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Orland Park

Located 25 miles southwest of Chicago’s Loop, Orland Park offers the best of both worlds: big city opportunities and vast green spaces. Orland Park is one of the premier communities in the State of Illinois that has been twice chosen by Money Magazine as one of America’s Best Places to Live and as one of the Chicago Area’s Best Places to Live by Chicago Magazine. The town routinely ranks as one of the top 10 safest cities in Illinois and offers amenities geared toward providing an excellent quality of life for residents. Orland Park features an extensive park system, biking and walking paths, community events, great shopping, restaurants, and more.

From the Community

Featured Trip Itineraries

Southland's Entertainment & Nightlife

Southland's Top Things To Do Outside

10 Fun Things To Do in Orland Park, Illinois

Recommendations

Outdoor4.6/5

Centennial Park, Orland Park

Located in Orland Park, Centennial Park is a traveler's paradise! With sprawling green lawns perfect for picnicking and relaxing, it's an ideal spot to unwind. The park offers a range of recreational activities, including sports courts, walking trails, and a fabulous splash pad for the little ones to cool off. Don't miss the beautiful gazebo, a perfect backdrop for Instagram-worthy moments. Visit Centennial Park and let the adventure begin!

Outdoor4.1/5

Lake Sedgewick

Nestled in the heart of Orland Park, Lake Sedgewick is a hidden gem for nature lovers. With its shimmering waters and lush greenery, this picturesque spot offers a soothing escape from the bustling city. Whether you're looking to paddleboard, picnic by the shore, or simply unwind with a leisurely stroll, this tranquil oasis has something for everyone. Get ready to dive into relaxation at Lake Sedgewick!

Shop4.3/5

Orland Square

Orland Square is a shopper's paradise in the heart of Orland Park! With over 150 stores, delicious dining options, and fun entertainment spots, it’s perfect for family outings or solo adventures. From chic boutiques to major brands, there’s something for everyone! Don't forget to catch a movie at the theater after a shopping spree. Happy exploring!

Landmark4.4/5

Marcus Orland Park Cinema

Welcome to Marcus Orland Park Cinema! Located in Orland Park, IL, this vibrant theater is a haven for movie lovers. With its prime location on South La Grange Road, it offers a fantastic selection of films, comfy seats, and delicious snacks. Prepare for an unforgettable movie experience that will leave you smiling and wanting more. Lights, camera, action!

Self Care4.2/5

Sportsplex

Looking for a sports haven in Orland Park? Look no further than Sportsplex! Located at 11351 W 159th St, this action-packed destination offers everything for the sports enthusiast - from basketball and volleyball courts to batting cages and a turf field. Get ready for an adrenaline rush like no other!

Outdoor4.4/5

Crescent Park

Crescent Park in Orland Park is a serene retreat featuring lush landscapes, picturesque walking trails, and inviting picnic spots, making it an ideal destination for families and nature lovers alike.

Shop

John Humphrey House

Nestled in Orland Park, the John Humphrey House is a charming historical site showcasing 19th-century architecture and local history, making it a delightful stop for history enthusiasts and curious travelers alike.

Landmark5/5

Stellwagen Farm

Stellwagen Farm in Orland Park is a charming destination, showcasing picturesque landscapes, vibrant community events, and an authentic farmhouse experience that captures the essence of Midwestern agriculture, making it a must-visit for locals and tourists alike.

Landmark5/5

Dean’s Greens

At Dean’s Greens, visitors can enjoy a beautiful garden center and nursery, offering an expansive selection of plants, expert gardening advice, and stunning landscapes that make it a local favorite for nature enthusiasts.

Landmark4.5/5

Jacob Hostert Log Cabins

Tucked away in Orland Park, Jacob Hostert Log Cabins offers a charming glimpse into early American architecture, featuring beautifully preserved log structures that invite visitors to appreciate history amidst a scenic natural backdrop.

Landmark4.2/5

Centennial Park Aquatic Center (Orland Park Pool)

Centennial Park Aquatic Center offers a vibrant aquatic experience with its stunning water slides, lazy river, and family-friendly amenities, making it a must-visit destination for summer fun in Orland Park.

Eat$$$3.9/5

Dave & Buster's Orland Park

At Dave & Buster's Orland Park, enjoy a vibrant blend of arcade games, delicious dining, and exciting sports viewing, making it the ultimate destination for fun and entertainment for all ages.

