Chicago holiday rentals

We found 4,256 holiday rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
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April 2024
Discover a selection of 1381 homes, 2461 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)
  • Adagio Teas (14.1 mi / 22.6 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)

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)
  • Union Park (1.9 mi / 3.1 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 best area to stay in Chicago when booking a holiday home?

One of the more sought-after locations to get a holiday home in Chicago is Near North Side. Spend your holiday here and you'll be a short distance from some top attractions including Navy Pier and Chicago Childrens Museum.

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

The most popular types of holiday homes in Chicago are apartments. Looking for something different? Stayz has many options to match the needs of our guests, so you'll see properties in lots of shapes and sizes. The ideal fit is waiting for you — lock in yours today.

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

Several things affect what you'll pay for a holiday home in Chicago, including the season, length of stay and type of property. However, all our holiday homes have one thing in common — exceptional value. Simply add your travel dates to find your dream escape.

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

The average price for a holiday home near the beach in Chicago depends on when you're travelling and the type and size of property you're looking for. You can find prices easily and quickly on Stayz by entering your destination and preferred travel dates. Then use our handy filter tool to select the number of bedrooms and amenities that you need, like WiFi, a pool and air conditioning.

Are there pet-friendly holiday homes in Chicago?

With 1 ,659 properties that host four-legged guests, your furry buddy can also come along on your Chicago break. Use the filter tool to browse our pet-friendly holiday homes and find the pawfect pad on Stayz.

Can I rent a house with a pool in Chicago?

Pack your swimsuit and inflatable swan, because there are 307 houses with a private pool in Chicago. Stay at one of these superb holiday homes and every day will be a pool day. Simply enter your dates into Stayz, then use the "pool" filter to find the perfect place to make a splash!

What are popular home amenities in Chicago?

When it comes to home amenities that people are looking for in Chicago, a chef, a fireplace and a nearby waterfront rank the highest. With Stayz holiday homes, you'll have options to suit your style and taste, whether you're planning to get away with family members, friends or even pets.

Are there large group holiday homes in Chicago?

With 131 properties that can host 10 or more guests in Chicago, there's no need to keep anyone off the invite list. From family holidays to special events like Christmas and birthday parties, Stayz can help you find a large group home to match the occasion.

Are there holiday homes in Chicago that welcome kids?

Chicago has 1 ,646 family-friendly holiday homes to choose from. And securing a stay that welcomes youngsters is super easy with our "Properties good for families" filter. As well as having the entire place to yourselves, you can also look forward to perks and amenities such as multiple bedrooms, pools and kitchens.

What are the top attractions for families in Chicago?

Keep your kids occupied at these popular family-friendly attractions in Chicago:

  • Navy Pier
  • Chicago Riverwalk
  • Shedd Aquarium

Are there one-bedroom holiday homes in Chicago?

There are 577 one-bedroom properties in Chicago to choose from. A one-bedroom holiday home is an excellent choice if it's just two of you or if you're travelling alone. Toss in more space, convenience and privacy than a regular hotel, and you've got the makings of a break to remember.

Can I find two-bedroom holiday homes in Chicago?

Gather your nearest and dearest and enjoy total privacy and comfort in one of the 442 two-bedroom holiday homes Chicago has to offer.

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