Chicago, IL Villas and Holiday homes | Best Deals on cozycozy

Chicago, IL

5 4

NZ$2958/nighttotal: NZ$5916 (2 )

Top 1 Rated 4br Lincoln Park House - King Bed

house - Chicago

This Lincoln Park residence is situated a short walk from North Avenue Beach and Lincoln Park Zoo, approximately 2.7km from the Water Tower Place.
The 1000 square metre property boasts a spacious four-bedroom layout sleeping up to 23 guests, complete with a fitness centre, garden, and fully equipped kitchen; laundry service is available.

9.5 58 reviews

Chicago, IL

2 3

NZ$580/nighttotal: NZ$2320 (4 )

Victorian Mansion In Garfield Park

house - Chicago

This three-bedroom house is situated in Chicago, just five miles from the city centre and a short distance from the United Center. The property has received excellent ratings for its cleanliness, location, and overall experience, making it a great choice for travellers.
The house provides 139 square metres of space, accommodating up to five guests. It features a fully equipped kitchen, a private patio and garden, air conditioning, and free Wi-Fi, ensuring a comfortable and enjoyable stay.

Chicago, IL

2 2

NZ$768/nighttotal: NZ$5376 (7 )

2 Br, 2 Bt, Uchicago Coachman's Guesthouse

cottage - Chicago

This detached coach house in Chicago's Hyde Park district is situated within 800 metres of the University of Chicago's main quad and two blocks from the Metra train, offering direct access to downtown Chicago's attractions.
This two-bedroom, two-bathroom property accommodates up to five guests and features a full kitchen, air conditioning, and off-street parking, with the nearby lakefront and museums providing further leisure opportunities.

9.6 1 review

Chicago, IL

1 1

NZ$681/nighttotal: NZ$3405 (5 )

Spacious Row Home Next Transit Near Downtown W Parking

house - Chicago

House listing with an excellent rating of 96% based on 1 reviews. You will stay in Chicago.
Services and facilities include a dish washer, an iron and air conditioning. This house in Chicago also has a terrace!

8.8 47 reviews

Chicago, IL

2 3

NZ$1059/nighttotal: NZ$4236 (4 )

Large Condo With Outdoor Deck In Historic Chicago District Home

house - Chicago

This charming house is located in the historic Old Town neighbourhood, just a short walk from Wells Street's shops and restaurants and a 5-minute walk from the Sedgwick Brown/Purple line station, offering easy access to the Loop in 20 minutes. The property has received very good ratings from previous guests.
The house is spread across three floors, providing ample space for families or groups of friends. It features a fully equipped kitchen with a fridge, microwave oven, and dishwasher, air conditioning, parking, and high-speed internet access.

Chicago, IL

1 4

NZ$639/nighttotal: NZ$8946 (14 )

Spacious Home With Modern Amenities - Charming Group Getaway

house - Berwyn

This detached house in Berwyn, Illinois, is situated a convenient 32 kilometres from downtown Chicago, with easy access to local amenities and Midway Airport.
The property offers accommodation for up to eight guests in four bedrooms and two bathrooms, featuring a fully equipped kitchen, a living room with a smart TV, on-site laundry, private garden, and garage parking, all supported by fast Wi-Fi.

8.7 54 reviews

Chicago, IL

2 1

NZ$210/nighttotal: NZ$840 (4 )

Lincoln Park Living - 3 Queen Beds - Sleeps 6

house - Chicago

This Lincoln Park holiday home in Chicago is ideally situated 1.9km from North Avenue Beach and 1.2km from Wrigley Field.
The 93 square metre property offers three queen-size beds sleeping six, a fully equipped kitchen with dishwasher, air conditioning, free Wi-Fi, and a private patio; guests can easily access Lincoln Park Zoo (2.6km).

