What are the top family-friendly attractions in Orland Park, IL?

The Orland Park Recreation Center offers a wide range of activities for kids, including swimming, sports, and arts and crafts. The Centennial Park is a great place for a picnic or a family walk, and it also has a playground and a splash pad. The Orland Park Public Library also hosts many family-friendly events throughout the year.

What are the best Airbnb and vacation rentals in Orland Park, IL?

Luxurious Townhome , Orland -Huntington Rental and Orland Park -Huntington Ct are the most popular Airbnb and vacation rentals in Orland Park, IL among travelers.

When is the best time to book a vacation rental in Orland Park, IL?

The best time to book a vacation rental in Orland Park is during the shoulder seasons, in the spring or fall. You'll avoid the crowds and the higher prices of the summer months, but you'll still enjoy pleasant weather. The summer months are popular for families with kids, and the fall is a great time to see the changing leaves.

What are the most popular Airbnbs in Orland Park, IL?

Among the Airbnbs in Orland Park, IL, Luxurious Townhome , Orland Park- Huntington Rental and Lovely 3 Bedroom Town House Fully Furnished/wi-fi are the most popular ones.

What events or festivals should visitors check out in and around Orland Park, IL?

The Orland Park Village Center hosts a variety of events throughout the year, including the Orland Park Summerfest and the Orland Park Holiday Festival. The nearby city of Tinley Park has the popular Route 66 Ribfest in June, and the Chicagoland Speedway hosts NASCAR events throughout the year.

What are the best vacation rentals with a pool in Orland Park, IL?

Luxury 1 Bedroom Near Orlandsquare Mall , Lovely - Spacious 2 Bedroom Unit and Orland Park Oasis are the best vacation rentals with a pool in Orland Park, IL.

What are the best budget-friendly activities in Orland Park, IL?

The Orland Park Public Library offers free programs and events for all ages, including book clubs, movie nights, and craft classes. The Centennial Park is a great place for a free picnic or walk, and it also has a playground and a splash pad. The Orland Park Village Center has a variety of free events throughout the year, like concerts and farmers markets.

What are the best rentals for families and kids in Orland Park, IL?

The best rentals for families and kids in Orland Park, IL are Orland -Huntington Rental , Orland Park -Huntington Ct and Orland Park- Huntington Rental .

What are the best restaurants with local dishes in Orland Park, IL?

Orland Park has a variety of restaurants serving local dishes, but you'll find a great selection of Chicago-style pizza. Some local favorites include Lou Malnati's Pizzeria, Gino's East, and Pizzeria Bebu. For a more casual experience, try the Orland Square Mall food court, with its variety of options.

What are the best rentals or Airbnbs with a jacuzzi in Orland Park, IL?

The best vacation rental or Airbnb with a jacuzzi in Orland Park, IL is Luxury 1 Bedroom Near Orlandsquare Mall .

What are the best walking or cycling routes in Orland Park, IL?

The Centennial Park has a paved walking and biking path that circles the park. You can also enjoy a scenic walk or bike ride along the Des Plaines River Trail, which runs through Orland Park. The Orland Park Village Center is a great place to start a walk or bike ride, with its many shops and restaurants.

Are there pet-friendly attractions in Orland Park, IL?

Centennial Park is a great option for pet owners, with its large open space, paved walking paths, and dog park. Many restaurants in the Orland Park Village Center have outdoor patios that are pet-friendly.

What are the benefits of choosing a vacation rental in Orland Park, IL?

Vacation rentals offer more space and privacy than hotels, making them a great option for families or groups. They often come with kitchens, allowing you to save money on dining out. You can also find rentals with amenities like pools, hot tubs, and fireplaces, which can enhance your stay.

Orland Park, IL Vacation rentals & Airbnb

Orland Park, IL

08/10 – 09/09

$194/nighttotal: $5820 (30 )

Grade A Safe Working Class Neighborhood - Brand New Just Updated.

3 2

apartment , Oak Lawn

This 3-bedroom, 2-bathroom Oak Lawn apartment accommodates up to 6 guests and is located near Lake Michigan and Marquette Park, with easy access to the Moraine Valley Community College Fine and Performing Arts Center.
Enjoy year-round comfort with air conditioning and heating in this spacious rental, featuring one king and two queen beds, and convenient amenities like hair dryers in each bathroom.

