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The best vacation homes in Chicago Metropolitan Area

Check out our selection of great vacation homes in Chicago Metropolitan Area

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Review Score

Wonderful: 9+ Very Good: 8+ Good: 7+ Pleasant: 6+
Our top picks Lowest Price First Star rating and price Top reviewed

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The Avondale Guesthouse

Chicago

Located in Chicago, 4.6 km from Wrigley Field and 5.5 km from Lincoln Park Zoo, The Avondale Guesthouse provides air-conditioned accommodation with a patio and free WiFi. This recently renovated holiday home is located 7.2 km from United Center and 8.1 km from 360 Chicago. On clear days, guests can head outside to enjoy the holiday home's outdoor fireplace or simply kick back and relax. Good suburban location with access to public transport into Downtown. Three bedrooms and excellent washing and drying facilities. Lovely veranda in the back yard to chill out in the evening.

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9.3
Wonderful
121 reviews
Price from
$360
per night

Stunning Condo #2 - Downtown River North

Near North Side, Chicago

The spacious holiday home has 3 bedrooms, a TV with cable channels and a fully equipped kitchen that provides guests with a dishwasher, an oven, a washing machine, a microwave and a fridge. Towels and bed linen are offered in the holiday home. For added privacy, the accommodation features a private entrance. Fantastic property very close to the downtown area of Chicago, near the metro and the bus stop. Beautifully done up interiors, Very spacious and can easily accommodate 12-14 people . Ample amount of coffee milk and sugar at disposal. Prompt replies from the owner for everything we needed.

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9.7
Exceptional
11 reviews
Price from
$149
per night

Stunning Duplex Condo #1 - Downtown River North

Near North Side, Chicago

The spacious holiday home has 2 bedrooms, a TV and a fully equipped kitchen that provides guests with a dishwasher, an oven, a washing machine, a microwave and a fridge. Towels and bed linen are offered in the holiday home. The apartment is lovely and has everything you need. The location was great for us. Lots of restaurants and shops close by. We really enjoyed our stay in the apartment and would definitely come back.

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9
Wonderful
5 reviews
Price from
$139
per night

Beautiful loft style townhouse-vaulted ceilings

Romeoville

This holiday home comes with 1 bedroom, a kitchen with an oven and a microwave, a flat-screen TV, a seating area and 2 bathrooms equipped with a walk-in shower. Towels and bed linen are provided in the holiday home. Everything awesome must go visit!!

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9.7
Exceptional
7 reviews
Price from
$129.60
per night

2-Acre Highland Park Retreat with Heated Pool ~ 5*

Highland Park

The spacious holiday home is located on the ground floor and is fitted with 6 bedrooms, a flat-screen TV with cable channels and a fully equipped kitchen that provides guests with a dishwasher, an oven, a washing machine, a microwave and a toaster. A private entrance leads guests into the holiday home, where they can enjoy some wine or champagne and chocolates or cookies. There is also a seating area and a fireplace. This property was extremely comfortable for our family. There were bedrooms and bathrooms on the main floor for our older family members, a place for young adults downstairs and a master suite to get away upstairs. It was beautiful, private and well maintained.

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9.9
Exceptional
7 reviews
Price from
$1,134
per night

Luxurious House, 25 min Downtown, 10min Midway

Burbank

The spacious holiday home has 4 bedrooms, a flat-screen TV with streaming services, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 2 bathrooms with a bath. Towels and bed linen are available in the holiday home. For added privacy, the accommodation features a private entrance. Our stay in Chicago was very enjoyable. This was the perfect home for our stay. We appreciated the cleanliness and how beautifully decorated it was with the modern touches. The bedrooms were comfortable and the garage parking was an added plus. We did not have to hassle with parking. The family room was just perfect for our evening down time. All our needs were met and we look forward to any future stays at this home. Thank you!

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10
Exceptional
5 reviews
Price from
$310.50
per night

Beautiful home in Beach Park IL

Beach Park

The holiday home features 3 bedrooms, a flat-screen TV, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 2 bathrooms with a shower. The accommodation offers a fireplace.

Carthage College is 24 km from the holiday home, while Tarble Center is 24 km away. The nearest airport is Chicago O'Hare International Airport, 58 km from Beautiful home in Beach Park IL. Nice place to stay if you’re visiting six flags park. Sauna was a great bonus! House was clean. Wifi, cable tv works great. Definitely worth the price.

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9.1
Wonderful
7 reviews
Price from
$168.75
per night

Spacious Row Home next Transit near Downtown w Parking

Chicago

The spacious holiday home with a balcony and garden views has 4 bedrooms, 3 living rooms, a flat-screen TV, an equipped kitchen with a dishwasher and an oven, and 3 bathrooms with a bath. Towels and bed linen are available in the holiday home. The property has an outdoor dining area. Very clean had everything we needed.

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9.4
Wonderful
7 reviews
Price from
$318.60
per night

Northside FAMLYNEST Lincoln Sq 4BR 2BA 2P Rare find

Chicago

The spacious holiday home is fitted with 4 bedrooms, 2 bathrooms, bed linen, towels, a flat-screen TV with streaming services, a dining area, a fully equipped kitchen, and a patio with garden views. A private entrance leads guests into the holiday home, where they can enjoy some fruits and chocolates or cookies. The property has an outdoor dining area. Staying at Northside FAMILYNEST Lincoln Sq was an absolute delight! From the cleanness,modern amenities to the beautifully decorated rooms and the delicious light snacks that were available to eat. Lastly our host Mr Ivan was great he made us feel right at home. I truly enjoyed our stay!

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9.8
Exceptional
24 reviews
Price from
$302.50
per night

Spacious 5-BR House near Transit w Parking

Chicago

The spacious holiday home has 5 bedrooms, a flat-screen TV, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 3 bathrooms with a walk-in shower. Featuring air conditioning, this unit has a dressing room and a fireplace. The property has an outdoor dining area. Plenty of room. Very spacious.

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9.7
Exceptional
7 reviews
Price from
$413
per night

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