Chicago holiday homes, IL, USA: holiday houses & more

Discover a selection of 1343 homes, 2462 apartments and other holiday rentals in Chicago that are perfect for your trip. Whether you’re staying in a holiday home with friends, family or just with your pet, you'll have the best amenities for spending time at your home away from home, which might include parking and a fireplace. At the end of the day, you're sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.

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Find the best place to stay - Chicago

51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi

Sleeps 4 · 1 bedroom · 1 bathroom

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Travel to vibrant Chicago

Take a holiday to Chicago and enjoy the area's theatre scene, architecture and museums. This city is cosmopolitan and scenic, recognised for its art, monuments and entertainment. Navy Pier and Michigan Avenue are a couple of places to search for that perfect souvenir. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in Chicago

Are you hoping to discover attractions to visit during your stay? Venture out of your holiday home and check out everything that makes Chicago a one-of-a-kind holiday spot. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

Dave & Buster's (1.4 mi / 2.3 km)
Lincoln Park Zoo (2.8 mi / 4.5 km)
Galloping Ghost (12.5 mi / 20.1 km)
The Dome at the Parkway Bank Sports Complex (14.4 mi / 23.2 km)
Oak Brook Golf Course (15.7 mi / 25.3 km)
Home Alone House (16.7 mi / 26.9 km)

Exploring the natural features in Chicago

Whether you're an outdoor enthusiast or just want to take in the scenery, Chicago is a great spot to appreciate mother nature. Here are some of the area’s most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

Grant Park (0.7 mi / 1 km)
Millennium Park (0.3 mi / 0.5 km)
Maggie Daley Park (0.5 mi / 0.8 km)
Ohio Street Beach (1.2 mi / 1.9 km)
Oak Street Beach (1.6 mi / 2.5 km)
Northerly Island (1.7 mi / 2.8 km)

Transport options to and around Chicago

Fly into Chicago Midway Airport (MDW), the closest airport, located 8.6 mi (13.9 km) from the city centre. If you're unable to find a flight that fits your schedule, you might consider flying into Chicago O'Hare International Airport (ORD), which is 15.7 mi (25.3 km) away.

If you're travelling by train, Millennium Station, Chicago Van Buren Street Station and Chicago Union Station are the main stations that serve the city. It's easy to get around Chicago by jumping on the metro at Monroe Station (Red Line), Monroe Station (Blue Line) or Adams-Wabash Station.

Frequently asked questions

What is the most popular type of holiday home accommodation in Cheltenham?

Apartments are the most popular style of holiday home in Cheltenham, according to our data. Even if you've got a different idea about what you want, Bookabach has holiday homes in many shapes and sizes. Explore our options to find your ideal match.

How much does it cost to rent a holiday home in Cheltenham?

A number of things affect the price of a holiday home in Cheltenham, like the type of property, length of stay and season. However, all our holiday homes have something in common — excellent value. Simply enter your travel dates to find your home away from home.

How much does it cost to rent a beach house in Cheltenham?

When you travel and the size and style of the property will determine the cost of your beachside holiday home. Type in your Cheltenham travel dates to view your available options on Bookabach. Can't live without a hot tub, or maybe a private pool? Use our filters to select the amenities and features you want.

What are popular home amenities in Cheltenham?

Off-street parking options, an oven and a playground top the list of most popular home amenities in Cheltenham. Whether you're planning to travel as a party of one, with your significant other or a group of friends, Bookabach will help you find a holiday home that matches your tastes with all the features you'll enjoy.

What are the top attractions for families in Cheltenham?

There's a ton of wonderful things to see and do with the family in Cheltenham, such as:

Shedd Aquarium
Field Museum of Natural History
Chicago Museum of Science and Industry

How old do you have to be to rent a holiday home in Cheltenham?

The minimum age is generally 16, 18 or 21. It can change from one property to another on Bookabach, so check the rules of your preferred Cheltenham holiday home before making a booking.

How long can I rent a holiday home in Cheltenham for?

The amount of time you can book a Cheltenham holiday home for is down to each property. Just enter your dates of travel to see options that offer extended stays. They include everything you need to make your extended trip more enjoyable and convenient, like kitchens and laundries. Some properties may also offer weekly or monthly discounted prices, so you can stick around for longer for less.