Landmark4.7/5

Crystal Tree Golf and Country Club

Nestled in Orland Park, Crystal Tree Golf and Country Club boasts a stunning championship golf course and luxurious amenities, making it a premier destination for golf enthusiasts and social gatherings alike.

Landmark4.5/5

Silver Lake Country Club

Nestled in Orland Park, Silver Lake Country Club boasts stunning fairways and a rich history, making it a premier destination for golf enthusiasts and a perfect backdrop for unforgettable events.

Outdoor4.6/5

Orland Grassland

Nestled in Tinley Park, Orland Grassland offers breathtaking prairies and diverse wildlife, making it a perfect spot for nature lovers and outdoor enthusiasts seeking tranquility and scenic beauty just moments away from urban life.

Outdoor4.8/5

Lake Katherine Nature Center

Nestled in Palos Heights, Lake Katherine Nature Center and Botanic Gardens is a hidden gem for nature enthusiasts. Explore the lush trails, canoe on the serene lake, or discover a variety of native plants and animals. This enchanting destination promises endless photo opportunities, captivating wildlife encounters, and a memorable adventure for all ages. Don't forget your binoculars and sense of wanderlust!

Eat$$$4.4/5

Cooper’s Hawk Winery & Restaurant

Nestled in the heart of Orland Park, Cooper's Hawk Winery & Restaurant is a traveler's paradise. With a lively and vibrant atmosphere, it's the perfect place to unwind after a long journey. From the moment you step in, you'll be greeted by friendly staff, exceptional wines, and a delectable menu that will tantalize your taste buds. It's a delightful escape that's not to be missed!

Eat$$$4.6/5

Bonefish Grill

Get ready to dive into deliciousness at Bonefish Grill in Orland Park! Located on South La Grange Road, this seafood hotspot will transport you to coastal dining heaven. Indulge in their famous Bang Bang Shrimp or savor their melt-in-your-mouth wood-grilled fish. With a lively atmosphere and friendly staff, Bonefish Grill is a must-visit for seafood lovers in the Chicago area!

Eat$$4.3/5

Carrabba's Italian Grill

Get ready to embark on a mouthwatering journey at Carrabba's Italian Grill! Located at 1001 75th St in Woodridge, IL, this charming eatery offers an authentic taste of Italy. Bite into their delicious wood-fired pizzas, savor their tantalizing pasta dishes, and don't miss their irresistible desserts. With a lively atmosphere and friendly staff, Carrabba's is the perfect spot to indulge in Italian delights!

Stays

Stay4.25/5

La Banque Hotel

Nestled in charming Homewood, IL, La Banque Hotel is a delightful blend of vintage elegance and modern comfort. Enjoy beautifully designed rooms, cozy lounges, and a trendy bar that pops with personality! Perfect for exploring local gems or just unwinding, this hotel invites travelers to kick back, relax, and soak in that warm hospitality. Check it out!

Stay4.2/5

Hampton Inn & Suites Chicago Southland-Matteson

Nestled in the heart of Matteson, the Hampton Inn & Suites Chicago Southland is your comfy haven away from home! With cozy rooms, a splashy indoor pool, and a delicious complimentary breakfast, you’ll start each day off right. Plus, it’s just a hop away from shopping and dining. Perfect for adventures or relaxation—your choice!

Stay4.15/5

Holiday Inn Chicago – Tinley Park by IHG

Welcome to Holiday Inn Chicago – Tinley Park, where comfort meets convenience! Delight in modern rooms and a splash of fun with the indoor pool. Kick back at the on-site restaurant and enjoy easy access to local attractions. Whether you’re here for business or pleasure, this hotel is your perfect home base for a fantastic adventure in Tinley Park!

Stay3.95/5

Homewood Suites by Hilton Orland Park

Get ready for a memorable stay at Homewood Suites by Hilton Orland Park! Located just off La Grange Road, this hotel is a traveler's dream. With spacious suites, free breakfast, and a refreshing indoor pool, it's perfect for families or solo adventurers. Plus, enjoy easy access to Orland Park's shopping and dining scene. Unwind, relax, and let the good times roll at Homewood Suites!

