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The best holiday homes in Chicago

Check out our pick of great holiday homes in Chicago

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Review score

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.

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

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9.3
Superb
122 reviews
Price from
1,756 lei
per night

The spacious holiday home has 3 bedrooms, a TV with cable channels and a fully equipped kitchen that provides guests with a dishwasher, an oven, a washing machine, a microwave and a fridge. Towels and bed linen are offered in the holiday home. For added privacy, the accommodation features a private entrance.

Fantastic property very close to the downtown area of Chicago, near the metro and the bus stop. Beautifully done up interiors, Very spacious and can easily accommodate 12-14 people . Ample amount of coffee milk and sugar at disposal. Prompt replies from the owner for everything we needed.

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9.6
Exceptional
8 reviews
Price from
1,884 lei
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
Superb
17 reviews
Price from
2,986 lei
per night

The spacious holiday home with a balcony and garden views has 4 bedrooms, 3 living rooms, a flat-screen TV, an equipped kitchen with a dishwasher and an oven, and 3 bathrooms with a bath. Towels and bed linen are available in the holiday home. The property has an outdoor dining area.

Very clean had everything we needed.

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9.4
Superb
7 reviews
Price from
2,194 lei
per night

The spacious holiday home is fitted with 4 bedrooms, 2 bathrooms, bed linen, towels, a flat-screen TV with streaming services, a dining area, a fully equipped kitchen, and a patio with garden views. A private entrance leads guests into the holiday home, where they can enjoy some fruits and chocolates or cookies. The property has an outdoor dining area.

Staying at Northside FAMILYNEST Lincoln Sq was an absolute delight! From the cleanness,modern amenities to the beautifully decorated rooms and the delicious light snacks that were available to eat. Lastly our host Mr Ivan was great he made us feel right at home. I truly enjoyed our stay!

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9.8
Exceptional
22 reviews
Price from
1,757 lei
per night

The spacious holiday home has 5 bedrooms, a flat-screen TV, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 3 bathrooms with a walk-in shower. Featuring air conditioning, this unit has a dressing room and a fireplace. The property has an outdoor dining area.

Plenty of room. Very spacious.

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9.7
Exceptional
7 reviews
Price from
2,372 lei
per night

The spacious holiday home is fitted with 3 bedrooms, a TV and a fully equipped kitchen that provides guests with a dishwasher, an oven, a washing machine, a microwave and a fridge. Towels and bed linen are offered in the holiday home.

I like the fact that it was close to bus stop and train stop. Overall nice building with roof top views. Garage parking.

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8.3
Very good
6 reviews
Price from
1,969 lei
per night

The spacious holiday home has 2 bedrooms, a TV and a fully equipped kitchen that provides guests with a dishwasher, an oven, a washing machine, a microwave and a fridge. Towels and bed linen are offered in the holiday home. The accommodation is non-smoking.

Very clean and fully equipped just for a missing iron. At the first sight from the outside you won’t expect that you’ll enter into a clean and reasonably well maintained place but as you step inside you’ll feel relaxed and satisfied.

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8
Very good
5 reviews
Price from
1,105 lei
per night

The spacious holiday home has 2 bedrooms, a TV with cable channels and a fully equipped kitchen that provides guests with a dishwasher, an oven, a washing machine, a microwave and a fridge. Towels and bed linen are offered in the holiday home. For added privacy, the accommodation features a private entrance.

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8
Very good
6 reviews
Price from
1,269 lei
per night

The spacious holiday home has 2 bedrooms, a TV and a fully equipped kitchen that provides guests with a dishwasher, an oven, a washing machine, a microwave and a fridge. Towels and bed linen are offered in the holiday home.

Very clean and cute decorations!

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8.9
Fabulous
8 reviews
Price from
1,419 lei
per night

Looking for a holiday home?

Great for families or large parties, holiday homes are privately owned accommodation, available for long or short-term rental. These homes are furnished and equipped with kitchen facilities for self-catering, although breakfast may be offered as an add-on. These properties have their own independent front door, which makes them different to apartments.
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Most booked holiday homes in Chicago this month

Enjoy breakfast in Chicago!

  • 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

  • Stunning Condo #2 - Downtown River North
    9.6
    Scored 9.6
    Exceptional
    Rated exceptional
     · 8 reviews

    Boasting air-conditioned accommodation with a patio, Stunning Condo #2 - Downtown River North is situated in Chicago.

    The location, the amount of bathrooms and bedrooms

  • Romantic 3 Bed Home In The Heart Of The Park
    8.7
    Scored 8.7
    Fabulous
    Rated fabulous
     · 17 reviews

    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...

  • Spacious Row Home next Transit near Downtown w Parking
    9.4
    Scored 9.4
    Superb
    Rated superb
     · 7 reviews

    Located in Chicago in the Illinois region, Spacious Row Home next Transit near Downtown w Parking features a patio.

