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Villas and Holiday home Rentals in Chicago, IL

Search among 23 available vacation houses in Chicago from 50+ providers

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6 adults
2 bedrooms
3 beds
View on map1700 yd from City Center500 yd from House of Blues Chicago
Featuring the views over Lake Michigan, this property offers a rooftop outdoor pool and a game room and video games for kids.
8.0
Great7 reviews
From   US$ 152 /nightSelect
Not available
10 adults
3 bedrooms
3 beds
View on map2.1 mi from City Center1800 yd from Lincoln Park Zoo
Positioned right next to The Richard H. Driehaus Museum, the venue with a fully equipped kitchen and a patio and a garden, available on site, waits for you.
From   US$ 399 /nightSelect
Not available
8 adults
3 bedrooms
5 beds
5.1 mi from City Center500 yd from Viaduct Center
The Richard H. Driehaus Museum is 4.4 miles from this villa that offers 3 bedrooms along with a kitchen.
From   US$ 146 /nightSelect
Not available
10 adults
3 bedrooms
4 beds
3.4 mi from City Center1.1 mi from United Center
Offering a fully equipped kitchen equipped with a microwave, a dishwasher and a cooktop, this villa is set near Garfield Park Fieldhouse.
From   US$ 283 /nightSelect
Not available
21 adults
4 bedrooms
8 beds
2.1 mi from City Center1800 yd from Lincoln Park Zoo
Placed in Old Town district, this self-catering villa has 4 bedrooms and can accommodate up to 21 guests.
From   US$ 699 /nightSelect
Not available
24 adults
5 bedrooms
11 beds
2.1 mi from City Center1600 yd from Lincoln Park Zoo
Featuring a play area and board games which are perfect for kids, this villa is situated 4 km away from the centre of Chicago.
From   US$ 838 /nightSelect
Not available
7 adults
2 bedrooms
3 beds
1.7 mi from City Center900 yd from McCormick Place
Featuring a sunny patio, this villa is located in South Loop district, 3 km away from city centre.
From   US$ 125 /nightSelect
Not available
8 adults
4 bedrooms
4 beds
8.8 mi from City Center500 yd from Jazz Unites Inc
Chicago Office of Tourism - Cultural Center is 10 miles from this villa that offers 4 bedrooms along with a fully equipped kitchen.
From   US$ 479 /nightSelect
Not available
12 adults
5 bedrooms
6 beds
7.8 mi from City Center1500 yd from Progressive Driving School Inc
This is a 5-bedroom villa, set in proximity to Our Lady Of Resurrection Ctr.
From   US$ 489 /nightSelect
Not available
10 adults
4 bedrooms
4 beds
3.1 mi from City Center400 yd from
Featuring a fully equipped kitchen along with 4 bathrooms, this villa is set in Bridgeport district.
From   US$ 688 /nightSelect
Not available
4 adults
500 yd from City Center600 yd from Chicago Theater
Set in Chicago Loop district and 1.2 miles from 360 Chicago Observation Deck, this villa provides a kitchen with a microwave, a dishwasher and kitchenware.
From   US$ 319 /nightSelect
Not available
6 adults
3.7 mi from City Center1600 yd from Lincoln Park Zoo
Set in Lincoln Park district and 0.3 miles from Elks National Memorial, this villa provides a kitchen with a microwave oven, a dishwasher and a refrigerator.
From   US$ 531 /nightSelect
Not available
2 adults
3.7 mi from City Center1600 yd from Lincoln Park Zoo
Just 550 feet from Wrightwood 659, the venue is set in Lincoln Park district.
From   US$ 243 /nightSelect
Not available
2 adults
3.7 mi from City Center1600 yd from Lincoln Park Zoo
Set in Lincoln Park district and 0.2 miles from Saint Clement Roman Catholic Church, this villa provides a kitchen with a dishwasher, a fridge and an oven.
From   US$ 267 /nightSelect
Not available
6 adults
3.7 mi from City Center1600 yd from Lincoln Park Zoo
Settled just 550 feet from Wrightwood 659, this villa features a sunny patio.
From   US$ 243 /nightSelect
Not available
2 adults
3.7 mi from City Center1600 yd from Lincoln Park Zoo
Set in Lincoln Park district and 0.2 miles from Saint Clement Roman Catholic Church, this villa provides a kitchen with a microwave, a dishwasher and kitchenware.
From   US$ 422 /nightSelect
Not available
4 adults
3.7 mi from City Center1600 yd from Lincoln Park Zoo
Located about 0.6 miles from Foster Avenue Beach, the vacation home offers accommodation for 4 guests.
From   US$ 265 /nightSelect
Not available
4 adults
3.7 mi from City Center1600 yd from Lincoln Park Zoo
Located about 0.5 miles from Lincoln Park Zoo, the villa offers accommodation for 4 guests.
From   US$ 555 /nightSelect
Not available
4 adults
3.7 mi from City Center1600 yd from Lincoln Park Zoo
Set in Lincoln Park district and 0.7 miles from Briar Street Theatre, this villa provides a kitchen with a microwave, a dishwasher and a fridge.
From   US$ 423 /nightSelect
Not available
8 adults
4 bedrooms
4 beds
7.7 mi from City Center1100 yd from
Rockefeller Memorial Chapel is 1.7 miles from this villa that offers 4 bedrooms along with a kitchen.
From   US$ 370 /nightSelect
Not available
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23 hotels found

