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Holiday Rentals in Chicago

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The best holiday rentals in Chicago

Check out our pick of great holiday rentals in Chicago

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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.

E
Ellen Requena
From
United States
Close to the subway, well-equipped kitchen, beautiful and safe neighborhood, free parking on the street.
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 193 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.

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, 129 reviews
Price from
US$238.21
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 9.3
Superb - What previous guests thought, 176 reviews
Price from
US$139.43
1 night, 2 adults

Historic Home with Outdoor Hot Tub Near Downtown in Public Transportation Hub

Chicago

A recently renovated holiday home situated in Chicago, Historic Home with Outdoor Hot Tub Near Downtown in Public Transportation Hub features a garden.

K
Kylie
From
United States
Loved the location/neighborhood with proximity to the downtown area but privacy while spending time at the house. The size is great, outside property very nice. Plenty of street parking for folks who drive, but easy public transportation access for folks who use that to get in/around.
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 8 reviews
Price from
US$300
1 night, 2 adults

Lincoln Park 3 BR Penthouse

Lincoln Park, Chicago

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

M
Melanos
From
France
A spacious home in a nice neighborhood, close to all amenities and the station I felt as if I was living in Chicago
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 61 reviews
Price from
US$180
1 night, 2 adults

1F Cozy Home in Little Italy near Downtown West Loop United Center

Chicago

Offering city views, 1F Cozy Home in Little Italy near Downtown West Loop United Center is an accommodation set in Chicago, 3.9 km from Union Station and 4.1 km from Depaul University.

N
Neil
From
United Kingdom
Cosy, well-appointed and presented apartment. Very close to shops, bars and restaurants on West Taylor Street. Also only 5 mins away from the Pink Line train at Polk, for safe travel into the city. Felt very safe. Highly recommended.
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 87 reviews
Price from
US$202.50
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.

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 9.5
Exceptional - What previous guests thought, 30 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 9.4
Superb - What previous guests thought, 49 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
All holiday rentals in Chicago

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

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Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 206 reviews

Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 5.6
Passable - What previous guests thought, 164 reviews

Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 331 reviews

Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 397 reviews

Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 322 reviews

Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 193 reviews

Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 330 reviews

Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 5.6
Passable - What previous guests thought, 400 reviews

Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 61 reviews

Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 2,016 reviews

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.

Set in the heart of Chicago, 1.7 km from Ohio Street Beach, Loop 1BR w Gym Pool WD nr Millennium Park CHI-226 offers air-conditioned accommodation with free WiFi and a TV.

Set in the heart of Chicago, 1.7 km from Ohio Street Beach, Loop Studio w Gym Pool nr Chicago Riverwalk CHI-240 offers air-conditioned accommodation with free WiFi and a TV.

Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 62 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...

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.

Set in the heart of Chicago, 2.4 km from Ohio Street Beach, Loop 1BR w Pool Gym nr Financial District CHI-282 offers 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 1BR w Gym Pool WD nr Financial District CHI-222 offers free WiFi, a shared lounge and air...

Holiday Rentals with swimming pools in Chicago and nearby

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 103 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 8.8
Fabulous - What previous guests thought, 2,016 reviews

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.

From US$266.01 per night

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 9.3
Superb - What previous guests thought, 3 reviews

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, 50 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.

Set right in the centre of Chicago, 700 metres from Field Museum Of Natural History, S Loop 1BR w Pool Gym nr Soldier Field CHI-350 offers air-conditioned accommodation with free WiFi and a TV.

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...

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

Located in the centre of Chicago, 300 metres from Willis Tower, Loop 1BR w Fitness center nr W Loop the L CHI-194 provides 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 8.8
Fabulous - What previous guests thought, 330 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 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.

Situated right in the heart of Chicago, 1.4 km from Oak Street Beach, River N 2BR wGym Deck Pool nr Mag Mile CHI-133 features air-conditioned accommodation with free WiFi and a TV.

Set right in the centre of Chicago, 1.7 km from Oak Street Beach, River North 1br w gym lounge roof nr Riverwalk CHI-900 offers air-conditioned accommodation with free WiFi and a TV.

Situated right in the heart of Chicago, 1.7 km from Oak Street Beach, River North 1br w gym lounge roof nr Riverwalk CHI-893 features air-conditioned accommodation with free WiFi and a TV.

Highly rated holiday rentals in Chicago and nearby

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 54 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 9.4
Superb - What previous guests thought, 19 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, 8 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, 24 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.

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 5 reviews

Right in the heart of Chicago, Luxurious Gold Coast 4BR 4-Story Villa with Parking Sleeps 12 Guests has garden views from the balcony.

Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 26 reviews

Set within 1.3 km of Union Station and 1.7 km of Willis Tower, Sage Modern Apartments Near Union Park in West Loop offers rooms with air conditioning and a private bathroom in Chicago.

Scored out of 10, guest rating 9.9
Exceptional - What previous guests thought, 17 reviews

Avenir West Loop Penthouses with Iconic City Views is situated in the West Town district in Chicago, and has a rooftop pool, a kitchen and city views.

Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 30 reviews

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.

From US$689.81 per night

FAQ about holiday rentals in Chicago

Holiday rentals that guests love in Chicago

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Avg. price/night: US$90
Scored out of 10, guest rating 6.9
Pleasant - What previous guests thought, 220 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
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 35 reviews
It's like a little courtyard villa in Montparnasse, with a wrought-iron balcony and birds singing in the garden. Great shower!
Guest review by
Mary
Solo traveller
Avg. price/night: US$248.36
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$248.36
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
gogless