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The 10 Best Holiday Rentals in Chicago, USA

Check out our pick of great holiday rentals in Chicago

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Superb: 9+ Very good: 8+ Good: 7+ Pleasant: 6+
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Sonder The Opal features accommodation within 700 metres of the centre of Chicago, with free WiFi, and a kitchen with a dishwasher, an oven and a microwave. The air-conditioned accommodation is 1.6 km from Oak Street Beach. North Avenue Beach is 2.8 km from the aparthotel and Shops at Northbridge is 700 metres away.

it’s a huge place, very well located, nice neighborhood. it’s near to greatest market places. it’s clean, with all equipment you need to stay comfortable. Linens are good quality. kitchens equipment are in great condition.

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9
Superb
121 reviews
Price from
£217
per night

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.

Everything was clean , working, and each detail to make your stay more cozy was provided

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9.3
Superb
121 reviews
Price from
£417
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.

Everything is high quality. Bedding is great. Place is very quiet. Breakfast is great and perfect to start a day.

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9.4
Superb
271 reviews
Price from
£164
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.

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.

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9.6
Exceptional
207 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
£86
per night

Situated in Chicago, 1.5 km from Oakwood Beach and 4.3 km from Museum of Science and Industry - Chicago, The Penthouse, Lux stay near Downtown, UofC & Lake features air-conditioned accommodation with a balcony and free WiFi. Guests can benefit from a patio and a sun terrace. The property is non-smoking and is located 4.8 km from Guaranteed Rate Field.

Great location, just what I was looking for.

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9.7
Exceptional
9 reviews
Price from
£190
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
£3,595
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
£461
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
Superb
11 reviews
Price from
£163
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 house was so beautifully decorated, enough space for all guests! It felt like we were in a movie.

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9.8
Exceptional
10 reviews
Price from
£425
per night

Most booked holiday rentals in Chicago this month

Enjoy breakfast in Chicago!

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

    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.

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

  • The Polo Inn Bridgeport U.S.A.
    9.4
    Scored 9.4
    Superb
    Rated superb
     · 65 reviews

    Just 6 miles south of the Chicago city centre, 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
    Superb
    Rated superb
     · 62 reviews

    Located 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.

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

  • House 5863- Chicago's Premier Bed and Breakfast
    8.9
    Scored 8.9
    Fabulous
    Rated fabulous
     · 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 5 km from Wrigley Field.

    Great spread, many options, lovely outdoor seating.

  • Wicker Park Inn
    8.8
    Scored 8.8
    Fabulous
    Rated fabulous
     · 35 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
    Superb
    Rated superb
     · 122 reviews

    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.

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

  • The Sono Chicago
    Breakfast options
    9.4
    Scored 9.4
    Superb
    Rated superb
     · 272 reviews

    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 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

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

These holiday rentals in Chicago have options with FREE cancellation

  • Sonder The Opal
    Free cancellation options available
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 121 reviews

    Sonder The Opal features accommodation within 700 metres of the centre of Chicago, with free WiFi, and a kitchen with a dishwasher, an oven and a microwave.

    The location was great and the apartment was clean

  • Sentral Michigan Avenue
    Free cancellation options available
    8.9
    Scored 8.9
    Fabulous
    Rated fabulous
     · 1,098 reviews

    Sentral Michigan Avenue offers accommodation within 1.8 km of the centre 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
     · 329 reviews

    Sonder Jewelers Row features accommodation within 700 metres of the centre 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
    8.4
    Scored 8.4
    Very good
    Rated very good
     · 253 reviews

    In the Lakeview district of Chicago, close to Wrigley Field, The Double Play, Wrigley Flats - Cubs! - Located Right next to Wrigley and Transit has free WiFi and a washing machine.

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

  • 5430 Happy Home
    Free cancellation options available
    8.5
    Scored 8.5
    Very good
    Rated very good
     · 257 reviews

    Featuring a garden, 5430 Happy Home is set in Chicago, within 4.4 km of Museum of Science and Industry - Chicago and 5 km of Guaranteed Rate Field. All common areas and bathrooms are shared.

    Facilities, location, staff's response, wonderful word

  • Sonder Greektown
    Free cancellation options available
    8.2
    Scored 8.2
    Very good
    Rated very good
     · 123 reviews

    In the West Loop district of Chicago, close to Union Station, Sonder Greektown has free WiFi and a washing machine.

