Skip to main content

The best vacation homes in Chicago

Check out our selection of great vacation homes in Chicago

Filter by:


Review Score

Wonderful: 9+ Very Good: 8+ Good: 7+ Pleasant: 6+
Our top picks Lowest Price First Star rating and price Top reviewed

See the latest prices and deals by choosing your dates.

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.

Show more Show less
9.3
Wonderful
121 reviews
Price from
£187
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.

Show more Show less
9.6
Exceptional
8 reviews
Price from
£109
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.

Show more Show less
9.4
Wonderful
7 reviews
Price from
£229
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.

The property was super clean and had a very good vibe altogether.

Show more Show less
9.8
Exceptional
22 reviews
Price from
£228
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.

Show more Show less
9.7
Exceptional
7 reviews
Price from
£254
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.

Show more Show less
8.3
Very Good
6 reviews
Price from
£156
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.

Show more Show less
8
Very Good
5 reviews
Price from
£86
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.

Show more Show less
8
Very Good
6 reviews
Price from
£117
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!

Show more Show less
8.9
Excellent
8 reviews
Price from
£149
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.

Show more Show less
8.7
Excellent
17 reviews
Price from
£281
per night

Looking for a vacation home?

Great for families or large parties, vacation homes are privately owned accommodations, available for long or short-term rental. These homes are furnished and equipped with kitchen facilities, though breakfast might be offered as an add-on. These properties have their own independent front door, which makes them different than apartments.
Search vacation homes in Chicago

Most booked vacation homes in Chicago this month

Enjoy breakfast in Chicago!

  • 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

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

    Stunning Condo #2 - Downtown River North offers accommodations in Chicago, 1.5 miles from Ohio Street Beach and 1.8 miles from North Avenue Beach.

    The location, the amount of bathrooms and bedrooms

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

    Spacious Row Home next Transit near Downtown w Parking offers accommodations in Chicago, 2 miles from United Center and 4 miles from Union Station.

    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 vacation home in Chicago where guests can make the most of the 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

    Offering a garden, Spacious 5-BR House near Transit w Parking offers accommodations in Chicago. 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

    Breathtaking Downtown Penthouse A - Sleeps 11 is located in Chicago, just 1.5 miles from Ohio Street Beach and 1.8 miles from North Avenue Beach.

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

    Suite 2 on Southport 4 Queen Beds is located in Chicago, just 1.8 miles from Wrigley Field and 3.4 miles from 360 Chicago. The air-conditioned accommodation is 1.7 miles from Lincoln Park Zoo.

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

    Central Chicago Suite2 Access to Patio offers accommodations in Chicago, 1.8 miles from Water Tower Chicago and 1.8 miles from United Center.

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

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

    Romantic 3 Bed Home In The Heart Of The Park is located in Chicago, just 2.3 miles from Museum of Science and Industry - Chicago and 3.8 miles from Guaranteed Rate Field.

  • 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 sustainable 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!

    Chicago Vacation Rental, 19 Mi to Downtown Area! is located in Chicago, just 14 miles from Guaranteed Rate Field and 17 miles from Field Museum of Natural History.

  • Chicago Big House
    Budget options available

    Chicago Big House is located in Chicago, just 7.1 miles from Wrigley Field and 8.8 miles from Lincoln Park Zoo. Both free Wifi and parking on-site are accessible at the vacation home free of charge.

  • Luxe SFH in the Heart of Old Town

    Luxe SFH in the Heart of Old Town offers accommodations in Chicago, 1.6 miles from 360 Chicago and 1.7 miles from Water Tower Chicago.

  • The Orleans - Floor 2 Private roof deck Patio

    The Orleans - Floor 2 Private roof deck Patio is located in Chicago, just 1.5 miles from Ohio Street Beach and 1.8 miles from North Avenue Beach.

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

    Brownstone in Gold Coast - Downtown is located in Chicago, just a 11-minute walk from Chicago Museum of Contemporary Art and 0.9 miles from Shops at Northbridge.

  • 2 Newly Built Luxury Condos with Private Roofdeck

    2 Newly Built Luxury Condos with Private Roofdeck is located in Chicago, just 1.5 miles from Ohio Street Beach and 1.8 miles from North Avenue Beach.

Great access to the city center! Check these vacation homes in Chicago

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

    Luxury Downtown Penthouse with Private Rooftop offers accommodations in Chicago, 1.5 miles from Ohio Street Beach and 1.7 miles from North Avenue Beach.

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

    Brownstone in Gold Coast - Downtown offers accommodations in Chicago, a 11-minute walk from Chicago Museum of Contemporary Art and 0.9 miles from Shops at Northbridge.

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

    Just 1.1 miles from North Avenue Beach and a 12-minute walk from 360 Chicago, Gold coast villa with free parking garage sleeps 10 features accommodations in Chicago with a garden.

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

    Beautiful Remodeled Penthouse Unit in Old Town offers accommodations in Chicago, 1.4 miles from 360 Chicago and 1.4 miles from Water Tower Chicago.

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

    Stunning 2 Floor Penthouse Downtown is located in Chicago, just 1.9 miles from Water Tower Chicago and 1.9 miles from United Center.

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

    Immaculate Brand New Penthouse Chicago is located in Chicago, just 1.8 miles from Union Station and 2.2 miles from CIBC Theatre.

  • 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 Chicago, just 2.6 miles from Chicago Museum of Contemporary Art and 2.8 miles from 360 Chicago.

