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 9.4
Wonderful - What previous guests thought, 131 reviews
Price from
$136.12
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.

Z
Zak
From
United States
Everything. The atmosphere, the staff, everything was incredible. I only wished I had stayed longer. Ashlee was very helpful and accommodating. I was upgraded to the room with a view and would highly recommend staying there.
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 184 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
Greg
From
New Zealand
Great personal service and cooked-to-order breakfast by the wonderful proprietors; very spacious and comfortable rooms (I has a two room suite). Although the McCormick Place Convention Centre where I was attending a conference is 4 miles away, they happily dropped me to the door each morning. Amazing - thanks!
Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 47 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 9.5
Exceptional - What previous guests thought, 31 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.

J
Juan Jose
From
Argentina
The apartment was great, with breathtaking lake, park, and city views. Ample and comfortable, also the swimming pool and indoor garden are beautiful and much enjoyable -- it's a whole floor#7 dedicated to the pool, garden, and shared dining room with barbecue facilities. The location was perfect, especially for us who love "walking the city", parks and lakeside trails. Staff was also very helpful, in particular, I shipped several small and large eBay/Amazon packages, all ok.
Scored out of 10, guest rating 8.8
Excellent - What previous guests thought, 2,043 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.

J
José Roberto
From
Mexico
The location was very clean, it was close to a subway station.
Scored out of 10, guest rating 8.1
Very Good - What previous guests thought, 362 reviews
Price from
$228.65
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.

N
Nelisbeth
From
Puerto Rico
Excellent location, spacious, clean and comfortable
Scored out of 10, guest rating 8.6
Excellent - What previous guests thought, 341 reviews
Price from
$216.75
1 night, 2 adults

Prime Location! - 1 Min Walk to Wrigley Field - 2BR Apts Perfect for Cubs Fans!

Lakeview, Chicago

Prime Location! - 1 Min Walk to Wrigley Field - 2BR Apts Perfect for Cubs Fans! offers accommodations in Chicago, a 3-minute walk from Wrigley Field and 2.4 miles from Lincoln Park Zoo.

W
William
From
Philippines
Location was outstanding and the host was helpful and cooperative and it was clean!
Scored out of 10, guest rating 8.6
Excellent - What previous guests thought, 327 reviews
Price from
$203.82
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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Highly rated vacation rentals in Chicago and nearby

  • Scored out of 10, guest rating 8.6
    Excellent - What previous guests thought, 52 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, 101 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 8.6
    Excellent - What previous guests thought, 341 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.

    From $204.67 per night
  • Scored out of 10, guest rating 8.7
    Excellent - What previous guests thought, 326 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 9.1
    Wonderful - What previous guests thought, 39 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 8.7
    Excellent - What previous guests thought, 46 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 8.2
    Very Good - What previous guests thought, 510 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.

Vacation Rentals with swimming pools in Chicago and nearby

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

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 9.5
    Exceptional - What previous guests thought, 31 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, 300 reviews
    Looks like a vacation house
    Guest review by
    Linh
    Young couple
  • Avg. price/night: $317.73
    Scored out of 10, guest rating 9.5
    Exceptional - What previous guests thought, 31 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