Skip to main content

Holiday Rentals in Chicago

Find the holiday rentals that appeal to you the most

Holiday Rentals for every style

Find the right holiday rental for you in Chicago

The best holiday rentals in Chicago

Check out our pick of great holiday rentals in Chicago

Show hotels on map

Filter by:

Review score

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.

L
LEO_DOUTLER
From
Canada
Everything was clean , working, and each detail to make your stay more cozy was provided
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 132 reviews
Price from
US$136.12
1 night, 2 adults
Check availability

Forrestville Ave Large Suite

Bronzeville, Chicago

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.

N
Niks
From
Latvia
Good location, close to transport lines. Clean, cozy. And the best part - super helpful and nice hosts.
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 106 reviews
Price from
US$126
1 night, 2 adults
Check availability

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.

D
David
From
Germany
Very unique place to stay. Staff is super friendly and helpful. this has been one of our best stays ever. Homemade Breakfast is extraordinary good!
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 182 reviews
Price from
US$199.19
1 night, 2 adults
Check availability

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.

G
Giovanni
From
Italy
Breakfast was amazing, the 0lace is super and location is great, with free and efficient parking. Great service also
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 29 reviews
Price from
US$419
1 night, 2 adults
Check availability

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.

M
Manjit
From
United Kingdom
A lovely apartment above a restaurant in a lovely area of Chicago. Really warm welcome from the team.
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 47 reviews
Price from
US$285
1 night, 2 adults
Check availability

Villa D' Citta

Lincoln Park, Chicago

Set just 2.2 km from North Avenue Beach, Villa D' Citta offers accommodation in Chicago with access to a tennis court, barbecue facilities, as well as a lift.

C
Carrie
From
United States
The beautiful courtyard where I ate breakfast, and sitting with my mug of tea on the upper deck. Beautiful old home. I also liked that the kitchen was fully available, and preparing breakfast from all the options set out and in the fridge felt like I was part of a home. You can easily make a packed lunch to take with. Really liked the large walk-in shower, and having a bottle of water available in the room. The hosts were very attentive. It is a great location with very convenient access to Fullerton Station, and right next to the DePaul University campus.
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 32 reviews
Price from
US$205.85
1 night, 2 adults
Check availability

Sentral Michigan Avenue

Hotel in Chicago Loop, Chicago

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

G
Gabriele
From
Austria
Michigan Ave 808 obviously is in a great location: next to Grant Park and to a METRA station (you are in 20 minutes at the University of Chicago), 15 Minutes to Lake Michigan (and a water taxi stop), 10 Minutes to the Art Institute (and there is a very nice bakery at the corner and a Trader Joe‘s not far). I enjoyed the studio I stayed in very much: much space, modern furniture, view (partly overlooking Grant Park), many lights and plug-ins, great WLAN, all kinds of kitchen utensils, big bathroom, good products (shampoo, body cream etc.) + the building feels very secure (entrance key, elevator key), you have your own mailbox, everything is top cleaned and there is small swimming pool at the 7th floor and even if you don‘t feel like swimming go there just for the view. What really stands out for me is the the friendliness and the competence of the staff. Everyone is very welcoming, they help you in no time with (seemingly) whatever question you have. I have stayed in lots of places — this for sure is one of the best.
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 2,055 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.

A
Alexander
From
Indonesia
Wonderful location in the middle of Chicago, right next to Union Station. Lou Mitchell next door is a huge plus for food lovers. Well appointed and designed interior and great facilities within the room too. Very clean as well. Highly recommended.
Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 368 reviews
Price from
US$218.45
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.

S
Sara
From
France
I really liked the size, the amenities, the fact that it wasn’t a hotel and where it was located. And I always felt safe!
Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 343 reviews
Price from
US$224.40
1 night, 2 adults
Check availability
All holiday rentals in Chicago

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

See all

Holiday Rentals with swimming pools in Chicago and nearby

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, 471 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...

  • Scored out of 10, guest rating 7.6
    Good - What previous guests thought, 369 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.

    From US$184.10 per night
  • Scored out of 10, guest rating 7.7
    Good - What previous guests thought, 145 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.

  • Scored out of 10, guest rating 7.4
    Good - What previous guests thought, 302 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 in Chicago, 500 metres from CIBC Theatre and 700 metres from Art Institute of Chicago, Loop 1BR w gym doorman same block as L CHI-672 provides accommodation with amenities such as free WiFi...

  • 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.

Highly rated holiday rentals in Chicago and nearby

  • Scored out of 10, guest rating 8.9
    Fabulous - What previous guests thought, 45 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$303.50 per night
  • Scored out of 10, guest rating 8.0
    Very good - What previous guests thought, 156 reviews

    Located within 2.8 km of Oakwood Beach and 1.4 km of Guaranteed Rate Field in Chicago, McCormick Place Guest House provides accommodation with seating area.

    From US$148 per night
  • 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, 41 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.

  • Scored out of 10, guest rating 8.8
    Fabulous - What previous guests thought, 49 reviews

    Aurelien Spacious Apartments in the Heart of Gold Coast provides accommodation within 1.1 km of the centre of Chicago, with free WiFi, and a kitchen with a microwave, a toaster and a fridge.

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

    Set 1.6 km from Union Station and 1.9 km from Willis Tower, K2 Sky High Apartments with Stunning Chicago Views in West Loop features free WiFi and units equipped with a kitchen, balcony and seating...

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

    Right in the centre of Chicago, situated within a short distance of Oak Street Beach and 360 Chicago, Historic luxury Townhouse in Downtown Chicago offers free WiFi, air conditioning and household...

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

    In the Downtown Chicago district of Chicago, close to 360 Chicago, Studio flat in the heart of Downtown Chicago features free WiFi and a washing machine.

Enjoy breakfast in Chicago and nearby

FAQ about holiday rentals in Chicago

Holiday rentals that guests love in Chicago

See all

  • Villa D' Citta

    Holiday Rental in Lincoln Park, Chicago
    Avg. price/night: US$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

  • Sonder by Marriott Bonvoy Market Hall Apartments West Loop

    Holiday Rental in West Loop, Chicago
    Scored out of 10, guest rating 7.4
    Good - What previous guests thought, 302 reviews
    Looks like a vacation house
    Guest review by
    Linh
    Young couple

  • Villa D' Citta

    Holiday Rental in Lincoln Park, Chicago
    Avg. price/night: US$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

Research, refine and make plans for your whole trip

Flights to Chicago

Book your tickets for this popular flight route in just a few simple steps.

Hotels in Downtown Chicago

Get to know one of the city's most popular neighbourhoods.

Hotels in River North

Get to know one of the city's most popular neighbourhoods.

Car hire in Chicago

Hire a car and hit the road.

Flights to Chicago Rockford International

Jet into this airport to explore Chicago at your leisure.

Flights to Chicago O'Hare International Airport

Jet into this airport to explore Chicago at your leisure.

Flights to Midway International Airport

Jet into this airport to explore Chicago at your leisure. Compare flights, fares and airlines – all in one place.

Hotels near McCormick Place

Places to stay near one of the top places to see.

Hotels near Union Station

Perfect for local transport links.