Orland Park, IL

06/27 – 07/04

$163/nighttotal: $1141 (7 )

Lowkey Getaway In Town

1 2

apartment , Matteson

This 2-bedroom, 1-bathroom condo in Matteson offers a peaceful retreat in a quiet neighborhood, providing convenient access to local amenities and serving as a perfect base for exploring the area. This apartment accommodates up to 4 guests and features internet, air conditioning, a kitchen, and parking, ideal for a relaxing family vacation.

Orland Park, IL

07/02 – 07/05

$759/nighttotal: $2277 (3 )

* Extended Stay* Country Club Hills Fhs Rental

1 6

apartment , Country Club Hills

This spacious home is located in the south suburbs, just minutes from I-57 and I-80, making it easy to explore the Chicago metropolitan area. The surrounding area offers a quiet and peaceful ambiance, perfect for a relaxing getaway.
This 5-bedroom, 3-bathroom house can comfortably accommodate up to 12 guests. The house is equipped with a fully stocked kitchen, a large backyard, and a variety of entertainment options, including an arcade cabinet, air hockey table, and pinball machine.

Orland Park, IL

07/02 – 07/05

$560/nighttotal: $1680 (3 )

Cozy 4br 2ba Worth Home

4 6

house , Worth

This Worth home is located 8.1 miles from Midway International Airport and offers convenient access to Chicago's major attractions, all within an 18-mile radius, including Guaranteed Rate Field and the Museum of Science and Industry.
This house provides 130 square feet of living space with four bedrooms, two bathrooms, and a fully equipped kitchen, accommodating up to 12 guests with air conditioning and free WiFi.

Orland Park, IL

06/27 – 07/04

$649/nighttotal: $4543 (7 )

Country Club Hills Fhs Rental

1 2

apartment , Country Club Hills

This spacious home is conveniently located in the south suburbs, just minutes from I-57 and I-80, making it easy to explore the surrounding areas of Tinley Park, Flossmoor, and Homewood. This 5-bedroom, 3.5-bathroom house comfortably accommodates up to 12 guests, perfect for families and groups. The home features a fully equipped kitchen, a dedicated gaming area with a 50" TV, arcade cabinet, air hockey table, and pinball machine, as well as over 50 board games and playing cards for hours of entertainment.

9.6 40 reviews

Orland Park, IL

07/02 – 07/05

$436/nighttotal: $1308 (3 )

Nice Suburban Living

4 6

apartment , Olympia Fields

This spacious Olympia Fields home, five blocks from both the Olympia Fields Country Club and the train station, offers convenient access to golf and public transportation.
The 2,600-square-foot house features a finished basement, a backyard with gazebo and grills, a fully equipped kitchen with dishwasher, and can comfortably accommodate eight guests with large-screen TVs and resort-style amenities including a spa.

9.2 45 reviews

Orland Park, IL

07/24 – 07/26

$305/nighttotal: $610 (2 )

Peaceful Two Bedroom Condo

1 7

apartment , Chicago Ridge

This two-bedroom apartment in Chicago Ridge is located in a safe and quiet neighborhood with easy access to public transportation. The apartment features a fully equipped kitchen, a comfortable living area, and a private garden, making it an ideal choice for families and groups of up to six.

9.8 8 reviews

Orland Park, IL

06/27 – 07/04

$400/nighttotal: $2800 (7 )

Richton Park Rental

1 2

apartment , Richton Park

This spacious four-bedroom, two-bathroom house in Richton Park offers a peaceful neighborhood setting with easy access to local amenities and attractions in the Chicago metropolitan area.
The 4-bedroom home comfortably sleeps 8 guests and features a fully equipped kitchen, multiple LCD TVs with streaming services, a private fenced yard, and ample parking, plus family-friendly amenities like a pack 'n play and highchair.

