Chicago vacation rentals

We found 4,232 vacation 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 1307 homes, 2494 apartments, and other vacation rentals in Chicago that are perfect for your trip. Whether you’re staying in a vacation home with friends, family, or even just your pets, you'll have the amenities you expect and more, which might include parking and a hot tub. Whatever you're looking for, you'll be able to choose a rental for everyone's needs, including a place that's non-smoking or offers accessibility.

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Travel to exciting Chicago

Take a vacation to Chicago and enjoy the area's theater scene, architecture and museums. This city is cosmopolitan and scenic, recognized 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 friends trip, vacation rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in Chicago

Are you hoping to find things to do during your stay? Venture out of your vacation home and check out everything that Chicago has to offer. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • 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)
  • The Glen Club (17.7 mi / 28.5 km)

Exploring the natural features in Chicago

Whether you're an active traveler or just want to spend some time taking in the scenery, Chicago is a great place to get outside. Here are some of the area’s most eye-catching natural features, all within 30 miles (48.2 km) of the city center:

  • 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)

Transportation options to and around Chicago

Fly into Chicago Midway Airport (MDW), the closest airport, located 8.6 mi (13.9 km) from the city center. If you can't find a flight that works for your travel itinerary, you could book a flight to Chicago O'Hare Intl. Airport (ORD), which is 15.7 mi (25.3 km) away.

If you're traveling by train, Millennium Station, Chicago Van Buren Street Station and Chicago Union Station are the main stations that serve the city. You can 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 vacation rental?

One of the more sought-after locations to get a vacation home in Chicago is Near North Side. Spend your vacation 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 vacation rental accommodation in Chicago?

The most popular types of vacation rentals in Chicago are apartments. Looking for something different? Vrbo 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 vacation rental in Chicago?

Several things affect what you'll pay for a vacation rental in Chicago, including the season, length of stay and type of property. However, all our vacation 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 vacation home near the beach in Chicago depends on when you're traveling and the type and size of property you're looking for. You can find prices easily and quickly on Vrbo 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 vacation rentals 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 vacation rentals and find the pawfect pad on Vrbo.

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 vacation rentals and every day will be a pool day. Simply enter your dates into Vrbo, then use the "pool" filter to find the perfect place to make a splash!

What are popular rental amenities in Chicago?

When it comes to rental amenities that people are looking for in Chicago, a chef, a fireplace and a nearby waterfront rank the highest. With Vrbo vacation rentals, 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 vacation rentals 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 vacations to special events like Christmas and birthday parties, Vrbo can help you find a large group rental to match the occasion.

Are there vacation rentals in Chicago that welcome kids?

Chicago has 1,646 family-friendly vacation rentals 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 vacation rentals in Chicago?

There are 577 one-bedroom properties in Chicago to choose from. A one-bedroom vacation home is an excellent choice if it's just two of you or if you're traveling 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 vacation rentals in Chicago?

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

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