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
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 9.1
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.

M
Maja
From
Norway
The apartment was exactly as described. The location was perfect - very central and yet felt like we were in a calm area. The check-in and check-out process was very straightforward. The building and the apartment had a very cozy vibe and it always felt like we were going home when returning there from the city. The apartment had everything we needed for our short stay and we would definitely stay there again next time we're in Chicago.
Scored out of 10, guest rating 8.8
Excellent - What previous guests thought, 2,041 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
Jacquelyn
From
United States
Fun location close to great eats and Union Station. Comfortable bed, chic style, nice amenities, and loved the view.
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.

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, 339 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.

M
Mechelina
From
Netherlands
the location was awesome, it was clean well stocked. literally 1 minute from Wrigley field. well thought out instructions on how to get in, parking passes available.
Scored out of 10, guest rating 8.6
Excellent - What previous guests thought, 327 reviews
Price from
$206.40
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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Vacation Rentals with swimming pools in Chicago and nearby

Enjoy breakfast in Chicago and nearby

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, 363 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 7.7
    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.

  • Streeterville 1BR w Gym Pool nr Navy Pier CHI-412 is located in Chicago, just a 13-minute walk from Water Tower Chicago and 0.8 miles from 360 Chicago. This apartment offers an elevator and free Wifi.

  • Streeterville 2BR w Deck Gym nr Beach Park CHI-589 is located in Chicago, just a 13-minute walk from Water Tower Chicago and 0.8 miles from 360 Chicago.

  • Scored out of 10, guest rating 8.6
    Excellent - What previous guests thought, 339 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 $225.24 per night
  • Kasa South Loop Chicago

    South Loop, Chicago
    Free cancellation options available
    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.

  • Level Chicago River North

    River North, Chicago
    Free cancellation options available
    Scored out of 10, guest rating 9.0
    Wonderful - What previous guests thought, 1 review

    Located in Chicago and with Oak Street Beach reachable within 1.5 miles, Level Chicago River North provides a seasonal outdoor swimming pool, non-smoking rooms, free WiFi throughout the property and a...

  • River N 2BR w Gym WD nr Magnificent Mile CHI-164 offers accommodations in Chicago, a 6-minute walk from Shops at Northbridge and one mile from Millennium Station.

Highly rated vacation rentals in Chicago and nearby

  • 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 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 8.7
    Excellent - What previous guests thought, 21 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.

  • Scored out of 10, guest rating 8.8
    Excellent - What previous guests thought, 5 reviews

    Just a 13-minute walk from Water Tower Chicago and 0.6 miles from 360 Chicago, Luxurious Gold Coast 4BR 4-Story Villa with Parking Sleeps 12 Guests features accommodations in Chicago with a garden.

  • Scored out of 10, guest rating 9.7
    Exceptional - What previous guests thought, 19 reviews

    Just a 15-minute walk from Union Station and 1.1 miles from Willis Tower, Sage Modern Apartments Near Union Park in West Loop features accommodations in Chicago, with a fitness center.

  • Scored out of 10, guest rating 9.9
    Exceptional - What previous guests thought, 10 reviews

    Avenir West Loop Penthouses with Iconic City Views features a garden and accommodations with a kitchen in Chicago, 1.6 miles from Water Tower Chicago.

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
  • Avg. price/night: $216.59
    Scored out of 10, guest rating 7.4
    Good - What previous guests thought, 298 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