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The best holiday rentals in Chicago

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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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.

Central to where wanted to visit. Large property that was very comfortable.

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9.3
Superb
120 reviews
Price from
MYR 2,456
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.

Staff kindness was much appreciated; room was clean and large; position was good and breakfast rich.

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9.5
Exceptional
280 reviews
Price from
MYR 1,130
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.

We LOVED this place! The house was adorable and cute. All the decor was so fun, Ashley was beyond friendly, the breakfast was incredible, snacks always downstairs. The neighborhood was great...we want to move in, please take us :))

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9.6
Exceptional
214 reviews
Price from
MYR 1,059
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. It is situated 1.2 km from Museum of Science and Industry - Chicago and provides full-day security. The property is non-smoking and is located 2.4 km from 63rd Street Beach.

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
MYR 553
per night

Set in Chicago, 1.9 km from Foster Beach and 2.1 km from Loyola University Chicago, Modern Vintage 2BR Walkable To Dining & Lakefront offers free WiFi and air conditioning. The property is around 9 km from Lincoln Park Zoo, 11 km from 360 Chicago and 11 km from Water Tower Chicago. The property is non-smoking and is located 6.1 km from Wrigley Field.

!000% one of the best places I've stayed .Would definitely recommend. Also great price.

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9.8
Exceptional
5 reviews
Price from
MYR 994
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
MYR 24,950
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
12 reviews
Price from
MYR 2,911
per night

Modern 2 BDRM Apartment in Chicago is situated in Chicago, 12 km from Union Station, 13 km from Willis Tower, as well as 13 km from DePaul University. Both free WiFi and parking on-site are available at the apartment free of charge. The property is non-smoking and is located 9.3 km from United Center.

Everything from beginning to end was wonderful. A nice low key spot in the middle of a quiet Chicago neighborhood. Two bedroom spacious, and full kitchen with large bathroom as well as wash room. Wonderful stay comfy beds and big screens in each room. Updated appliances and modern look and feel. Wonderful married couple host who mind their business. Will for sure be back. Book here. U won't be sorry. Close to Jazz rn club and wonderful fish fry place and 24 hour store around corner. Like 10 mins from Walmart and great shopping centers. About 30 mins from main downtown.

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9.8
Exceptional
5 reviews
Price from
MYR 796
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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9.2
Superb
12 reviews
Price from
MYR 1,265
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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9.5
Exceptional
11 reviews
Price from
MYR 2,503
per night

Most booked holiday rentals in Chicago this month

Enjoy breakfast in Chicago!

  • The Polo Inn Bridgeport U.S.A.
    9.4
    Scored 9.4
    Superb
    Rated superb
     · 68 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.

  • Wicker Park Inn
    8.8
    Scored 8.8
    Fabulous
    Rated fabulous
     · 38 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 Sono Chicago
    Breakfast options
    9.5
    Scored 9.5
    Exceptional
    Rated exceptional
     · 280 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

  • Ray's Bucktown Bed and Breakfast
    9.6
    Scored 9.6
    Exceptional
    Rated exceptional
     · 214 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.

  • 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.

  • Modern Vintage 2BR Walkable To Dining & Lakefront
    9.8
    Scored 9.8
    Exceptional
    Rated exceptional
     · 5 reviews

    Set in Chicago, 1.9 km from Foster Beach and 2.1 km from Loyola University Chicago, Modern Vintage 2BR Walkable To Dining & Lakefront offers free WiFi and air conditioning.

    Proximity to family and sites very clean perfect two bedroom apartment

  • Fully Furnished Apts at The Mag mile -Cloud9 - 747
    9.9
    Scored 9.9
    Exceptional
    Rated exceptional
     · 7 reviews

    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.

    Exactly as pictured. Beautiful, comfortable and clean

These holiday rentals in Chicago have options with FREE cancellation

  • The Blue Golden Luxury Modern 3- Bedroom Apartment in Chicago
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 52 reviews

    Set in Chicago, 8.3 km from Wrigley Field and 11 km from Loyola University Chicago, The Blue Golden Luxury Modern 3- Bedroom Apartment in Chicago offers free WiFi and air conditioning.

    Great location, went to a Cubs game. Clean and roomy.

