Beginning of main content

Featured Vacation Rentals in Chicago

Estimated price for 1 night/2 adults

House with 2 King Beds, 4K TV & Wifi
House with 2 King Beds, 4K TV & Wifi
3.5 out of 5.0 22 W Franklin Ave, Naperville, IL
Located in the heart of Naperville, this vacation home is within 9 mi (15 km) of Blackwell Forest Preserve, Morton Arboretum, and College of Dupage. Wheaton ...
Gold Coast Historic Living-private Room in a House
Gold Coast Historic Living-private Room in a House
Chicago, IL
Located in River North, this vacation home is within a 5-minute walk of Newberry Library and State Street. John Hancock Center and Water Tower Place are also ...
Lovely 2 Bedroom w/ Balcony and 2 car Garage in Great Neighborhood Chicago, IL
Lovely 2 Bedroom w/ Balcony and 2 car Garage in Great Neighborhood Chicago, IL
Chicago, IL
Located in West Ridge, this vacation home is 1.2 mi (2 km) from Loyola University Chicago and 2.3 mi (3.7 km) from Aragon Entertainment Center. Wrigley Field ...
Newly Renovated 1200 Sq/ft Apartment. Sleeps 5
Newly Renovated 1200 Sq/ft Apartment. Sleeps 5
Elmwood Park, IL
Situated in Elmwood Park, this historic vacation home is 2.9 mi (4.6 km) from Frank Lloyd Wright Home and Studio and within 6 mi (10 km) of Rosemont Theatre ...
2 King BED Downtown Home in a Million Dollar Locality 58" 4K TV Fast Wifi
2 King BED Downtown Home in a Million Dollar Locality 58" 4K TV Fast Wifi
Naperville, IL
Situated in Naperville, this historic vacation home is within a 15-minute walk of Centennial Beach and Moser Tower and Millennium Carillon. Naper Settlement ...
Map

Vacation Rentals

Book vacation rentals 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 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 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

Estimated price for 1 night/2 adults