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

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, 131 reviews
Price from
US$136.12
1 night, 2 adults

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.

T
Tiffany
From
United States
We only met the hosts when we checked in, but they were very nice and welcoming. We were given a tour of the property, then left to ourselves. We were very comfortable and don't have a single complaint. I'd happily stay again. The beds were comfortable, unlike hotel beds, and we all slept very well. It was quiet and we had everything we needed. The neighborhood is close enough to everything, but in a quiet and safe area. It was really ideal.
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 106 reviews
Price from
US$126
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 4.9 km of Lincoln Park Zoo and 5.1 km of Wrigley Field.

i
idan
From
Belgium
every thing was above my expectations super nice location amazing breakfast and super kind owner and crew
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 181 reviews
Price from
US$199.19
1 night, 2 adults

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

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

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

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.

j
janice
From
United Kingdom
Beautiful villa with homely feel . Absolute gorgeous breakfast all home made in the morning as well as cereal , fruit etc Bedroom was excellent with everything you need such as extra towels , dressing gowns and slippers for the Hot Tub .
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 32 reviews
Price from
US$205.85
1 night, 2 adults

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.

A
Alessio
From
Italy
Great apartment with all the services. Great location in the Loop with view of the lake, near bus and metro lines.
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 2,052 reviews
Price from
US$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 accommodation within 1.6 km of the centre of Chicago, with free WiFi, and a kitchen with a dishwasher, an oven and a microwave.

J
Jeroen
From
Netherlands
I stayed at Sonder The Burnham for 3 weeks and had a great stay. It's located in the middle of Downtown Chicago close to Union Station. I had a large clean apartment with all the amenities I needed. There's a large well-equipped kitchen, a washer/dryer, quiet air conditioner and a great bed. It was clean and there was not too much noise from the street, which can be an issue in Chicago, with the elevated metro lines. Large screen with Roku tv or HDMI connection and good Wi-Fi. Little to complain about, 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

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.

M
Maria
From
Russia
Wonderful location, close to all main attractions. Spacious, clean and comfortable apartment, well quipped for both short and long stay.
Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 344 reviews
Price from
US$224.40
1 night, 2 adults
All holiday rentals in Chicago

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

See all

Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 7.4
Good - What previous guests thought, 303 reviews

Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 326 reviews

Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 314 reviews

Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 392 reviews

Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 210 reviews

Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 7.9
Good - What previous guests thought, 160 reviews

Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 8.2
Very good - What previous guests thought, 507 reviews

Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 5.6
Passable - What previous guests thought, 416 reviews

Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 325 reviews

Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 2,045 reviews

Holiday Rentals with swimming pools in Chicago and nearby

Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 53 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...

Set in the heart of Chicago, 2.4 km from Ohio Street Beach, Loop 1BR w Pool Gym nr Financial District CHI-281 offers air-conditioned accommodation with free WiFi and a TV.

Situated right in the heart of Chicago, 2.4 km from Ohio Street Beach, Loop 1BR w Pool Gym nr Theatre District CHI-277 features air-conditioned accommodation with free WiFi and a TV.

Situated right in the heart of Chicago, 2.4 km from Ohio Street Beach, Loop 1BR w Pool Gym nr Financial District CHI-261 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...

Located in a central area of Chicago, 2.4 km from Ohio Street Beach, Loop 1BR w Pool Gym nr the L Riverwalk CHI-242 provides air-conditioned accommodation with free WiFi and a TV.

Set in the centre of Chicago, 2.4 km from Ohio Street Beach and less than 1 km from Willis Tower, Loop Studio w gym pool lounge 1 block from L CHI-694 offers free WiFi, an indoor pool and air...

Set in the centre of Chicago, 2.4 km from Ohio Street Beach and less than 1 km from Willis Tower, Loop 1BR w Gym Pool WD nr Financial District CHI-222 offers free WiFi, a shared lounge and air...

Highly rated holiday rentals in Chicago and nearby

Scored out of 10, guest rating 8.2
Very good - What previous guests thought, 507 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$163.53 per night
Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 45 reviews

Situated in Chicago, 2.1 km from Fullerton Beach and 1.8 km from Lincoln Park Zoo, Lincoln Park Apartment with Backyard! features air-conditioned accommodation with a patio and free WiFi.

From US$180.23 per night

5430 Happy Home

Chicago
8.0+ review score
Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 392 reviews

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.

From US$220.95 per night
Scored out of 10, guest rating 9.4
Superb - 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 8.7
Fabulous - What previous guests thought, 325 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, 42 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, 52 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 9.2
Superb - What previous guests thought, 18 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...

Enjoy breakfast in Chicago and nearby

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, 1.7 km from Ohio Street Beach and 300 metres from Millennium Station, Loop 2br w lounge gym nr Chicago Riverwalk CHI-959 offers free WiFi, a shared lounge and air...

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.

Situated right in the heart of Chicago, 300 metres from Willis Tower, Loop 1BR w Gym Roof Lounge same block as L CHI-670 features air-conditioned accommodation with free WiFi and a TV.

Set in Chicago, less than 1 km from Shops at Northbridge and a 11-minute walk from Chicago Museum of Contemporary Art, Streeterville 1BR w Gym Pool nr Navy Pier CHI-412 provides accommodation with...

Set in the heart of Chicago, 300 metres from Ohio Street Beach, Streeterville 2BR w Deck Gym nr Beach Park CHI-589 offers air-conditioned accommodation with free WiFi and a TV.

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, 470 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$142.96 per night
Scored out of 10, guest rating 7.6
Good - What previous guests thought, 367 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$163.53 per night
Scored out of 10, guest rating 7.4
Good - What previous guests thought, 303 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.

From US$132.68 per night

Located in a central area of Chicago, 1.8 km from Oak Street Beach, River North jr 1br w game room nr beach L CHI-971 provides air-conditioned accommodation with free WiFi and a TV.

Located in the centre of Chicago, 1.8 km from Oak Street Beach, River N 1BR w Gym WD nr Mag Mile by Bluegound CHI-127 provides air-conditioned accommodation with free WiFi and a TV.

Level Chicago River North

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

Set in Chicago and with Oak Street Beach reachable within 2.4 km, Level Chicago River North offers a seasonal outdoor swimming pool, non-smoking rooms, free WiFi throughout the property and a fitness...

Located in the centre of Chicago, 1.4 km from Oak Street Beach, River N 2BR w Gym WD nr Magnificent Mile CHI-164 provides air-conditioned accommodation with free WiFi and a TV.

Located in a central area of Chicago, 1.4 km from Oak Street Beach, River N 2BR w Gym WD nr Magnificent Mile CHI-160 provides air-conditioned accommodation with free WiFi and a TV.

FAQ about holiday rentals in Chicago

Holiday rentals that guests love in Chicago

See all
Avg. price/night: US$117
Scored out of 10, guest rating 6.9
Pleasant - What previous guests thought, 221 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
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
Avg. price/night: US$132.68
Scored out of 10, guest rating 7.4
Good - What previous guests thought, 303 reviews
Looks like a vacation house
Guest review by
Linh
Young couple
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