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Vacation Rentals in Chicago

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The best vacation rentals in Chicago

Check out our selection of great vacation rentals in Chicago

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Review score

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

Chicago

2F Chicago's Little Italy near West Loop & Downtown offers accommodations in Chicago, 1.9 miles from Union Station and 2 miles from Willis Tower.

D
Debbie
From
United Kingdom
Outstanding accommodation. Fabulously comfortable beds. Great shared area. Super bathrooms. Incredibly stocked with bedding, toiletries, kitchen equipment etc. Very clean. Great location near lovely restaurants and L stations to get you into the city. Highly recommended for a trip to Chicago. Great communication from owners.
Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 195 reviews
Price from
$180
1 night, 2 adults

The Avondale Guesthouse

Chicago

The Avondale Guesthouse is located in Chicago, just 2.8 miles from Wrigley Field and 3.6 miles from Lincoln Park Zoo.

K
Kam
From
United States
Easy access to a nice property in a good location. The hosts were amazing and easy to communicate with. Noemi was so nice and decorated the house for the holiday- it was so cool! We had a blast!
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 128 reviews
Price from
$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 3.1 miles of Lincoln Park Zoo and 3.2 miles of Wrigley Field.

Z
Zak
From
United States
Everything. The atmosphere, the staff, everything was incredible. I only wished I had stayed longer. Ashlee was very helpful and accommodating. I was upgraded to the room with a view and would highly recommend staying there.
Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 173 reviews
Price from
$169.31
1 night, 2 adults

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

Chicago

A recently renovated vacation home, Historic Home with Outdoor Hot Tub Near Downtown in Public Transportation Hub offers accommodations in Chicago.

K
Krystyna
From
Canada
Located reasonably close to downtown.Kept clean and had a homey feeling.located in the very nice old neighbourhood..Our car was parked right in front of our porch.The porch was the best.The breakfasts on the porch in the shade of the old tree. Thank you Andrea. We will come back.
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 8 reviews
Price from
$300
1 night, 2 adults

Cozy Chicago Apartment next to the River

Bridgeport, Chicago

Cozy Chicago Apartment next to the River is located in Chicago, just 3.4 miles from United Center and 3.6 miles from Field Museum of Natural History.

s
simorangel
From
Brazil
The place was incredibly clean and tidy. The host's are very particular about some things, can be restrictive if you have a problem with it - but in my opinion just makes the place really great and reliable to stay.
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 15 reviews
Price from
$144.90
1 night, 2 adults

Lincoln Park 3 BR Penthouse

Lincoln Park, Chicago

Lincoln Park 3 BR Penthouse is located in Chicago, just 1.6 miles from Fullerton Beach and 1.3 miles from Wrigley Field.

M
Maria Jose
From
Ecuador
An amazing experience. The place is beautiful and it was really easy to communicate with the host. Cleanliness was wonderful and I felt right at home. I would definitely consider coming back.
Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 67 reviews
Price from
$180
1 night, 2 adults

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

Chicago

1F Cozy Home in Little Italy near Downtown West Loop United Center is located in Chicago, just 1.1 miles from United Center and 2.4 miles from Willis Tower.

C
CHUNSIK
From
South Korea
There is not many accomodation which also has free parking area in Chicago. The location is also good and safe, so you can just walk down the road about 5 minutes then you can have access to the subway and to the loop(downtown). The room condition was also great and clean so much, each different 3 room has its own comfortable facility.
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 88 reviews
Price from
$202.50
1 night, 2 adults

Designer Themed 4 Bedroom in Best Location with Patio and Fireplace

Near North Side, Chicago

Offering a garden, Designer Themed 4 Bedroom in Best Location with Patio and Fireplace offers accommodations in Chicago.

S
Strand
From
United States
This was our first attempt at a non-hotel location. I was surprised how much we appreciated the home's amenities away from home. Amenities like; multiple bathrooms, full kitchen, private off-street parking and a pleasant neighborhood.
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 30 reviews
Price from
$419
1 night, 2 adults

4 Bedroom Home in Best Location Parking Fireplace Back Yard Pets Welcome

Near North Side, Chicago

A 19-minute walk from Oak Street Beach in Chicago, 4 Bedroom Home in Best Location Parking Fireplace Back Yard Pets Welcome provides accommodations with access to spa facilities and fitness room.

