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

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The best vacation rentals in Chicago

Check out our selection of great 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.

K
Kam
From
United States
Easy access to a nice property in a good location. The hosts were amazing and easy to communicate with. Noemi was so nice and decorated the house for the holiday- it was so cool! We had a blast!
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 132 reviews
Price from
$136.12
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.

S
Steven
From
United Kingdom
Wonderful size and comfort and easy to grab an Uber too and from into Chicago. Rail station is also close by. Host was amazing from the moment we arrived and we could not fault anything.
Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 106 reviews
Price from
$126
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.

M
Marcus
From
Canada
Like going back to the university hostel of long forgotten days. People could be staying there for a night, but it looks like they stayed there longer. The kitchen is always open, so it is a big plus for hungry and thirsty travelers. Anyone can just grab something there and make yourself at home like you did in your own kitchen, excellent. The location is a real plus and sunset walk nearby give you a good feel of American lives seeing couples young and old taking their dogs for a walk. Somewhat, the building around reminds me of Boston or Montreal.
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 182 reviews
Price from
$199.19
1 night, 2 adults

Designer Themed 4 Bedroom in Best Location with Patio and Fireplace

Near North Side, Chicago

Offering a garden, Designer Themed 4 Bedroom in Best Location with Patio and Fireplace offers accommodations in Chicago.

S
Strand
From
United States
This was our first attempt at a non-hotel location. I was surprised how much we appreciated the home's amenities away from home. Amenities like; multiple bathrooms, full kitchen, private off-street parking and a pleasant neighborhood.
Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 29 reviews
Price from
$419
1 night, 2 adults

4 Bedroom Home in Best Location Parking Fireplace Back Yard Pets Welcome

Near North Side, Chicago

A 19-minute walk from Oak Street Beach in Chicago, 4 Bedroom Home in Best Location Parking Fireplace Back Yard Pets Welcome provides accommodations with access to spa facilities and fitness room.

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 5 reviews
Price from
$499
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.

G
Garcia
From
United States
Great location in Bridgeport; excellent breakfast and hospitality! A true old school bed and breakfast.
Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 46 reviews
Price from
$285
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.

M
Marcia M
From
United States
I loved the kitchen, the room, the courtyard, everything about it! Best B&B ever!
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 32 reviews
Price from
$205.85
1 night, 2 adults

Sentral Michigan Avenue

Hotel in Chicago Loop, Chicago

Sentral Michigan Avenue has a fitness center, garden, a shared lounge and restaurant in Chicago. This 3-star hotel offers a shared kitchen, a 24-hour front desk and free WiFi.

C
Christine
From
Germany
The view was outstanding. The facility had all what was needed to make the stay wonderful.
Scored out of 10, guest rating 8.8
Excellent - What previous guests thought, 2,055 reviews
Price from
$169
1 night, 2 adults

Sonder by Marriott Bonvoy The Burnham Apartments Loop

West Loop, Chicago

Sonder by Marriott Bonvoy The Burnham Apartments Loop offers accommodations within one mile of the center of Chicago, with free Wifi and a kitchen with a dishwasher, an oven, and a microwave.

V
Valter
From
France
I really enjoyed my stay at the Sonder! This was my second time here, and it was wonderful once again. What I like most is the self check-in, it’s so practical, easy and safe. I will definitely be staying here again!
Scored out of 10, guest rating 8.1
Very Good - What previous guests thought, 368 reviews
Price from
$218.45
1 night, 2 adults

Sonder by Marriott Bonvoy The Opal Apartments River North

River North, Chicago

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.

L
Linda
From
United States
Very clean, comfortable and great location. Your online chat was very efficient
Scored out of 10, guest rating 8.6
Excellent - What previous guests thought, 343 reviews
Price from
$224.40
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 7.6
    Good - What previous guests thought, 370 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.

    From $225.24 per night
  • Scored out of 10, guest rating 7.7
    Good - What previous guests thought, 145 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.

    From $194.39 per night
  • Scored out of 10, guest rating 8.2
    Very Good - What previous guests thought, 506 reviews

    Sonder by Marriott Bonvoy South Wabash Apartments South Loop offers accommodations in Chicago, 1.2 miles from Art Institute of Chicago and 1.2 miles from Chicago Symphony Orchestra.

  • Scored out of 10, guest rating 7.4
    Good - What previous guests thought, 301 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.

  • Scored out of 10, guest rating 7.6
    Good - What previous guests thought, 471 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...

  • 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.

  • Scored out of 10, guest rating 8.7
    Excellent - What previous guests thought, 53 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,...

  • Loop 1BR w WD Gym Rooftop Pool 2 blocks to L CHI-382 offers accommodations in Chicago, a 11-minute walk from Cloud Gate – The Bean and half a mile from Chicago Symphony Orchestra.

Vacation Rentals with swimming pools in Chicago and nearby

Highly rated vacation rentals in Chicago and nearby

  • Scored out of 10, guest rating 8.9
    Excellent - What previous guests thought, 45 reviews

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

    From $303.50 per night
  • Scored out of 10, guest rating 8.0
    Very Good - What previous guests thought, 156 reviews

    McCormick Place Guest House in Chicago provides accommodations with a garden and a shared lounge.

    From $154 per night
  • Scored out of 10, guest rating 8.7
    Excellent - What previous guests thought, 327 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 9.0
    Wonderful - What previous guests thought, 41 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 8.8
    Excellent - What previous guests thought, 49 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.

  • Scored out of 10, guest rating 9.3
    Wonderful - What previous guests thought, 17 reviews

    Just a 19-minute walk from Union Station and 1.2 miles from Willis Tower, K2 Sky High Apartments with Stunning Chicago Views in West Loop features accommodations in Chicago, with a shared lounge.

  • Scored out of 10, guest rating 9.8
    Exceptional - What previous guests thought, 7 reviews

    Historic luxury Townhouse in Downtown Chicago is located in Chicago, just a 15-minute walk from Shops at Northbridge and 1.4 miles from Millennium Station.

  • Scored out of 10, guest rating 8.8
    Excellent - What previous guests thought, 22 reviews

    Studio flat in the heart of Downtown Chicago offers accommodations in Chicago, a 15-minute walk from Shops at Northbridge and 1.4 miles from Millennium Station.

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: $317.73
    Scored out of 10, guest rating 9.6
    Exceptional - What previous guests thought, 32 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 7.4
    Good - What previous guests thought, 301 reviews
    Looks like a vacation house
    Guest review by
    Linh
    Young couple
  • Avg. price/night: $317.73
    Scored out of 10, guest rating 9.6
    Exceptional - What previous guests thought, 32 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