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Holiday homes in Chicago You’ll Love

Top-Rated Chicago Holiday homes for Every Budget and Style!

Looking for a holiday home in Chicago (Illinois)? Browse a wide range of vacation rentals – from cozy retreats to spacious family homes – starting at just $53.00 per night. Whether you are planning a weekend getaway or a longer stay, you will find the perfect home away from home in the heart of Chicago.

We found 48 Holiday-homes in Chicago and the surrounding area (within 20 miles)

Hamaline Luxury & Tranquil Home in Chicago, USA

Hamaline Luxury & Tranquil Home

Villa in Chicago, Illinois , 76 East 37th Street
Hamaline Luxury & Tranquil Home is located in Chicago, just a 17-minute walk from Guaranteed Rate Field and 3.7 miles from Art Institute of Chicago.
  • Parking
  • Family rooms
  • Allergy-free room

Good 8 Reviews 7.6

from $298.03 Show details »

Villa GoldCoast King Bed Garage Netflix PingPong Pets OK in Chicago, USA

Villa GoldCoast King Bed Garage Netflix...

Villa in Chicago, Illinois , 1153 North Cambridge Avenue
Villa GoldCoast King Bed Garage Netflix PingPong Pets OK offers accommodations in Chicago, 1.1 miles from Oak Street Beach and 1.5 miles from North Av...
  • Parking
  • Pets allowed
  • Family rooms

no reviews

from $87.00 Show details »

Featured in Chicago Socials Most Luxurious Airbnbs in Chicago, USA

Featured in Chicago Socials Most Luxurio...

Villa in Chicago, Illinois , 1545 West Nelson Street
Featured in Chicago Socials Most Luxurious Airbnbs is located in Chicago, just 2.3 miles from Lincoln Park Zoo and 4.2 miles from United Center.
  • Parking

no reviews

from $100.00 Show details »

The Black And White Suite in Chicago, USA

The Black And White Suite

Holiday home in Chicago, Illinois , 611 East 41st Street
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.
  • Parking
  • Pets allowed
  • Family rooms

Good 20 Reviews 7.0

from $362.36 Show details »

Stylish Chicago Duplex Close to Parks and Dtwn in Chicago, USA

Stylish Chicago Duplex Close to Parks an...

Holiday home in Chicago, Illinois
Stylish Chicago Duplex Close to Parks and Dtwn offers accommodations in Chicago, 3.7 miles from United Center and 5 miles from Union Station.
  • Parking
  • Spa and wellness centre

Okay 3 Reviews 5.7

from $211.84 Show details »

Chic Chicago Retreat home in Chicago, USA

Chic Chicago Retreat home

Holiday home in Chicago, Illinois
Chic Chicago Retreat home offers accommodations in Chicago, 3.5 miles from United Center and 4.7 miles from Guaranteed Rate Field.
  • Parking

Fabulous 6 Reviews 8.7

from $224.58 Show details »

West Pilsen Hideaway in Chicago, USA

West Pilsen Hideaway

Holiday home in Chicago, Illinois , 2334 South Hoyne
West Pilsen Hideaway offers accommodations in Chicago, 3.8 miles from Union Station and 4.3 miles from Field Museum of Natural History.
  • Parking
  • Pets allowed

Exceptional 1 Reviews 10.0

from $97.00 Show details »

Spacious 5-BR House near Transit w Parking in Chicago, USA

Spacious 5-BR House near Transit w Parki...

Holiday home in Chicago, Illinois , 1868 South Millard Avenue
Offering a garden, Spacious 5-BR House near Transit w Parking offers accommodations in Chicago.
  • Parking
  • Pets allowed
  • Family rooms

Fabulous 17 Reviews 8.6

from $345.51 Show details »

Modern SFH Near McCormick Place & Soldier Field in Chicago, USA

Modern SFH Near McCormick Place & Soldie...

