grant Park, Museums 2bd-2ba #5
2 3
house , Chicago
This downtown Chicago vacation rental is located near Grant Park, a 10-minute walk from the Field Museum and an 18-minute walk from DePaul University, with the Adler Planetarium & Astronomy Museum 1.1 miles away. This 1050 square foot, 2-bedroom, 2-bathroom house accommodates up to 8 guests and features a kitchen with a fridge, microwave, and dishwasher, plus complimentary WiFi and lake views from the patio.
Chicago
09/01 – 09/05
$184/nighttotal: $736 (4 )
Modern 2br Gem Free Parking-10 Min Midway Airport-15 Min Dtwn
2 2
house , Cicero
This Cicero house offers convenient access to Chicago attractions, situated 5.1 miles from the United Center and 6.7 miles from Union Station, with Midway Airport just 3.7 miles away. This property accommodates up to 7 guests with 2 bedrooms, 1 bathroom, complimentary Wi-Fi, a full kitchen, and free on-site parking.
9.9 132 reviews
Chicago
06/24 – 06/26
$183/nighttotal: $366 (2 )
O'malley Oasis!
1 2
house , Oak Park
This charming coach house is located in a central Oak Park neighborhood, just a short walk from downtown Oak Park and public transportation. The studio apartment receives excellent ratings for location, cleanliness, and user experience. The apartment is perfect for two guests and features a private entrance, parking, and a comfortable living area with a recliner, leather couch, and big screen TV. Enjoy the fully equipped kitchen, charming porch, high ceilings, and skylights.
Chicago
07/08 – 07/12
$595/nighttotal: $2380 (4 )
Spacious 5br 2ba Berwyn Home
1 2
house , Berwyn
This Berwyn house is situated 7.5 miles from the United Center, with downtown Chicago attractions such as Union Station and Willis Tower located 9.2 miles away. This 130 square foot, 5-bedroom, 2-bathroom home accommodates up to 14 guests and features a fully equipped kitchen, air conditioning, and free WiFi.
10 3 reviews
Chicago
09/01 – 09/05
$593/nighttotal: $2372 (4 )
Modern 2-bedroom Townhome In Chicago With Private Patio
1 2
apartment , Chicago
This Bucktown townhome is located on a quiet corner block, steps from the bustling Six Corners intersection of North, Milwaukee, and Damen Avenues. The 1800-square-foot property features two bedrooms, two bathrooms, sleeps up to nine guests, and includes a private patio with a fire pit, a game room with shuffleboard and Connect Four, and a fully equipped kitchen.
Chicago
09/09 – 09/14
$291/nighttotal: $1455 (5 )
Classic Forest Park Foursquare < 1 Mi To Blue Line
3 3
house , Forest Park
This Forest Park accommodation offers a prime location within 5,280 feet of the Blue Line for easy transit to downtown Chicago, and is 7.9 miles from the United Center. This 1,120 square foot house features 3 bedrooms, 2 living rooms, a fully equipped kitchen with a dishwasher and coffee machine, air conditioning, complimentary WiFi, and outdoor patio space for up to 13 guests.
Chicago
07/05 – 07/10
$734/nighttotal: $3670 (5 )
Giant 5br, Pool Table, 15 Min To Cubs & Mag Mile
5 2
house , Chicago
This 2500 sq ft, 5-bedroom house in Chicago is located 3.8 miles from Wrigley Field and a 15-minute drive to the Cubs and Magnificent Mile, with Lincoln Park Zoo 5.8 miles away. This allergy-free, non-smoking residence accommodates 27 guests with 3 bathrooms, a fully equipped kitchen, air conditioning, and free WiFi, plus a pool table for entertainment.
9.7 23 reviews
Chicago
08/01 – 10/31
$52/nighttotal: $4732 (91 )
Lakefront English Basement W/ Workspace
1 2
house , Chicago
This charming bed and breakfast is located in a peaceful residential neighborhood on the outskirts of Chicago, just a short drive from the city's vibrant downtown and beautiful lakefront parks. The property has received excellent ratings for its cleanliness, location, and overall guest experience. The bed and breakfast occupies the top floor of a three-story townhouse, offering a private and quiet retreat for up to two guests. Amenities include a fully equipped kitchen, a private garden, a fitness center, and reserved parking for an additional fee.
Chicago
09/09 – 09/14
$428/nighttotal: $2140 (5 )
Spacious 5 Bed 2 Bath House
1 3
house , Northlake
This vacation home is located in a district providing easy access to local attractions and amenities in Northlake. This 130-square-foot house features 1 bedroom, 2 bathrooms, and accommodates up to 14 guests, offering complimentary Wi-Fi, air conditioning, and a fully equipped kitchen.
