The 10 best holiday rentals in Chicago, USA | Booking.com
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The best holiday rentals in Chicago

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The Avondale Guesthouse

Chicago

Located in Chicago, 4.5 km from Wrigley Field and 5.8 km from Lincoln Park Zoo, The Avondale Guesthouse provides air-conditioned accommodation with a patio and free WiFi.

A
Ann
From
United Kingdom
The apartment was clean and tidy, and there were local bars nearby. The bed was very comfy.
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 132 reviews
Price from
US$136.12
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 4.9 km of Lincoln Park Zoo and 5.1 km of Wrigley Field.

H
Howard
From
United Kingdom
Ray's B & B, was great. Full arrival arrangements were relayed to me before I arrived. The place was quirky, clean and the staff were very willing and thoughtful. Everything was thought of to make my stay an enjoyable one.
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 187 reviews
Price from
US$199.19
1 night, 2 adults
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Designer Themed 4 Bedroom in Best Location with Patio and Fireplace

Near North Side, Chicago

In the Old Town district of Chicago, close to 360 Chicago, Designer Themed 4 Bedroom in Best Location with Patio and Fireplace features a garden and a washing machine.

M
Martinusz
From
Belgium
Walkable location, well equipped. Inna, our host, was exceptionally helpful with tips and ideas and she was always available for communication.
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 29 reviews
Price from
US$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

Boasting a patio with city views, a garden and barbecue facilities, 4 Bedroom Home in Best Location Parking Fireplace Back Yard Pets Welcome can be found in Chicago, close to Oak Street Beach and 2.2...

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 5 reviews
Price from
US$499
1 night, 2 adults
Check availability

The Polo Inn Bridgeport U.S.A.

Bridgeport, Chicago

Situated within 1.8 km of Guaranteed Rate Field and 6.1 km of Field Museum Of Natural History, The Polo Inn Bridgeport U.S.A. Features rooms with air conditioning and a private bathroom in Chicago.

D
David (Ao)
From
Canada
The breakfast at the Inn was amazing, the owner Dave Samber was very friendly and I had a great stay.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 47 reviews
Price from
US$285
1 night, 2 adults
Check availability

Sentral Michigan Avenue

Chicago Loop, Chicago

Set in Chicago, 800 metres from Grant Park and 1.8 km from the centre, Sentral Michigan Avenue offers air-conditioned accommodation with free WiFi, and an infinity pool.

N
Nuttanai
From
Thailand
My recent stay at Sentral Michigan Ave was absolutely outstanding! From the moment I arrived, the staff was warm and welcoming, making me feel right at home. The apartment was spacious, modern, and fully equipped with everything I needed – from high-quality kitchen appliances to cozy, stylish furniture. Plus, the floor-to-ceiling windows offered incredible views of the Chicago skyline, which was a perfect way to start and end each day. The building’s amenities were also a major highlight. The gym was well-equipped, and I loved spending time in the rooftop lounge – it's an amazing spot to relax or connect with friends. The location couldn’t be better, with easy access to public transport, fantastic restaurants, and some of Chicago’s most iconic attractions just minutes away. I felt perfectly situated to explore the city while also having a cozy and quiet retreat to return to. If you’re looking for a place to stay in Chicago, I can’t recommend Sentral Michigan Ave enough. It felt like a home away from home, and I’m already looking forward to my next visit. Highly recommended!
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 2,049 reviews
Price from
US$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 accommodation within 1.6 km of the centre of Chicago, with free WiFi, and a kitchen with a dishwasher, an oven and a microwave.

L
Li
From
United Kingdom
Well equipped, comfortable and stylish apartment, which was perfect as a chance to recharge and catch up on laundry after a week of staying in hotels on a business trip. Right next to an amazing breakfast restaurant that's a Chicago institution, and within walking distance of lots of interesting places including Symphony Hall and theatre district. Sonder app is well worth downloading as it gives lots of functionality, including early check-in (for a fee),, virtual fee and other information about your booking. Extremely good value when I stayed.
Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 360 reviews
Price from
US$228.65
1 night, 2 adults
Check availability

Sonder by Marriott Bonvoy The Opal Apartments River North

River North, Chicago

Sonder by Marriott Bonvoy The Opal Apartments River North features accommodation within 700 metres of the centre of Chicago, with free WiFi, and a kitchen with a dishwasher, an oven and a microwave.

G
Grainne
From
Ireland
Absolutely fantastic property. Perfect location for walking around the city. So clean. Plenty of fresh towels, kitchen towels, even salt and pepper etc and facilities for washing clothes including detergent! Check in was contactless and there are even lockers to store your luggage after check out.
Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 340 reviews
Price from
US$227.80
1 night, 2 adults
Check availability

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

Lakeview, Chicago

In the Lakeview district of Chicago, close to Wrigley Field, Cubs! Prime Location! - 1 Min Walk to Wrigley Field - 2BR Apts Perfect for Cubs Fans! has free WiFi and a washing machine.