FAQs about vacation houses and cabins in Chicago

To know more about vacation homes in Chicago, read these 10 answers to FAQs.

Which pet-friendly vacation houses in Chicago allow dogs?

According to Booked.net travel data, there are 15 accommodations that welcome pets. Check Old Town-Gold Coast Amazing 3 Bedroom Home/ Free Parking/ Breakfast/ Backyard/ Walk Everywhere/ Pets Ok at the cost of 399US$ per night, featuring board games, live performances and ironing on site. Another great option is The Avondale Guesthouse at the cost of 146US$ per one night. Other suitable properties are Beautiful Room In, Penthouse Level, Stunning Wrigley Stay and 2142 West Walton Apartment.

What are the best budget villas in Chicago?

Budget travelers might select one of 18 properties. Among villas, we recommend Swank Victorian Near United Center W/ Backdeck with a free parking lot, ironing and a free private parking lot on site. It's set 10 minutes' walk from Jackson Boulevard Christian Church and costs about 283US$ per night. Old Town-Gold Coast Elegant 4 Br-4 Bath Home/ Free Parking/ Breakfast/ Backyard/ Walk Everywhere is one more great deal at the cost of 699US$ for those searching for a budget stay.

What are the best budget holiday homes in Chicago with weekly rates?

Among the best apartments in Chicago, you may book Grand Plaza Suites at the cost of 1064US$ per week. It's located 1 miles from Willis Tower and provides video games and ironing.

Which Chicago vacation houses are family-friendly?

For a perfect family stay, check one of available deals on Booked.net.

What are the best vacation houses in Chicago providing hot tubes?

If you want to relax during your stay, Booked.net offers some deals with a jacuzzi for you. You may like The Boom Boom Room offering shopping service, a Jacuzzi and complimentary parking at the price of 439US$ per one night.

What are the the most popular vacation houses among couples in Chicago?

According to Booked.net travel data, there are 5 deals for couples. Another great apartment is Perfect Place To Enjoy The City Or Just Relax rated 7.4/10 with free private parking and a free parking lot. You may book it for 115US$ per night.

What are the best vacation houses in Chicago with kitchenettes?

To stay at the top vacation house with a kitchen, Booked.net offers 3 properties to select from. Customers who enjoy cooking may like Oakwood 200 Squared (rating: 8.0/10) with an indoor swimming pool, concierge service and a gym. This property is set 1750 feet from Goodman Theatre.

What are the most popular budget Chicago vacation houses offering free parking?

According to Booked.net travel data, there are 10 apartments to select from. For instance, you may book Old Town-Gold Coast Amazing 3 Bedroom Home/ Free Parking/ Breakfast/ Backyard/ Walk Everywhere/ Pets Ok rated 8.0/10 with board games, live performances and ironing. It's set a 5-minute walk from Thomas Masters Gallery and costs 399US$ per night.

What are the top vacation houses in Chicago near Millennium Park?

According to Booked.net travel data, there are 5 deals to select from. For instance, consider booking Modern 2Br/2Bath Apt In Streeterville rated 8.0/10 for about 371US$ per night, a top apartment with fitness and ironing. Another great deal is Oakwood 200 Squared rated 8.0/10 with an indoor swimming pool, concierge service and a gym on site. It's situated 0.8 miles from the landmark and costs 205US$ per night.

What are the best luxury vacation houses in Chicago?

According to Booked.net travel data, one of the top villas is Massive 3 Floor Townhouse In Loop By Domio! set 1550 feet from The Shops at Roosevelt Collection. It costs 936US$ per night.

Guest reviews of hotels in Chicago