Chicago
06/29 – 07/02
$457/nighttotal: $1371 (3 )
4br Modern Urban Escape Walk To Zoo Lakefront & Red Line
1 2
house , Chicago
This urban escape is located in Chicago, offering city views and convenient proximity to Zoo Lakefront and the Red Line, just 1.7 miles from North Avenue Beach and 2 miles from Water Tower Chicago. This vacation home spans 1210 square feet with 4 bedrooms and 3 bathrooms, accommodating up to 16 guests with amenities including a dishwasher, microwave oven, fridge, and air conditioning, plus access to an on-site water park and nearby cycling.
10 2 reviews
Chicago
08/20 – 08/23
$2256/nighttotal: $6768 (3 )
Stunning 5br Home In Heart Of Chicago With 2 Rooftops
5 2
house , Chicago
This five-bedroom Chicago home is centrally located, approximately 3.4 miles from Lincoln Park Zoo and 3.6 miles from Water Tower Place, offering easy access to major attractions. This 4,000-square-foot residence boasts two rooftop terraces, a private garden, and accommodates up to 26 guests with amenities including a fully equipped kitchen, fireplace, and in-unit laundry.
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.
Chicago
09/11 – 09/17
$266/nighttotal: $1596 (6 )
Sleeps7 • 2br • Coffee Station • Backyard W/ Grill
2 1
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.
Chicago
01/05 – 02/28
$250/nighttotal: $13500 (54 )
102 M² House ∙ 3 Bedrooms ∙ 6 Guests
3 2
house , Des Plaines
Vacation rental for up to 6 people. You will be in Des Plaines. Facilities and services: a freeze, a kitchen and a fridge. Enjoy free parking with this accommodation in Des Plaines!
9.7 35 reviews
Chicago
09/16 – 09/23
$427/nighttotal: $2989 (7 )
Andersonville Luxe Pool Escape
1 2
house , Chicago
This Andersonville pool house, a short walk from a beach and near Ashland Avenue, offers easy access to Andersonville's shops and restaurants. The one-bedroom, one-bathroom unit features a full kitchen, queen bed, private heated pool and spa, in-unit laundry, high-speed Wi-Fi, and parking; it comfortably sleeps two guests and offers optional pool and yard rentals for parties.
Chicago
08/10 – 10/10
$425/nighttotal: $25925 (61 )
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
9.6 335 reviews
Chicago
12/24 – 12/28
$2295/nighttotal: $9180 (4 )
Historic Luxury Townhouse In Downtown Chicago
4 8
house , Chicago
This townhouse is located in Downtown Chicago, just a short walk from Oak Street Beach and other nearby beaches, offering easy access to the city's most popular attractions. It has excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. This home offers 5 bedrooms and 3 bathrooms, providing ample space for families or groups. The fully equipped kitchen includes a dishwasher and oven, and the house features air conditioning, free Wi-Fi, and a spa, making it ideal for relaxation and entertainment.
9.9 293 reviews
Chicago
07/14 – 07/18
$373/nighttotal: $1492 (4 )
The Nancy’s Gorgeous , Spacious Urban Getaway
1 5
house , Chicago
This newly renovated townhouse is located in Edgewater, a neighborhood in Chicago, just four miles from Evanston and Northwestern University. The house has excellent user, location, and cleanliness ratings. This three-bedroom home is perfect for families or groups of up to 10 guests. The house has a fully equipped kitchen, a finished basement, a fitness room, a garden, and parking.
10 2 reviews
Chicago
01/05 – 02/28
$1221/nighttotal: $65934 (54 )
The Grand Kimball Lodge, Logan Square, Sleeps 20
5 2
apartment , Chicago
This Chicago apartment is located in Logan Square, a neighborhood with a lively atmosphere, just a short walk from Wrigley Field and the United Center. This 5-bedroom, 4-bathroom home spans 2,990 square feet and can comfortably accommodate up to 20 guests. The apartment features a spacious layout with multiple living areas, a chef's kitchen, a wood-burning sauna, and a glamping tent for a unique experience.
9.7 50 reviews
Chicago
08/06 – 08/10
$350/nighttotal: $1400 (4 )
Victorian Mansion In Garfield Park
3 3
house , Chicago
This Chicago vacation rental is located just 5 miles from downtown and 2.3 miles from the United Center, offering easy access to the city's attractions. The property boasts excellent ratings for user experience, location, and cleanliness, making it a top choice for travelers. This 3-bedroom home offers 1500 square feet of space, comfortably accommodating up to 5 guests. Enjoy modern amenities including a fully equipped kitchen, air conditioning, and a private balcony or patio, perfect for relaxing after a day of exploring the city.