8.4 22 reviews

Chicago, IL

4 2

NZ$441/nighttotal: NZ$1323 (3 )

Lincoln Park Living - Suite 2

house - Chicago

This Lincoln Park house rental is ideally located in Chicago, 1.9km from Wrigley Field and 2.6km from Lincoln Park Zoo, offering easy access to beaches and downtown.
The 93 square metre property features two bedrooms, two bathrooms, sleeps up to ten guests, and includes a fully equipped kitchen, air conditioning, private patio, free Wi-Fi, and in-unit laundry.

10 2 reviews

Chicago, IL

5 1

NZ$897/nighttotal: NZ$1794 (2 )

Beautiful Home In Bridgeview!

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.

Chicago, IL

2 4

NZ$1170/nighttotal: NZ$37440 (32 )

139 M² House ∙ 4 Bedrooms ∙ 8 Guests

house - Elmwood Park

Holiday rental listing for up to 8 people. You will be based in Elmwood Park.
Services and facilities include a dish washer, a kitchen and a washing machine. Enjoy free parking with this accommodation in Elmwood Park!

9.5 109 reviews

Chicago, IL

2 4

NZ$1104/nighttotal: NZ$7728 (7 )

Charming & Comfy Gem ~ 10 Mins To Downtown ~Patio!

apartment - Chicago

This four-bedroom Chicago house, situated less than 6.4 km from the city centre, offers easy access to major attractions.
The spacious property sleeps ten guests, boasting a fully equipped kitchen, six 55" Smart TVs, a private patio with Solostove and smoker, and free on-street parking; breed restrictions and fees apply for pets.

Chicago, IL

9 1

NZ$1114/nighttotal: NZ$4456 (4 )

Stunning Duplex Condo #1 - Downtown River North

house - Chicago

Accommodation. Your accommodation will be located in Chicago.
Facilities and services: a washing machine, an iron and a dish washer. Take advantage of the Free Parking with this accommodation.

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

9.9 31 reviews

Chicago, IL

4 2

NZ$1039/nighttotal: NZ$2078 (2 )

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

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.

Chicago, IL

1 2

NZ$667/nighttotal: NZ$4002 (6 )

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.

Chicago, IL

9 5

NZ$1613/nighttotal: NZ$8065 (5 )

Stylish Escape With Spacious Living Area And Modern Comforts - Chic Retreat

house - Chicago

This South Shore dwelling is situated a 5-minute walk from Lake Michigan, offering convenient access to Hyde Park, the Museum of Science and Industry, and the future Obama Presidential Library.
This spacious five-bedroom house accommodates up to 12 guests, featuring a fully equipped kitchen, a living area with a fireplace, air conditioning, a swimming pool, and parking, with the option of a Pack 'n Play/Travel Crib and on-site laundry for families.

Chicago, IL

2 2

NZ$726/nighttotal: NZ$45012 (62 )

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

9.9 117 reviews

Chicago, IL

4 2

NZ$599/nighttotal: NZ$1797 (3 )

Cozy & Bright Townhome Near Ohare -Self Check In-

house - Chicago

This Montclare house, situated in a quiet residential area of Chicago's Northwest side, offers convenient access to major roads.
The two-bedroom, two-bathroom property sleeps six guests and features a fully equipped kitchen with stainless steel appliances, a comfortable living area with a gas fireplace, in-unit laundry, and a private deck; Smart TVs with Netflix are provided in the bedrooms and living room.

Chicago, IL

2 7

NZ$4640/nighttotal: NZ$18560 (4 )

Spacious Backyard Oasis And Entertainment Haven - Elegant Luxury Retreat

house - Chicago

This seven-bedroom Bridgeport dwelling is situated in Chicago's Pilsen district, offering convenient access to the city centre via the Ashland Orange Line, approximately 32 to 48 kilometres from Midway Airport and 64 to 96 kilometres from O'Hare Airport by car.
This family-friendly house accommodates up to 16 guests and features two kitchens, a pool table, a private garden with a barbecue, and is equipped with air conditioning, a jacuzzi, and a sauna for your comfort.

