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Holiday Villas and Holiday homes for rent in Chicago, IL

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

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6 adults
2 bedrooms
3 beds
View on map1.5 km from City Centre500 m from House of Blues Chicago
Set 15 km from Midway Airport, this property features 2 bedrooms facing the garden and a sun terrace with a sitting area.
8.0
Great7 reviews
From   C$ 189 /nightSelect
Not available
21 adults
4 bedrooms
8 beds
View on map3.3 km from City Centre1.6 km from Lincoln Park Zoo
Located 3 km from Millennium Park, the self-catering villa consists of 4 bedrooms, a mini-kitchen and 4 bathrooms equipped with a bath, a rain shower and a bidet.
From   C$ 870 /nightSelect
Not available
10 adults
4 bedrooms
4 beds
4.9 km from City Centre300 m from
Situated 450 metres from Ashland tube station, the property is composed of a fully equipped kitchen and 4 bathrooms.
From   C$ 856 /nightSelect
Not available
4 adults
5.9 km from City Centre1.4 km from Lincoln Park Zoo
Located about 2.3 km from Chicago History Museum, the villa offers accommodation for 4 guests.
From   C$ 691 /nightSelect
Not available
6 adults
5.9 km from City Centre1.4 km from Lincoln Park Zoo
Set in Lincoln Park district and 0.9 km from Jonquil Park, this villa provides a kitchen with a dishwasher, a refrigerator and a microwave oven.
From   C$ 661 /nightSelect
Not available
8 adults
4 bedrooms
4 beds
12.4 km from City Centre1000 m from
Located 3.7 km from Museum of Science and Industry, the holiday home features a flat screen TV and a cable flat-screen.
From   C$ 473 /nightSelect
Not available
12 adults
5 bedrooms
6 beds
12.5 km from City Centre1.3 km from Progressive Driving School Inc
This is a 5-bedroom villa, set in proximity to Chicago National College.
From   C$ 609 /nightSelect
Not available
10 adults
3 bedrooms
3 beds
3.3 km from City Centre1.6 km from Lincoln Park Zoo
Located in Old Town district, this villa features a terrace along with a mini-kitchen.
From   C$ 497 /nightSelect
Not available
16 adults
6 bedrooms
6 beds
8.7 km from City Centre800 m from
Composed of 6 bedrooms and 4 bathrooms, this holiday home is set only 1.3 km from California & Milwaukee.
Select
Not available
4 adults
5.9 km from City Centre1.4 km from Lincoln Park Zoo
Located about 3.9 km from 360 Chicago Observation Deck, the holiday home offers accommodation for 4 guests.
From   C$ 330 /nightSelect
Not available
2 adults
5.9 km from City Centre1.4 km from Lincoln Park Zoo
Located about 2.3 km from Wrigley Field, the holiday home offers accommodation for 2 guests.
From   C$ 525 /nightSelect
Not available
2 adults
5.9 km from City Centre1.4 km from Lincoln Park Zoo
Located about 0.9 km from Jonquil Park, the holiday home offers accommodation for 2 guests.
From   C$ 302 /nightSelect
Not available
19 adults
1 bedroom
3 beds
3.5 km from City Centre1.3 km from Lincoln Park Zoo
Situated less than 5 minutes' drive from 360 Chicago Observation Deck, this villa features a flat screen TV, a cable flat-screen and a bar.
Select
Not available
4 adults
500 m from City Centre500 m from Chicago Theater
Set in Chicago Loop district and 0.8 km from The Art Institute of Chicago, this villa provides a kitchen with a dishwasher, a refrigerator and a microwave.
From   C$ 397 /nightSelect
Not available
10 adults
3 bedrooms
4 beds
5.4 km from City Centre1.8 km from United Center
Offering a fully equipped kitchen complete with a microwave oven, a dishwasher and a fridge, this villa is located close to Willis Tower.
From   C$ 352 /nightSelect
Not available
4 adults
5.9 km from City Centre1.4 km from Lincoln Park Zoo
Set in Lincoln Park district and 4.4 km from The Magnificent Mile, this villa provides a kitchen with dishwasher, fridges and a microwave.
From   C$ 527 /nightSelect
Not available
6 adults
5.9 km from City Centre1.4 km from Lincoln Park Zoo
Featuring a patio, this villa is located in Lincoln Park district, 6 km away from city centre.
From   C$ 302 /nightSelect
Not available
8 adults
3 bedrooms
5 beds
8.2 km from City Centre500 m from Viaduct Center
Featuring a terrace along with 3 bedrooms, this villa is set 2.6 km from Sheil Park.
From   C$ 182 /nightSelect
Not available
10 adults
5 bedrooms
5 beds
2.6 km from City Centre700 m from Michigan Avenue
Composed of 5 bedrooms and 3 bathrooms, this holiday home is set only 0.9 km from The Magnificent Mile.
Select
Not available
2 adults
5.9 km from City Centre1.4 km from Lincoln Park Zoo
Set in Lincoln Park district and 0.8 km from Peggy Notebaert Nature Museum, this villa provides a kitchen with dishwasher, a fridge and kitchenware.
From   C$ 332 /nightSelect
Not available
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23 hotels found