Stay3.95/5

DoubleTree by Hilton Hotel Chicago - Alsip

Nestled in a vibrant location, DoubleTree by Hilton Hotel Chicago - Alsip offers a warm welcome with its famous chocolate chip cookies, modern amenities, and exceptional service, making it an ideal destination for both business and leisure travelers.

Stay3.5/5

Comfort Inn & Suites near Tinley Park Amphitheater

Nestled just a hop away from the Tinley Park Amphitheater, Comfort Inn & Suites is your cozy retreat! Enjoy spacious rooms, a complimentary breakfast, and friendly vibes. After an epic concert, unwind in the indoor pool or recharge with free Wi-Fi. Perfect for music lovers and adventurers alike—pack your bags for a memorable stay! 🎶✨

Stay2.8/5

Red Roof Inn Chicago - Alsip

Welcome to the vibrant Red Roof Inn Chicago - Alsip! Conveniently located at 12340 S Cicero Ave, our hotel is a haven for explorers. With comfy rooms, free Wi-Fi, and pet-friendly policies, we've got you covered. Grab a tasty bite at nearby restaurants and dive into the lively city scene. Get ready for an unforgettable adventure in Alsip, IL!

Stay4.7/5

Sybaris Frankfort

Experience the perfect getaway at Sybaris Frankfort! Nestled in beautiful Frankfort, IL, this adults-only haven offers luxurious suites with private pools, whirlpools, and steam rooms. Indulge in a romantic, indulgent escape, complete with cozy fireplaces and enchanting ambiance. With its convenient location and exquisite amenities, Sybaris Frankfort is a paradise for couples seeking a memorable retreat.

Stay3.9/5

The Champagne Lodge & Luxury Suites

Welcome to The Champagne Lodge, a luxurious getaway nestled in Willowbrook, IL. This adult-only boutique hotel is the perfect spot for those seeking a romantic and indulgent stay. With beautifully-themed suites featuring whirlpool tubs, fireplaces, and saunas, you'll be transported to a world of pure relaxation. Indulge in a glass of bubbly while enjoying the unique amenities of this enchanting retreat. Cheers to a memorable experience at The Champagne Lodge!

Things To Do
Provided by

5/5

Personalized Private Driving Tour of Chicago for 1-3 People

Looking for a convenient way to see Chicago rain or shine? Discover Chicago and its remarkable landmarks in a unique way with a private tour designed just for you. Enjoy the comfort of a private car as a friendly local guide takes you through the city’s iconic architecture, vibrant neighborhoods, and scenic drives. This tour allows you to explore at your own pace while receiving insider tips and local insights. - Private tour for 1-3 people with a local guide - Explore iconic landmarks and vibrant neighborhoods - Flexible itinerary tailored to your interests - Enjoy the comfort of a private car with scenic drives

$395.00

5/5

Chicago Small Group City Tour

Experience Chicago like never before on your all-inclusive small group city tour, led by an expert guide. Discover iconic landmarks, hidden gems, and vibrant neighborhoods with personalized attention and insider knowledge. Enjoy a hassle-free day with transportation, tickets, and lunch included. Explore Millennium Park, Navy Pier, and more, with plenty of photo opportunities and fascinating stories. Book now for an unforgettable Chicago adventure!

$465.00

4.6/5

Chicago City Private Tours

Ready to explore Chicago like never before? Whether you have just a couple of hours or a full day, my personalized city tours offer a unique and unforgettable experience, customizable from 2 to 8 hours. From the iconic skyline to hidden gems off the beaten path, I’ll take you on a journey that captures the heart and soul of this incredible city. I’ll also capture professional photos along the way, so you can take home memories of your adventure. With flexible pickup options, including quick tours during layovers at O'Hare, I make it easy to see the best of Chicago, no matter how much time you have. Book your tour today and let me show you the Windy City through the eyes of a local!

$199.00

4.5/5

4 h 30 mins

Small-Group Tour of Chicago Neighborhoods: North and South Side

This unique tour of Chicago will allow for tourist to see most of Chicago’s 77 neighborhoods and city parks. There is no other tour that tours multiple neighborhoods in Chicago. Some tours show 1 or 2 neighborhoods, we travel through the South Side, North Side, Southwest, Northwest and a portion of Downtown showing more then 10 neighborhoods and attractions.

