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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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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.

E
Eduardo
From
Puerto Rico
Space, accomodations, and location
Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 181 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 9.5
Exceptional - What previous guests thought, 131 reviews
Price from
$136.12
1 night, 2 adults

Forrestville Ave Large Suite

Bronzeville, Chicago

Forrestville Ave Large Suite is located in Chicago, just 2.8 miles from Museum of Science and Industry - Chicago and 4.5 miles from Field Museum of Natural History.

S
Steven
From
United Kingdom
Wonderful size and comfort and easy to grab an Uber too and from into Chicago. Rail station is also close by. Host was amazing from the moment we arrived and we could not fault anything.
Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 106 reviews
Price from
$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 3.1 miles of Lincoln Park Zoo and 3.2 miles of Wrigley Field.

C
Carlos
From
Spain
Lots of personality. Everyone working there has a great attitude. Happy people who make you feel happy! Breakfast is amazing
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 181 reviews
Price from
$199.19
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 9.3
Wonderful - What previous guests thought, 29 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
Garcia
From
United States
Great location in Bridgeport; excellent breakfast and hospitality! A true old school bed and breakfast.
Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 47 reviews
Price from
$285
1 night, 2 adults

Villa D' Citta

Lincoln Park, Chicago

Villa D' Citta enjoys a location in Chicago, 1.4 miles from North Avenue Beach and a 18-minute walk from Lincoln Park Zoo.

M
Marcia M
From
United States
I loved the kitchen, the room, the courtyard, everything about it! Best B&B ever!
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 32 reviews
Price from
$205.85
1 night, 2 adults

Sentral Michigan Avenue

Hotel in Chicago Loop, Chicago

Sentral Michigan Avenue has a fitness center, garden, a shared lounge and restaurant in Chicago. This 3-star hotel offers a shared kitchen, a 24-hour front desk and free WiFi.

J
Juan Jose
From
Argentina
The apartment was great, with breathtaking lake, park, and city views. Ample and comfortable, also the swimming pool and indoor garden are beautiful and much enjoyable -- it's a whole floor#7 dedicated to the pool, garden, and shared dining room with barbecue facilities. The location was perfect, especially for us who love "walking the city", parks and lakeside trails. Staff was also very helpful, in particular, I shipped several small and large eBay/Amazon packages, all ok.
Scored out of 10, guest rating 8.8
Excellent - What previous guests thought, 2,052 reviews
Price from
$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 accommodations within one mile of the center of Chicago, with free Wifi and a kitchen with a dishwasher, an oven, and a microwave.

J
José Roberto
From
Mexico
The location was very clean, it was close to a subway station.
Scored out of 10, guest rating 8.1
Very Good - What previous guests thought, 368 reviews
Price from
$218.45
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 7.4
Good - What previous guests thought, 303 reviews

Popular with guests booking vacation rentals in Chicago

Scored out of 10, guest rating 8.6
Excellent - What previous guests thought, 329 reviews

Popular with guests booking vacation rentals in Chicago

Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 314 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 9.0
Wonderful - What previous guests thought, 210 reviews

Popular with guests booking vacation rentals in Chicago

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

Popular with guests booking vacation rentals in Chicago

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

Popular with guests booking vacation rentals in Chicago

Scored out of 10, guest rating 5.6
Fair - What previous guests thought, 415 reviews

Popular with guests booking vacation rentals in Chicago

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

Popular with guests booking vacation rentals in Chicago

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

Vacation Rentals with swimming pools in Chicago and nearby

Scored out of 10, guest rating 8.7
Excellent - What previous guests thought, 53 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 Pool Gym nr Financial District CHI-281 provides 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 Theatre District CHI-277 provides 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 Financial District CHI-261 offers accommodations in Chicago, a 15-minute walk from Millennium Park and 0.9 miles from DePaul University.

