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The best holiday homes in Chicago

Check out our pick of great holiday homes in Chicago

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The Avondale Guesthouse, hotel in Chicago

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

The location was perfect, it was also very clean and the owner was really very attentive, I would recommend it
Scored 9.3
9.3
Rated superb
Superb
141 reviews
4 bedroom in Best Location Parking Fireplace Back Yard Home office Pets Welcome, hotel in Chicago

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...

Scored 9.6
9.6
Rated exceptional
Exceptional
5 reviews
Lincoln Park Living - Suite 1, hotel in Chicago

Located in Chicago, 2.5 km from Fullerton Beach and 3 km from North Avenue Beach, Lincoln Park Living - Suite 1 provides air-conditioned accommodation with a patio and free WiFi.

Just like the pictures! Everything was very clean, we had a great time
Scored 9.3
9.3
Rated superb
Superb
16 reviews
The Black And White Suite, hotel in Chicago

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...

Scored 9.0
9.0
Rated superb
Superb
6 reviews
Stunning Condo #2 - Downtown River North, hotel in Chicago

Situated within the Near North Side district in Chicago, Stunning Condo #2 - Downtown River North has air conditioning, a patio, and city views.

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.
Scored 9.2
9.2
Rated superb
Superb
21 reviews
Stunning 2 Floor Penthouse Downtown, hotel in Chicago

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.

Scored 9.2
9.2
Rated superb
Superb
13 reviews
Beautifully Renovated House 10 mins from Downtown, hotel in Chicago

Located within the Bronzeville district in Chicago, Beautifully Renovated House 10 mins from Downtown has air conditioning, a balcony, and garden views.

It’s a huge house with four floors, six rooms, five bathrooms, two laundries and many other things. Two steps away from a metro station (green line) and 20 minutes from the main attractions of the city. Huge TV and sofas help to relax after a long day of visiting.
Scored 9.4
9.4
Rated superb
Superb
5 reviews
Spacious Luxury Retreat 8 Bed Oasis with 6 Baths, hotel in Chicago

Situated within the Bridgeport district in Chicago, Spacious Luxury Retreat 8 Bed Oasis with 6 Baths has air conditioning, a patio, and city views.

All the facilities were amazing and functional.
Scored 9.2
9.2
Rated superb
Superb
5 reviews
Spacious Row Home next Transit near Downtown w Parking, hotel in Chicago

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

Very clean had everything we needed.
Scored 9.5
9.5
Rated exceptional
Exceptional
11 reviews
Northside FAMLYNEST Lincoln Sq 4BR 2BA 2P Rare find, hotel in Chicago

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.

Exceptionally well maintained place. Ivan was an excellent host. The place was stocked up with small things that just made it feels so homely. He was always happy to service any request that you had. Overall an amazing stay. Definitely going back.
Scored 9.8
9.8
Rated exceptional
Exceptional
36 reviews
All holiday homes in Chicago
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.

Most booked holiday homes in Chicago this month

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Enjoy breakfast in Chicago!

  • The Avondale Guesthouse
    Scored 9.3
    9.3
    Rated superb
    Superb
     · 141 reviews

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

    The size of the apartment was large. Parking was free.

  • Lincoln Park Living - Suite 1
    Scored 9.3
    9.3
    Rated superb
    Superb
     · 16 reviews

    Located in Chicago, 2.5 km from Fullerton Beach and 3 km from North Avenue Beach, Lincoln Park Living - Suite 1 provides air-conditioned accommodation with a patio and free WiFi.

    Location, spacious, lots of beds, big kitchen, free street parking.

  • Stunning Condo #2 - Downtown River North
    Scored 9.2
    9.2
    Rated superb
    Superb
     · 21 reviews

    Situated within the Near North Side district in Chicago, Stunning Condo #2 - Downtown River North has air conditioning, a patio, and city views.

    The location, the amount of bathrooms and bedrooms

  • Stunning 2 Floor Penthouse Downtown
    Scored 9.2
    9.2
    Rated superb
    Superb
     · 13 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.

    It was very spacious! I enjoyed the view from the private balcony.