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

    The Village Inn by Dakota Gal Digs is located in Chicago, just 1.8 miles from Fullerton Beach and 1.8 miles from North Avenue Beach.

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

    Luxe Urban Retreat Near United Center offers accommodations in Chicago, 3.1 miles from Union Station and 3.7 miles from Millennium Station.

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

    Lincoln Park Living - 3 Queen Beds - Sleeps 6 is located in Chicago, just 1.5 miles from Fullerton Beach and 1.9 miles from North Avenue Beach.

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

    River North Hideaway with Amazing Views and Parking offers accommodations in Chicago, 1.6 miles from North Avenue Beach and a 11-minute walk from 360 Chicago.

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

    Just 1.1 miles from North Avenue Beach and a 12-minute walk from 360 Chicago, Luxurious classic Gold coast villa for 12 guests features accommodations in Chicago with a garden.

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

    A 19-minute walk from Oak Street Beach in Chicago, 4 bedroom in Best Location Parking Fireplace Back Yard Home office Pets Welcome provides accommodations with access to spa facilities and fitness...

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

    Immaculate Brand New Condo Downtown offers accommodations in Chicago, 1.8 miles from Union Station and 2.2 miles from CIBC Theatre.

  • Breathtaking Downtown Penthouse B - Sleeps 11
    9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 1 review

    Breathtaking Downtown Penthouse B - Sleeps 11 is located in Chicago, just 1.5 miles from Ohio Street Beach and 1.8 miles from North Avenue Beach.

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

    Beautiful 5br home for 14 guests with free parking offers accommodations in Chicago, 1.3 miles from Oak Street Beach and 1.7 miles from North Avenue Beach.

  • Upscale Penthouse Private Balcony
    9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 1 review

    Upscale Penthouse Private Balcony is located in Chicago, just 1.7 miles from United Center and 2.5 miles from Water Tower Chicago.

  • Spacious Wicker Park Hideaway with Parking!
    9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 2 reviews

    Spacious Wicker Park Hideaway with Parking! offers accommodations in Chicago, 2.4 miles from United Center and 2.5 miles from Lincoln Park Zoo.

  • Lincoln Park Living - Suite 2
    9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 3 reviews

    Lincoln Park Living - Suite 2 offers accommodations in Chicago, 1.5 miles from Fullerton Beach and 1.9 miles from North Avenue Beach.

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

    Chic Green l Near Downtown & IL Medical District offers accommodations in Chicago, 3.1 miles from Union Station and 3.2 miles from Willis Tower.

  • The Black And White Suite
    8.7
    Scored 8.7
    Excellent
    Rated excellent
     · 3 reviews

    The Black And White Suite is located in Chicago, just 4.3 miles from Adler Planetarium & Astronomy Museum and 4.6 miles from Art Institute of Chicago.

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

    Historic luxury Townhouse in Downtown Chicago is located in Chicago, just a 8-minute walk from Water Tower Chicago and half a mile from Chicago Museum of Contemporary Art.

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

    Just 1.1 miles from North Avenue Beach and a 12-minute walk from 360 Chicago, Luxurious Gold Coast villa with parking for up to 12 guests features accommodations in Chicago with a garden.

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

    Stunning Duplex Condo #1 - Downtown River North is located in Chicago, just 1.5 miles from Ohio Street Beach and 1.8 miles from North Avenue Beach.

  • A terrific house for a large group.
    8.2
    Scored 8.2
    Very Good
    Rated very good
     · 4 reviews

    A terrific house for a large group. Is located in Chicago, just 7 miles from Wrigley Field and 8.8 miles from Lincoln Park Zoo.

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

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

  • Brownstone in Gold Coast
    8.0
    Scored 8.0
    Very Good
    Rated very good
     · 3 reviews

    Brownstone in Gold Coast offers accommodations in Chicago, a 9-minute walk from Water Tower Chicago and 0.6 miles from Chicago Museum of Contemporary Art.

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

    5 Bedroom House in Best Location Parking Fireplace Back Yard Home office offers accommodations in Chicago, 1.5 miles from Fullerton Beach and 1.3 miles from 360 Chicago.

FAQ about vacation homes in Chicago




Vacation Homes That Guests Love in Chicago

  • Avg. price/night: £289.71
    8.6
    Scored 8.6
    Excellent
    Rated excellent
     · 1,554 reviews
    Very clean, nice bedrooms & excellent location
    Loraine
    Solo traveler
  • Avg. price/night: £281.23
    8.5
    Scored 8.5
    Very Good
    Rated very good
     · 2,201 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: £220.27
    6.9
    Scored 6.9
    Pleasant
    Rated pleasant
     · 500 reviews
    Very clean. Nice small gym. Room utlta clean. Staff friendly.
    Hugues GM
    Young couple
  • Avg. price/night: £234.17
    7.5
    Scored 7.5
    Good
    Rated good
     · 6,701 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: £202.76
    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: £281.23
    8.5
    Scored 8.5
    Very Good
    Rated very good
     · 2,201 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: £359.57
    9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 1,776 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: £267.83
    8.2
    Scored 8.2
    Very Good
    Rated very good
     · 3,072 reviews
    The size of the accommodation it was also very clean
    David
    Young couple
  • Avg. price/night: £131.79
    8.2
    Scored 8.2
    Very Good
    Rated very good
     · 7,983 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 traveler
  • Avg. price/night: £88.48
    8.3
    Scored 8.3
    Very Good
    Rated very good
     · 4,077 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 traveler

Research, refine, and make plans for your whole trip