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Holiday homes in Chicago

Enjoy your stay and find the best Holiday homes in Chicago at affordable prices

Searching for a holiday home in Chicago (Illinois)? Explore a great selection of vacation homes in Chicago to find the one that best fits to your needs, starting from $144.57 per night. Holiday homes offer a relaxing escape, providing a cozy retreat for vacationers seeking a home away from home.

Holiday-homes in Chicago and region (40 miles)
Prime Location Old Town Chicago Townhome! in Chicago, USA

Prime Location Old Town Chicago Townhome...

Holiday home in Chicago, Illinois
Prime Location Old Town Chicago Townhome! is situated in the Lincoln Park district of Chicago, 2.3 km from Fullerton Beach, 2.3 km from Oak Street Bea...
  • Parking
  • Pets allowed

no reviews

from $144.57 Show details »

Chic and Spacious Chicago Townhouse with Patio! in Chicago, USA

Chic and Spacious Chicago Townhouse with...

Holiday home in Chicago, Illinois
Chic and Spacious Chicago Townhouse with Patio! is set in the West Town district of Chicago, 4 km from Union Station, 4 km from Water Tower Chicago an...
  • Parking
  • Pets allowed

no reviews

from $206.00 Show details »

Modern Chicago Home Near The Loop and Lake MI! in Chicago, USA

Modern Chicago Home Near The Loop and La...

Holiday home in Chicago, Illinois
Modern Chicago Home Near The Loop and Lake MI! is located in the West Town district of Chicago, 4 km from Union Station, 4 km from Water Tower Chicago...
  • Parking
  • Pets allowed

Very good 3 Reviews 8.3

from $301.67 Show details »

Flat in Lincoln Park 2-Flat Central to Everything in Chicago, USA

Flat in Lincoln Park 2-Flat Central to E...

Villa in Chicago, Illinois , 2645 North Dayton Street
Featuring garden views, Flat in Lincoln Park 2-Flat Central to Everything offers accommodation with a terrace and a balcony, around 2.5 km from North ...
  • Parking
  • Pets allowed

Exceptional 5 Reviews 9.6

from $418.00 Show details »

Griffin Mansion with Yard, 5 Mi to Dtwn Chicago! in Chicago, USA

Griffin Mansion with Yard, 5 Mi to Dtwn...

Holiday home in Chicago, Illinois
Griffin Mansion with Yard, 5 Mi to Dtwn Chicago! is located in Chicago, 3.8 km from United Center, and provides a balcony, garden, and free WiFi.
  • Parking
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Very good 2 Reviews 8.5

from $256.67 Show details »

The Avondale Guesthouse in Chicago, USA

The Avondale Guesthouse

Holiday home in Chicago, Illinois , 2973 North Elston Avenue
Located in Chicago, just 4.6 km from Wrigley Field, The Avondale Guesthouse provides accommodation with a garden, a terrace, barbecue facilities and f...
  • Parking
  • Pets allowed
  • Family rooms
  • Tea/Coffee maker
  • Shower

Superb 127 Reviews 9.3

from $460.00 Show details »

Oak Park House - 11 Mi From Downtown Chicago! in Oak Park, USA

Oak Park House - 11 Mi From Downtown Chi...

Holiday home in Oak Park near Chicago, Illinois
Set in Oak Park, 14 km from United Center and 16 km from Lincoln Park Zoo, Oak Park House - 11 Mi From Downtown Chicago! provides accommodation with a...
  • Parking

no reviews

from $512.67 Show details »

Charming Oak Park Home with Private Fire Pit! in Oak Park, USA

Charming Oak Park Home with Private Fire...

Holiday home in Oak Park near Chicago, Illinois
Situated in Oak Park, 14 km from United Center and 16 km from Lincoln Park Zoo, Charming Oak Park Home with Private Fire Pit! provides accommodation w...
  • Parking

no reviews

from $452.33 Show details »

Chicago Home with Spacious Yard 14 Mi to Dtwn in Chicago, USA

Chicago Home with Spacious Yard 14 Mi to...

Holiday home in Chicago, Illinois
Chicago Home with Spacious Yard 14 Mi to Dtwn is set in Chicago, 16 km from Guaranteed Rate Field, 20 km from Field Museum of Natural History, as well...
  • Parking

no reviews

from $225.67 Show details »

Chicago Home with Spacious Backyard! in Chicago, USA

Chicago Home with Spacious Backyard!

