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Vacation Homes in Chicago, IL

Search among 45 available vacation homes in Chicago from 50+ providers

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Vacation Homes in Chicago essential information

🏨 Vacation Homes in Chicago 45
👛 Lowest price 107 USD
27Sept2023Wednesday
28Sept2023Thursday
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10 adults
3 bedrooms
3 beds
View on map2.1 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.
From   US$ 519 /nightSelect
Not available
8 adults
3 bedrooms
5 beds
View on map4.9 mi from City Center500 yd from Viaduct Center
From   US$ 107 /nightSelect
Not available
7.7 mi from City Center600 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.
From   US$ 246 /nightSelect
Not available
6.3 mi from City Center1.0 mi from University of Chicago
Guaranteed Rate Field is about 2.9 miles from the Romantic 3 Bed Home In The Heart Of The Park and Hyde Park is around 1.7 miles away.
From   US$ 293 /nightSelect
Not available
6.1 mi from City Center1600 yd from Cannella School of Hair Design
Half Italian is around 1.8 miles from the Home 6 Bd 4 Ba Home With 2 Car Garage Parking Chicago, while City Lit Books is approximately 1.8 miles away.
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Not available
3.8 mi from City Center500 yd from
Wrigley Field is 1.3 miles from the Flat In Lincoln Park 2-Flat Central To Everything Chicago, while Trader Joe's is just an 8-minute walk away.
From   US$ 602 /nightSelect
Not available
6.1 mi from City Center800 yd from Kindred Hospital-Chicago North
Set within 1.5 miles of Fellger Park, the rooms in the Large, Upscale Beautiful Home Perfect For Entertaining, Near Wrigley Chicago have views of garden.
From   US$ 1 000 /nightSelect
Not available
3.5 mi from City Center300 yd from
From   US$ 345 /nightSelect
Not available
2.9 mi from City Center1.1 mi from United Center
From   US$ 401 /nightSelect
Not available
11.9 mi from City Center1400 yd from Ridge Historical Society
From   US$ 293 /nightSelect
Not available
2.0 mi from City Center1600 yd from United Center
Eckhart Park is 15 minutes' walk away and Skydeck Chicago can be reached within 10 minutes by car.
From   US$ 421 /nightSelect
Not available
4.2 mi from City Center200 yd from
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.
From   US$ 319 /nightSelect
Not available
21 adults
4 bedrooms
8 beds
2.1 mi from City Center1.1 mi from Michigan Avenue
Placed in Old Town district, this self-catering villa has 4 bedrooms and can accommodate up to 21 guests.
From   US$ 499 /nightSelect
Not available
9.4 mi from City Center700 yd from Wright College
From   US$ 186 /nightSelect
Not available
10 adults
5 bedrooms
5 beds
1.9 mi from City Center800 yd from Michigan Avenue
Located about 1.3 miles from Millennium Park, the vacation home offers accommodation for 10 guests.
From   US$ 879 /nightSelect
Not available
3.8 mi from City Center700 yd from
Skydeck Chicago and Garfield Park Conservatory are located 3.8 miles and 0.6 miles from the Griffin Mansion With Yard, 5 Mi To Dtwn Chicago! respectively.
From   US$ 201 /nightSelect
Not available
24 adults
5 bedrooms
11 beds
2.2 mi from City Center1.1 mi from Michigan Avenue
Millennium Park is within 2.1 miles of the 5 Bedroom House In Best Location Parking Fireplace Back Yard Home Office and Lincoln Park Zoo is about 20 minutes' walk away.
From   US$ 616 /nightSelect
Not available
4.2 mi from City Center200 yd from
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Not available
3.0 mi from City Center700 yd from
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Not available
12.9 mi from City Center1400 yd from Roseland Community Hospital
From   US$ 132 /nightSelect
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45 hotels found

FAQs about vacation houses in Chicago

Read these 9 answers to find a vacation house 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.

Guest reviews of hotels in Chicago