The 10 best vacation rentals in Chicago, US | Booking.com
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The best vacation rentals in Chicago

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The Avondale Guesthouse

Chicago

The Avondale Guesthouse is located in Chicago, just 2.8 miles from Wrigley Field and 3.6 miles from Lincoln Park Zoo.

A
Adams
From
United States
Great house, great location! Enjoyed our stay, thank you!
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 134 reviews
Price from
$249
1 night, 2 adults

Forrestville Ave Large Suite

Bronzeville, Chicago

Forrestville Ave Large Suite is located in Chicago, just 2.8 miles from Museum of Science and Industry - Chicago and 4.5 miles from Field Museum of Natural History.

T
Tserentamir
From
United States
It was a spacious and nice apartment, extremely spacious and quiet. I needed a nice break, and I definitely got it while staying in the apartment.
Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 104 reviews
Price from
$126
1 night, 2 adults

The Sono Chicago

Near North Side, Chicago

The Sono Chicago is located in The Old Town neighborhood of Chicago. Lincoln Park Zoo is only 0.7 mi away. Parking is free with permit provided by The Sono Chicago.

J
JAN
From
United States
Beautiful home-like surroundings. Spotlessly clean. Manager is outstanding; very responsive to any requests; meets & greets for our check-in & helps with luggage. Breakfast buffet has many healthy choices & freshly baked croissants. The common area & patio is welcoming with areas for small or large conversation. Highly recommend!
Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 326 reviews
Price from
$187.20
1 night, 2 adults

Ray's Bucktown Bed and Breakfast

Logan Square, Chicago

Ray's Bucktown Bed and Breakfast provides a sauna and free private parking, and is within 3.1 miles of Lincoln Park Zoo and 3.2 miles of Wrigley Field.

G
Gill
From
United States
The room was cozy and clean. The location was nice and the breakfast was amazing.
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 194 reviews
Price from
$199.19
1 night, 2 adults

Historic Home with Outdoor Hot Tub Near Downtown in Public Transportation Hub

Chicago

A recently renovated vacation home, Historic Home with Outdoor Hot Tub Near Downtown in Public Transportation Hub offers accommodations in Chicago.

S
Seagle
From
United States
Everything was fantastic!
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 8 reviews
Price from
$450
1 night, 2 adults

1F Cozy Home in Little Italy near Downtown West Loop United Center

Chicago

1F Cozy Home in Little Italy near Downtown West Loop United Center is located in Chicago, just 1.1 miles from United Center and 2.4 miles from Willis Tower.

A
Anonymous
From
United States
A truly wonderful home. Beautifully decorated and exceeded all of our expectations. Many extras provided that made the house feel like a home.
Scored out of 10, guest rating 9.9
Exceptional - What previous guests thought, 78 reviews
Price from
$166.50
1 night, 2 adults

The Avondale Attic

Chicago

The Avondale Attic offers accommodations in Chicago, 3.4 miles from Wrigley Field and 4.9 miles from Lincoln Park Zoo. Both free Wifi and parking on-site are available at the apartment free of charge....

T
Thomas
From
United States
Very nicely appointed and excellent use of the available space. We would definitely stay again.
Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 13 reviews
Price from
$130
1 night, 2 adults

The Polo Inn Bridgeport U.S.A.

Bridgeport, Chicago

Offering air-conditioned rooms in the Bridgeport district of Chicago, The Polo Inn Bridgeport U.S.A. Is 1.1 miles from Guaranteed Rate Field.

J
Julien
From
United States
We stayed only one night but had a good time. The breakfast was very good (the toasted cinnamon bread is really special).
Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 51 reviews
Price from
$270
1 night, 2 adults

Villa D' Citta

Lincoln Park, Chicago

Villa D' Citta enjoys a location in Chicago, 1.4 miles from North Avenue Beach and a 18-minute walk from Lincoln Park Zoo.

K
Krystal
From
United States
This place was stunning! The location is great, the building is beautiful, the owners were so kind and the food was delicious. We had zero complaints and will most definitely be back again.
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 34 reviews
Price from
$205.85
1 night, 2 adults

Sentral Michigan Avenue

Chicago Loop, Chicago

Sentral Michigan Avenue offers accommodations within 1.1 miles of the center of Chicago, with free Wifi and a kitchen with a dishwasher, an oven, and a microwave.

J
Jaime
From
United States
This was a great location, right on Michigan Ave. We walked EVERYWHERE! So many restaurants and bars very near to the condo/building. The patio at the pool was also a really cool bonus!
Scored out of 10, guest rating 8.8
Excellent - What previous guests thought, 2,018 reviews
Price from
$169
1 night, 2 adults
All vacation rentals in Chicago

Most booked vacation rentals in Chicago and surrounding area in the past month

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These vacation rentals in Chicago and nearby have options with free cancellation

  • Scored out of 10, guest rating 7.5
    Good - What previous guests thought, 460 reviews

    Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park features accommodations within half a mile of the center of Chicago, with free Wifi and a kitchen with a dishwasher, a microwave, and a...

  • Scored out of 10, guest rating 7.7
    Good - What previous guests thought, 367 reviews

    Located in Chicago, within 1.4 mi of Ohio Street Beach and 1969 feet of Chicago Board of Trade Building, The Plymouth, Sonder Apartments by Marriott Bonvoy features free WiFi.

