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The 10 Best Vacation Rentals in Chicago, USA

Check out our selection of great vacation rentals in Chicago

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Review Score

Wonderful: 9+ Very Good: 8+ Good: 7+ Pleasant: 6+
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Located in Chicago, 4.6 km from Wrigley Field and 5.5 km from Lincoln Park Zoo, The Avondale Guesthouse provides air-conditioned accommodation with a patio and free WiFi. This recently renovated holiday home is located 7.2 km from United Center and 8.1 km from 360 Chicago. On clear days, guests can head outside to enjoy the holiday home's outdoor fireplace or simply kick back and relax.

Good suburban location with access to public transport into Downtown. Three bedrooms and excellent washing and drying facilities. Lovely veranda in the back yard to chill out in the evening.

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9.3
Wonderful
121 reviews
Price from
£191
per night

The Sono Chicago is located in The Old Town neighborhood of Chicago. Lincoln Park Zoo is only 1.2 km away. Parking is free with permit provided by The Sono Chicago.

The rooms are fitted with a flat-screen TV with premium cable channels. Each room has an en suite bathroom with a large shower.

It’s located in a residential neighborhood so it’s very peaceful and perfect to walk around during this time of the year. Everything thing is clean and very well decorated. I came with my sister for one night and wished we could have stayed longer. Highly recommended!

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9.5
Exceptional
275 reviews
Price from
£124
per night

Located near numerous restaurants and shops in the Bucktown neighbourhood of Chicago, Ray's Bucktown features a communal sauna, free WiFi, and in-room breakfast service. Live entertainment at the Congress Theatre is 800 metres away.

amazing breakfast amazing staff

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9.6
Exceptional
208 reviews
Price from
£149
per night

Set in Chicago, 1.4 km from 57th Street Beach, Studio with private bath room offers recently renovated accommodation with free WiFi and a garden. The air-conditioned accommodation is 2.4 km from 63rd Street Beach. The property is non-smoking and is located 1.2 km from Museum of Science and Industry - Chicago.

Very comfortable, quaint and cozy and clean. I felt safe in the neighborhood. The worst part is that I only stayed 2 days. I hope this property is available for my next visit.

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10
Exceptional
8 reviews
Price from
£73
per night

Fully Furnished Apts at The Mag mile -Cloud9 - 747 offers accommodation within less than 1 km of the centre of Chicago, with free WiFi, and a kitchen with a microwave, a fridge and kitchenware. Less than 1 km from Oak Street Beach and a 17-minute walk from Ohio Street Beach, the property provides a rooftop pool and a garden. Private parking can be arranged at an extra charge.

Exactly as pictured. Beautiful, comfortable and clean

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9.9
Exceptional
7 reviews
Price from
£2,823
per night

Fully Furnished Apt Near Millenium Park- 29 features accommodation within less than 1 km of the centre of Chicago, with free WiFi, and a kitchen with a dishwasher, an oven and a microwave. 2.7 km from Ohio Street Beach and 400 metres from CIBC Theatre, the property offers a seasonal outdoor swimming pool and a garden. Private parking can be arranged at an extra charge.

This property is at a great location. It is nice and roomy. The kitchen is all furnished. Both the unit and the public areas are clean and easy to access.

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9.8
Exceptional
11 reviews
Price from
£303
per night

Located in Chicago, 1.9 km from United Center and 5.1 km from Union Station, Cozy 2 brm apartment mins away from United Center offers air conditioning. Both free WiFi and parking on-site are available at the apartment free of charge. The property is non-smoking and is set 6.2 km from Millennium Station.

Everything was clean and cozy, you’ll find everything you need - washing machine and dryer, hair dryer too, host was also really nice and prompt with respond

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9.3
Wonderful
11 reviews
Price from
£92
per night

The Twin Lions: Bespoke Travel Lodge w/ Speakeasy* is a recently renovated apartment in Chicago, where guests can make the most of its garden and bar. Among the facilities at this property are a concierge service and room service, along with free WiFi throughout the property. The property is non-smoking and is set 3.4 km from Lincoln Park Zoo.

The whole place was so tastefully decorated. Everything you could need or want was there provided for you. The location was great and free parking out front made it very comfortable.

