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.
Chicago, IL
13/09 – 14/09
NZ$1494/nightfor 1 night
Whispering Oaks Retreat
1 9
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.
9.2 5 reviews
Chicago, IL
09/08 – 11/08
NZ$865/nighttotal: NZ$1730 (2 )
House In The Park 5 Min From O'hare
4 4
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.
Chicago, IL
09/10 – 14/10
NZ$3818/nighttotal: NZ$19090 (5 )
Portage Park, Jacuzzi, Movie Theater, Games & Arcade
5 8
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.
8.2 21 reviews
Chicago, IL
13/09 – 16/09
NZ$936/nighttotal: NZ$2808 (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.
9.9 41 reviews
Chicago, IL
26/08 – 30/08
NZ$505/nighttotal: NZ$2020 (4 )
Updated Bungalow With Koi Pond Oasis
1 2
bungalow , Maywood
This Maywood detached house offers excellent access to Downtown Chicago, situated 17.7 kilometres away and reachable via the 290 expressway or the Blue Line, and is also conveniently located near Brookfield Zoo and The Shops of Downtown Oak Park. This property boasts a spacious 11,000 sq ft lot with an 11,000-gallon Koi pond, a shaded gazebo with a waterfall, a 'Man Cave' featuring shuffleboard and air hockey, and a state-of-the-art kitchen, accommodating up to 4 guests with 1 bedroom and 1 bathroom.
9.4 29 reviews
Chicago, IL
26/06 – 30/06
NZ$304/nighttotal: NZ$1216 (4 )
Modern Midway Stay
1 2
house , Chicago
This Archer Heights flat is situated near Midway Airport (approximately 2.4km away) and the CTA Orange Line Pulaski station, offering easy access to Chicago's city centre. The 600 sq ft property features one bedroom, one bathroom, sleeps four guests, and includes a fully equipped kitchen, air conditioning, parking, and high-speed internet; ideal for business travellers or families.
Chicago, IL
15/12 – 15/01
NZ$2092/nighttotal: NZ$64852 (31 )
8br Kids Room, Game Room, Gym Andtheater
8 5
house , Chicago
This Chicago holiday home is located 9.6 kilometres from Wrigley Field, offering easy access to attractions such as Lincoln Park Zoo (14.2 km) and Union Station (15.1 km). This spacious property spans 1000 square metres, accommodating up to 18 guests across 8 bedrooms, and features a dedicated gym, a games room with billiards and table tennis, and a cinema.
9.7 17 reviews
Chicago, IL
01/01 – 31/01
NZ$834/nighttotal: NZ$25020 (30 )
Breathtaking Downtown Penthouse B - Sleeps 11
1 6
house , Chicago
This downtown Chicago penthouse, approximately 2.4 kilometres from Ohio Street Beach and 2.9 kilometres from North Avenue Beach, offers easy access to attractions such as the Oak Street Beach and the Museum of Contemporary Art. This 167 square metre three-bedroom, three-bathroom dwelling sleeps eleven, features a fully equipped kitchen, patio, free Wi-Fi, and parking, making it ideal for large groups or families visiting the city.
10 1 review
Chicago, IL
09/08 – 12/08
NZ$981/nighttotal: NZ$2943 (3 )
Envitae Hotel 4br Luxury Modern Apartments
4 2
house , Chicago
This spacious four-bedroom apartment in Chicago offers convenient access to North Avenue Beach, located 2.7 kilometres away, and is within 3.4 kilometres of Water Tower Chicago and the Museum of Contemporary Art. This property provides a fully equipped kitchen, air conditioning, free WiFi, a fitness centre, and on-site casino and water park facilities, with a floor area of 130 square metres and capacity for 15 guests.
Chicago, IL
05/07 – 08/07
NZ$1230/nighttotal: NZ$3690 (3 )
Wicker Park 6bd 4ba, Steps From Cta, Parking Incl Home
6 4
house , Chicago
This Wicker Park residence offers excellent access to Chicago's public transport, situated just 3.7 kilometres from the United Centre and 4.2 kilometres from the Water Tower Chicago. This spacious property provides six bedrooms, four bathrooms, and parking for up to twenty-three guests, featuring air conditioning, a fully equipped kitchen with a dishwasher and microwave, and complimentary WiFi.
9.7 393 reviews
Chicago, IL
09/08 – 13/08
NZ$582/nighttotal: NZ$2328 (4 )
The Avondale Guesthouse
3 2
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.
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
Chicago, IL
01/01 – 31/01
NZ$571/nighttotal: NZ$17130 (30 )
102 M² House ∙ 3 Bedrooms ∙ 6 Guests
3 6
house , Des Plaines
Holiday house to rent for 6 people. You will be in Des Plaines. Facilities and services: a garden, a terrace and free parking. This house in Des Plaines also has air conditioning!
9.9 23 reviews
Chicago, IL
25/06 – 28/06
NZ$651/nighttotal: NZ$1953 (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.
Chicago, IL
17/08 – 22/08
NZ$434/nighttotal: NZ$2170 (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.
Chicago, IL
10/08 – 10/10
NZ$730/nighttotal: NZ$44530 (61 )
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.
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
9.6 265 reviews
Chicago, IL
19/07 – 25/07
NZ$662/nighttotal: NZ$3972 (6 )
Chicago Bungalow Near Wrigley Field W/ King Suite
1 8
bungalow , Chicago
This Chicago bungalow is situated just a short distance from Wrigley Field, in a safe and friendly neighbourhood with plenty of pubs and restaurants nearby. The property has received excellent ratings for its location, cleanliness and overall experience. The three-bedroom house comfortably sleeps up to nine guests and offers a fully equipped kitchen, a private garden with access until 9pm, and super-fast internet. You’ll also find a separate entrance, a smart lock for easy access, and air conditioning for your comfort.
