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Vacation Rentals in Chicago

Find the vacation rentals that appeal to you the most

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Vacation Rentals for every style

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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.

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
₪ 579.98
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.

M
Marcus
From
Canada
Like going back to the university hostel of long forgotten days. People could be staying there for a night, but it looks like they stayed there longer. The kitchen is always open, so it is a big plus for hungry and thirsty travelers. Anyone can just grab something there and make yourself at home like you did in your own kitchen, excellent. The location is a real plus and sunset walk nearby give you a good feel of American lives seeing couples young and old taking their dogs for a walk. Somewhat, the building around reminds me of Boston or Montreal.
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 172 reviews
Price from
₪ 545.53
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
₪ 966.63
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.

T
Todd
From
Canada
3 bedroom and all the amemities.
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 88 reviews
Price from
₪ 652.48
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
₪ 1,350.06
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
₪ 1,607.83
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 9.4
Wonderful - What previous guests thought, 49 reviews
Price from
₪ 918.30
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, 33 reviews
Price from
₪ 663.27
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.

R
Reham
From
Saudi Arabia
The staff were very nice especially Femi, he was nice & cooperative and he deserves 5 stars!
Scored out of 10, guest rating 8.8
Excellent - What previous guests thought, 2,016 reviews
Price from
₪ 544.53
1 night, 2 adults

Prime Location! - Modern 2BR Apts Right Next to Wrigley Field & Transit!

Lakeview, Chicago

Prime Location! - Modern 2BR Apts Right Next to Wrigley Field & Transit! offers accommodations in Chicago, a 3-minute walk from Wrigley Field and 2.4 miles from Lincoln Park Zoo.

L
Luisa
From
United States
The location on the corner of the block was even more convenient for us. It was literally just steps away from the train station where you can easily take the red line to downtown! Even though we were close to the train station I didn’t find any noise to be absurd or overly loud. It was 5 of us and we all slept well and cozy! Wrigley field is just about two blocks up the road along with tons of restaurants, bars, and stores all around. Super safe area and police station is right up the road. Unit #2 was great for our family. Super clean, open, comfortable beds, couch, and it had the comforts of a Keurig with Keurig cups. One thing I most appreciated is that this host is the most responsive and accommodating host I’ve ever dealt with, and I’ve used air bnb a lot! Quick to respond and answer all questions. I would absolutely stay here again and recommend it to our friends visiting Chicago!
Scored out of 10, guest rating 8.6
Excellent - What previous guests thought, 333 reviews
Price from
₪ 540.35
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 9.4
Wonderful - What previous guests thought, 172 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 8.9
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, 331 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, 391 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 8.9
Excellent - What previous guests thought, 63 reviews

Popular with guests booking vacation rentals in Chicago

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

Highly rated vacation rentals in Chicago and nearby

Scored out of 10, guest rating 8.6
Excellent - What previous guests thought, 161 reviews

Perfect place to enjoy the city or just relax offers accommodations in Chicago, 2.7 miles from United Center and 4.4 miles from Union Station.

Scored out of 10, guest rating 8.7
Excellent - What previous guests thought, 109 reviews

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.

Scored out of 10, guest rating 8.7
Excellent - What previous guests thought, 31 reviews

Hyde Park Modern Private Room - Near Univ of Chicago is located in Chicago, just 1.5 miles from Oakwood Beach and 2.3 miles from Museum of Science and Industry - Chicago.

From ₪ 419.49 per night
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,...

Scored out of 10, guest rating 9.3
Wonderful - 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.

Scored out of 10, guest rating 8.8
Excellent - What previous guests thought, 331 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.

Vacation Rentals with swimming pools in Chicago and nearby

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.

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.

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...

Scored out of 10, guest rating 7.6
Good - What previous guests thought, 7 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.

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.

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.

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.

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.

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.

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.

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

W Loop 1BR w Deck Pool Gym 3 blocks to L CHI-646 is located in Chicago, just 1.1 miles from Millennium Station and 1.3 miles from DePaul University.

W Loop 1BR w Deck Pool Gym 3 blocks to L CHI-645 offers accommodations in Chicago, 1.1 miles from Millennium Station and 1.3 miles from DePaul University.

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.

Gold Coast 2BR w Gym Roof nr Water Tower CHI-389 is located in Chicago, just a 13-minute walk from Shops at Northbridge and 1.2 miles from Millennium Station.

Just a 5-minute walk from Water Tower Chicago and 500 yards from 360 Chicago, Gold Coast Convertible w Lounge nr Oak St CHI-83 features accommodations in Chicago with a shared lounge.

Just a 5-minute walk from Water Tower Chicago and 500 yards from 360 Chicago, Gold Coast 1BR w Gym Pool nr Magnificent Mile CHI-221 features accommodations in Chicago with a shared lounge.

FAQ about vacation rentals in Chicago

Vacation Rentals That Guests Love in Chicago

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Avg. price/night: ₪ 405.98
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 traveler
Avg. price/night: ₪ 1,783.76
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: ₪ 1,783.76
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
gogless