Holiday home in Chicago, Illinois
Chicago Home with Spacious Backyard! is situated in Chicago, 17 km from Guaranteed Rate Field, 22 km from United Center, and 22 km from Field Museum o...
  • Parking

no reviews

from $239.00 Show details »

Bright Westchester Escape about 13 Mi to Downtown in Westchester, USA

Bright Westchester Escape about 13 Mi to...

Holiday home in Westchester near Chicago, Illinois
Set 22 km from Union Station, 22 km from Willis Tower and 22 km from DePaul University, Bright Westchester Escape about 13 Mi to Downtown offers accom...
  • Parking

no reviews

from $236.00 Show details »

Cozy Westmont Home Walk to Metra Station! in Westmont, USA

Cozy Westmont Home Walk to Metra Station...

Holiday home in Westmont near Chicago, Illinois
Set 34 km from Guaranteed Rate Field, 35 km from Union Station and 36 km from Field Museum of Natural History, Cozy Westmont Home Walk to Metra Statio...
  • Parking

no reviews

from $289.00 Show details »

The Katerina Residence in Calumet City, USA

The Katerina Residence

Holiday home in Calumet City near Chicago, Illinois , 1582 Wentworth Avenue
Spacious Modern Getaway Mins From Major Retail is set in Calumet City, 36 km from Field Museum of Natural History, 37 km from Adler Planetarium & Astr...
  • Parking

Fabulous 13 Reviews 8.8

from $167.64 Show details »

Davids Vacation Escapes Hideaway Home Sleeps 12 in Addison, USA

Davids Vacation Escapes Hideaway Home Sl...

Holiday home in Addison near Chicago, Illinois , 3N555 Central Court
Hideaway Chicago Western Suburbs Sleeps 10 is situated in Addison, 35 km from United Center, 38 km from Union Station, as well as 38 km from Willis To...
  • Parking

no reviews

from $216.33 Show details »

The Clay Hideaway in Downers Grove, USA

The Clay Hideaway

Holiday home in Downers Grove near Chicago, Illinois , 1116 Adelia Street
Set in Downers Grove, within 41 km of United Center and 41 km of Guaranteed Rate Field, The Clay Hideaway offers accommodation with free WiFi, air con...
  • Parking
  • Pets allowed
  • Bar
  • Family rooms

no reviews

from $315.00 Show details »

Executive Family Home in quiet Culdesac in Hazel Crest, USA

Executive Family Home in quiet Culdesac

Villa in Hazel Crest near Chicago, Illinois , 3208 172nd Court
Set in Hazel Crest in the Illinois region, Executive Family Home in quiet Culdesac has a patio.
  • Parking
  • Pets allowed
  • Family rooms

Exceptional 5 Reviews 10.0

from $209.67 Show details »

Cozy three bedroom home in Munster , Indiana. in Munster, USA

Cozy three bedroom home in Munster , Ind...

Holiday home in Munster near Chicago, Illinois , 8006 Columbia Avenue
Set in Munster, just 33 km from Museum of Science and Industry - Chicago, Cozy three bedroom home in Munster, Indiana.
  • Parking
  • Restaurant
  • Pets allowed
  • Family rooms

no reviews

from $323.00 Show details »

Glendale Heights Home with Office and Backyard! in Glendale Heights, USA

Glendale Heights Home with Office and Ba...

Holiday home in Glendale Heights near Chicago, Illinois
Glendale Heights Home with Office and Backyard! is set in Glendale Heights, 48 km from Union Station, 48 km from Willis Tower, and 48 km from DePaul U...
  • Parking

Disappointing 1 Reviews 4.0

from $295.33 Show details »

Arlington Heights Townhome 33 Mi to Chicago in Arlington Heights, USA

Arlington Heights Townhome 33 Mi to Chic...

Holiday home in Arlington Heights near Chicago, Illinois
Set in Arlington Heights, 34 km from Six Flags Great America and 35 km from Loyola University Chicago, Arlington Heights Townhome 33 Mi to Chicago pro...
  • Parking

no reviews

from $309.33 Show details »

Dream Retreat Indiana Dunes National Park in Tolleston, USA

Dream Retreat Indiana Dunes National Par...

Holiday home in Tolleston near Chicago, Illinois , 701 North Howard Street
Situated in Tolleston in the Indiana region, with Marquette Park Beach and Lake Street Beach nearby, Dream Retreat Dunes Natl Pk Hot Tub Volleyball Fi...
  • Parking
  • Pets allowed
  • Sauna
  • Family rooms
  • Tea/Coffee maker

Fabulous 1 Reviews 9.0

from $498.16 Show details »

Home with Yard and Patio about 30 Mi to Downtown Chicago in Matteson, USA

Home with Yard and Patio about 30 Mi to...