  • Scored out of 10, guest rating 7.8
    Good - What previous guests thought, 146 reviews

    Sonder by Marriott Bonvoy Greektown Apartments enjoys a location in Chicago, 1.3 miles from Art Institute of Chicago and one mile from DePaul University. This 4-star condo hotel offers free Wifi.

  • Scored out of 10, guest rating 7.7
    Good - What previous guests thought, 278 reviews

    Sonder by Marriott Bonvoy Market Hall Apartments West Loop offers accommodations in Chicago, a 13-minute walk from United Center and 1.7 miles from Union Station.

  • 5430 Happy Home

    Chicago
    Free cancellation options available
    Scored out of 10, guest rating 7.9
    Good - What previous guests thought, 383 reviews

    5430 Happy Home enjoys a location in Chicago, 2.8 miles from Museum of Science and Industry - Chicago and 3 miles from Guaranteed Rate Field. This homestay offers a shared kitchen and free Wifi.

  • Loop 1BR w Lounge Rooftop nr Art Institute CHI-103 offers accommodations in Chicago, a 1-minute walk from Chicago Symphony Orchestra and half a mile from Willis Tower.

  • Just a 3-minute walk from Millennium Station and 500 yards from Millennium Park, Loop 2br w gym playroom pool close to L CHI-960 features accommodations in Chicago with a shared lounge.

  • Loop 1BR w Gym Pool WD nr Millennium Park CHI-236 offers accommodations in Chicago, a 9-minute walk from Chicago Symphony Orchestra and half a mile from Shops at Northbridge.

Highly rated vacation rentals in Chicago and nearby

  • Scored out of 10, guest rating 8.9
    Excellent - What previous guests thought, 48 reviews

    Wicker Park Inn enjoys a location in Chicago, 2.3 miles from United Center and 2.8 miles from Water Tower Chicago.

  • Scored out of 10, guest rating 9.0
    Wonderful - What previous guests thought, 51 reviews

    Offering air-conditioned rooms in the Bridgeport district of Chicago, The Polo Inn Bridgeport U.S.A. Is 1.1 miles from Guaranteed Rate Field.

  • Scored out of 10, guest rating 8.7
    Excellent - What previous guests thought, 42 reviews

    Experience Downtown Chicago at Millennium - Luxury Apartments in The Loop features accommodations within half a mile of the center of Chicago, with free Wifi and a kitchen with a microwave, a toaster,...

  • Scored out of 10, guest rating 9.3
    Wonderful - What previous guests thought, 100 reviews

    Located in the heart of downtown Chicago, just 3 blocks away from the Magnificent Mile, this self-catering apartment features a balcony with iconic views of the city. Free WiFi access is available.

  • Scored out of 10, guest rating 8.7
    Excellent - What previous guests thought, 319 reviews

    Sonder by Marriott Bonvoy The Opal Apartments River North features accommodations within 0.4 miles of the center of Chicago, with free Wifi and a kitchen with a dishwasher, an oven, and a microwave.

  • Scored out of 10, guest rating 8.6
    Excellent - What previous guests thought, 322 reviews

    Just a 18-minute walk from Art Institute of Chicago and 0.9 miles from Chicago Symphony Orchestra, Kasa South Loop Chicago features accommodations in Chicago, with a shared lounge.

  • Scored out of 10, guest rating 9.2
    Wonderful - What previous guests thought, 28 reviews

    The Bernardin Gold Coast Luxury Apartments Near Magnificent Mile is an apartment featuring rooms with free Wifi and air conditioning in the center of Chicago.

  • Scored out of 10, guest rating 8.6
    Excellent - What previous guests thought, 42 reviews

    Aurelien Spacious Apartments in the Heart of Gold Coast provides accommodations within 0.7 miles of the center of Chicago, with free Wifi and a kitchen with a microwave, a toaster, and a fridge.

Enjoy breakfast in Chicago and nearby

FAQ about vacation rentals in Chicago

Vacation Rentals That Guests Love in Chicago

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  • Avg. price/night: $231.67
    Scored out of 10, guest rating 5.6
    Fair - What previous guests thought, 203 reviews
    Im so happy i came across Villa Dubois Guesthouse. The whole property is clean and organized, free street parking, neighborhood is quiet. I love the full functional kitchen where you can prepare meals.security cameras around the common area for safety.If you dont mind sharing a space with strangers,this a nice budget friendly place to stay😊
    Guest review by
    LIW-LIWA
    Young couple
  • Avg. price/night: $387.11
    Scored out of 10, guest rating 9.6
    Exceptional - What previous guests thought, 34 reviews
    Rosa & Edith were attentive to our needs and expectations. The entire staff was friendly, accommodating and engaging. The Villa was at our disposal, and we were able to enjoy the amenities with our daughter and her husband who live nearby.
    Guest review by
    Nosal
    Young couple
  • Scored out of 10, guest rating 7.7
    Good - What previous guests thought, 278 reviews
    Looks like a vacation house
    Guest review by
    Linh
    Young couple
  • Avg. price/night: $387.11
    Scored out of 10, guest rating 9.6
    Exceptional - What previous guests thought, 34 reviews
    The Villa is lovely and the host was great. They have great options for breakfast which you prepare yourself. Location was really nice - lovely the neighborhood. Loved the wine on tap!
    Guest review by
    Sydney
    Group

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