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.

A
Aurora
From
Netherlands
Spacious, clean and comfortable stay for a group of 4 people. It was nice to have two bathrooms. The owner communicated well and made sure we had a parking pass upon request. We would love to stay here again!
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 197 reviews
Price from
US$180
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.

J
Jessika
From
Italy
Incredible staff first and foremost who made my stay welcoming from the beginning. There was community space and yet complete privacy and autonomy. There were tiny touches all around, such as a selection of curated treats up front, bottled water as you needed, and a back porch that offered beautiful mornings with coffee. Enjoyed most the good feelings of walking in and coming to my room. I want to visit Chicago again simply to bring my daughter to this location- thank you all again.
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 173 reviews
Price from
US$169.31
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

Cozy Chicago Apartment next to the River

Bridgeport, Chicago

Situated in Chicago, 5.4 km from United Center and 5.7 km from Field Museum Of Natural History, Cozy Chicago Apartment next to the River offers air conditioning.

J
Jeffrey
From
United Kingdom
The location was really good as it was only a short walk to the nearest Loop network train station. It was very quiet, so great at night, and had some lovely views of the nearby river and the city skyline in the distance. The attention to detail and little welcoming touches that the owners had put into the apartment were amazing. It felt better than a home-from-home.
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 15 reviews
Price from
US$144.90
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 9.1
Superb - What previous guests thought, 73 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.

J
Jennifer
From
South Africa
We liked the quiet neighborhood and the "local feel" of staying in an apartment. We walked to Little Italy for dinner. The train stations and bus stops were close by to get into the city easily. We were blessed with large jars of treats!
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 91 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.

O
Omar Leon
From
Mexico
I really enjoyed the whole experience. The breakfast was simply delicious. Excellent attention and service. The room is lovely and warm.
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.

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, 33 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

See all

Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 7.9
Good - What previous guests thought, 165 reviews

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 9.3
Superb - What previous guests thought, 197 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 8.8
Fabulous - What previous guests thought, 333 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 8.1
Very good - What previous guests thought, 393 reviews

Popular with guests booking holiday rentals in Chicago

Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 73 reviews

Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 2,020 reviews

Holiday Rentals with swimming pools in Chicago and nearby

Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 65 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 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...

Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 102 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.

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, 53 reviews

An apartment nestled in the centre of Chicago, The Bernardin Gold Coast Luxury Apartments Near Magnificent Mile features private parking, free WiFi, a rooftop pool and fitness centre.

Scored out of 10, guest rating 7.8
Good - What previous guests thought, 8 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.

Located in the centre of Chicago, 700 metres from Field Museum Of Natural History, S Loop Studio w Pool Gym Spa nr Grant Park CHI-739 provides air-conditioned accommodation with free WiFi and a TV.

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 Studio w Gym Pool nr Chicago Riverwalk CHI-240 offers 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.

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 the heart of Chicago, 300 metres from Willis Tower, Loop 1BR w Deck Gym WD nr W Loop the L CHI-220 offers 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 Studio w Gym Pool nr Navy Pier CHI-410 provides accommodation with...

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...

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 333 reviews

Providing city views, Kasa South Loop Chicago is located in the South Loop district of Chicago, 1.1 km from Depaul University and 1.4 km from Willis Tower.

Highly rated holiday rentals in Chicago and nearby

Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 110 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.

From US$173.50 per night
Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 31 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.

From US$122.65 per night
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 56 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 9.5
Exceptional - What previous guests thought, 21 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, 9 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 9.0
Superb - What previous guests thought, 25 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, 6 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, 29 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.

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

Situated right in the heart of Chicago, 1.8 km from Oak Street Beach, River N 1BR w Gym Pool WD nr L CHI-124 features air-conditioned accommodation with free WiFi and a TV.

Set in the centre of Chicago, 1.8 km from Oak Street Beach and 500 metres from Water Tower Chicago, River N 1BR w Gym Lounge Roof 1 block to L CHI-660 offers free WiFi, a shared lounge and air...

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.

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 in Chicago, 1.1 km from Union Station and 1.4 km from Willis Tower, W Loop 1BR w Deck Pool Gym 3 blocks to L CHI-646 offers a rooftop pool and air conditioning.

Situated in Chicago, 1.1 km from Union Station and 1.4 km from Willis Tower, W Loop 1BR w Deck Pool Gym 3 blocks to L CHI-645 offers a rooftop pool and air conditioning.

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...

FAQ about holiday rentals in Chicago

Holiday rentals that guests love in Chicago

See all
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, 36 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, 33 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, 33 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