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 5 reviews
Price from
$499
1 night, 2 adults

The Polo Inn Bridgeport U.S.A.

Bridgeport, Chicago

Offering air-conditioned rooms in the Bridgeport district of Chicago, The Polo Inn Bridgeport U.S.A. Is 1.1 miles from Guaranteed Rate Field.

G
Greg
From
New Zealand
Great personal service and cooked-to-order breakfast by the wonderful proprietors; very spacious and comfortable rooms (I has a two room suite). Although the McCormick Place Convention Centre where I was attending a conference is 4 miles away, they happily dropped me to the door each morning. Amazing - thanks!
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 49 reviews
Price from
$285
1 night, 2 adults
All vacation rentals in Chicago

Top picks for Chicago hotels

Explore our most popular hotels in Chicago

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Review score

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

Chicago

2F Chicago's Little Italy near West Loop & Downtown offers accommodations in Chicago, 1.9 miles from Union Station and 2 miles from Willis Tower.

D
Debbie
From
United Kingdom
Outstanding accommodation. Fabulously comfortable beds. Great shared area. Super bathrooms. Incredibly stocked with bedding, toiletries, kitchen equipment etc. Very clean. Great location near lovely restaurants and L stations to get you into the city. Highly recommended for a trip to Chicago. Great communication from owners.
Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 195 reviews
Price from
$180
1 night, 2 adults

The Avondale Guesthouse

Chicago

The Avondale Guesthouse is located in Chicago, just 2.8 miles from Wrigley Field and 3.6 miles from Lincoln Park Zoo.

K
Kam
From
United States
Easy access to a nice property in a good location. The hosts were amazing and easy to communicate with. Noemi was so nice and decorated the house for the holiday- it was so cool! We had a blast!
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 128 reviews
Price from
$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 3.1 miles of Lincoln Park Zoo and 3.2 miles of Wrigley Field.

Z
Zak
From
United States
Everything. The atmosphere, the staff, everything was incredible. I only wished I had stayed longer. Ashlee was very helpful and accommodating. I was upgraded to the room with a view and would highly recommend staying there.
Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 173 reviews
Price from
$169.31
1 night, 2 adults

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

Chicago

A recently renovated vacation home, Historic Home with Outdoor Hot Tub Near Downtown in Public Transportation Hub offers accommodations in Chicago.

K
Krystyna
From
Canada
Located reasonably close to downtown.Kept clean and had a homey feeling.located in the very nice old neighbourhood..Our car was parked right in front of our porch.The porch was the best.The breakfasts on the porch in the shade of the old tree. Thank you Andrea. We will come back.
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 8 reviews
Price from
$300
1 night, 2 adults

Cozy Chicago Apartment next to the River

Bridgeport, Chicago

Cozy Chicago Apartment next to the River is located in Chicago, just 3.4 miles from United Center and 3.6 miles from Field Museum of Natural History.

s
simorangel
From
Brazil
The place was incredibly clean and tidy. The host's are very particular about some things, can be restrictive if you have a problem with it - but in my opinion just makes the place really great and reliable to stay.
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 15 reviews
Price from
$144.90
1 night, 2 adults

Lincoln Park 3 BR Penthouse

Lincoln Park, Chicago

Lincoln Park 3 BR Penthouse is located in Chicago, just 1.6 miles from Fullerton Beach and 1.3 miles from Wrigley Field.

M
Maria Jose
From
Ecuador
An amazing experience. The place is beautiful and it was really easy to communicate with the host. Cleanliness was wonderful and I felt right at home. I would definitely consider coming back.
Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 67 reviews
Price from
$180
1 night, 2 adults

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

Chicago

1F Cozy Home in Little Italy near Downtown West Loop United Center is located in Chicago, just 1.1 miles from United Center and 2.4 miles from Willis Tower.

C
CHUNSIK
From
South Korea
There is not many accomodation which also has free parking area in Chicago. The location is also good and safe, so you can just walk down the road about 5 minutes then you can have access to the subway and to the loop(downtown). The room condition was also great and clean so much, each different 3 room has its own comfortable facility.
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 88 reviews
Price from
$202.50
1 night, 2 adults

Designer Themed 4 Bedroom in Best Location with Patio and Fireplace

Near North Side, Chicago

Offering a garden, Designer Themed 4 Bedroom in Best Location with Patio and Fireplace offers accommodations in Chicago.