Holiday home in Chicago, Illinois , 1614 S Desplaines St
Modern SFH Near McCormick Place & Soldier Field is located in Chicago, just 1.8 miles from Union Station and 1.8 miles from Willis Tower.
  • Parking
  • Pets allowed
  • Family rooms

Exceptional 1 Reviews 10.0

from $1.013.89 Show details »

5 Mi to Millennium Park Apartment with Fireplaces in Chicago, USA

5 Mi to Millennium Park Apartment with F...

Holiday home in Chicago, Illinois
5 Mi to Millennium Park Apartment with Fireplaces offers accommodations in Chicago, 2.3 miles from United Center and 4.7 miles from Union Station.
  • Parking

Exceptional 3 Reviews 9.7

from $244.58 Show details »

Luxe Urban Retreat Near United Center in Chicago, USA

Luxe Urban Retreat Near United Center

Holiday home in Chicago, Illinois , 2705 W Warren Blvd
Luxe Urban Retreat Near United Center offers accommodations in Chicago, 3.1 miles from Union Station and 3.7 miles from Millennium Station.
  • Pets allowed
  • Family rooms

no reviews

from $72.00 Show details »

4 Mi to Dtwn Chicago Modern Home with Outdoor Space in Chicago, USA

4 Mi to Dtwn Chicago Modern Home with Ou...

Holiday home in Chicago, Illinois
4 Mi to Dtwn Chicago Modern Home with Outdoor Space offers accommodations in Chicago, 2.6 miles from Union Station and 3.1 miles from CIBC Theatre.
  • Parking

no reviews

from $54.00 Show details »

Central Downtown Location-Modern 2BR Condo in Chicago, USA

Central Downtown Location-Modern 2BR Con...

Holiday home in Chicago, Illinois , 210 North Wells Street Unit 1401
Just a 9-minute walk from Millennium Station and 0.4 miles from CIBC Theatre, Central Downtown Location-Modern 2BR Condo features accommodations in Ch...
  • Fitness centre

Pleasant 1 Reviews 6.0

from $317.24 Show details »

Spacious Row Home next Transit near Downtown w Parking in Chicago, USA

Spacious Row Home next Transit near Down...

Holiday home in Chicago, Illinois , 3133 West Fulton Street
Spacious Row Home next Transit near Downtown w Parking offers accommodations in Chicago, 2 miles from United Center and 4 miles from Union Station.
  • Parking
  • Pets allowed
  • Family rooms

Very good 20 Reviews 8.5

from $363.07 Show details »

The Chicago Retreat Just 10 mins from Chicago Bulls Arena in Chicago, USA

The Chicago Retreat Just 10 mins from Ch...

Holiday home in Chicago, Illinois , 545 North Wood Street
The Chicago Retreat Just 10 mins from Chicago Bulls Arena is located in Chicago, just a 17-minute walk from United Center and 2.6 miles from Union Sta...
  • Parking

Pleasant 3 Reviews 6.7

from $301.33 Show details »

Luxe 4BR with Hot Tub & Game Room in Chicago, USA

Luxe 4BR with Hot Tub & Game Room

Holiday home in Chicago, Illinois , 1654 West Ohio Street
Luxe 4BR with Hot Tub & Game Room offers accommodations in Chicago, 2.5 miles from Union Station and 2.6 miles from Shops at Northbridge.
  • Parking
  • Pets allowed

Fabulous 5 Reviews 9.0

from $328.00 Show details »

Spacious West Town Oasis with Parking! in Chicago, USA

Spacious West Town Oasis with Parking!

Holiday home in Chicago, Illinois , 1656 West Erie Street
Spacious West Town Oasis with Parking! is located in Chicago, just 1.1 miles from United Center and 2.5 miles from Union Station.
  • Parking
  • Pets allowed

no reviews

from $72.00 Show details »

River North Hideaway with Amazing Views and Parking in Chicago, USA

River North Hideaway with Amazing Views...