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9.8
Exceptional
10 reviews
Price from
£223
per night

Offering garden views, Chicago Charm is an accommodation set in Chicago, 11 km from Lincoln Park Zoo and 13 km from 360 Chicago. The air-conditioned accommodation is 2.6 km from Loyola University Chicago, and guests can benefit from private parking available on site and free WiFi. The property is non-smoking and is located 6.6 km from Wrigley Field.

Very clean, comfortable, and homey. Can highly recommend .Smooth transaction and seamless visit.

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9.7
Exceptional
35 reviews
Price from
£137
per night

Situated 6.2 km from Guaranteed Rate Field, 11 km from Art Institute of Chicago and 11 km from Field Museum of Natural History, Romantic 3 Bed Home In The Heart Of The Park features accommodation located in Chicago. The air-conditioned accommodation is 3.8 km from Museum of Science and Industry - Chicago, and guests can benefit from on-site private parking and complimentary WiFi. Adler Planetarium & Astronomy Museum is 11 km away and Willis Tower is 12 km from the holiday home.

The property had a lot of space and the host was a good host.

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9.1
Wonderful
16 reviews
Price from
£286
per night

Most booked vacation rentals in Chicago this month

Enjoy breakfast in Chicago!

  • Ray's Bucktown Bed and Breakfast
    9.6
    Scored 9.6
    Exceptional
    Rated exceptional
     · 209 reviews

    Located near numerous restaurants and shops in the Bucktown neighborhood of Chicago, Ray's Bucktown features a communal sauna, free WiFi, and in-room breakfast service.

    Super unique and interesting plenty to do on and off property.

  • The Polo Inn Bridgeport U.S.A.
    9.4
    Scored 9.4
    Wonderful
    Rated wonderful
     · 66 reviews

    Just 6 miles south of the Chicago city center, this Bridgeport B&B is 3 minutes’ drive from U.S. Cellular Field, home of baseball’s White Sox.

    It was cozy,charming and in such a perfect location.

  • Villa D' Citta
    9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 62 reviews

    In the heart of Lincoln Park’s shopping and dining district, this modernized Chicago B&B features a private grotto and garden with BBQ facilities. Each romantic guest room comes with free Wi-Fi.

    The feel of the home is solid, stately, yet welcoming.

  • House 5863- Chicago's Premier Bed and Breakfast
    8.9
    Scored 8.9
    Excellent
    Rated excellent
     · 19 reviews

    Modern and urban style décor is featured at this bed and breakfast in Chicago’s Andersonville neighborhood. Offering free WiFi access, Chicago’s Premier Bed and Breakfast is 3.1 mi from Wrigley Field.

    Great spread, many options, lovely outdoor seating.

  • Wicker Park Inn
    8.8
    Scored 8.8
    Excellent
    Rated excellent
     · 36 reviews

    Located near the Blue Line transportation station in Chicago's Wicker Park neighborhood, the Wicker Park Inn offers easy access to downtown's top attractions, including the Magnificent Mile and...

    Very classy restoration of a great building. Spotlessly clean

  • The Avondale Guesthouse
    9.3
    Scored 9.3
    Wonderful
    Rated wonderful
     · 122 reviews

    The Avondale Guesthouse is a recently renovated vacation home in Chicago where guests can make the most of the garden and barbecue facilities.

    i like the games,couches and smart tv with good inter

  • The Sono Chicago
    Breakfast options
    9.5
    Scored 9.5
    Exceptional
    Rated exceptional
     · 275 reviews

    The Sono Chicago is located in The Old Town neighborhood of Chicago. Lincoln Park Zoo is only 0.7 mi away. Parking is free with permit provided by The Sono Chicago.

    The flushing of toilet in next room was sometimes a bit of a bother

  • Studio with private bath room
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 8 reviews

    Just a 16-minute walk from 57th Street Beach and 0.8 miles from Museum of Science and Industry - Chicago, Studio with private bath room features accommodations in Chicago with a garden.

    The privacy, the silence. The neighborhood was very calm. It was close to the places I visited.

These vacation rentals in Chicago have options with FREE cancellation

  • Sentral Michigan Avenue
    Free cancellation options available
    8.9
    Scored 8.9
    Excellent
    Rated excellent
     · 1,120 reviews

    Sentral Michigan Avenue offers accommodations within 1.1 miles of the center of Chicago, with free Wifi and a kitchen with a dishwasher, an oven, and a microwave.

