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)
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...
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...
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...
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 ...
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...
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...
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...
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...
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...
Spacious Row Home next Transit near Downtown w Parking offers accommodations in Chicago, 2 miles from United C...
Parking
Pets allowed
Family rooms
from $363.07
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