9.8 37 reviews

Chicago, IL

6 4

NZ$1006/nighttotal: NZ$3018 (3 )

Northside Famlynest Lincoln Sq 4br 2ba 2p Rare Find

house - Chicago

This spacious home is located in Lincoln Square on Chicago's Northside, just 5.6 kilometres from Lincoln Park Zoo and 3.7 kilometres from Wrigley Field, offering easy access to the city's attractions and a peaceful residential setting. The property has consistently received excellent ratings for its location, cleanliness and overall experience.
The house spans 149 square metres and can accommodate up to 17 guests, with 4 bedrooms and 2 bathrooms. Guests can enjoy a private garden, tennis court, outdoor fireplace, and a well-equipped kitchen, as well as a range of entertainment options, including darts and cycling in the surrounding area.

Chicago, IL

2 5

NZ$1162/nighttotal: NZ$2324 (2 )

Stylish Rooftops And Sauna - Chic Urban Oasis

house - Chicago

This Wicker Park residence is situated just steps from shops and nightlife, offering a 10-20 minute drive or transit ride to downtown Chicago landmarks such as Millennium Park and the Magnificent Mile.
This spacious 5-bedroom property accommodates up to 16 guests, featuring a kitchen with a fridge, freezer, microwave, and dishwasher, air conditioning, a jacuzzi, terrace, sauna, and private parking, alongside an entertainment basement with air hockey and foosball.

Frequently asked questions about villa rentals in Chicago, IL

What are the must-see attractions in Chicago, IL?
You can't miss the iconic Willis Tower, formerly known as the Sears Tower, for stunning views of the city. The Art Institute of Chicago is a must for art lovers, with works by Monet and Van Gogh. And no trip to Chicago is complete without a stroll along Navy Pier, a vibrant entertainment complex with a Ferris wheel and shops.
What are the best villa rentals in Chicago, IL?
Among the villa rentals in Chicago, IL, Polk Street Coach House Apartment - Little Italy/medical Dist, Couture Themed 3 Bedroom In Prime Spot With Patio - Parking - Fireplace - Pets Welcome and The Albany Park Room At The Cape Cod In Riverside are the most popular ones.
What indoor activities for families are available in Chicago, IL on rainy days?
The Field Museum is a great option, with dinosaur exhibits and a fantastic collection of cultural artifacts. The Shedd Aquarium is another popular choice, featuring a wide variety of aquatic life. And for a bit of fun, the Museum of Science and Industry offers interactive exhibits for all ages.
What are the best villa rentals with a pool in Chicago, IL?
Long Term Rental-delightful One Bdrm Pool House, Sweet Home Chicago (House) - Free Parking - Pool and Beautiful Townhome Mins To Downtown are the best villa rentals with a pool in Chicago, IL.
What are the best activities in Chicago, IL?
Chicago is a city that offers something for everyone. You could spend a day exploring Millennium Park, taking in the iconic Cloud Gate sculpture and the Crown Fountain. For a taste of Chicago's history, visit the Chicago Cultural Center, a beautiful building with free concerts and exhibitions. And don't forget to catch a Cubs game at Wrigley Field, a true Chicago experience.
What are the best villa rentals with a jacuzzi in Chicago, IL?
The best villa rentals with a jacuzzi in Chicago, IL are Couture Themed 3 Bedroom In Prime Spot With Patio - Parking - Fireplace - Pets Welcome, The Avondale Guesthouse and Private Coach House Near Lincoln Square.
What are the advantages of renting a house or a villa in Chicago, IL
Renting a house or villa in Chicago can provide more space and privacy compared to a hotel. You'll often have access to a kitchen, which allows you to prepare your own meals and save money. Some rentals also offer amenities like a backyard or a balcony, providing more opportunities to relax and enjoy your surroundings.
What are the best villa rentals for families and kids in Chicago, IL?
The best villa rentals for families and kids in Chicago, IL are Couture Themed 3 Bedroom In Prime Spot With Patio - Parking - Fireplace - Pets Welcome, The Avondale Guesthouse and Chicago’s Dickens Place A Trendy Centralized Flat.
What food festivals or culinary events take place in and around Chicago, IL?
Chicago has a vibrant food scene, with several festivals throughout the year. The Taste of Chicago is a popular event, showcasing local restaurants and food vendors. The Chicago Gourmet Festival is another highlight, featuring cooking demonstrations and wine tastings. And for a taste of the city's Polish heritage, check out the Taste of Polonia.
What are the best pet friendly villa rentals in Chicago, IL?
The best pet friendly villa rentals in Chicago, IL are Couture Themed 3 Bedroom In Prime Spot With Patio - Parking - Fireplace - Pets Welcome, The Avondale Guesthouse and Chicago’s Dickens Place A Trendy Centralized Flat.
What exclusive experiences are available when visiting Chicago, IL?
For a unique experience, consider a private tour of the Wrigleyville neighborhood, home to the iconic Wrigley Field. You can also book a private boat tour on Lake Michigan, enjoying stunning views of the city skyline. Or for a taste of Chicago's nightlife, try a speakeasy tour, exploring hidden bars and cocktail lounges.
What are the best villa rentals with parking in Chicago, IL?
Polk Street Coach House Apartment - Little Italy/medical Dist, Couture Themed 3 Bedroom In Prime Spot With Patio - Parking - Fireplace - Pets Welcome and The Albany Park Room At The Cape Cod In Riverside are the best villa rentals with parking in Chicago, IL.
Which part of Chicago, IL would be ideal for a villa rental?
Lincoln Park is a great choice for a villa rental, offering a mix of residential areas, parks, and attractions. You'll be close to the Lincoln Park Zoo, the Lincoln Park Conservatory, and the vibrant shops and restaurants of Lincoln Avenue. The Gold Coast is another option, known for its luxury homes and proximity to the Magnificent Mile.