    Very nice room, great kitchen. And there was everything you needed.

  • Sonder Jewelers Row
    Free cancellation options available
    8.1
    Scored 8.1
    Very Good
    Rated very good
     · 335 reviews

    Sonder Jewelers Row features accommodations within half a mile of the center of Chicago, with free Wifi and a kitchen with a dishwasher, a microwave, and a toaster.

    Location was good, property was clean and as pictured

  • The Double Play, Wrigley Flats - Cubs! - Located Right next to Wrigley and Transit
    8.3
    Scored 8.3
    Very Good
    Rated very good
     · 256 reviews

    The Double Play, Wrigley Flats - Cubs! - Located Right next to Wrigley and Transit offers accommodations in Chicago, a 2-minute walk from Wrigley Field and 2.3 miles from Lincoln Park Zoo.

    Around the corner from Wrigley. Clean. Safe. Awesome!

  • Sonder South Wabash
    Free cancellation options available
    8.5
    Scored 8.5
    Very Good
    Rated very good
     · 500 reviews

    Sonder South Wabash offers accommodations in Chicago, 1.2 miles from Chicago Symphony Orchestra and 1.4 miles from CIBC Theatre. This condo hotel features an elevator and free Wifi.

    Location, everything works well within the apartment

  • Sonder The Burnham
    Free cancellation options available
    8.4
    Scored 8.4
    Very Good
    Rated very good
     · 69 reviews

    Sonder The Burnham offers accommodations within one mile of the center of Chicago, with free Wifi and a kitchen with a dishwasher, an oven, and a microwave.

    Good location, clean and nice fully equipped kitchen.

  • Sonder Market Hall
    Free cancellation options available
    8.4
    Scored 8.4
    Very Good
    Rated very good
     · 91 reviews

    Sonder Market Hall enjoys a location in Chicago, a 13-minute walk from United Center and 1.7 miles from Union Station.

    Easy entrance, great location, clean and beautiful.

  • Wrigleyville Friends Unit - 5bdrm
    Free cancellation options available
    8.7
    Scored 8.7
    Excellent
    Rated excellent
     · 12 reviews

    Wrigleyville Friends Unit - 5bdrm offers accommodations in Chicago, 1.7 miles from Fullerton Beach and a 9-minute walk from Wrigley Field.

    No breakfast. Location was good for us it’s an easy balk to Wrigley field.

  • Sonder The Plymouth
    Free cancellation options available
    7.9
    Scored 7.9
    Good
    Rated good
     · 242 reviews

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

    Style, location. Value for money. Super comfy beds!!!

Highly-rated vacation rentals in Chicago

  • Casa Cerca De La Playa
    8.5
    Scored 8.5
    Very Good
    Rated very good
     · 17 reviews

    Providing a garden, Casa Cerca De La Playa provides accommodations in Chicago. This beachfront property offers access to free Wifi and free private parking.

    Friendly. Told me what he expected and was a nice person.

  • Contemporary 1BR Apartment with Wi-Fi! - Lockwood 1 & 2
    8.2
    Scored 8.2
    Very Good
    Rated very good
     · 5 reviews

    Contemporary 1BR Apartment with Wi-Fi! - Lockwood 1 & 2 offers accommodations in Chicago, 6.5 miles from United Center and 6.7 miles from Lincoln Park Zoo.

  • Stylish Studio Apartment with a Modern Kitchen- Wilson 418
    8.1
    Scored 8.1
    Very Good
    Rated very good
     · 12 reviews

    Stylish Studio Apartment with a Modern Kitchen- Wilson 418 is located in Chicago, just 1.2 miles from Montrose Beach and 1.3 miles from Foster Beach.

    Right next to Wilson station. Coffee and food in walking distance.

  • Charming 1BR Apt in North Center Near Shops- Larchmont 3
    8.0
    Scored 8.0
    Very Good
    Rated very good
     · 19 reviews

    Charming 1BR Apt in North Center Near Shops- Larchmont 3 is located in Chicago, just 5.5 miles from United Center and 5.8 miles from 360 Chicago.

    Great value for money. Easy check in instructions and good proximity to public transport.