Just a 11-minute walk from Willis Tower and 0.6 miles from CIBC Theatre, Loop 2BR w Pool Gym nr Financial District L CHI-247 features accommodations in Chicago with a shared lounge.

Loop 1BR w Pool Gym nr the L Riverwalk CHI-242 is located in Chicago, just a 15-minute walk from Millennium Park and 0.9 miles from DePaul University.

Loop Studio w gym pool lounge 1 block from L CHI-694 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 8.2
Very Good - What previous guests thought, 507 reviews

Sonder by Marriott Bonvoy South Wabash Apartments South Loop offers accommodations in Chicago, 1.2 miles from Art Institute of Chicago and 1.2 miles from Chicago Symphony Orchestra.

From $163.53 per night
Scored out of 10, guest rating 8.7
Excellent - What previous guests thought, 45 reviews

Lincoln Park Apartment with Backyard! is located in Chicago, just 1.3 miles from Fullerton Beach and 1.1 miles from Lincoln Park Zoo.

From $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

5430 Happy Home enjoys a location in Chicago, 2.8 miles from Museum of Science and Industry - Chicago and 3 miles from Guaranteed Rate Field. This homestay offers a shared kitchen and free Wifi.

From $220.95 per night
Scored out of 10, guest rating 9.4
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 8.7
Excellent - What previous guests thought, 325 reviews

Just a 18-minute walk from Art Institute of Chicago and 0.9 miles from Chicago Symphony Orchestra, Kasa South Loop Chicago features accommodations in Chicago, with a shared lounge.

Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 42 reviews

The Bernardin Gold Coast Luxury Apartments Near Magnificent Mile is an apartment featuring rooms with free Wifi and air conditioning in the center of Chicago.

Scored out of 10, guest rating 8.8
Excellent - What previous guests thought, 52 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 9.2
Wonderful - What previous guests thought, 18 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.

Enjoy breakfast in Chicago and nearby

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.

Just a 9-minute walk from Chicago Symphony Orchestra and half a mile from Shops at Northbridge, Loop 2br w lounge gym nr Chicago Riverwalk CHI-959 features accommodations in Chicago with a shared...

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 gym doorman same block as L CHI-672 is located in Chicago, just a 7-minute walk from Chicago Symphony Orchestra and 0.4 miles from Willis Tower.

Loop 2BR w Gym Doorman same block as L CHI-674 is located in Chicago, just a 7-minute walk from Chicago Symphony Orchestra and 0.4 miles from Willis Tower.

Loop 1BR w Gym Roof Lounge same block as L CHI-670 offers accommodations in Chicago, a 15-minute walk from Grant Park and 0.7 miles from Art Institute of 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.

These vacation 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 accommodations within half a mile of the center of Chicago, with free Wifi and a kitchen with a dishwasher, a microwave, and a...

From $142.96 per night
Scored out of 10, guest rating 7.6
Good - What previous guests thought, 367 reviews

Located in Chicago, within 1.4 mi of Ohio Street Beach and 1969 feet of Chicago Board of Trade Building, The Plymouth, Sonder Apartments by Marriott Bonvoy features free WiFi.

From $163.53 per night
Scored out of 10, guest rating 7.4
Good - What previous guests thought, 303 reviews

Sonder by Marriott Bonvoy Market Hall Apartments West Loop offers accommodations in Chicago, a 13-minute walk from United Center and 1.7 miles from Union Station.

From $132.68 per night

River North jr 1br w game room nr beach L CHI-971 is located in Chicago, just a 7-minute walk from Shops at Northbridge and one mile from Millennium Station.

River N 1BR w Gym WD nr Mag Mile by Bluegound CHI-127 offers accommodations in Chicago, a 7-minute walk from Shops at Northbridge and one mile from Millennium Station.

Level Chicago River North

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

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.

FAQ about vacation rentals in Chicago

Vacation Rentals That Guests Love in Chicago

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Avg. price/night: $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: $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: $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: $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