    Everything was clean and comfortable for 5 adults and 11 kids

  • Northside FAMLYNEST Lincoln Sq 4BR 2BA 2P Rare find
    9.8
    Scored 9.8
    Exceptional
    Rated exceptional
     · 22 reviews

    Northside FAMLYNEST Lincoln Sq 4BR 2BA 2P Rare find is a recently renovated holiday home in Chicago, where guests can make the most of its garden and tennis court.

    The place is in a very cute neighborhood and was super clean.

  • Spacious 5-BR House near Transit w Parking
    9.7
    Scored 9.7
    Exceptional
    Rated exceptional
     · 7 reviews

    Located in Chicago in the Illinois region, Spacious 5-BR House near Transit w Parking features a balcony. This property offers access to a terrace, free private parking and free WiFi.

    I came for my son’s birthday and he loved it very spacious and great communication

  • Breathtaking Downtown Penthouse A - Sleeps 11
    8.3
    Scored 8.3
    Very good
    Rated very good
     · 6 reviews

    Boasting air-conditioned accommodation with a patio, Breathtaking Downtown Penthouse A - Sleeps 11 is set in Chicago.

  • Suite 2 on Southport 4 Queen Beds
    8.0
    Scored 8.0
    Very good
    Rated very good
     · 5 reviews

    Situated in Chicago, 2.9 km from Wrigley Field and 5.5 km from 360 Chicago, Suite 2 on Southport 4 Queen Beds offers air conditioning.

Save money on holiday homes in Chicago – budget options available!

  • Central Chicago Suite2 Access to Patio
    8.0
    Scored 8.0
    Very good
    Rated very good
     · 6 reviews

    Situated in Chicago, 2.8 km from Water Tower Chicago and 2.9 km from United Center, Central Chicago Suite2 Access to Patio features air-conditioned accommodation with a patio and free WiFi.

  • 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.

  • Chicago Vacation Rental, 19 Mi to Downtown Area!

    Situated in Chicago, 19 km from Museum of Science and Industry - Chicago and 23 km from Guaranteed Rate Field, Chicago Vacation Rental, 19 Mi to Downtown Area! offers air conditioning.

  • The Black And White Suite
    8.7
    Scored 8.7
    Fabulous
    Rated fabulous
     · 3 reviews

    The Black And White Suite is situated in the Bronzeville district of Chicago, 3.2 km from Guaranteed Rate Field, 5.4 km from Museum of Science and Industry - Chicago and 6.3 km from Field Museum of...

  • Chicago Big House
    Budget options available

    Set in Chicago in the Illinois region, Chicago Big House has a terrace and garden views. Both free WiFi and parking on-site are accessible at the holiday home free of charge.

  • Luxe SFH in the Heart of Old Town

    Set in Chicago, 1.2 km from North Avenue Beach and 2 km from Fullerton Beach, Luxe SFH in the Heart of Old Town offers air conditioning.

  • The Orleans - Floor 2 Private roof deck Patio

    Featuring air-conditioned accommodation with a patio, The Orleans - Floor 2 Private roof deck Patio is set in Chicago.

  • Brownstone in Gold Coast - Downtown
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    Situated in the centre of Chicago, 600 metres from Oak Street Beach and 1.6 km from North Avenue Beach, Brownstone in Gold Coast - Downtown offers free WiFi and air conditioning.

Great access to the city centre! Check these holiday homes in Chicago

  • Luxury Downtown Penthouse with Private Rooftop
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 2 reviews

    Boasting air-conditioned accommodation with a patio, Luxury Downtown Penthouse with Private Rooftop is set in Chicago.

  • Brownstone in Gold Coast - Downtown
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 3 reviews

    Located in the centre of Chicago, 600 metres from Oak Street Beach and 1.6 km from North Avenue Beach, Brownstone in Gold Coast - Downtown offers free WiFi and air conditioning.

  • Gold coast villa with free parking garage sleeps 10
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    In the centre of Chicago, located within a short distance of Oak Street Beach and North Avenue Beach, Gold coast villa with free parking garage sleeps 10 offers free WiFi, air conditioning and...

  • Beautiful Remodeled Penthouse Unit in Old Town
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    Located in Chicago, 1.7 km from Oak Street Beach and 1.9 km from Fullerton Beach, Beautiful Remodeled Penthouse Unit in Old Town offers air conditioning.

  • Stunning 2 Floor Penthouse Downtown
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 4 reviews

    Featuring air-conditioned accommodation with a patio, Stunning 2 Floor Penthouse Downtown is located in Chicago. Both free WiFi and parking on-site are available at the holiday home free of charge.

  • Immaculate Brand New Penthouse Chicago
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    Situated in Chicago, 600 metres from United Center and 2.8 km from Union Station, Immaculate Brand New Penthouse Chicago offers air conditioning.