  • Charming Bowmanville 1BR Apt with Roomy Living Room - Foster 1S
    8.7
    Scored 8.7
    Excellent
    Rated excellent
     · 7 reviews

    Charming Bowmanville 1BR Apt with Roomy Living Room - Foster 1S in Chicago offers accommodations with free Wifi, 1.9 miles from Foster Beach, 2.8 miles from Loyola University Chicago, and 2.9 miles...

  • Lakeview 1BR Apt, Near Shops, Easy Transportation - Oakdale 204
    8.2
    Scored 8.2
    Very Good
    Rated very good
     · 20 reviews

    Lakeview 1BR Apt, Near Shops, Easy Transportation - Oakdale 204 offers accommodations in Chicago, 1.3 miles from North Avenue Beach and 1.3 miles from Wrigley Field.

  • 3BR Apartment Cozy Modern Living - Division 201W
    8.0
    Scored 8.0
    Very Good
    Rated very good
     · 26 reviews

    3BR Apartment Cozy Modern Living - Division 201W offers accommodations in Chicago, 3.3 miles from Union Station and 3.3 miles from Chicago Museum of Contemporary Art.

    Great service, clean, beds are comfortable 👌 I recommend it 100%

  • Relaxing 1BR Apt in Lakeview near Best Restaurants - Belmont H6
    8.1
    Scored 8.1
    Very Good
    Rated very good
     · 26 reviews

    Relaxing 1BR Apt in Lakeview near Best Restaurants - Belmont H6 offers accommodations in Chicago, 4.3 miles from 360 Chicago and 4.5 miles from Water Tower Chicago.

    It was a cozy and nice apartment. It was definitely worth it.

FAQ about vacation rentals in Chicago









Vacation Rentals That Guests Love in Chicago

  • Avg. price/night: £180.05
    8.6
    Scored 8.6
    Excellent
    Rated excellent
     · 907 reviews
    The location was excellent for our travel plans. We were there to hear music at Buddy Guy's Legends and do some sight seeing during the day. The stadium tour of Wriggley Field was a high light. The Italian Village was a nice surprise with fantastic food. My partner is gluten free and the options they had were outstanding. The restaurant is a bit pricey.
    EJAYBICK
    Young couple
  • Avg. price/night: £276.22
    9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 62 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.
    Nosal
    Young couple
  • 10
    Scored 10
    Exceptional
    Rated exceptional
     · 1 review
    One of the nicest vacation rental apartments I have stayed in. Very well appointed, kitchen had everything you could need including a full size washer and dryer. Having the back balcony was great.
    Marguerite
    Solo traveler
  • Avg. price/night: £146.66
    8.4
    Scored 8.4
    Very Good
    Rated very good
     · 91 reviews
    Looks like a vacation house
    L
    Linh
    Young couple
  • 9.3
    Scored 9.3
    Wonderful
    Rated wonderful
     · 43 reviews
    Updated, well maintained. Nearby is a cozy little Italian village with restaurants and outdoor seating that was great! Overall it was beautiful, cozy and comfortable.
    Dawn
    Travelers with friends
  • Avg. price/night: £276.22
    9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 62 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!
    Sydney
    Group
  • Avg. price/night: £180.05
    8.6
    Scored 8.6
    Excellent
    Rated excellent
     · 907 reviews
    Breakfast was convenient. Location can't be beaten. Rooms are unexpectedly roomy. The staff was extremely friendly and helpful. We enjoyed the Grillroom Chophouse (reasonable prices) across the street and the Italian Village (whimsical interior) down the block -- both recommended.
    Wilson
    Young couple
  • Avg. price/night: £219.17
    8.7
    Scored 8.7
    Excellent
    Rated excellent
     · 361 reviews
    The location was convenient to restaurants, and most importantly, to our family members in Ukrainian Village. The staff was friendly and helpful. Our room was very comfortable, very functional, and had an excellent shower.
    Joanne
    Young couple
  • Avg. price/night: £555
    8.8
    Scored 8.8
    Excellent
    Rated excellent
     · 20 reviews
    Great location for us. Our daughter and family also live in Roscoe Village
    Sue
    Young couple
  • Avg. price/night: £179.43
    6.9
    Scored 6.9
    Pleasant
    Rated pleasant
     · 228 reviews
    Loved the way the villa was decorated and gave a homely vibe.
    T
    Tikisha
    Solo traveler

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