Orland Park, IL

08/10 – 09/09

$270/nighttotal: $8100 (30 )

Large Mcm Hideaway In The Forest

1 2

apartment , Palos Park

This Palos Park mid-century modern home, situated on 1.25 acres near Swallow Cliff Forest Preserve and its trails, offers easy access to both nature and downtown Chicago (20 miles away).
This four-bedroom, three-bathroom house features a chef's kitchen, fireplaces, a finished basement, and accommodates up to 10 guests, perfect for families or groups enjoying biking, horseback riding, or exploring nearby attractions.

Orland Park, IL

07/02 – 07/05

$727/nighttotal: $2181 (3 )

Matteson Fhs Rental

1 6

apartment , Matteson

**Matteson Apartment**
This apartment is perfect for families or groups visiting Matteson. It is located in a quiet neighborhood, just a short walk from the city center. The apartment has two bedrooms, two bathrooms, and can accommodate up to 12 guests. It is fully equipped with a kitchen, air conditioning, and a garden. Guests can also enjoy free Wi-Fi and parking.
The apartment is also pet-friendly, so you can bring your furry friends along on your vacation. The garden is perfect for relaxing or playing with the kids. And the free parking is a great convenience, especially if you are renting a car.

8.0 2 reviews

Orland Park, IL

06/27 – 07/04

$302/nighttotal: $2114 (7 )

Soothing 3-bedroom House With Ac In Richton Park

3 2

apartment , Richton Park

This 3-bedroom, 1-bathroom vacation home in Richton Park is conveniently located near Odyssey Fun World and Orland Square, with Space Golf and Centennial Park Aquatic Center also a short drive away. This residence accommodates up to 6 guests and features a jetted bathtub, air conditioning, and heating for year-round comfort.

Orland Park, IL

07/24 – 07/26

$774/nighttotal: $1548 (2 )

Extended Stay Richton Park Fhs Rental

1 7

apartment , Richton Park

This spacious Richton Park house, ideal for families, offers four bedrooms, two bathrooms, and sleeps eight guests, boasting a fenced yard and convenient street parking.
The property features a fully equipped kitchen, five LCD TVs with streaming services, numerous board games, and child-friendly amenities including a pack 'n play, stroller, highchair, and booster seat.

Compare Vacation Rentals for Families in Orland Park, IL

Make family travel to Orland Park, IL seamless with spacious vacation rentals located just minutes from top city attractions.

10 44 reviews

Orland Park, IL

06/27 – 07/04

$406/nighttotal: $2842 (7 )

3br/2ba + Pull Out Sofa Bed + No Stairs + Backyard

1 2

apartment , Worth

This stylish 3-bedroom vacation rental is located in Worth, just a short distance from the city's main attractions, such as the Worth Museum and the Worth Riverwalk. The home features a fully equipped kitchen, a spacious living area, two bathrooms, a private garden, and parking for up to two vehicles, perfect for a family vacation or a group getaway.

Orland Park, IL

06/27 – 07/04

$542/nighttotal: $3794 (7 )

Richton Park Fhs Rental

1 2

apartment , Richton Park

This 761-square-foot Richton Park home, located in a quiet neighborhood, offers easy access to local amenities and major roadways.
The four-bedroom, two-bathroom house sleeps eight guests and features a fully equipped kitchen, high-speed internet, a fenced yard, and ample entertainment options including multiple TVs, board games, and an arcade cabinet.

Orland Park, IL

08/10 – 09/09

$424/nighttotal: $12720 (30 )

71 M² House ∙ 4 Bedrooms ∙ 10 Guests

4 2

house , Richton Park

House listing for 10 guests. This accommodation is located in Richton Park.
Facilities and services: a dish washer, air conditioning and a washing machine. Take advantage of the Free Parking with this accommodation.

10 4 reviews

Orland Park, IL

07/24 – 07/26

$856/nighttotal: $1712 (2 )

Quaint Ranch With A Gym

1 7

apartment , Mokena

This farm is located in Mokena, a short drive from Chicago, near the I&M Canal, the Mokena Public Library, and the Mokena Park District. The area offers a peaceful escape from the city while being close to amenities.
This rural retreat provides a spacious, relaxing environment for up to 10 guests. It features a fully equipped kitchen, air conditioning, a garden, a fitness center, and parking.