$125.00

4.4/5

African American Heritage Tour of Chicago

This tour visits the homes of Louis Farrakhan, the former home of Elijah Muhammad and the former home of Muhammad Ali. We will pass by and take pictures at the home the 44th President of the Unites States, Barack Obama. Visitors will see the home of Reverend Jessie Jackson and Ida B. Wells along with Thomas Dorsey and Mahalia Jackson. Visitors have the option to stop at the new Obama Presidential Library for 3 hours. We give a chronological history of blacks coming to Chicago after the civil war to today. We provide facts, figure and insight. The tour guide was part of the Great Migration; it is like listening to his story firsthand. You will get well thought-out analysis on why Chicago is like it is today. This is a dialogue driven tour where you are given information and asked questions. You will be a part of this tour. Most importantly, you will laugh. After the tour, if wanted, we will stop at a soul food restaurant to dine for an hour. Come tour with us!

$125.00

4/5

Chicago Explorer Pass: 35+ Things To Do - Includes 360 CHICAGO

Access top Chicago attractions, tours and activities with Go City's Explorer Pass. Save on entry to your choice of up to seven top things to do. Hop-on a Big Bus tour for an introduction to the city, check out the panoramic views from the 103rd floor at SkyDeck Chicago or 94th floor of 360 CHICAGO, take in the stunning cityscape on an Architecture River Cruise - with over 35 options, there's something for everyone and 30 days validity means you can explore at your own pace. Choose your pass type (2, 3, 4, 5, 6 or 7 attractions), review your digital guide to plan your adventure and make reservations where needed, then enjoy direct entry by simply showing the QR code for admission. Explore Chicago knowing that you've saved on your sightseeing compared to buying attraction tickets separately - it really is the best Chicago pass for flexibility and savings.

$84.00

3.5/5

Chicago Attractions Pass: Save up to 50% - Includes 360 CHICAGO

Enjoy admission to more than 30 of Chicago's most popular attractions with Go City's All-Inclusive Pass. Go City lets you create your own itinerary and save far more than if you were to purchase individual attraction tickets. Take a hop-on hop-off bus tour of the Windy City, admire the stunning views from Skydeck Chicago, and much more. You can visit as many attractions as you like over the course of 1, 2, 3 or 5 days. Access your Pass in the Go City App and simply simply show it at the gate or ticket office to gain admission. The App acts as your digital guidebook including attraction information and details on which attractions require reservations in advance.

$149.00

3/5

One Day Galena and Dubuque Tour from Chicago

Explore the charming towns of Dubuque and Galena on this enriching day trip from Chicago. Begin your journey along the scenic Mississippi River in Dubuque, where you can enjoy free time to stroll, have lunch, or even take a cable car ride for breathtaking views. Continue to Galena, a beautifully preserved historic town where 80% of the buildings are listed on the National Register of Historic Places. Here, you’ll visit the Ulysses S. Grant Home and take in the serene beauty of Grant Park. With a total travel distance of 325 km from Chicago, this tour offers the perfect blend of history, scenery, and relaxation before heading back to the city.

$450.00

Private Shopping Tour from Chicago to Chicago Premium Outlets

Comfortable Roundtrip Tour from your hotel in Chicago to Chicago Premium Outlets - plays host to luxury boutiques and stores selling everything from clothes and accessories to cosmetics and home essentials. Its world-class boutiques showcasing collections from prestigious local and international designers make for a truly memorable shopping experience. Add to all these a unbeatable prices, and a handful of trendy cafés and restaurants, and what you’ll get is one of the best shopping destinations in and around the Chicago. After you finish your shopping you will be picked up and will be delivered directly to your hotel in Chicago. All our vehicles are fully licensed and insured. We are happy to provide child seats in our cars for all ages upon request. Vehicles are clean inside and outside; our drivers are well-dressed and unfailingly attentive to our guests. They speak English. They will greet you with a name sign and will help with luggage.

$291.57

5 h

Private Shopping Tour from Chicago to Fashion Outlets of Chicago

Comfortable Roundtrip Tour from your hotel in Chicago to Fashion Outlets of Chicago - plays host to luxury boutiques and stores selling everything from clothes and accessories to cosmetics and home essentials. Its world-class boutiques showcasing collections from prestigious local and international designers make for a truly memorable shopping experience. Add to all these a unbeatable prices, and a handful of trendy cafés and restaurants, and what you’ll get is one of the best shopping destinations in and around the Chicago. After you finish your shopping you will be picked up and will be delivered directly to your hotel in Chicago. All our vehicles are fully licensed and insured. We are happy to provide child seats in our cars for all ages upon request. Vehicles are clean inside and outside; our drivers are well-dressed and unfailingly attentive to our guests. They speak English. They will greet you with a name sign and will help with luggage.