  • Beautifully Renovated House 10 mins from Downtown
    Scored 9.4
    9.4
    Rated superb
    Superb
     · 5 reviews

    Located within the Bronzeville district in Chicago, Beautifully Renovated House 10 mins from Downtown has air conditioning, a balcony, and garden views.

    Excellent location, beautiful, clean and spacious house with all amenities needed. Fantastic communication and friendly service, would love to stay here again.

  • Spacious Luxury Retreat 8 Bed Oasis with 6 Baths
    Scored 9.2
    9.2
    Rated superb
    Superb
     · 5 reviews

    Situated within the Bridgeport district in Chicago, Spacious Luxury Retreat 8 Bed Oasis with 6 Baths has air conditioning, a patio, and city views.

  • Spacious Row Home next Transit near Downtown w Parking
    Scored 9.5
    9.5
    Rated exceptional
    Exceptional
     · 11 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
    Scored 9.8
    9.8
    Rated exceptional
    Exceptional
     · 36 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.

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

  • Spacious 5-BR House near Transit w Parking
    Scored 9.8
    9.8
    Rated exceptional
    Exceptional
     · 11 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.

    Excellent, it was close to downtown and the airport.

  • 4 bedroom in Best Location Parking Fireplace Back Yard Home office Pets Welcome
    Scored 9.6
    9.6
    Rated exceptional
    Exceptional
     · 5 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...

  • Beautiful Remodeled Penthouse Unit in Old Town
    Scored 8.7
    8.7
    Rated fabulous
    Fabulous
     · 9 reviews

    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.

  • Lincoln Park Living - 3 Queen Beds - Sleeps 6
    Scored 8.6
    8.6
    Rated fabulous
    Fabulous
     · 10 reviews

    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.

    Everything was wonderful could have used a few more pans for cooking like a skillet.

  • Lincoln Park Living - Suite 2
    Scored 8.4
    8.4
    Rated very good
    Very good
     · 9 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.

    Arrangement was done nicely and house supplies were enough for everyone

  • Suite 2 on Southport 4 Queen Beds
    Scored 8.4
    8.4
    Rated very good
    Very good
     · 15 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.

    Lokalizacja, standard apartamentu, wyposażenie lokalu

  • A terrific house for a large group.
    Scored 8.8
    8.8
    Rated fabulous
    Fabulous
     · 6 reviews

    Set in Chicago, 11 km from Wrigley Field and 14 km from Lincoln Park Zoo, A terrific house for a large group. Offers air-conditioned accommodation with a terrace and free WiFi.

  • Chicago Home with Spacious Yard 14 Mi to Dtwn
    Scored 8.6
    8.6
    Rated fabulous
    Fabulous
     · 9 reviews

    Set in Chicago, 12 km from Museum of Science and Industry - Chicago and 16 km from Guaranteed Rate Field, Chicago Home with Spacious Yard 14 Mi to Dtwn offers air conditioning.

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

  • Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 1 review

    Set in Chicago, 6.8 km from Museum of Science and Industry - Chicago and 15 km from Guaranteed Rate Field, Cozy 4bd House Fireplace and Pond offers a garden and air conditioning.

  • Historic luxury Townhouse in Downtown Chicago
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 3 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...

  • Gold coast villa with free parking garage sleeps 10
    Scored 10.0
    10.0
    Rated exceptional
    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...

  • Modern SFH Near McCormick Place & Soldier Field
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 1 review

    Set in Chicago, 2.8 km from Union Station and 3 km from Willis Tower, Modern SFH Near McCormick Place & Soldier Field offers air-conditioned accommodation with a patio and free WiFi.

  • Old Town Pied-a-Terre with Private Terrace and Parking!
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 1 review

    Boasting air-conditioned accommodation with a patio, Old Town Pied-a-Terre with Private Terrace and Parking! is situated in Chicago. It is located 1.2 km from North Avenue Beach and features a lift.

  • Luxury Retreat with Home Theater
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 1 review

    Set within the Wicker Park district in Chicago, Luxury Retreat with Home Theater has air conditioning, a patio, and city views.

  • Chicago Mid-Century Gem By United Center
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 1 review

    Boasting air-conditioned accommodation with a patio, Chicago Mid-Century Gem By United Center is situated in Chicago.

  • The Village Inn by Dakota Gal Digs
    Scored 10.0
    10.0
    Rated exceptional
    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.