Best Orland Park, IL vacation rentals with parking

10 1 review

Orland Park, IL

07/02 – 07/05

$418/nighttotal: $1254 (3 )

Serenity 3bd Home Free Parking&wine Oversized Yard

2 6

house , Burbank

This house in Burbank offers 2 bedrooms and 1 bathroom, with complimentary WiFi and on-site parking, situated approximately 3.1 miles from Midway International Airport and 10-13 miles from Chicago attractions including Guaranteed Rate Field and the United Center.
This accommodation accommodates up to 13 guests and features a fully equipped kitchen, an oversized yard, and is a non-smoking property managed by a private host.

Orland Park, IL

06/27 – 07/04

$577/nighttotal: $4039 (7 )

Best View And Luxury Style, Located In Downtown

1 2

apartment , Oak Lawn

This Oak Lawn apartment rental boasts stunning panoramic views of Wacker Drive, Lake Michigan, Navy Pier, the Chicago River, and Trump Tower, offering convenient access to downtown Chicago attractions.
The one-bedroom, one-bathroom unit sleeps two guests and features a king-sized bed, fully equipped kitchen, high-speed Wi-Fi, large TV, and access to a swimming pool, jacuzzi, fitness center, and sauna.

10 3 reviews

Orland Park, IL

08/10 – 09/09

$216/nighttotal: $6480 (30 )

Grade A Working Class Safe Neighborhood 3br Up To 6 Guests. Updated & Best Price

3 2

apartment , Burbank

This Burbank vacation rental is conveniently located near Chicago Midway International Airport, a 25-minute drive from downtown Chicago, offering easy access to parks like Cook County Forest Preserves and attractions such as the Museum of Science and Industry and Art Institute.
This three-bedroom, one-bathroom home sleeps six guests comfortably, featuring a full kitchen with dishwasher, washer/dryer, smart TV, free Wi-Fi, ample parking, and enhanced security with three Ring cameras.

10 2 reviews

Orland Park, IL

07/02 – 07/05

$455/nighttotal: $1365 (3 )

Cozy/private 3 Br Nestled On An Acre Of Serenity

3 6

apartment , Tinley Park

This renovated three-bedroom apartment rental in Tinley Park, Illinois, is less than a quarter-mile from I-80, providing easy access to Chicago and nearby attractions like Odyssey Fun World and Centennial Park Aquatic Center.
The 1000-square-foot unit sleeps eight guests and features a fully equipped kitchen with a fridge, microwave, and dishwasher, plus a swimming pool, spa, and on-site parking.

