Chicago holiday homes

We found 4,229 holiday rentals — enter your dates for availability

your current months are April, 2024 and May, 2024.
April 2024
May 2024
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.

Find spaces that suit your style

  • 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 Cuyler?

The most desirable types of holiday homes in Cuyler are apartments. Searching for something different? Bookabach has a variety of options to match our guests' needs, so you'll see holiday properties in loads of sizes and shapes. The perfect fit is ready and waiting for you — lock in yours today.

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

A number of things determine how much you'll pay for a holiday home in Cuyler, like the type of property, length of stay and season. But, all Bookabach homes have something in common — amazing value. Just enter your travel dates to find your ideal match.

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

When you travel and the style and size of the property will determine the cost of your beachside escape. Type in your Cuyler travel dates to see all your options on Bookabach. Did someone just say "private pool"? Use the filters to pick the features and amenities you need.

Are there pet-friendly holiday homes in Cuyler?

You're in luck. There are. You can choose from three holiday homes that roll out the welcome mat in Cuyler on Bookabach. Our furry kids also need a break, so simply use our search function for pet-friendly holiday homes to find a pad where your pooch can get in on the fun.

What are popular home amenities in Cuyler?

When it comes to home amenities that people are looking for in Cuyler, an oven, a fridge and a stovetop are the most popular. With Bookabach holiday homes, you'll find options to suit your taste and style, whether you're going away with family members, friends or even pets.

Are there holiday homes in Cuyler that welcome kids?

Bring the whole group together for the adventure of a lifetime in Cuyler at one of our three family-friendly holiday properties. These stays come with amenities that are great for trips with youngsters, like kitchens, living rooms and swimming pools. Just click on the "Properties good for families" filter box and choose your favourite option.

What are the top attractions for families in Cuyler?

Keep the kids busy at these top family-friendly attractions in Cuyler:

  • Navy Pier
  • Chicago Riverwalk
  • Shedd Aquarium

Are there one-bedroom holiday homes in Cuyler?

Yes, you can choose from two one-bedroom homes in Cuyler. Whether you'd prefer a cosy cottage or a condo, Bookabach's one-bedroom properties are great if you don't require a lot of space. One of the main perks of having your own digs? You'll never have to share your trip with strangers.

How can I find holiday homes with air conditioning in Cuyler?

Cuyler has three holiday homes where you'll be able to spend your days in air-conditioned comfort. To find a property on Bookabach featuring this perk, enter your travel dates and use the filter tool to select the "air conditioning" box.

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

You'll need to check with the Cuyler holiday home you're looking at on Bookabach as age restrictions vary. However, it's generally 16, 18 or 21.

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

It all depends on the Cuyler property. To browse available options offering extended stays, simply type your dates and number of guests into Bookabach. You can enjoy having the property to yourself, as well as amenities such as a kitchen, air conditioning and outdoor spaces where your little ones can play. Keep your eyes peeled for any long-term stays that offer discounted weekly or monthly prices.

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