S
Strand
From
United States
This was our first attempt at a non-hotel location. I was surprised how much we appreciated the home's amenities away from home. Amenities like; multiple bathrooms, full kitchen, private off-street parking and a pleasant neighborhood.
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 30 reviews
Price from
$419
1 night, 2 adults

4 Bedroom Home in Best Location Parking Fireplace Back Yard Pets Welcome

Near North Side, Chicago

A 19-minute walk from Oak Street Beach in Chicago, 4 Bedroom Home in Best Location Parking Fireplace Back Yard Pets Welcome provides accommodations with access to spa facilities and fitness room.

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 5 reviews
Price from
$499
1 night, 2 adults

The Polo Inn Bridgeport U.S.A.

Bridgeport, Chicago

Offering air-conditioned rooms in the Bridgeport district of Chicago, The Polo Inn Bridgeport U.S.A. Is 1.1 miles from Guaranteed Rate Field.

G
Greg
From
New Zealand
Great personal service and cooked-to-order breakfast by the wonderful proprietors; very spacious and comfortable rooms (I has a two room suite). Although the McCormick Place Convention Centre where I was attending a conference is 4 miles away, they happily dropped me to the door each morning. Amazing - thanks!
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 49 reviews
Price from
$285
1 night, 2 adults
All vacation rentals in Chicago

Most booked vacation rentals in Chicago and surrounding area in the past month

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Popular with guests booking vacation rentals in Chicago

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

Popular with guests booking vacation rentals in Chicago

Scored out of 10, guest rating 8.9
Excellent - What previous guests thought, 208 reviews

Popular with guests booking vacation rentals in Chicago

Scored out of 10, guest rating 8.8
Excellent - What previous guests thought, 332 reviews

Popular with guests booking vacation rentals in Chicago

Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 195 reviews

Popular with guests booking vacation rentals in Chicago

Scored out of 10, guest rating 8.6
Excellent - What previous guests thought, 333 reviews

Popular with guests booking vacation rentals in Chicago

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

Popular with guests booking vacation rentals in Chicago

Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 321 reviews

Popular with guests booking vacation rentals in Chicago

Popular with guests booking vacation rentals in Chicago

Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 67 reviews

Popular with guests booking vacation rentals in Chicago

Scored out of 10, guest rating 8.8
Excellent - What previous guests thought, 2,017 reviews

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

Loop 1BR w Lounge Rooftop nr Art Institute CHI-103 offers accommodations in Chicago, a 1-minute walk from Chicago Symphony Orchestra and half a mile from Willis Tower.

Loop Studio w Gym Pool nr Chicago Riverwalk CHI-240 is located in Chicago, just a 9-minute walk from Chicago Symphony Orchestra and half a mile from Shops at Northbridge.

Scored out of 10, guest rating 8.5
Very Good - What previous guests thought, 64 reviews

Experience Downtown Chicago at Millennium - Luxury Apartments in The Loop features accommodations within half a mile of the center of Chicago, with free Wifi and a kitchen with a microwave, a toaster,...

Loop 1BR w WD Gym Rooftop Pool 2 blocks to L CHI-382 offers accommodations in Chicago, a 11-minute walk from Cloud Gate – The Bean and half a mile from Chicago Symphony Orchestra.

Loop 1BR w Pool Gym nr Financial District CHI-282 is located in Chicago, just a 15-minute walk from Millennium Park and 0.9 miles from DePaul University.

Loop 2BR w Pool Gym nr Financial District L CHI-247 features accommodations in the center of Chicago, 1.5 miles from Ohio Street Beach and a 11-minute walk from Willis Tower.

Loop 1BR w Pool Gym nr the L Riverwalk CHI-242 features accommodations in the center of Chicago, 1.5 miles from Ohio Street Beach and a 11-minute walk from Willis Tower.

Just a 15-minute walk from Millennium Park and 0.9 miles from DePaul University, Loop 1BR w Gym Pool WD nr Financial District CHI-222 features accommodations in Chicago with a shared lounge.

Highly rated vacation rentals in Chicago and nearby

Scored out of 10, guest rating 9.3
Wonderful - 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 8.8
Excellent - What previous guests thought, 332 reviews

Kasa South Loop Chicago enjoys a location in Chicago, a 16-minute walk from Grant Park and one mile from Art Institute of Chicago.

Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 53 reviews

Just a 2-minute walk from Water Tower Chicago and 500 yards from 360 Chicago, The Bernardin Gold Coast Luxury Apartments Near Magnificent Mile features accommodations in Chicago, with a fitness center...

Scored out of 10, guest rating 8.9
Excellent - What previous guests thought, 56 reviews

Aurelien Spacious Apartments in the Heart of Gold Coast provides accommodations within 0.7 miles of the center 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

Just a 19-minute walk from Union Station and 1.2 miles from Willis Tower, K2 Sky High Apartments with Stunning Chicago Views in West Loop features accommodations in Chicago, with a shared lounge.

Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 9 reviews

Historic luxury Townhouse in Downtown Chicago is located in Chicago, just a 16-minute walk from Shops at Northbridge and 1.4 miles from Millennium Station.

Scored out of 10, guest rating 8.9
Excellent - What previous guests thought, 25 reviews

Studio flat in the heart of Downtown Chicago offers accommodations in Chicago, a 16-minute walk from Shops at Northbridge and 1.4 miles from Millennium Station.

Scored out of 10, guest rating 8.8
Excellent - What previous guests thought, 6 reviews

Just a 13-minute walk from Water Tower Chicago and 0.6 miles from 360 Chicago, Luxurious Gold Coast 4BR 4-Story Villa with Parking Sleeps 12 Guests features accommodations in Chicago with a garden.

Enjoy breakfast in Chicago and nearby

Streeterville Studio w Gym Pool nr Navy Pier CHI-445 is located in Chicago, just a 13-minute walk from Water Tower Chicago and 0.8 miles from 360 Chicago.

Streeterville 1BR w Gym Pool nr Navy Pier CHI-412 is located in Chicago, just a 13-minute walk from Water Tower Chicago and 0.8 miles from 360 Chicago. This apartment offers an elevator and free Wifi.

Streeterville 2BR w Deck Gym nr Beach Park CHI-589 is located in Chicago, just a 13-minute walk from Water Tower Chicago and 0.8 miles from 360 Chicago.

River North 1br w gym lounge roof nr L CHI-838 offers accommodations in Chicago, a 7-minute walk from Shops at Northbridge and one mile from Millennium Station.

Just a 7-minute walk from Shops at Northbridge and one mile from Millennium Station, River N 1BR w Gym Lounge Roof 1 block to L CHI-660 features accommodations in Chicago with a shared lounge.

Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 3 reviews

Located in Chicago and with Oak Street Beach reachable within 1.5 miles, Level Chicago River North provides a seasonal outdoor swimming pool, non-smoking rooms, free WiFi throughout the property and a...

River N 2BR w Gym WD nr Magnificent Mile CHI-164 offers accommodations in Chicago, a 6-minute walk from Shops at Northbridge and one mile from Millennium Station.

River N 2BR w Gym WD nr Magnificent Mile CHI-160 offers accommodations in Chicago, a 6-minute walk from Shops at Northbridge and one mile from Millennium Station.

Vacation Rentals with swimming pools in Chicago and nearby

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

A 3-minute walk from Union Station in the center of Chicago, Jeffjack Heated Pool Penthouse in Chicago's West Loop provides accommodations with access to a hot tub, fitness room, and indoor pool.

S Loop 1BR w Pool Gym nr Soldier Field CHI-350 features accommodations in the center of Chicago, a 8-minute walk from Field Museum of Natural History and 0.7 miles from Grant Park.

S Loop 2BR w Pool Gym Spa nr Grant Park CHI-740 offers accommodations in the center of Chicago, a 8-minute walk from Field Museum of Natural History and 0.7 miles from Grant Park.

A 8-minute walk from Field Museum of Natural History in the center of Chicago, S Loop 1BR w pool gym spa nr Grant Park CHI-744 offers accommodations with access to an indoor pool.

A 8-minute walk from Field Museum of Natural History in the center of Chicago, S Loop 1BR w Pool Gym Spa nr Grant Park CHI-741 features accommodations with access to an indoor pool.

FAQ about vacation rentals in Chicago

Vacation Rentals That Guests Love in Chicago

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Avg. price/night: $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 traveler
Avg. price/night: $248.36
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 34 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: $248.36
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 34 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