  • Hamaline Luxury & Tranquil Home
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 1 review

    Located in Chicago, 1.4 km from Guaranteed Rate Field and 6 km from Art Institute of Chicago, Hamaline Luxury & Tranquil Home provides air-conditioned accommodation with a balcony and free WiFi.

  • ENTIRE BUILDING-Walk to Lincoln Park or The Beach
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 1 review

    Situated in Chicago, 2.5 km from Fullerton Beach and 3 km from North Avenue Beach, ENTIRE BUILDING-Walk to Lincoln Park or The Beach offers air conditioning.

  • The Urban Manor by Luxuri365
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 1 review

    Set in Chicago, 1.5 km from Oakwood Beach and 4 km from Guaranteed Rate Field, The Urban Manor by Luxuri365 offers air-conditioned accommodation with a balcony and free WiFi.

  • The Logandale: HUGE Mid-Century Home, sleeps 15
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 4 reviews

    Situated in Chicago, 6.5 km from Wrigley Field and 7.4 km from Lincoln Park Zoo, The Logandale: HUGE Mid-Century Home, sleeps 15 offers air conditioning.

  • Stylish Chicago Retreat Walk to Loyola University
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 1 review

    Located in Chicago, 700 metres from Loyola University Chicago and 5.7 km from Wrigley Field, Stylish Chicago Retreat Walk to Loyola University offers air conditioning.

  • River North Hideaway with Amazing Views and Parking
    Scored 9.7
    9.7
    Rated exceptional
    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
    Scored 9.5
    9.5
    Rated exceptional
    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...

  • Chicago Treasure 4 Bed Getaway
    Scored 9.5
    9.5
    Rated exceptional
    Exceptional
     · 4 reviews

    Located in Chicago, 3 km from Water Tower Chicago and 3.3 km from Chicago Museum of Contemporary Art, Chicago Treasure 4 Bed Getaway offers air conditioning.

  • Windy City Getaway - 3BR 2BA Chicago Townhouse home
    Scored 9.5
    9.5
    Rated exceptional
    Exceptional
     · 2 reviews

    Boasting air-conditioned accommodation with a patio, Windy City Getaway - 3BR 2BA Chicago Townhouse home is situated in Chicago. This property offers access to a balcony and free private parking.

  • Chicago Home Near Navy Pier and Shedd Aquarium!
    Scored 9.5
    9.5
    Rated exceptional
    Exceptional
     · 4 reviews

    Located in Chicago, 9.3 km from Museum of Science and Industry - Chicago and 14 km from Guaranteed Rate Field, Chicago Home Near Navy Pier and Shedd Aquarium! offers air conditioning.

  • The Black And White Suite
    Scored 9.0
    9.0
    Rated superb
    Superb
     · 6 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...

    Casa muy amplia, cómoda , limpia barrio muy tranquilo

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

    Featuring a patio with inner courtyard views, a garden and barbecue facilities, Couture Themed 3 Bedroom in Prime Spot with Patio, Parking, Fireplace, Pets Welcome can be found in Chicago, close to...

    Breakfast was amazing, the 0lace is super and location is great, with free and efficient parking. Great service also

  • Luxurious Gold Coast villa with parking for up to 12 guests
    Scored 8.5
    8.5
    Rated very good
    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.

  • 5 Mi to Millennium Park Apartment with Fireplaces
    Scored 8.5
    8.5
    Rated very good
    Very good
     · 2 reviews

    Located in Chicago, 3.8 km from United Center and 7.6 km from Union Station, 5 Mi to Millennium Park Apartment with Fireplaces provides air-conditioned accommodation with a balcony and free WiFi.

  • Chic 4-Bedroom Haven: Designer's Dream Home
    Scored 8.0
    8.0
    Rated very good
    Very good
     · 2 reviews

    Set within the West Town district in Chicago, Chic 4-Bedroom Haven: Designer's Dream Home has air conditioning, a patio, and city views.

  • Chic Chicago Retreat home
    Scored 8.0
    8.0
    Rated very good
    Very good
     · 2 reviews

    Set in Chicago, 5.7 km from United Center and 7.6 km from Guaranteed Rate Field, Chic Chicago Retreat home offers air-conditioned accommodation with a patio and free WiFi.

