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Chicago, IL holiday homes
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634 Villa rentals in Chicago, IL

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

102 M² House ∙ 3 Bedrooms ∙ 6 Guests - Chicago, IL
No reviews

102 M² House ∙ 3 Bedrooms ∙ 6 Guests

house, Des Plaines
House to rent for up to 6 people. Your accommodation will be located in Des Plaines.
Facilities and services: a dish washer, a washing machine and a garden. This house also has air conditioning!
Top-floor Oasis: 2br In Heart Of Fulton Market - Chicago, IL
10 1 review

Top-floor Oasis: 2br In Heart Of Fulton Market

apartment, Chicago
This downtown Chicago flat is situated less than 1.6km from Union Park and the United Centre, and under 3.2km from the Chicago Riverwalk and Michigan Avenue.
The 125 square metre property offers two bedrooms, two bathrooms, sleeps five, and includes a balcony, fitness centre access, and a fully equipped kitchen; nearby attractions include the University of Illinois Chicago.
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.
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 634 accommodations in Chicago, IL, here are the 4 best family friendly villas and holiday homes

70 M² House ∙ 5 Bedrooms ∙ 12 Guests - Chicago, IL
No reviews

70 M² House ∙ 5 Bedrooms ∙ 12 Guests

house, Des Plaines
Accommodation for up to 12 people. This accommodation is based in Des Plaines.
Services and facilities: air conditioning, a kitchen and a washing machine. Take advantage of the Free Parking with this accommodation in Des Plaines!
Northside Famlynest Lincoln Sq 4br 2ba 2p Rare Find - Chicago, IL
No reviews

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

house, Chicago
House listing. You will be located in Chicago.
Facilities and services: a terrace, a washing machine and an iron. This house also has air conditioning!
4 Bed/1.5 Bath Townhouse In Flw Historic District! - Chicago, IL
9.6 43 reviews

4 Bed/1.5 Bath Townhouse In Flw Historic District!

house, Oak Park
This four-bedroom duplex is located in Oak Park's Frank Lloyd Wright District, on the same street as the William E. Martin House, and is 0.8km from local restaurants and the Green Line 'L' train station.
This spacious 150m² property offers a comfortable home-from-home experience for up to seven guests, boasting a private garden, parking, and all modern amenities including a dishwasher and air conditioning.
Victorian Mansion In Garfield Park - Chicago, IL
9.7 52 reviews

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.

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Best Chicago, IL villas and holiday homes with parking

Cheerful 3 Story Townhouse Old Town/lp - Chicago, IL
9.7 238 reviews

Cheerful 3 Story Townhouse Old Town/lp

house, Chicago
This three-storey townhouse is ideally located in Lincoln Park, Chicago, within easy reach (less than 1.6 km) of Lincoln Park Zoo, Lake Michigan, the Magnificent Mile, and Old Town's restaurants and shops.
Offering two bedrooms with queen-size beds and a cot, plus a sofa bed, sleeping up to six guests, this property features a private patio, in-unit laundry, free off-street parking, and central air conditioning and heating.
Perfect Location Across From Park & Train Station - Chicago, IL
8.9 10 reviews

Perfect Location Across From Park & Train Station

house, Chicago
This Chicago holiday home enjoys a prime location near a park and train station, approximately 8 kilometres from downtown attractions including Cloud Gate and the Water Tower Place.
The 209 square metre property boasts five bedrooms, four bathrooms, two living rooms, and accommodates up to 25 guests, offering a fully equipped kitchen, free Wi-Fi, private parking, and a garden.
Gallery Loft Of Oak Park #1 Top Host In Il - Chicago, IL
9.8 267 reviews

Gallery Loft Of Oak Park #1 Top Host In Il

house, Oak Park
This studio apartment is located in Oak Park, just a short walk from the Ernest Hemingway birthplace and the Frank Lloyd Wright Home and Studio, offering easy access to these historical landmarks and the charming surrounding neighbourhood. It has consistently received excellent ratings for its cleanliness, location and overall guest experience.
The studio can accommodate up to four guests and is furnished with vintage mid-century modern pieces, giving it a unique and stylish feel. It features a well-equipped kitchen, a private porch, a firepit, and easy street parking, making it a comfortable and convenient base for exploring Oak Park.
Modern 4 Bedroom Greystone | White Sox - Chicago, IL
8.7 75 reviews

Modern 4 Bedroom Greystone | White Sox

apartment, Chicago
This Greystone house is situated in a desirable Chicago neighbourhood, less than 1.6km from Guaranteed Rate Field, home of the Chicago White Sox.
The four-bedroom property, sleeping up to nine guests, boasts a spacious three-storey layout with granite countertops, stainless steel appliances, and a private garden; free street parking is available.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL villas and holiday homes with a garden

A Pleasant Stay In Oak Park - Chicago, IL
10 71 reviews

A Pleasant Stay In Oak Park

house, Oak Park
This Oak Park townhouse, situated in a residential neighbourhood, is a short walk (less than 0.16 km) from the Chicago ‘L’ train station, 0.32 km from the Oak Park Arts District, and 0.16 km from Barrie Park.
The self-catering property sleeps six guests in two bedrooms and one bathroom, featuring a king-size bed, modern kitchen with dishwasher, three smart TVs, free high-speed Wi-Fi, a washer/dryer, off-street parking and a private garden.
Entire House W/ Free Parking, Close To Wrigley! - Chicago, IL
9.9 123 reviews

Entire House W/ Free Parking, Close To Wrigley!

house, Chicago
This five-bedroom Lakeview house, a highly sought-after Chicago neighbourhood, is minutes (less than 1.6km) from Wrigley Field, Lincoln Park, and the city centre.
Sleeping up to 15 guests, this property boasts a fully equipped kitchen, three-and-a-half bathrooms, in-unit laundry, and ample entertainment options including a pool table, arcade games, and a backyard patio; two covered parking spaces are also available.
Downtown Penthouse - Mich Ave 2bd Gym And Views #12 - Chicago, IL
No reviews

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

house, Chicago
This downtown Chicago penthouse is situated a mere 11-minute walk from the Art Institute of Chicago, 700 metres from the Chicago Symphony Orchestra, and a 9-minute walk from Grant Park, placing you within 2 kilometres of the city centre.
This penthouse offers 65 square metres of living space with two bedrooms and two bathrooms, accommodating up to seven guests with amenities including a fully equipped kitchen with a dishwasher, air conditioning, and complimentary WiFi, alongside access to an on-site fitness centre.
Lincoln Park 2 Bedroom Condo Wmid Century Flair - Chicago, IL
9.8 82 reviews

Lincoln Park 2 Bedroom Condo Wmid Century Flair

house, Chicago
This two-bedroom apartment is located in Lincoln Park, Chicago, a peaceful residential area just three miles from 360 Chicago and Water Tower Chicago. It has received excellent reviews from previous guests.
The apartment is 121 square metres and can accommodate up to four guests. Amenities include a fully equipped kitchen, free Wi-Fi, air conditioning, a terrace, a garden, and private parking.
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