Destination guide

Get a Chicago pad with a difference in Orland Park

Just a 30-minute drive down the freeways from the Loop and Little Italy, bustling Chinatown and the pretty gardens that line Lake Michigan, Orland Park offers a green and leafy base in the Windy City. Its streets are well pruned and wide, fringed with homes on the National Register of Historic Places and interspersed with recreational lakes. Hardy Irish pubs can be found in nearby Beverly, while nature preserves cling to the courses of the babbling Des Plaines River. This diverse landscape makes Orland Park vacation rentals a quiet and peaceful option on the edge of this great Midwestern metropolis.

Things to do

Orland Park offers Chicago from a different angle

Orland Park vacation rentals are a ticket to the enjoyments of Chicago's south side. Just a short drive from your doorstep, you could be hopping between the Irish pubs of Beverly or exploring the rooms of the stone-faced Givens Castle, all steeped in spine-tingling ghost tales and Gaelic history. This area is also home to the acclaimed Beverly Arts Center of Chicago, which hosts regular touring exhibits, filmmaking workshops, visual arts installations, theater troupes, festive Christmas events and local live music acts – the list goes on.


Park hopping in Orland Park

Orland Park is one of the greenest suburbs of Chicago. It's packed with nature preserves, parks and little lakes where locals love to kick back with a picnic in the warmer months. From the swaying woods of Orland Grove to the gravel trails and blooming meadows of Cap Sauers, there are miles of walking paths to stroll and biking routes to rumble over. Throw in a smattering of golf courses and country clubs, and you might just even forget that you're vacationing in the 3rd largest city in the United States.


Get outside in Orland Park

A winter jaunt to stay at one of many Orland Park vacation rentals is certainly doable – just be ready to wrap up warm and wade through some snowdrifts in the local parks. That's the reason most folk head this way in the summertime, usually between May and August. This is when the temperature climbs to the mid-70s most days, and when the green spaces and nature preserves are at their best. April and late September are good alternative options if you're looking to save a few dollars on your stay.

Natural features

Refreshing greenery in Orland Park

Orland Park is known as one of the greenest corners of the Windy City. The Orland Grove Forest Preserve sits right at its heart, home to the wading birds and wetlands of the wide McGinnis Slough. The Tampier Slough Woods are also close by, offering boating lakes and isolated fishing spots between their lawns and oaks. Keep going north and you'll eventually reach the Des Plaines River, fringed with floodplain forests and pockets of sugar maples that come alive with wildflowers every spring.

How to get there

Traveling to and around Orland Park

Fly into Chicago, IL (MDW-Midway Intl.), the closest airport, located 13.2 mi (21.2 km) from the city center. If you can't find a flight that works for your travel itinerary, you can also fly into Chicago, IL (ORD-O'Hare Intl.), which is 24.7 mi (39.8 km) away.

If you're traveling by train, make your way to Orland Park 143rd Street Station or Orland Park 153rd Street Station to see more of the city.

Where to stay around Orland Park?

Our 2019 property listings offer a large selection of 28 vacation rentals near Orland Park. From 16 Houses to 11 Condos/Apartments, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Orland Park for a holiday or a weekend are on HomeAway.

What is the best area to stay when traveling to Orland Park?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Orland Park:

  • Chicago Loop: 765 vacation rentals
  • Lincoln Park: 676 vacation rentals
  • River North: 501 vacation rentals
  • Magnificent Mile: 553 vacation rentals
  • Wicker Park: 688 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular points of interest near where I can stay when traveling to Orland Park?

HomeAway offers a large selection of vacation rentals near lovely places in Orland Park. From HomeAway travelers, the most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Centennial Park Aquatic Center: 196 vacation rentals
  • Orland Park 143rd Street Station: 315 vacation rentals
  • Orland Park 153rd Street Station: 175 vacation rentals
  • Orland Park Sportsplex: 122 vacation rentals
  • Space Golf: 230 vacation rentals

But there are many other points of interest around Orland Park listed on HomeAway where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Orland Park?

Yes, of course. HomeAway has 16 Houses in Orland Park. Our other popular types of vacation rentals in Orland Park include:

  • Condos/Apartments: 11 rentals available
  • Studios: 8 rentals available

Can I find a vacation rental with pool in Orland Park?

Yes, you can select your preferred vacation rental with pool among our 4 vacation rentals with pool available in Orland Park. Please use our search bar to access the selection of vacation rentals available.

    Explore destinations around Orland Park

    1,712 vacation rentals
    159 vacation rentals
    Oak Park
    1,497 vacation rentals
    18 vacation rentals
    Tinley Park
    24 vacation rentals
    78 vacation rentals
    Downers Grove
    77 vacation rentals
    82 vacation rentals
    64 vacation rentals
    124 vacation rentals
    Elmwood Park
    1,271 vacation rentals
    Oak Brook
    119 vacation rentals
    Glen Ellyn
    69 vacation rentals
    Oakbrook Terrace
    99 vacation rentals
    West Chicago
    79 vacation rentals
    Oak Lawn
    177 vacation rentals
    1,608 vacation rentals
    37 vacation rentals
    15 vacation rentals
    Forest Park
    1,375 vacation rentals