Holiday home in Chicago, Illinois , 1 E Huron St
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 ...
  • Parking
  • Pets allowed

Exceptional 2 Reviews 10.0

from $56.00 Show details »

Chicago Treasure 4 Bed Getaway in Chicago, USA

Chicago Treasure 4 Bed Getaway

Holiday home in Chicago, Illinois , 712 North Willard Court
Chicago Treasure 4 Bed Getaway offers accommodations in Chicago, 1.9 miles from Water Tower Chicago and 2 miles from Chicago Museum of Contemporary Ar...
  • Parking

Good 8 Reviews 7.8

from $192.56 Show details »

Cute and Cozy Chicago Modern Condo in Chicago, USA

Cute and Cozy Chicago Modern Condo

Holiday home in Chicago, Illinois , 1625 W Superior St 3F, Chicago, IL 60622, USA
Cute and Cozy Chicago Modern Condo is located in Chicago, just 2.4 miles from Water Tower Chicago and 2.5 miles from Chicago Museum of Contemporary Ar...

no reviews

from $281.33 Show details »

Spacious Ukrainian Village Retreat in Chicago, USA

Spacious Ukrainian Village Retreat

Holiday home in Chicago, Illinois , 2148 West Chicago
Spacious Ukrainian Village Retreat offers accommodations in Chicago, 2.9 miles from Water Tower Chicago and 3.1 miles from Chicago Museum of Contempor...
  • Parking
  • Pets allowed
  • Fitness centre

Passable 2 Reviews 5.5

from $57.00 Show details »

Stunning Condo #2 - Downtown River North in Chicago, USA

Stunning Condo #2 - Downtown River North

Holiday home in Chicago, Illinois , 811 N Sedgwick St
Stunning Condo #2 - Downtown River North is located in Chicago, just 1.5 miles from Ohio Street Beach and 1.8 miles from North Avenue Beach.
  • Parking

Fabulous 34 Reviews 8.6

from $298.63 Show details »

Hidden East Village Gem in Chicago, USA

Hidden East Village Gem

Holiday home in Chicago, Illinois , 869 N Marshfield Ave
1.6 miles from United Center in Chicago, Hidden East Village Gem provides accommodations with access to a hot tub.
  • Family rooms

Good 2 Reviews 7.0

from $96.00 Show details »

Chicago New 2BR Home w 3 Beds and HighSpeed Internet in Chicago, USA

Chicago New 2BR Home w 3 Beds and HighSp...

Holiday home in Chicago, Illinois , West Potomac Avenue 1731
Chicago New 2BR Home w 3 Beds and HighSpeed Internet offers accommodations in Chicago, 2.7 miles from Water Tower Chicago and 2.8 miles from Chicago M...
  • Parking

Good 4 Reviews 7.8

from $59.00 Show details »

Stunning 5BR Home in Heart of Chicago with 2 Rooftops in Chicago, USA

Stunning 5BR Home in Heart of Chicago wi...

Holiday home in Chicago, Illinois , 1307 North Bell Avenue
Stunning 5BR Home in Heart of Chicago with 2 Rooftops is located in Chicago, just 3.4 miles from Lincoln Park Zoo and 3.6 miles from Water Tower Chica...

Exceptional 2 Reviews 10.0

from $396.06 Show details »

Number of Holiday homes in Chicago 48
Number of guest ratings 216,870
Average price per night $250.00
Lowest price per night $53,00
Highest price per night $1.440,48

Top 10 Most Popular Holiday-homes in Chicago

Explore the Most Popular Holiday-homes in Chicago – Ranked by Average Guest Ratings.

Top 10 Cheapest Holiday-homes in Chicago

Discover the Cheapest Holiday-homes in Chicago – Ranked by Lowest Nightly Rates.

Top 10 Most Booked Holiday-homes in Chicago

Check out the Most Booked Holiday-homes in Chicago – Based on Guest Popularity.

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