  • Chic Green l Near Downtown & IL Medical District
    Scored 7.7
    7.7
    Rated good
    Good
     · 18 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.

    Die Wohnung ist wirklich schön eingerichtet, und war sehr sauber.

  • 5 Bedroom House in Best Location Parking Fireplace Back Yard Home office
    Scored 7.5
    7.5
    Rated good
    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...

  • Chicago New 2BR Home w 3 Beds and HighSpeed Internet
    Scored 7.0
    7.0
    Rated good
    Good
     · 3 reviews

    Located in Chicago, 4.3 km from Water Tower Chicago and 4.5 km from Chicago Museum of Contemporary Art, Chicago New 2BR Home w 3 Beds and HighSpeed Internet offers a casino and air conditioning.

  • Central Downtown Location-Modern 2BR Condo
    Scored 6.0
    6.0
    Rated pleasant
    Pleasant
     · 1 review

    Conveniently located in the centre of Chicago, Central Downtown Location-Modern 2BR Condo offers a balcony, air conditioning, free WiFi and TV. This holiday home also has a private pool.

FAQ about holiday homes in Chicago

Holiday homes that guests love in Chicago

See all
  • Avg. price/night: £101.72
    Scored 8.2
    8.2
    Rated very good
    Very good
     · 1,888 reviews
    Very clean. Conveniently located.
    Pier Luca
    Young couple
  • Avg. price/night: £125.17
    Scored 7.2
    7.2
    Rated good
    Good
     · 383 reviews
    Convenient location, room was a decent size for a solo traveller. Entire place was very clean. The mobile phone key to unlock the doors were also very useful. I also liked the TV + aircon unit, and the view from the room.
    Patricia
    Solo traveller
  • Scored 7.5
    7.5
    Rated good
    Good
     · 45 reviews
    Everything about this was perfect. The cute little apartment was very clean and comfortable. Fully equipped kitchen so we were able to have breakfast in and save a few quid! The location was in a quiet and safe neighbourhood with very simple and affordable access to the city. Probably my favourite stay throughout my travels around the states thus far. The owner was very easy to contact and very helpful in regard to any questions or queries we had or any help we needed while we were there.
    Julia
    People with friends
  • Avg. price/night: £121.32
    Scored 8.5
    8.5
    Rated very good
    Very good
     · 3,318 reviews
    The design of the hotel is amazing! There is breakfast at the River North Bistro (not expensive). The room view is a must! They keep the hotel very clean all the time, and they are very welcoming! The gyn is well-equipped. The shower was strong pressured (i loved it). I would recommend to every one, great experience.
    Matheus
    Solo traveller
  • Avg. price/night: £170.90
    Scored 9.1
    9.1
    Rated superb
    Superb
     · 2,015 reviews
    The location is very good! It has a bus station 50 meters from the entrance that goes to blue line(for the Airport). The room was very clean and big. The breakfast has decaf that it is very rare.
    Lampros
    Young couple
  • Scored 9.4
    9.4
    Rated superb
    Superb
     · 10 reviews
    The apartment is large, well equipped, and very clean. What we liked best of all was the fridge, where you could get cold and excellent tasting water directly from the tap, as well as ice cubes and crushed ice.
    Barbara
    Family with young children
  • Avg. price/night: £181.99
    Scored 9.0
    9.0
    Rated superb
    Superb
     · 1,749 reviews
    Location very central, very comfortable beds and very clean room
    Lucy
    Group
  • Avg. price/night: £94.39
    Scored 8.2
    8.2
    Rated very good
    Very good
     · 4,030 reviews
    Very clean
    Marlena
    Family with young children
  • Avg. price/night: £97.05
    Scored 8.3
    8.3
    Rated very good
    Very good
     · 5,456 reviews
    Amazing view, very clean, best location and polite staff.
    Kameliya
    Young couple
  • Scored 8.5
    8.5
    Rated very good
    Very good
     · 14 reviews
    The unit itself was renovated and lovely. Very clean and cozy space. The host was very receptive when we brought up mild concerns (tiny leak in faucet, shower temp concerns).
    Alexandra
    Family with young children

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