Holiday home in Matteson near Chicago, Illinois
Situated in Matteson, 42 km from Museum of Science and Industry - Chicago and 44 km from Guaranteed Rate Field, Quiet Home with Patio, Smart TVs 30 Mi...
  • Parking
  • Hairdryer
  • Iron
  • Refrigerator
  • Fan

Exceptional 2 Reviews 10.0

from $413.67 Show details »

Secluded Fenced Cottage W Dune Top Hot Tub Near Hiking Dog Friendly in Miller, USA

Secluded Fenced Cottage W Dune Top Hot T...

Holiday home in Miller near Chicago, Illinois , 246 N Hancock
Secluded Fenced Cottage W Dune Top Hot Tub Near Hiking Dog Friendly, a property with a garden and a terrace, is set in Miller, 1.1 km from Marquette P...
  • Parking
  • Pets allowed
  • Family rooms
  • Internet facilities
  • TV

Good 7 Reviews 7.9

from $336.81 Show details »

Pet Friendly Ranch Home 30 mins from O'Hare in Schaumburg, USA

Pet Friendly Ranch Home 30 mins from O'H...

Holiday home in Schaumburg near Chicago, Illinois , 1300 Kingston Lane
Pet Friendly Ranch Home 30 mins from OHare, a property with a garden, is located in Schaumburg, 47 km from Loyola University Chicago, 48 km from Unite...
  • Parking
  • Pets allowed
  • Family rooms

Exceptional 6 Reviews 9.7

from $169.20 Show details »

Immaculate Family Townhome - Walk to Beach! in Gary, USA

Immaculate Family Townhome - Walk to Bea...

Holiday home in Gary near Chicago, Illinois
Set 1.3 km from West Beach, 1.6 km from Marquette Park Beach and 48 km from Museum of Science and Industry - Chicago, Immaculate Family Townhome - Wal...
  • Parking

Pleasant 1 Reviews 7.0

from $267.43 Show details »

Pet-Friendly Lake Getaway 1 Block to Beach! in Gary, USA

Pet-Friendly Lake Getaway 1 Block to Bea...

Holiday home in Gary near Chicago, Illinois
Situated in Gary, 300 metres from Well Streets Beach and 1.1 km from West Beach, Pet-Friendly Lake Getaway 1 Block to Beach! provides accommodation wi...
  • Parking
  • Pets allowed

no reviews

from $274.67 Show details »

Number of Holiday homes in Chicago 30
Number of guest ratings 216492
Average price per night $588.15
Lowest price per night $144.57
Highest price per night $1.190.67

Most popular Holiday-homes in Chicago

The most popular Holiday-homes in Chicago based on average guest rating (Top 10).

Cheapest Holiday-homes in Chicago

The cheapest Holiday-homes in Chicago based on room rate per night (Top 10).

Most booked Holiday-homes in Chicago

The most booked Holiday-homes in Chicago based on popularity with guests (Top 10).

Holiday homes in Chicago (Illinois), comfortable and familiar

Staying in a holiday or vacation home in Chicago can be a great alternative to a hotel or resort. They can range from small cottages to luxurious villas, and are often located in popular tourist destinations such as beaches or mountains. One of the main benefits is the privacy and flexibility that comes with having your own space. Unlike a hotel room, a holiday home provides you with a living area, kitchen, and sometimes even outdoor space, allowing you to cook your own meals, relax in comfort, and enjoy the company of your friends or family without the interruptions of other guests.

Holiday homes often offer more space than a hotel room. This can be particularly useful for families or groups of friends traveling together, who may need more than one room or want to avoid the cramped feeling of a single hotel room. They can also provide a more authentic travel experience, allowing guests to immerse themselves in the local culture and lifestyle. This can be particularly appealing for those who prefer to stay in quieter, residential areas away from the hustle and bustle of tourist hotspots.

Find the best Holiday home in Chicago for your needs

Holiday homes should offer a comfortable and enjoyable stay, providing all the necessary amenities and conveniences to make your vacation experience memorable. At a minimum, your holiday home in Chicago should offer a clean and well-maintained living space with comfortable furnishings, adequate lighting, and climate control.

In addition to basic amenities such as a fully equipped kitchen, comfortable bedding, and clean linens and towels, holiday homes should also offer modern conveniences such as Wi-Fi, cable or streaming TV, and laundry facilities. A private outdoor space, such as a balcony or terrace, can also add to the overall enjoyment. They can also offer additional features such as a swimming pool, hot tub, or outdoor grill. Location is also important, for example, close to popular tourist attractions, restaurants and shopping areas.

Accommodation data and pictures provided by Booking.com