Popular destinations

Best Chicago, IL villas and holiday homes with parking

9.5 23 reviews

Chicago, IL

2 1

NZ$369/nighttotal: NZ$738 (2 )

Coach House | Step Outside To Architectural Icons!

house - Oak Park

This private coach house is located in Oak Park's Frank Lloyd Wright Historic District, offering a peaceful retreat just steps from renowned architecture, museums, dining, shopping, parks, and transit, with easy access to Chicago.
This one-bedroom, one-bathroom dwelling accommodates up to three guests and provides internet, air conditioning, and parking, serving as an ideal base for architecture enthusiasts and city explorers.

Chicago, IL

2 3

NZ$1245/nighttotal: NZ$2490 (2 )

Spacious Oasis With Deck And Backyard - Stylish Comfort Retreat

house - Chicago

This three-bedroom flat in Chicago's Near West Side is a 10-minute walk from the United Center, a 4-minute drive from the Illinois Medical District, and a 6-minute drive from the University of Illinois Chicago.
This professionally managed property offers 140 square metres of living space for up to six guests, featuring a fully equipped kitchen, high-speed Wi-Fi, Smart TVs, a washer/dryer, and a deck with a garden.

Chicago, IL

2 3

NZ$899/nighttotal: NZ$54839 (61 )

113 M² House ∙ 3 Bedrooms ∙ 6 Guests

house - Westchester

Holiday house rental for up to 6 guests. You will be in Westchester.
Services and facilities: a fridge, a kitchen and free parking.

9.5 157 reviews

Chicago, IL

2 4

NZ$6869/nighttotal: NZ$20607 (3 )

East Village 4-level-house With 5 Baths & Covered Attached Garage

apartment - Chicago

This four-storey townhouse is located in Chicago's East Village, a short walk from the Milwaukee 'L' station and a 12-minute subway ride from the Loop, Michigan Avenue, and the Lakefront. It has consistently received excellent user ratings for location, cleanliness, and overall experience.
The property offers 223 square metres of living space, comprising four bedrooms and five bathrooms. Guests can enjoy a range of amenities, including a fully equipped kitchen, private terraces, a spa-like bathroom, a fireplace, games, and a Sonos sound system.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL villas and holiday homes with a garden

