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Vacation Homes in Chicago, IL

Search among 106 available vacation homes in Chicago from 50+ providers

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1-20 out of 106
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8 adults
3 bedrooms
5 beds
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4.9 mi from City Center494 yd from Viaduct Center
FromUS$ 180 /nightSelect
8.8
Great18 reviews
10 adults
3 bedrooms
3 beds
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2.1 mi from City Center1.1 mi from Michigan Avenue
Set 1.4 miles from Chicago-style pizza, the 3 Bedroom In Best Location Parking Fireplace Patio Home Office Pets Welcome lies in the Old Town district.
FromUS$ 279 /nightSelect
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7.7 mi from City Center534 yd from Swedish Covenant Hospital
The Rare Find Cozy Family Gem Lincoln Square 4Br 1 And Half Bath 2 Parking is located 16 miles from Chicago O'Hare International airport and just 400 feet from California & Balmoral NB bus stop.
FromUS$ 270 /nightSelect
7.0
Very good1 review
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1.4 mi from City Center1293 yd from Michigan Avenue
FromUS$ 39 /nightSelect
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1.9 mi from City Center
FromUS$ 599 /nightSelect
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2.4 mi from City Center1415 yd from United Center
The Art Institute of Chicago is 15 minutes' drive from the Chic Green l Near Downtown & IL Medical District, while Willis Tower is about 2.9 miles away.
FromUS$ 181 /nightSelect
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3.7 mi from City Center
FromUS$ 199 /nightSelect
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3.5 mi from City Center
FromUS$ 438 /nightSelect
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4.2 mi from City Center
The Spacious 5-Br House Near Transit W Parking is located 0.5 miles from Midway International airport and 450 feet from 16th Street & Hamlin bus stop.
FromUS$ 598 /nightSelect
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3.9 mi from City Center
FromUS$ 301 /nightSelect
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4.0 mi from City Center1.1 mi from Wrigley Field
FromUS$ 149 /nightSelect
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2.4 mi from City Center1.2 mi from Michigan Avenue
FromUS$ 149 /nightSelect
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9.4 mi from City Center679 yd from Wright College
FromUS$ 156 /nightSelect
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1.9 mi from City Center1131 yd from Michigan Avenue
Nestled in the Near North Side district of Chicago, the Luxurious Classic Gold Coast Villa For 12 Guests is 25 minutes by foot from Millennium Park.
FromUS$ 938 /nightSelect
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1.9 mi from City Center1142 yd from Michigan Avenue
This villa in Near North Side district is composed of 5 bedrooms, a kitchen and 1 bathrooms.
FromUS$ 2 577 /nightSelect
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10.4 mi from City Center453 yd from Tuley Park
FromUS$ 159 /nightSelect
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2.1 mi from City Center1.2 mi from United Center
FromUS$ 224 /nightSelect
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1.4 mi from City Center352 yd from Michigan Avenue
FromUS$ 264 /nightSelect
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2.6 mi from City Center1.1 mi from United Center
FromUS$ 311 /nightSelect
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3.1 mi from City Center
FromUS$ 397 /nightSelect

FAQs about vacation houses in Chicago

In these 9 answers, you will find our recommendations about different vacation houses in Chicago.

What are the top pet-friendly vacation houses in Chicago?

If you want to stay with pets, you'll find 15 deals on Booked.net. Check Old Town-Gold Coast Amazing 3 Bedroom Home/ Free Parking/ Breakfast/ Backyard/ Walk Everywhere/ Pets Ok, offering board games, ironing and live performances on site. Another great option is The Avondale Guesthouse at the cost of 146US$ per one night. Other suitable properties are ✪ Cozy 1 Bedroom Close To Downtown ✪, Lowest Rates! Spacious Duplex With Free Parking! Howard Johnson Inn -.

What are the best budget villas in Chicago?

If you'd like to spend your trip to Chicago in an economical way, select among 17 villas on Booked.net. 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 5 minutes' walk from Pleasant Grove Missionary Baptist Church and costs about 283US$ per night.

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

According to Booked.net travel data, there are 8 deals with hot tubes. You may like The Boom Boom Room offering shopping service, a Jacuzzi and a free parking lot at the price of 439US$ per one night.

What are the top Chicago vacation houses next to a lake?

One of the top accommodations is Old Town-Gold Coast Amazing 3 Bedroom Home/ Free Parking/ Breakfast/ Backyard/ Walk Everywhere/ Pets Ok at the cost of 399US$ per night, it offers board games, ironing and live performances.

What are the best vacation houses in Chicago for couples?

According to Booked.net travel data, there are 22 deals for couples. You may book Grand Plaza Suites rated 8.0/10 for 152US$ per night. This villa is set a 5-minute walk from Marina City and provides video games and ironing on site. Another great villa is Old Town-Gold Coast Amazing 3 Bedroom Home/ Free Parking/ Breakfast/ Backyard/ Walk Everywhere/ Pets Ok at the price of 399US$ per night. Other suitable options for couples are Modern Stylish 1Br Apt In Lincoln Sq - Steps Away Brown Line Ea3, Stunning Penthouse and Charming Apartments Near Downtown.

What are the best vacation houses in Chicago with kitchenettes?

To enjoy your own meal during an comfortable stay, Booked.net offers 3 options to select from. Customers who enjoy cooking may check Oakwood 200 Squared (rating: 8.0/10), located 10 minutes' walk from Goodman Theatre for 205US$ per night.

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

If you want to stay at the place with free parking, Booked.net 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 1.9 miles from Skydeck Chicago. It features board games, ironing and live performances. Alternatively, you may book The Avondale Guesthousefor about 146US$ per night. This villa provides cribs, a free parking lot and a laundry room on site.

What are the most popular vacation houses in Chicago next to Millennium Park?

According to Booked.net travel data, there are 5 deals to select from. Check Modern 2Br/2Bath Apt In Streeterville (rating: 8.0/10) with fitness and ironing. It costs 371US$ per night and is set 0.9 miles from the attraction. Also you may book Stay Alfred At Park Michigan (rating: 8.0/10) for 713US$ per night. It's set 20 minutes' walk away.

What are the top luxury vacation houses in Chicago?

According to Booked.net travel data, one of the top villas is Envitae 3Br Huge Luxury Loft In Chicago'S Best Building, situated 1450 feet from House Of Blues. It costs 299US$ per night.

Vacation Homes in Chicago essential information

🏨 Vacation Homes in Chicago 106
👛 Lowest price 18 USD
✍️ Vacation Homes Reviews 19
Guest reviews of hotels in Chicago