$264.53

Private Shopping Tour from Chicago to Lighthouse Place Outlets

Comfortable Roundtrip Tour from your hotel in Chicago to Lighthouse Place Premium Outlets - plays host to luxury boutiques and stores selling everything from clothes and accessories to cosmetics and home essentials. Its world-class boutiques showcasing collections from prestigious local and international designers make for a truly memorable shopping experience. Add to all these a unbeatable prices, and a handful of trendy cafés and restaurants, and what you’ll get is one of the best shopping destinations in and around the Chicago. After you finish your shopping you will be picked up and will be delivered directly to your hotel in Chicago. All our vehicles are fully licensed and insured. We are happy to provide child seats in our cars for all ages upon request. Vehicles are clean inside and outside; our drivers are well-dressed and unfailingly attentive to our guests. They speak English. They will greet you with a name sign and will help with luggage.

$370.34

5 h

Private Tour Art Institute of Chicago Guided Museum

Experience our Private Excursion tailored exclusively for you! Embark on a serene journey through the picturesque landscapes of USA as you make your way to the heart of the city. Upon your arrival, meet your seasoned tour guide, ready to lead you on an enchanting tour of Art Institute of Chicago. Discover the awe-inspiring allure of Art Institute of Chicago, marvel at the grandeur of Chicago, and capture iconic moments and many more. Leave the details to us as we escort you on an extraordinary adventure, crafting memories that will stand the test of time!

$1,058.12

Chicago VIP Private Tour

Discover the very best of New York City in one unforgettable experience! From the majestic Statue of Liberty and the historic Brooklyn Bridge to famous neighborhoods, hidden gems, and picture-perfect skyline views — this tour captures it all. Enjoy guided stops at iconic landmarks, learn fascinating stories from your local guide, and experience the true energy of the city that never sleeps. Perfect for first-time visitors or anyone wanting to see it all, this experience blends history, culture, and unbeatable photo ops at every turn. Come ready to explore, snap amazing pictures, and make lasting memories on the ultimate NYC adventure!

$499.00

Guided Hike at Starved Rock and Matthiessen Park

Reconnect with nature on a rejuvenating day trip through Starved Rock and Matthiessen State Parks. This guided adventure blends relaxation with light hiking, perfect for entrepreneurs and anyone seeking a mental reset. Discover scenic canyons and stunning waterfalls as you explore the great outdoors, and wind down with a group dinner at Starved Rock Lodge Lounge, where stories and reflections are shared. Conclude your day with a stop for souvenir shopping and ice cream, leaving you refreshed and inspired. - Enjoy guided exploration of Starved Rock’s trails and Matthiessen’s waterfalls - Group dinner at Starved Rock Lodge Lounge (meals not included) - Suitable for ages 16+, with a total hiking duration of 4 hours - Includes bottled water and light snacks, with optional photo sessions

$45.00

Chicago-Milwaukee Small Group Tour

Discover the charm of Milwaukee on a small group day trip from Chicago! Enjoy a guided city tour, explore iconic landmarks, and experience the legendary Miller Brewery with exclusive behind-the-scenes access and tastings. With comfortable transport, expert local insights, and a friendly group atmosphere, this all-inclusive adventure is perfect for curious travelers. Book now for a memorable escape to Milwaukee's culture and flavors!

$485.00

Chicago Private Tour to Lake Geneva and Anderson Japanese Gardens

Discover the natural beauty of Lake Geneva and the tranquil Anderson Japanese Gardens on this private 10‑hour getaway from Chicago. Begin your day with convenient pickup and enjoy a scenic drive as your expert guide shares insights about the region. Once at Lake Geneva, you’ll have free time to explore its picturesque lakeside paths, historic estates, and even take an optional cruise. Afterward, immerse yourself in the serene pathways of Anderson Japanese Gardens, where elegant bridges, koi ponds, and peaceful landscapes await. This personalized tour offers a relaxing and enriching experience, perfect for couples, families, and small groups seeking a nature‑filled escape.