Frequently Asked Questions about vacation rentals in Orland Park, IL

What are the top family-friendly attractions in Orland Park, IL?
The Orland Park Recreation Center offers a wide range of activities for kids, including swimming, sports, and arts and crafts. The Centennial Park is a great place for a picnic or a family walk, and it also has a playground and a splash pad. The Orland Park Public Library also hosts many family-friendly events throughout the year.
What are the best Airbnb and vacation rentals in Orland Park, IL?
Luxurious Townhome, Orland -Huntington Rental and Orland Park -Huntington Ct are the most popular Airbnb and vacation rentals in Orland Park, IL among travelers.
When is the best time to book a vacation rental in Orland Park, IL?
The best time to book a vacation rental in Orland Park is during the shoulder seasons, in the spring or fall. You'll avoid the crowds and the higher prices of the summer months, but you'll still enjoy pleasant weather. The summer months are popular for families with kids, and the fall is a great time to see the changing leaves.
What are the most popular Airbnbs in Orland Park, IL?
Among the Airbnbs in Orland Park, IL, Luxurious Townhome, Orland Park- Huntington Rental and Lovely 3 Bedroom Town House Fully Furnished/wi-fi are the most popular ones.
What events or festivals should visitors check out in and around Orland Park, IL?
The Orland Park Village Center hosts a variety of events throughout the year, including the Orland Park Summerfest and the Orland Park Holiday Festival. The nearby city of Tinley Park has the popular Route 66 Ribfest in June, and the Chicagoland Speedway hosts NASCAR events throughout the year.
What are the best vacation rentals with a pool in Orland Park, IL?
Luxury 1 Bedroom Near Orlandsquare Mall, Lovely - Spacious 2 Bedroom Unit and Orland Park Oasis are the best vacation rentals with a pool in Orland Park, IL.
What are the best budget-friendly activities in Orland Park, IL?
The Orland Park Public Library offers free programs and events for all ages, including book clubs, movie nights, and craft classes. The Centennial Park is a great place for a free picnic or walk, and it also has a playground and a splash pad. The Orland Park Village Center has a variety of free events throughout the year, like concerts and farmers markets.
What are the best rentals for families and kids in Orland Park, IL?
The best rentals for families and kids in Orland Park, IL are Orland -Huntington Rental, Orland Park -Huntington Ct and Orland Park- Huntington Rental.
What are the best restaurants with local dishes in Orland Park, IL?
Orland Park has a variety of restaurants serving local dishes, but you'll find a great selection of Chicago-style pizza. Some local favorites include Lou Malnati's Pizzeria, Gino's East, and Pizzeria Bebu. For a more casual experience, try the Orland Square Mall food court, with its variety of options.
What are the best rentals or Airbnbs with a jacuzzi in Orland Park, IL?
The best vacation rental or Airbnb with a jacuzzi in Orland Park, IL is Luxury 1 Bedroom Near Orlandsquare Mall.
What are the best walking or cycling routes in Orland Park, IL?
The Centennial Park has a paved walking and biking path that circles the park. You can also enjoy a scenic walk or bike ride along the Des Plaines River Trail, which runs through Orland Park. The Orland Park Village Center is a great place to start a walk or bike ride, with its many shops and restaurants.
Are there pet-friendly attractions in Orland Park, IL?
Centennial Park is a great option for pet owners, with its large open space, paved walking paths, and dog park. Many restaurants in the Orland Park Village Center have outdoor patios that are pet-friendly.
What are the benefits of choosing a vacation rental in Orland Park, IL?
Vacation rentals offer more space and privacy than hotels, making them a great option for families or groups. They often come with kitchens, allowing you to save money on dining out. You can also find rentals with amenities like pools, hot tubs, and fireplaces, which can enhance your stay.

Destinations nearby

Choose the Right Vacation Rentals with a Terrace in Orland Park, IL

Enjoy a Orland Park, IL vacation rental with a balcony and stunning city skyline views for a truly memorable stay.

Orland Park, IL

07/24 – 07/26

$868/nighttotal: $1736 (2 )

Ranch Single Level Home Near Downtown Tinley Park

3 7

house , Tinley Park

This ranch home in Tinley Park is located 16 miles from Midway International Airport and within 26 miles of downtown Chicago attractions, including Union Station and the Field Museum.
This 120 square foot dwelling offers 1 bedroom, 1 bathroom, accommodates up to 10 guests, and features a fully equipped kitchen, air conditioning, and complimentary WiFi.

Best Orland Park, IL vacation rentals with air conditioning

Orland Park, IL

06/27 – 07/04

$400/nighttotal: $2800 (7 )

Matteson Rental

1 2

apartment , Matteson

This Matteson apartment is a great choice for travelers seeking a comfortable and convenient stay. With its pet-friendly policy, family-friendly amenities, and ample parking, it caters to a wide range of guests.
The apartment features two bathrooms, accommodating up to 12 guests. It boasts a fully equipped kitchen with modern appliances, air conditioning, and a private garden. Guests can also enjoy access to high-speed internet and a variety of entertainment options.

Orland Park, IL

06/27 – 07/04

$567/nighttotal: $3969 (7 )

Crestwood Fhs Rental

3 2

apartment , Crestwood

This 1,400 square foot ranch-style house is located in Crestwood, IL, a family-friendly southwest suburb of Chicago, offering a quiet neighborhood setting.
This 3-bedroom, 2-bathroom rental accommodates up to 4 guests and features a master suite, a well-equipped kitchen with stainless steel appliances, high-speed internet, and a fenced backyard, making it ideal for families with children.

