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

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

Chicago

Offering quiet street views, 2F Chicago's Little Italy near West Loop & Downtown is an accommodation situated in Chicago, 3.1 km from Willis Tower and 4.2 km from Depaul University.

K
Ken
From
United Kingdom
We stayed at this property for just over a week. The property is in a great location, a couple of blocks from the pink line at Polk station. The host made everything extremely easy from checking in to checking out and provided coffees, teas, sweets and the kitchen has every thing needed if you decide to cook. The area is quiet and friendly and literally a block from Taylor Street where there are numerous places to eat and drink. We actually walked from the apartment to Willis tower on our first morning, (jet lag) and even that with our 12 year old took less than half an hour. Grocery store is minutes away. We as a family found the apartment was very clean and met all our needs and with four good sized bedrooms was ideal. Would highly recommend anyone thinking of travelling to Chicago especially with family to stay here and I know when I return I will be staying here again. Thank you to John for making everything extremely simple and messaging with updates before arrival and during our stay.
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 183 reviews
Price from
US$180
1 night, 2 adults

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.

T
Tony
From
Italy
Central to where wanted to visit. Large property that was very comfortable.
Scored out of 10, guest rating 9.4
Superb - 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.

L
Laura
From
United Kingdom
Fantastic hosts - respond quickly to messages and were excellent meeting us on arrival and showing us around the property. Good space and spotlessly clean. Good neighbourhood about 20 mins drive from the centre of Chicago and on street parking was easy.
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 108 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.

A
Anna
From
Russia
We LOVED this place! The house was adorable and cute. All the decor was so fun, Ashley was beyond friendly, the breakfast was incredible, snacks always downstairs. The neighborhood was great...we want to move in, please take us :))
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 177 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 9.4
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 9.3
Superb - What previous guests thought, 48 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.

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

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.

C
Caroline
From
United Kingdom
The location was excellent. The whole process of checking in/out and contact with Sentral prior to my stay was simple and timely. The actual building and facilities were amazing.
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 2,035 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.

D
David
From
El Salvador
The space, the design, the cleaning, the location.
Scored out of 10, guest rating 8.2
Very good - What previous guests thought, 382 reviews
Price from
US$218.45
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, 304 reviews

Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 8.2
Very good - What previous guests thought, 382 reviews

Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 395 reviews

Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 7.9
Good - What previous guests thought, 162 reviews

Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 317 reviews

Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 211 reviews

Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 5.6
Passable - What previous guests thought, 413 reviews

Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 327 reviews

Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 8.2
Very good - What previous guests thought, 505 reviews

Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 2,035 reviews

Highly rated holiday rentals in Chicago and nearby

Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 347 reviews

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.

From US$163.53 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 54 reviews

Located within the Lincoln Park district in Chicago, Lincoln Park 3 BR Penthouse has air conditioning, a balcony, and city views.

Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 164 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 8.6
Fabulous - What previous guests thought, 329 reviews

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

From US$246.80 per night
Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 34 reviews

Set in Chicago, 2.3 km from Oakwood Beach and 3.8 km from Museum of Science and Industry - Chicago, Hyde Park Modern Private Room - Near Univ of Chicago offers a garden and air conditioning.

5430 Happy Home

Chicago
8.0+ review score
Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 395 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$170.76 per night
Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 57 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 9.4
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.

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, 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...

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 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...

Holiday Rentals with swimming pools in Chicago and nearby

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...

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.

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...

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 45 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 7.6
Good - What previous guests thought, 7 reviews

An apartment nestled in the centre of Chicago, Jeffjack Heated Pool Penthouse in Chicago's West Loop features private parking, free WiFi, a rooftop pool and fitness centre.

Situated right in the centre of Chicago, 700 metres from Field Museum Of Natural History, S Loop 2BR w Pool Gym Spa nr Grant Park CHI-740 features air-conditioned accommodation with free WiFi and a TV...

Set right in the centre of Chicago, 700 metres from Field Museum Of Natural History, S Loop 1BR w Pool Lounge nr CTA Trains CHI-353 offers air-conditioned accommodation with free WiFi and a TV.

Set in the heart of Chicago, 700 metres from Field Museum Of Natural History, S Loop 1BR w Pool Gym Spa nr Grant Park CHI-741 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, 472 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 7.7
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$142.96 per night
Scored out of 10, guest rating 7.8
Good - What previous guests thought, 147 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$142.96 per night
Scored out of 10, guest rating 7.4
Good - What previous guests thought, 304 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$122.39 per night

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...

Kasa South Loop Chicago

South Loop, Chicago
Free cancellation options 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.

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.

FAQ about holiday rentals in Chicago

Holiday rentals that guests love in Chicago

See all
Avg. price/night: US$97
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$122.39
Scored out of 10, guest rating 7.4
Good - What previous guests thought, 304 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