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'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
9.0 48 reviews
Chicago
09/23 – 09/28
$262/nighttotal: $1310 (5 )
Lincoln Park Living - 3 Queen Beds - Sleeps 6
1 4
house , Chicago
This Lincoln Park vacation rental is ideally located near Wrigley Field (1.2 miles), Lincoln Park Zoo (1.6 miles), and beaches (1.5-1.9 miles). This 1000-square-foot house features three queen beds sleeping up to six guests, a fully equipped kitchen with a dishwasher, free Wi-Fi, and a private patio; easy access to public transportation enhances exploration of Chicago.
Chicago
06/28 – 07/01
$807/nighttotal: $2421 (3 )
Wicker Park 6bd 4ba, Steps From Cta, Parking Incl Home
6 2
house , Chicago
This six-bedroom house in Chicago's Wicker Park neighborhood offers easy access to the CTA, placing you within a short distance of attractions like the United Center and Water Tower Place. The 2,800-square-foot property boasts four bathrooms, accommodates up to 23 guests, and includes a fully equipped kitchen, free parking, and Wi-Fi.
Chicago
08/01 – 10/31
$596/nighttotal: $54236 (91 )
113 M² House ∙ 3 Bedrooms ∙ 6 Guests
3 2
house , Westchester
House rental for up to 6 guests. Your accommodation will be located in Westchester. Facilities and services: a fridge, a freeze and an iron. Take advantage of the Free Parking with this accommodation in Westchester!
Chicago
10/14 – 12/14
$242/nighttotal: $14762 (61 )
2 Mi To Red Line: Chicago Home Near Sherman Park
5 1
house , Chicago
This Chicago house rental near Sherman Park offers convenient access to the Red Line (2 miles), providing easy transportation to downtown and attractions like the United Center (6.8 miles), Willis Tower (7 miles), Museum of Science and Industry (4.3 miles), Guaranteed Rate Field (3.8 miles), and Midway International Airport (5 miles). This 1,190-square-foot property features five bedrooms, two bathrooms, and sleeps up to 17 guests, boasting a fully equipped kitchen, free Wi-Fi, a private entrance, and on-site parking, plus a spa.
Neighborhoods and points of interest in Chicago
Best Chicago houses with a garden
9.4 63 reviews
Chicago
07/30 – 08/03
$638/nighttotal: $2552 (4 )
Walk To The Beach And Golf From Our 3 Story Home.
1 7
house , Chicago
This spacious 2700 sqft, 3-story house is located in a Chicago district, offering convenient access to local attractions, with specific distances not provided. This family-friendly, pet-friendly home accommodates up to 8 guests with 2 bathrooms, a fully stocked chef's kitchen, a master suite with a jacuzzi tub, and rooftop deck access, perfect for group travel to Chicago.
9.8 78 reviews
Chicago
08/26 – 08/30
$905/nighttotal: $3620 (4 )
Lincoln Park 2 Bedroom Condo Wmid Century Flair
2 2
house , Chicago
This Chicago apartment is located in Lincoln Park, just three miles from both 360 Chicago and the Water Tower, offering easy access to the city's iconic landmarks and attractions. Guests consistently rate this rental as excellent, highlighting its comfortable and convenient features. The apartment has two bedrooms and two bathrooms, accommodating up to four guests in a spacious 1,300 square feet. Enjoy amenities like free Wi-Fi, a washing machine, and a fully equipped kitchen, making your stay comfortable and hassle-free.
9.2 94 reviews
Chicago
09/10 – 09/15
$478/nighttotal: $2390 (5 )
Classic Oak Park Home, 11 Mi To Downtown Chicago!
4 1
house , Oak Park
This 4-bedroom vacation home is located in Oak Park, just 11 miles from downtown Chicago, making it a great base for exploring the city and its surrounding attractions. The home has received excellent ratings for cleanliness, location, and overall user experience. This spacious vacation rental offers 1780 square feet of living space, comfortably accommodating up to 8 guests. It features a fully equipped kitchen, a private patio, air conditioning, and free Wi-Fi, ensuring a comfortable and enjoyable stay.
Chicago
06/24 – 07/31
$284/nighttotal: $10508 (37 )
90s Condo| King Bed | 65” Smart Tv | Arcade Game
2 2
house , Elmwood Park
This Elmwood Park condo is conveniently located near O'Hare International Airport (5 miles) and within 10-11 miles of Chicago attractions like Wrigley Field, Lincoln Park Zoo, and the United Center. This 5,380-square-foot home features two bedrooms, one bathroom, and sleeps up to ten guests, offering a fully equipped kitchen, in-unit laundry, free Wi-Fi, and a private garden.