9.8 111 reviews
Chicago, IL
13/07 – 15/07
NZ$479/nighttotal: NZ$958 (2 )
Wicker Park Crash Pad + 7 Beds
1 6
house , Chicago
This spacious two-level apartment is located in Chicago's Wicker Park neighbourhood, less than 1.6km from Downtown, Lincoln Park, and Wrigleyville. The 7-bed dwelling, sleeping up to 8 guests, boasts two bathrooms, two living areas, a fully equipped kitchen with complimentary food items, a shared patio, Wi-Fi, DISH network TV with DVR, and Sirius Satellite Radio.
9.4 63 reviews
Chicago, IL
27/06 – 04/07
NZ$657/nighttotal: NZ$4599 (7 )
Walk To The Beach And Golf From Our 3 Story Home.
1 8
house , Chicago
This spacious Chicago house, ideal for groups, offers four bedrooms and two bathrooms sleeping up to twelve guests, and boasts a 251-square-metre floor area across three floors. The property includes a fully equipped kitchen, rooftop deck with city views, and convenient access to Chicago's attractions, though precise distances to landmarks are not specified.
Chicago, IL
09/09 – 12/09
NZ$1740/nighttotal: NZ$5220 (3 )
Hello Again, Chicago!
1 2
house , Chicago
This Chicago residence is situated approximately 1.8 kilometres from the United Centre and 4.3 kilometres from Union Station, with the Chicago Museum of Contemporary Art and Shops at Northbridge also around 4.8 kilometres away. This spacious holiday home, spanning 418 square metres, accommodates up to 31 guests and offers four bathrooms, complimentary private parking, and free WiFi, alongside a fully equipped kitchen and a balcony.
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 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?
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?
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?
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?
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?
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.
Destinations nearby
Best Chicago, IL villas and holiday homes with parking
9.5 253 reviews
Chicago, IL
05/07 – 06/07
NZ$910/nightfor 1 night
Pearly Gates | 3 Bed | Sleeps 5 | W/ 2-car Garage
3 6
apartment , Forest Park
This charming house is located in Forest Park, just 1.6km from Madison Street, a bustling area with shops, restaurants, and bars, and a 3-block walk from the CTA Blue Line "L" station, providing easy access to downtown Chicago. The property has received excellent ratings for its location, cleanliness, and overall user experience. The house features three bedrooms and one bathroom. Amenities include a fully equipped kitchen, air conditioning, parking, a fenced backyard, a washer and dryer, and flexible check-in/check-out options.
10 2 reviews
Chicago, IL
30/07 – 02/08
NZ$5544/nighttotal: NZ$16632 (3 )
Stunning 5br Home In Heart Of Chicago With 2 Rooftops
1 3
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.
9.7 54 reviews
Chicago, IL
25/06 – 28/06
NZ$1331/nighttotal: NZ$3993 (3 )
3-story Townhome, Free Parking, Private Patio, Was
1 4
house , Chicago
This southeast Lincoln Park townhouse, a short walk from Lincoln Park Zoo and approximately 1.6 km from downtown Chicago and Wrigley Field, offers convenient access to Chicago's key attractions. The three-storey property sleeps eight guests in two bedrooms and one bathroom, boasting a fully equipped kitchen, private patio with barbecue and smoker, in-unit laundry, and additional amenities including bicycles and beach equipment.
10 2 reviews
Chicago, IL
15/08 – 17/08
NZ$915/nighttotal: NZ$1830 (2 )
Beautiful Home In Bridgeview!
1 2
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.
Neighborhoods and points of interest in Chicago, IL
Best Chicago, IL villas and holiday homes with a garden
Chicago, IL
11/09 – 16/09
NZ$8642/nighttotal: NZ$43210 (5 )
Downtown Mich Ave - 6 Penthouses, Sleep 25
10 4
house , Chicago
This expansive penthouse is located in Downtown Chicago, offering a 9-minute walk to Grant Park and a 17-minute walk to Cloud Gate, placing it near the Art Institute of Chicago and the Chicago Symphony Orchestra. This property boasts a 310 square meter floor area, with 10 bedrooms and 9 bathrooms suitable for up to 36 guests, and includes a fitness centre and lake views.
8.2 13 reviews
Chicago, IL
21/09 – 24/09
NZ$1354/nighttotal: NZ$4062 (3 )
Beautifully Renovated House 10 Mins From Downtown
6 2
house , Chicago
This renovated house is situated in Chicago, just 1.6km from Oakwood Beach and 3.2km from Guaranteed Rate Field, offering easy access to the city's attractions and a peaceful neighbourhood setting. The property has received excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. This spacious home spans 297 square metres and comfortably accommodates up to 29 guests, making it ideal for large families or groups. The house offers a fully equipped kitchen, a terrace, a garden, a dedicated kids' pool, an indoor play area, and outdoor play equipment, ensuring a relaxing and entertaining stay for everyone.
Chicago, IL
10/08 – 10/10
NZ$332/nighttotal: NZ$20252 (61 )
Charming Andersonville Coach House 3br 2,5ba
3 2
house , Chicago
This private, two-storey coach house in Chicago is located on a quiet, tree-lined street, less than 300 metres from the dining, shopping, and café options on North Clark. This dwelling offers three bedrooms, two and a half bathrooms, and accommodates up to five guests, with internet, air conditioning, and a kitchen equipped with a fridge, microwave, and dishwasher, plus it allows pets for an additional fee.
Chicago, IL
25/11 – 29/11
NZ$682/nighttotal: NZ$2728 (4 )
Classic Forest Park Foursquare Less Than 1 Mi To Blue Line
3 2
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.