Beginning of main content

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Vacation Homes in Chicago

Beautiful House in Round Lake Park
Beautiful House in Round Lake Park
Round Lake, IL
This vacation home is a smoke-free vacation home.
Essence Suite W/spa Bath
Essence Suite W/spa Bath
South Holland, IL
At this vacation home, guests have access to features like an arcade/game room.
Luxury Family Home Near Down Town
Luxury Family Home Near Down Town
Addison, IL
This vacation home is a smoke-free vacation home.
Cambridge Estates
Cambridge Estates
4.0 out of 5.0 Cambridge Court, Darien, IL
Guests of this vacation home enjoy features like an outdoor pool, free WiFi in public areas, and laundry facilities. If you decide to drive, there's free ...
Columbia Bay Compound, Two Homes Great Groups And Families On The Chain'o'lakes!
Columbia Bay Compound, Two Homes Great Groups And Families On The Chain'o'lakes!
Antioch, IL
$350
This vacation home is a smoke-free vacation home.
Quaint Bungalow, Near Great Lakes Naval Base
Quaint Bungalow, Near Great Lakes Naval Base
Mundelein, IL
At this vacation home, guests have access to a garden.
Downtown Home in the heart of Naperville
Downtown Home in the heart of Naperville
2.5 out of 5.0 681 W Benton Ave, Naperville, IL
This vacation home features free WiFi in public areas, express check-in, and laundry facilities. You can put free parking to good use if you drive.
Map

Chicago Vacation Homes

Book vacation homes in Chicago
Next time you take a group getaway top Chicago, don’t confine your friends and family to one or two hotel rooms. Instead, snag a deal on a full-sized house and get the best of both worlds. Vacation home rentals are perfect for families and large groups that want to live like locals on vacation. Whether you are searching for a villa that pulls out all the stops or a four-bedroom house to host the best summer vacation ever, Orbitz has a variety of Chicago vacation homes for rent that are ideal for you. Your perfect pad is only a few clicks away.

Homes for every Chicago vacation
If you’re planning a vacation with a lot of people, you’ll want room to stretch out, and a rental home has plenty of space. Many vacation homes also come with everything you’ll need for a proper getaway, like kitchens with every gadget you can think of, along with updated furnishings, fancy spa tubs and balconies. You may even wind up in a rental home that has a sprawling backyard for barbecues, games and general relaxation. These rentals offer the added bonus of putting you right in the thick of things in Chicago; instead of going to a small hotel room at the end of a busy day, you’re going home.

Vacations are all about creating lasting memories, and a Chicago rental home makes it easy to create good ones. Whether you’re getting the college crowd back together or bringing along your folks and your kids, a trip to Chicago is sure to be a winner.

Hotel Options in Chicago

See all 1,941 Properties in Chicago
*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.