P
Pudvah
From
United States
Location was absolutely unbeatable if you're hitting a Cubs game or Wrigleyville in general. Host was very communicative and was easily reachable. Parking pass in Wrigleyville was a huge benefit and was included in the rental.
Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 326 reviews
Price from
US$205.11
1 night, 2 adults
Check availability

5430 Happy Home

Chicago

Set within 4.5 km of Museum of Science and Industry - Chicago and 4.8 km of Guaranteed Rate Field in Chicago, 5430 Happy Home offers accommodation with free WiFi and seating area.

A
Amber
From
Australia
Hosts were so accomodating!! Thanks so much to Dee who facilitated my requests! The area can feel a little dicey, especially from the station at night alone but cannot beat it for the price! Thanks :)
Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 384 reviews
Price from
US$88
1 night, 2 adults
Check availability
All holiday rentals in Chicago

Most booked holiday rentals in Chicago and surroundings in the past month

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Highly rated holiday rentals in Chicago and nearby

  • Scored out of 10, guest rating 8.2
    Very good - What previous guests thought, 514 reviews

    In the South Loop district of Chicago, close to Field Museum Of Natural History, Sonder by Marriott Bonvoy South Wabash Apartments South Loop has free WiFi and a washing machine.

    From US$216.59 per night
  • Scored out of 10, guest rating 8.9
    Fabulous - What previous guests thought, 43 reviews

    Featuring garden views, Wicker Park Inn offers accommodation with patio, around 3.6 km from United Center. The 3-star bed and breakfast has air-conditioned rooms with a private bathroom and free WiFi.

    From US$331.22 per night
  • Scored out of 10, guest rating 8.5
    Very good - What previous guests thought, 165 reviews

    Set in Chicago, 4.4 km from United Center and 7.1 km from Union Station, Perfect place to enjoy the city or just relax offers accommodation with free WiFi in a historic building.

  • Scored out of 10, guest rating 8.9
    Fabulous - What previous guests thought, 104 reviews

    Located in Chicago, 2.3 km from Oakwood Beach and 3.8 km from Guaranteed Rate Field, Forrestville Ave Large Suite provides accommodation with free WiFi in a historic building.

  • Scored out of 10, guest rating 8.6
    Fabulous - What previous guests thought, 50 reviews

    Experience Downtown Chicago at Millennium - Luxury Apartments in The Loop features accommodation within less than 1 km of the centre of Chicago, with free WiFi, and a kitchen with a microwave, a...

  • Scored out of 10, guest rating 9.3
    Superb - 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
    Fabulous - What previous guests thought, 327 reviews

    Featuring 4-star accommodation, Kasa South Loop Chicago is located in Chicago, 1.4 km from Willis Tower and 1.3 km from CIBC Theatre.

  • Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 38 reviews

    Situated conveniently in the centre of Chicago, The Bernardin Gold Coast Luxury Apartments Near Magnificent Mile offers air-conditioned rooms with free WiFi and private parking.

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

  • Scored out of 10, guest rating 7.6
    Good - What previous guests thought, 465 reviews

    Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park features accommodation within 700 metres of the centre of Chicago, with free WiFi, and a kitchen with a dishwasher, a microwave and a...

    From US$225.24 per night
  • Scored out of 10, guest rating 7.6
    Good - What previous guests thought, 366 reviews

    Situated in Chicago, within 2.2 km of Ohio Street Beach and 600 metres 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, 146 reviews

    In the West Loop district of Chicago, close to Union Station, Sonder by Marriott Bonvoy Greektown Apartments has free WiFi and a washing machine.

    From US$328.09 per night
  • Scored out of 10, guest rating 7.5
    Good - What previous guests thought, 295 reviews

    Located within 1.1 km of United Center and 2.8 km of Union Station, Sonder by Marriott Bonvoy Market Hall Apartments West Loop provides rooms with air conditioning and a private bathroom in Chicago.

  • Located in the centre of Chicago, 2.5 km from Ohio Street Beach, Loop 1BR w Lounge Rooftop nr Art Institute CHI-103 provides air-conditioned accommodation with free WiFi and a TV.

  • Located in the centre of Chicago, 2.8 km from Ohio Street Beach, Loop 1BR w WD Gym Rooftop Pool 2 blocks to L CHI-382 provides air-conditioned accommodation with free WiFi and a TV.

  • Situated right in the heart of Chicago, 2.9 km from Ohio Street Beach, Loop 2BR w Gym Doorman same block as L CHI-674 features air-conditioned accommodation with free WiFi and a TV.

  • Located in the centre of Chicago, 2.4 km from Ohio Street Beach and less than 1 km from Willis Tower, Loop 2BR w Pool Gym nr Financial District L CHI-247 offers free WiFi, a shared lounge and air...

Enjoy breakfast in Chicago and nearby

FAQ about holiday rentals in Chicago

Holiday rentals that guests love in Chicago

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  • Villa D' Citta

    Holiday Rental in Lincoln Park, Chicago
    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

  • Sonder by Marriott Bonvoy Market Hall Apartments West Loop

    Holiday Rental in West Loop, Chicago
    Scored out of 10, guest rating 7.5
    Good - What previous guests thought, 295 reviews
    Looks like a vacation house
    Guest review by
    Linh
    Young couple

  • Villa D' Citta

    Holiday Rental in Lincoln Park, Chicago
    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