    Space including storage. Quiet apart from a/c unit.

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

    Sonder The Burnham offers accommodation within 1.6 km of the centre 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
     · 89 reviews

    Located within 1.2 km of United Center and 2.8 km of Union Station, Sonder Market Hall provides rooms with air conditioning and a private bathroom in Chicago.

    Easy entrance, great location, clean and beautiful.

Highly rated holiday rentals in Chicago

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

    Set in Chicago, 6.9 km from Museum of Science and Industry - Chicago and 14 km from Guaranteed Rate Field, Casa Cerca De La Playa offers a garden and air conditioning.

    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

    Situated in Chicago, 10 km from United Center and 11 km from Lincoln Park Zoo, Contemporary 1BR Apartment with Wi-Fi! - Lockwood 1 & 2 offers air conditioning.

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

    Set 5.5 km from Lincoln Park Zoo, 6.7 km from Loyola University Chicago and 8.9 km from United Center, Charming 1BR Apt in North Center Near Shops- Larchmont 3 provides accommodation situated in...

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

  • Cozy 1 bedroom, 1 min from Irving Park Blue line, free parking
    8.7
    Scored 8.7
    Fabulous
    Rated fabulous
     · 40 reviews

    Located in Chicago, 7 km from Wrigley Field and 10 km from Lincoln Park Zoo, Cozy 1 bedroom, 1 min from Irving Park Blue line, free parking provides air-conditioned accommodation with a balcony and...

    Very comfortable and very clean place, I recommend it 100%

  • Lakeview 1BR Apt, Near Shops, Easy Transportation - Oakdale 204
    8.1
    Scored 8.1
    Very good
    Rated very good
     · 19 reviews

    Lakeview 1BR Apt, Near Shops, Easy Transportation - Oakdale 204 is situated in the Lakeview district of Chicago, 2.1 km from North Avenue Beach, 2.1 km from Wrigley Field and 2.4 km from Lincoln Park...

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

    Situated in Chicago, 5.1 km from Water Tower Chicago and 5.4 km from Union Station, 3BR Apartment Cozy Modern Living - Division 201W offers air conditioning.

    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

    Located in Chicago, 3.7 km from Lincoln Park Zoo and 7 km from 360 Chicago, Relaxing 1BR Apt in Lakeview near Best Restaurants - Belmont H6 offers air conditioning.

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

  • Penthouse of Joy with over 4000 games!
    8.3
    Scored 8.3
    Very good
    Rated very good
     · 7 reviews

    Penthouse of Joy with over 4000 games! is located in the South Loop district of Chicago, 2.6 km from DePaul University, 2.9 km from Art Institute of Chicago and 2.9 km from Chicago Symphony Orchestra.

FAQ about holiday rentals in Chicago








Holiday rentals that guests love in Chicago

  • Avg. price/night: £308.52
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 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 traveller
  • Avg. price/night: £209.33
    8.4
    Scored 8.4
    Very good
    Rated very good
     · 89 reviews
    Looks like a vacation house
    L
    Linh
    Young couple
  • 9.3
    Scored 9.3
    Superb
    Rated superb
     · 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
    People with friends
  • Avg. price/night: £308.52
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 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: £220.34
    8.6
    Scored 8.6
    Fabulous
    Rated fabulous
     · 905 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
  • 8.7
    Scored 8.7
    Fabulous
    Rated fabulous
     · 365 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
  • 7.2
    Scored 7.2
    Good
    Rated good
     · 892 reviews
    Location, close to the Loop and in the middle of the Hellenic village
    Josue
    Solo traveller
  • 9.8
    Scored 9.8
    Exceptional
    Rated exceptional
     · 30 reviews
    Magnolia Studios exceeded my expectations. The location was superb, and was perfect for a few days in town. Parking was never a problem. The studio itself was clean, comfortable, and quiet. Kitchen was adequately stocked with everything you may need for cooking a simple meal, and making a fresh cup of coffee with the Kuerig. As long as you read all instructions it's very simple to find the entrance. As an owner of my own vacation rental I would highly recommend Magnolia Studios.
    Amy
    Family with young children
  • Avg. price/night: £305.82
    8.0
    Scored 8.0
    Very good
    Rated very good
     · 26 reviews
    Location is great. Our daughter lives in Ukrainian Village very convenient. The property is large enough, new and clean. Beds are very comfy!
    Michael
    Solo traveller

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