  • Lincoln Park Aparment with Backyard!
    9.2
    Scored 9.2
    Superb
    Rated superb
     · 33 reviews

    Situated in Chicago, 2 km from Fullerton Beach and 2.1 km from North Avenue Beach, Lincoln Park Aparment with Backyard! offers free WiFi, a garden and air conditioning.

    Great place for a quick one night stay. Hosts are very responsive.

  • Sentral Michigan Avenue
    Free cancellation options available
    8.9
    Scored 8.9
    Fabulous
    Rated fabulous
     · 1,174 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 The Opal
    Free cancellation options available
    8.8
    Scored 8.8
    Fabulous
    Rated fabulous
     · 146 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

  • Sonder Jewelers Row
    Free cancellation options available
    8.1
    Scored 8.1
    Very good
    Rated very good
     · 356 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
    8.3
    Scored 8.3
    Very good
    Rated very good
     · 261 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!

  • Sonder Greektown
    Free cancellation options available
    8.2
    Scored 8.2
    Very good
    Rated very good
     · 125 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.

  • 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%

Highly rated holiday rentals in Chicago

  • The Avondale Guesthouse
    9.3
    Scored 9.3
    Superb
    Rated superb
     · 121 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

  • Casa Cerca De La Playa
    8.7
    Scored 8.7
    Fabulous
    Rated fabulous
     · 19 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.

  • ✪ Cozy 1 Bedroom close to Downtown Chicago ✪
    8.9
    Scored 8.9
    Fabulous
    Rated fabulous
     · 31 reviews

    Set in Chicago, 4.3 km from 360 Chicago and 4.3 km from Water Tower Chicago, ✪ Cozy 1 Bedroom close to Downtown Chicago ✪ offers air conditioning.

    The closeness to public transport and cute neighborhood.

  • Couture Themed 3 Bedroom in Prime Spot with Patio, Parking, Fireplace, Pets Welcome
    8.5
    Scored 8.5
    Very good
    Rated very good
     · 24 reviews

    Featuring a garden and inner courtyard views, this holiday home is well located in Chicago, close to landmarks like North Avenue Beach and Lincoln Park Zoo.

    The location is excellent. Great for a group. Garage parking. Clean.

  • Wrigleyville Friends Unit - 5bdrm
    8.7
    Scored 8.7
    Fabulous
    Rated fabulous
     · 12 reviews

    Boasting air-conditioned accommodation with a balcony, Wrigleyville Friends Unit - 5bdrm is situated in Chicago.

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

  • Roscoe Village Guesthouse
    8.7
    Scored 8.7
    Fabulous
    Rated fabulous
     · 21 reviews

    3.1 km from Wrigley Field in Chicago, Roscoe Village Guesthouse features accommodation with access to a fitness room. Both free WiFi and parking on-site are accessible at the apartment free of charge.

  • Fully Furnished Apt Near Millenium Park- 29
    9.8
    Scored 9.8
    Exceptional
    Rated exceptional
     · 12 reviews

    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.

    Great location. Easy to book. Clean and 24 hour security

  • Modern 2 BDRM Apartment in Chicago
    9.8
    Scored 9.8
    Exceptional
    Rated exceptional
     · 5 reviews

    Modern 2 BDRM Apartment in Chicago is situated in Chicago, 12 km from Union Station, 13 km from Willis Tower, as well as 13 km from DePaul University.

FAQ about holiday rentals in Chicago









Holiday rentals that guests love in Chicago

  • Avg. price/night: MYR 1,052.76
    6.9
    Scored 6.9
    Pleasant
    Rated pleasant
     · 233 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😊
    LIW-LIWA
    Young couple
  • 9.8
    Scored 9.8
    Exceptional
    Rated exceptional
     · 33 reviews
    It's like a little courtyard villa in Montparnasse, with a wrought-iron balcony and birds singing in the garden. Great shower!
    Mary
    Solo traveller
  • Avg. price/night: MYR 1,505.79
    8.6
    Scored 8.6
    Fabulous
    Rated fabulous
     · 912 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: MYR 1,620.65
    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: MYR 1,440.68
    8.3
    Scored 8.3
    Very good
    Rated very good
     · 102 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: MYR 1,620.65
    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: MYR 1,505.79
    8.6
    Scored 8.6
    Fabulous
    Rated fabulous
     · 912 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: MYR 1,800.87
    8.7
    Scored 8.7
    Fabulous
    Rated fabulous
     · 347 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

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