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

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2F Chicago's Little Italy near West Loop & Downtown

Chicago

2F Chicago's Little Italy near West Loop & Downtown offers accommodations in Chicago, 1.9 miles from Union Station and 2 miles from Willis Tower.

E
Eduardo
From
Puerto Rico
Space, accomodations, and location
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 176 reviews
Price from
$225
1 night, 2 adults
Check availability

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.

C
Camila
From
Colombia
It’s located in a residential neighborhood so it’s very peaceful and perfect to walk around during this time of the year. Everything thing is clean and very well decorated. I came with my sister for one night and wished we could have stayed longer. Highly recommended!
Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 319 reviews
Price from
$289.20
1 night, 2 adults
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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, 187 reviews
Price from
$191.99
1 night, 2 adults
Check availability

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.

A
Ashley
From
United States
This is truly a home away from home. We felt at ease the entire stay and even though we had a jam-packed trip, coming back to the house felt like coming home. The neighborhood is great for walking, and feels extremely safe. There are fantastic coffee shops and restaurants all throughout the neighborhood, and the street parking is plentiful, which makes staying in the city so much easier. I had exactly 30 minutes to myself during the trip, and while everyone else rested, I got in the hot tub and really recharged for the rest of our evening. It was cool outside and perfect in the tub. I cannot more highly recommend this home, and I can't thank Andrea enough. The house is historic and beautiful, and very clean. The beds are so comfortable, and having more than one bathroom is such a bonus. We ended up needing to use the dryer, and it's so nice to have laundry facilities when you accidentally end up with a wet shoe and socks! There's a fireplace and seating for hanging out inside when it's chilly, and it's super cozy. There's a Keurig for coffee and Andrea even offered to get us milk for coffee, but we opted to walk down to the local spots and soak in the neighborhood. I've said a lot but I still feel like I'm not capturing how great the property really is. If you've found this one, stop scrolling!
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 8 reviews
Price from
$450
1 night, 2 adults
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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
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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
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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 9.1
Wonderful - What previous guests thought, 48 reviews
Price from
$270
1 night, 2 adults
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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, 33 reviews
Price from
$205.85
1 night, 2 adults
Check availability

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.

n
nicola
From
United Kingdom
Great to have a 7th floor swimming pool, hot tub and outdoor deck. Excellent gym and fitness facilities. Comfortable, smart apartment, good air conditioning, very well equipped kitchen. Superb location, convenient for the city centre and overlooking the park and lake front.
Scored out of 10, guest rating 8.8
Excellent - What previous guests thought, 2,048 reviews
Price from
$169
1 night, 2 adults
Check availability

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, 346 reviews
Price from
$245.65
1 night, 2 adults
Check availability
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, 46 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, 331 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, 320 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 8.1
    Very Good - What previous guests thought, 346 reviews

    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.

  • Scored out of 10, guest rating 9.3
    Wonderful - What previous guests thought, 32 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, 45 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.

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

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FAQ about vacation rentals in Chicago

Vacation Rentals That Guests Love in Chicago

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  • Villa Dubois Guest House

    Vacation Rental in Bronzeville, Chicago
    Avg. price/night: $231.67
    Scored out of 10, guest rating 6.5
    Pleasant - What previous guests thought, 216 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

  • Villa D' Citta

    Vacation Rental in Lincoln Park, Chicago
    Avg. price/night: $317.73
    Scored out of 10, guest rating 9.5
    Exceptional - What previous guests thought, 33 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

  • Sonder by Marriott Bonvoy Market Hall Apartments West Loop

    Vacation Rental in West Loop, Chicago
    Scored out of 10, guest rating 7.6
    Good - What previous guests thought, 289 reviews
    Looks like a vacation house
    Guest review by
    Linh
    Young couple

  • Villa D' Citta

    Vacation Rental in Lincoln Park, Chicago
    Avg. price/night: $317.73
    Scored out of 10, guest rating 9.5
    Exceptional - What previous guests thought, 33 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