Orland Park, IL

06/27 – 07/04

$333/nighttotal: $2331 (7 )

Comfortable And Cozy 4br 2ba Home In Worth

1 2

apartment , Worth

This 4-bedroom, 2-bathroom house in Worth, IL offers a spacious retreat with newly installed flooring and central air conditioning, perfect for families and groups seeking a comfortable stay. Located in a tranquil suburban community, it provides easy access to local amenities and is a short drive from Chicago's attractions.
This single-family home accommodates up to 8 guests and features generously sized bedrooms with ample closet space, making it ideal for long-term stays. Pets are welcome, and the property includes internet and a kitchen for your convenience.

9.5 4 reviews

Orland Park, IL

07/24 – 07/26

$725/nighttotal: $1450 (2 )

Ranch Single Level Home Near Downtown Tinley Park

1 7

apartment , Tinley Park

This ranch-style rental is centrally located in Tinley Park, offering convenient access to the Tinley Park Convention Center and a short walk to downtown Tinley Park.
This open-concept dwelling accommodates up to 7 guests across four bedrooms and one bathroom, featuring air conditioning, internet, and a full kitchen for a comfortable stay.

Search vacation rentals in Orland Park, IL from 100+ sites!

Best Vacation rentals and Airbnb offers in Orland Park, IL

Grade A Safe Working Class Neighborhood - Brand New Just Updated.

Lowkey Getaway In Town

* Extended Stay* Country Club Hills Fhs Rental

Cozy 4br 2ba Worth Home

Country Club Hills Fhs Rental

Nice Suburban Living

Peaceful Two Bedroom Condo

Richton Park Rental

Large Mcm Hideaway In The Forest

Matteson Fhs Rental

Soothing 3-bedroom House With Ac In Richton Park

Extended Stay Richton Park Fhs Rental

Compare Vacation Rentals for Families in Orland Park, IL

3br/2ba + Pull Out Sofa Bed + No Stairs + Backyard

Richton Park Fhs Rental

71 M² House ∙ 4 Bedrooms ∙ 10 Guests

Quaint Ranch With A Gym

Best Orland Park, IL vacation rentals with parking

Serenity 3bd Home Free Parking&wine Oversized Yard

Best View And Luxury Style, Located In Downtown

Grade A Working Class Safe Neighborhood 3br Up To 6 Guests. Updated & Best Price

Cozy/private 3 Br Nestled On An Acre Of Serenity

Frequently Asked Questions about vacation rentals in Orland Park, IL

Destinations nearby

Choose the Right Vacation Rentals with a Terrace in Orland Park, IL

Ranch Single Level Home Near Downtown Tinley Park

Best Orland Park, IL vacation rentals with air conditioning

Matteson Rental

Crestwood Fhs Rental

Comfortable And Cozy 4br 2ba Home In Worth

Ranch Single Level Home Near Downtown Tinley Park

Search vacation rentals in Orland Park, IL from 100+ sites!

Best Vacation rentals and Airbnb offers in Orland Park, IL

Grade A Safe Working Class Neighborhood - Brand New Just Updated.

Lowkey Getaway In Town

* Extended Stay* Country Club Hills Fhs Rental

Cozy 4br 2ba Worth Home

Country Club Hills Fhs Rental

Nice Suburban Living

Peaceful Two Bedroom Condo

Richton Park Rental

Large Mcm Hideaway In The Forest

Matteson Fhs Rental

Soothing 3-bedroom House With Ac In Richton Park

*Extended Stay* Richton Park Fhs Rental

3br/2ba + Pull Out Sofa Bed + No Stairs + Backyard

Richton Park Fhs Rental

71 M² House ∙ 4 Bedrooms ∙ 10 Guests

Quaint Ranch With A Gym

Serenity 3bd Home Free Parking&wine Oversized Yard

Best View And Luxury Style, Located In Downtown

Grade A Working Class Safe Neighborhood 3br Up To 6 Guests. Updated & Best Price

Cozy/private 3 Br Nestled On An Acre Of Serenity

Ranch Single Level Home Near Downtown Tinley Park

Matteson Rental

Crestwood Fhs Rental

Comfortable And Cozy 4br 2ba Home In Worth

Ranch Single Level Home Near Downtown Tinley Park

Extended Stay Richton Park Fhs Rental