10 7 reviews

Chicago, IL

4 3

NZ$8532/nightfor 1 night

Historic Hales Mansion Near Frank Lloyd Wright

castle - Oak Park

This Tudor Revival mansion, situated in North Oak Park within walking distance of Oak Park's town centre, offers a unique castle-like experience.
Sleeping up to 16 guests, this four-bedroom, three-bathroom property boasts a performance hall, formal dining room, jacuzzis, four fenced second-floor porches, on-site parking for three vehicles, and event catering equipment (100 chairs, 100 place settings), with additional rooms and beds available on request; all proceeds benefit the Language and Music School's scholarship fund.

8.5 34 reviews

Chicago, IL

2 3

NZ$1417/nighttotal: NZ$4251 (3 )

Stunning Condo #2 - Downtown River North

house - Chicago

This River North apartment is ideally located 2.4km from Ohio Street Beach and 2.9km from North Avenue Beach, offering easy access to Chicago's downtown attractions including the Water Tower and the Museum of Contemporary Art.
The 167 square metre, three-bedroom condo sleeps 27 guests and features a fully equipped kitchen, private patio, in-unit laundry, and free Wi-Fi; enjoy nearby beaches and city exploration.

Chicago, IL

5 3

NZ$600/nighttotal: NZ$1200 (2 )

Classic Forest Park Foursquare < 1 Mi To Blue Line

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.

10 1 review

Chicago, IL

2 5

NZ$721/nighttotal: NZ$3605 (5 )

Whispering Oaks Retreat

house - Forest Park

Whispering Oaks Retreat, a Forest Park house, is conveniently located approximately 16 kilometres from both Union Station and DePaul University, offering easy access to major Chicago attractions.
This 177 square metre property sleeps up to 14 guests, boasting two bathrooms, a fully equipped kitchen, free Wi-Fi, a fireplace, and air conditioning; Midway International Airport is 13 kilometres away.

Search Chicago, IL villas and holiday homes

772 Villa rentals in Chicago, IL

Top 1 Rated 4br Lincoln Park House - King Bed

Victorian Mansion In Garfield Park

2 Br, 2 Bt, Uchicago Coachman's Guesthouse

Spacious Row Home Next Transit Near Downtown W Parking

Large Condo With Outdoor Deck In Historic Chicago District Home

Spacious Home With Modern Amenities - Charming Group Getaway

Lincoln Park Living - 3 Queen Beds - Sleeps 6

Lincoln Park Living - Suite 2

Beautiful Home In Bridgeview!

139 M² House ∙ 4 Bedrooms ∙ 8 Guests

Charming & Comfy Gem ~ 10 Mins To Downtown ~Patio!

Stunning Duplex Condo #1 - Downtown River North

Best Chicago, IL villas and holiday homes with a pool

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

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

Stylish Escape With Spacious Living Area And Modern Comforts - Chic Retreat

Extended Stay: Walk To Uic Campus & Train!

Best family friendly Chicago, IL villas and holiday home

Cozy & Bright Townhome Near Ohare -Self Check In-

Spacious Backyard Oasis And Entertainment Haven - Elegant Luxury Retreat

Northside Famlynest Lincoln Sq 4br 2ba 2p Rare Find

Stylish Rooftops And Sauna - Chic Urban Oasis

Frequently asked questions about villa rentals in Chicago, IL

Popular destinations

Best Chicago, IL villas and holiday homes with parking

Coach House | Step Outside To Architectural Icons!

Spacious Oasis With Deck And Backyard - Stylish Comfort Retreat

113 M² House ∙ 3 Bedrooms ∙ 6 Guests

East Village 4-level-house With 5 Baths & Covered Attached Garage

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL villas and holiday homes with a garden

Historic Hales Mansion Near Frank Lloyd Wright

Stunning Condo #2 - Downtown River North

Classic Forest Park Foursquare < 1 Mi To Blue Line

Whispering Oaks Retreat