Chicago vacation rentals

We found 4,267 vacation 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 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.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
  • More for less
    More space, more privacy, more amenities — more value
  • A place for everyone
    We stand for diversity, inclusion and families everywhere.
    Learn more

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:

  • 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 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?

Among the most sought-after neighborhoods to enjoy a vacation rental in Chicago is Near North Side. When you stay here, you'll be near top attractions like Navy Pier and Chicago Childrens Museum.

What is the most popular type of vacation rental accommodation in Chicago?

The most desirable types of vacation rentals in Chicago are apartments. After something a little different? Vrbo has plenty of options to match our guests' diverse needs, so you'll see vacation properties in all shapes and sizes. The perfect home away from home is waiting for you — get yours today.

How much does it cost to rent a vacation rental in Chicago?

The average price for a vacation home in Chicago can vary based on factors like property type, length of stay and time of year. Whether you're thinking about a sprawling villa with a pool or a quaint cabin ideal for just you and the kids, just enter your dates of travel to see stays that offer great value.

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

The average price for a vacation home by the beach in Chicago depends on when you're going and the type and size of property you're searching for. You can find prices easily and quickly on Vrbo by entering your dates of travel. Then use the filters to select the number of bedrooms and amenities important to you, such as a pool, air conditioning and WiFi.

Are there pet-friendly vacation rentals in Chicago?

With 2,074 properties that allow pets, your furry buddy can join in the fun on your Chicago getaway. Use our filter tool to search our pet-friendly vacation rentals and find a stay that'll set tails wagging on Vrbo.

Can I rent a house with a pool in Chicago?

Add a whole other level of fun to your getaway by booking one of the 392 houses with a private pool in Chicago. Use our search filter to find properties with pools on Vrbo, then spend your days splish-splashing around in a swimming pool that's just for you.

What are popular rental amenities in Chicago?

A firepit, nearby museums and a barbecue grill head the list of most popular rental amenities in Chicago. Whether you plan to travel solo, with a partner or a bunch of friends, Vrbo will help you find a vacation home that suits your style with a load of extras you'll love.

Are there large group vacation rentals in Chicago?

Take your pick of 185 vacation properties in Chicago that can host 10 or more people. Whether you're planning a vacation with extended family or an event like a birthday party, there's enough space to get your group together under the same roof.

Are there vacation rentals in Chicago that welcome kids?

With 2,058 family-friendly vacation rentals to select from in Chicago, there's never been a better time to introduce your little ones to the magic of travel. Just check our "Properties good for families" filter box to look for stays loaded with amenities perfect for vacationing families, such as kitchens, outdoor spaces, entertainment areas and hot tubs.

What are the top attractions for families in Chicago?

Keep your kids busy at these fabulous family-friendly attractions in Chicago:

  • Navy Pier
  • Chicago Riverwalk
  • Shedd Aquarium

Are there one-bedroom vacation rentals in Chicago?

Yes, you can pick from 670 one-bedroom rentals in Chicago. Whether you'd like a comfy cottage or a cabin, our one-bedroom properties are perfect if you don't require tons of space. One of the best parts about having your own digs? You'll never need to share your adventure with strangers.

Can I find two-bedroom vacation rentals in Chicago?

You can select from 568 two-bedroom vacation homes in Chicago. Give the kids the second room or fill it with a couple of your best buddies. There's ample space for whoever's lucky enough to be joining your adventure.

More Vacation Rentals ideas

People also search for

Vacation Rental options in Chicago (and vicinity)