  • Luxe Penthouse with Home Theater and Amazing City
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    Luxe Penthouse with Home Theater and Amazing City is located in the West Town district of Chicago, 4 km from Water Tower Chicago, 4.2 km from Union Station and 4.3 km from Chicago Museum of...

  • The Village Inn by Dakota Gal Digs
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 2 reviews

    Featuring air-conditioned accommodation with a patio, The Village Inn by Dakota Gal Digs is set in Chicago. Both free WiFi and parking on-site are available at the holiday home free of charge.

  • Luxe Urban Retreat Near United Center
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 2 reviews

    Located in Chicago, 5 km from Union Station and 6 km from Millennium Station, Luxe Urban Retreat Near United Center offers air conditioning.

  • Lincoln Park Living - 3 Queen Beds - Sleeps 6
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    Set in Chicago, 2.5 km from Fullerton Beach and 3 km from North Avenue Beach, Lincoln Park Living - 3 Queen Beds - Sleeps 6 offers air-conditioned accommodation with a patio and free WiFi.

  • River North Hideaway with Amazing Views and Parking
    9.7
    Scored 9.7
    Exceptional
    Rated exceptional
     · 3 reviews

    In a central area of Chicago, located within a short distance of Oak Street Beach and Ohio Street Beach, River North Hideaway with Amazing Views and Parking offers free WiFi, air conditioning and...

  • Luxurious classic Gold coast villa for 12 guests
    9.5
    Scored 9.5
    Exceptional
    Rated exceptional
     · 2 reviews

    In the heart of Chicago, set within a short distance of Oak Street Beach and North Avenue Beach, Luxurious classic Gold coast villa for 12 guests offers free WiFi, air conditioning and household...

  • 4 bedroom in Best Location Parking Fireplace Back Yard Home office Pets Welcome
    9.5
    Scored 9.5
    Exceptional
    Rated exceptional
     · 4 reviews

    Boasting a patio with city views, a garden and barbecue facilities, 4 bedroom in Best Location Parking Fireplace Back Yard Home office Pets Welcome can be found in Chicago, close to Oak Street Beach...

  • Immaculate Brand New Condo Downtown
    9.5
    Scored 9.5
    Exceptional
    Rated exceptional
     · 2 reviews

    Set in Chicago, 600 metres from United Center and 2.8 km from Union Station, Immaculate Brand New Condo Downtown offers air conditioning.

  • Breathtaking Downtown Penthouse B - Sleeps 11
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 1 review

    Featuring air-conditioned accommodation with a patio, Breathtaking Downtown Penthouse B - Sleeps 11 is set in Chicago.

  • Beautiful 5br home for 14 guests with free parking
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 2 reviews

    Featuring city views, Beautiful 5br home for 14 guests with free parking offers accommodation with a patio, around 2 km from Oak Street Beach.

  • Upscale Penthouse Private Balcony
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 1 review

    Boasting a spa bath, Upscale Penthouse Private Balcony is set in Chicago. Among the facilities at this property are a concierge service and an ATM, along with free WiFi throughout the property.

  • Spacious Wicker Park Hideaway with Parking!
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 2 reviews

    Offering city views, Spacious Wicker Park Hideaway with Parking! is an accommodation situated in Chicago, 4 km from Lincoln Park Zoo and 4.6 km from Water Tower Chicago.

  • Lincoln Park Living - Suite 2
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 3 reviews

    Located in Chicago, 2.5 km from Fullerton Beach and 3 km from North Avenue Beach, Lincoln Park Living - Suite 2 provides air-conditioned accommodation with a patio and free WiFi.

  • Chic Green l Near Downtown & IL Medical District
    8.9
    Scored 8.9
    Fabulous
    Rated fabulous
     · 8 reviews

    Set in Chicago, 1.8 km from United Center and 5 km from Union Station, Chic Green l Near Downtown & IL Medical District offers air conditioning.

  • Historic luxury Townhouse in Downtown Chicago
    8.5
    Scored 8.5
    Very good
    Rated very good
     · 4 reviews

    Right in the centre of Chicago, situated within a short distance of Oak Street Beach and Ohio Street Beach, Historic luxury Townhouse in Downtown Chicago offers free WiFi, air conditioning and...

  • Luxurious Gold Coast villa with parking for up to 12 guests
    8.5
    Scored 8.5
    Very good
    Rated very good
     · 2 reviews

    Right in the heart of Chicago, Luxurious Gold Coast villa with parking for up to 12 guests has garden views from the balcony. This property offers access to a terrace and free private parking.

  • Stunning Duplex Condo #1 - Downtown River North
    8.3
    Scored 8.3
    Very good
    Rated very good
     · 3 reviews

    Boasting air-conditioned accommodation with a patio, Stunning Duplex Condo #1 - Downtown River North is situated in Chicago.