FAQs about holiday houses and cottages in Chicago

To know more about holiday homes in Chicago, read these 8 answers to FAQs.

What are the most popular pet-friendly holiday houses in Chicago?

If you want to stay with pets, iBooked.ca offers 15 options to choose from. We recommend Old Town-Gold Coast Amazing 3 Bedroom Home/ Free Parking/ Breakfast/ Backyard/ Walk Everywhere/ Pets Ok (rating: 8.0/10), a perfect villa with board games, ironing and live performances. It's set a 5-minute walk from UP Comedy Club. Another great option is Webster House at the cost of 235C$ per one night. Other suitable properties are Charming Apartments Near Downtown Howard Johnson Inn -.

What are the top holiday houses in Chicago with hot tubs?

If you want to relax during your trip, there are 8 deals featuring jacuzzi on iBooked.ca. You may like The Boom Boom Room offering shopping service, a Jacuzzi and 24-hour front desk assistance at the price of 557C$ per one night.

What are the top lakefront holiday houses in Chicago?

Find out Old Town-Gold Coast Amazing 3 Bedroom Home/ Free Parking/ Breakfast/ Backyard/ Walk Everywhere/ Pets Ok at the price of 506C$ per night.

What are the top holiday houses in Chicago that are good for couples?

According to iBooked.ca travel data, there are 5 deals for couples. To make your stay fantastic, book Howard Johnson Inn - with massage treatments and restaurant. This high-rated holiday house is set 700 metres from Oak Street and costs 156C$ per night.

What are the top holiday houses in Chicago offering a kitchenette?

To stay at the top holiday house with a kitchen, iBooked.ca offers 3 properties to choose from. Customers who enjoy cooking may like Oakwood 200 Squared with an outdoor swimming pool, an indoor swimming pool and a gym, situated 700 metres from Ford Center Theater.

Which holiday houses in Chicago provide free parking?

If you want to stay at the place with free parking, iBooked.ca has 10 deals to offer. For instance, Old Town-Gold Coast Amazing 3 Bedroom Home/ Free Parking/ Breakfast/ Backyard/ Walk Everywhere/ Pets Ok, a good choice located 3 km from Willis Tower. It features board games, ironing and live performances. Alternatively, you may book The Avondale Guesthouse for about 185C$ per night. This villa provides cots, laundry and cars on site.

What are the most popular holiday houses in Chicago not far from Millennium Park?

If you wish to stay not far from this tourist destination, on iBooked.ca you can easily book one of 6 accommodations. For instance, find out Stay Alfred At Park Michigan rated 8.0/10, located a 20-minute walk from the attraction for 904C$ per night. Another good option is Modern 2Br/2Bath Apt In Streeterville providing fitness classes and ironing for 471C$ per night.

What are the most popular luxury holiday houses in Chicago?

According to iBooked.ca travel data, one of the top accommodations is Printers Penthouse 450 metres from Wabash Arts Corridor. It costs 778C$ per night.

Guest reviews of hotels in Chicago