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Featured Vacation Rentals in Chicago

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
Situated in the city center, this vacation home is in the same area as Morton Arboretum, Blackwell Forest Preserve, and College of Dupage. Regional attractions ...
Sunny Woodstock Home
Sunny Woodstock Home
Woodstock
Situated in Woodstock, this vacation home is close to McHenry County Fairgrounds, Woodstock City Hall, and Woodstock Opera House. Also nearby are Woodstock Square ...
Beautifully Rehabbed House in Brookfield -16 Miles From Downtown Chicago
Beautifully Rehabbed House in Brookfield -16 Miles From Downtown Chicago
Brookfield
$50
Situated in La Grange Park, this vacation home is close to Brookfield Zoo. Area attractions also include Toyota Park and Oakbrook Center Mall.
Downtown Home In Million Dollar Locality
Downtown Home In Million Dollar Locality
2.5 out of 5.0 681 W Benton Ave, Naperville
$102
Situated near the airport, in the city center, this vacation home is close to Centennial Beach, Naperville Convention & Visitors Bureau, and Moser Tower and ...
"the Greenleaf House" - Whole House
"the Greenleaf House" - Whole House
Chicago
Located in Rogers Park, this vacation home is 1.1 mi (1.7 km) from Loyola University Chicago and 3 mi (4.8 km) from Aragon Entertainment Center. Northwestern ...
Exotic House - Few Minutess From O'hare and Chicago
Exotic House - Few Minutess From O'hare and Chicago
Des Plaines
$199
Located in the heart of Des Plaines, this historic vacation home is within 6 mi (10 km) of Lake Park, Allstate Arena, and Rivers Casino. Donald E. Stephens Convention ...
Cozy Warm Aptnear Stephens CC Rosemontkids & Dogsfree Parkingquiet Area
Cozy Warm Aptnear Stephens CC Rosemontkids & Dogsfree Parkingquiet Area
Chicago
$69
This family-friendly vacation home is in the center of Chicago, within 6 mi (10 km) of Portage Park, Rosemont Theatre, and Ernest Hemingway Museum and House. ...
Studio Room, on River, Newly Remodelled, Patio, and Dock Access
Studio Room, on River, Newly Remodelled, Patio, and Dock Access
St. Charles
$125
Situated in St. Charles, this vacation home is close to Fine Line Creative Arts Center, Dellora A. Norris Cultural Arts Center, and Durant House Museum. Area ...
Cambridge Estates
Cambridge Estates
4.0 out of 5.0 Cambridge Court, Darien
Situated in Darien, this vacation home is within 6 mi (10 km) of National Shrine of St. Therese, Promenade Bolingbrook, and Willowbrook Community Park. Boughton ...
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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.

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