  • Tranquil Urban Retreat
    8.0
    Scored 8.0
    Very good
    Rated very good
     · 2 reviews

    A recently renovated holiday home in Chicago, Tranquil Urban Retreat offers outdoor fireplace, parking on-site and sports facilities.

  • 5 Bedroom House in Best Location Parking Fireplace Back Yard Home office
    7.5
    Scored 7.5
    Good
    Rated good
     · 2 reviews

    Featuring a patio with city views, a garden and barbecue facilities, 5 Bedroom House in Best Location Parking Fireplace Back Yard Home office can be found in Chicago, close to North Avenue Beach and...

  • Brownstone in Gold Coast
    7.0
    Scored 7.0
    Good
    Rated good
     · 2 reviews

    Located in the centre of Chicago, 600 metres from Oak Street Beach and 1.6 km from North Avenue Beach, Brownstone in Gold Coast offers free WiFi and air conditioning.

  • Suite 1 on Southport 4 Queen Beds
    6.7
    Scored 6.7
    Pleasant
    Rated pleasant
     · 3 reviews

    Located in Chicago, 2.9 km from Wrigley Field and 5.5 km from 360 Chicago, Suite 1 on Southport 4 Queen Beds offers air conditioning.

  • Lincoln Park Living - Suite 1
    1.0
    Scored 1.0
    Very poor
    Rated very poor
     · 1 review

    Set in Chicago, 2.5 km from Fullerton Beach and 2.7 km from North Avenue Beach, Lincoln Park Living - Suite 1 offers air-conditioned accommodation with a patio and free WiFi.

FAQ about holiday homes in Chicago





Holiday homes that guests love in Chicago

  • Avg. price/night: 1,669.18 lei
    8.6
    Scored 8.6
    Fabulous
    Rated fabulous
     · 1,560 reviews
    Very clean, nice bedrooms & excellent location
    Loraine
    Solo traveller
  • Avg. price/night: 1,645.17 lei
    8.5
    Scored 8.5
    Very good
    Rated very good
     · 2,203 reviews
    Very clean comfortable room,excellent rain forest shower and toiletries. Hotel is in very convenient location easy access for Magnificent Mile and shoreline,felt safe and was very clean not too busy.
    WENDY
    Young couple
  • Avg. price/night: 1,288.54 lei
    6.9
    Scored 6.9
    Pleasant
    Rated pleasant
     · 498 reviews
    Very clean. Nice small gym. Room utlta clean. Staff friendly.
    Hugues GM
    Young couple
  • Avg. price/night: 1,369.88 lei
    7.5
    Scored 7.5
    Good
    Rated good
     · 6,681 reviews
    Very good hotel with perfect location in the hearth of Chicago. Very clean and comfortable. Very good equipped fitness room.
    Lukasz
    Family with young children
  • Avg. price/night: 1,114.93 lei
    8.5
    Scored 8.5
    Very good
    Rated very good
     · 1,850 reviews
    Great location! It's next to a lot of nice restaurants and bars and also attractions. Good value of the price considering its location. Very clean.
    楊千漾
    Group
  • Avg. price/night: 1,645.17 lei
    8.5
    Scored 8.5
    Very good
    Rated very good
     · 2,203 reviews
    beautiful suite, very clean, very comfortable. Great view of the city. roof terrace was good for a pre-night out drink staff friendly located right in the heart of the city within 2 minutes of good restaurants and pubs. 15 minute walk to a beautiful sandy beach and shopping malls
    Mick
    Family with young children
  • Avg. price/night: 2,103.44 lei
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 1,774 reviews
    Alex on the front desk has been very helpful to us for the late checkout. Will stay there again just because of this. Not everyone's priority but Gym is also very good, clean and easy to use with enough equipment. Rooms are also very clean.
    Yağız
    Young couple
  • Avg. price/night: 1,630.46 lei
    8.2
    Scored 8.2
    Very good
    Rated very good
     · 3,070 reviews
    The size of the accommodation it was also very clean
    David
    Young couple
  • Avg. price/night: 749.40 lei
    8.2
    Scored 8.2
    Very good
    Rated very good
     · 7,963 reviews
    The room is very clean. The staff is professional and it seems everyone is trying their best every day. The location is premium and super easy to access from the airport. The breakfast is among the worst I've had in any hostel, but the staff were busy making sure it was the best, so I give them that.
    Hugo Eder
    Solo traveller
  • Avg. price/night: 517.57 lei
    8.3
    Scored 8.3
    Very good
    Rated very good
     · 4,066 reviews
    The bathrooms and kitchen are very clean, and there is a patio where you can enjoy the weather if it is mild. Despite being far from all tourist attractions, there is a subway station a 12-minute walk away, and a bus stop one block away.
    Lisandra
    Solo traveller

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