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Crestwood

Welcome to Crestwood, IL—a charming suburban gem! This community boasts vibrant parks, cozy cafes, and delightful shops. Enjoy family-friendly attractions like the nearby Chicago Ridge Mall or take a stroll through the scenic Crestwood Park. With a friendly vibe and convenient access to the Windy City, Crestwood is perfect for a delightful day trip or a weekend getaway!

From the Community

Recommendations

Attraction4.6/5

Ozinga Field

Step up to Ozinga Field, where baseball dreams come alive! Nestled in Crestwood, IL, this charming ballpark is home to the Windy City ThunderBolts. With delightful concessions and a lively atmosphere, the sun-soaked stands are perfect for family fun or a romantic date. Grab a hot dog, cheer loud, and soak in the local sports vibe! ⚾️✨

Outdoor4.3/5

Walker Park

Outdoor4.6/5

Playfield Park

Nestled in Midlothian, Playfield Park offers a vibrant blend of lush greenery, scenic walking paths, and engaging playgrounds, making it a cherished gathering spot for families and nature lovers alike.

Outdoor5/5

Caesar Park

Landmark3.6/5

Crestwood Illinois Soccer Club

Outdoor4.1/5

Nancy Benedetto Dog Park

Self Care3.9/5

Southwest Ice Arena

Landmark4.8/5

Kiki's Gaming Lounge

Culture4.2/5

Crestwood Public Library

Crestwood Public Library is a community gem, offering a welcoming atmosphere, extensive collections, and engaging programs that inspire lifelong learning and creativity, making it a must-visit destination for residents and visitors alike.

Landmark3.4/5

Village of Crestwood

Drink$$$4.5/5

Thirsty Beaver

Drink$$$4.7/5

The Point Sports Bar & Grill

Eat$$4.4/5

The Brazen Head

Eat$$$4.4/5

Culver’s

At Culver’s in Crestwood, savor the iconic ButterBurgers and fresh, creamy frozen custard, all served with genuine Midwestern hospitality, making it a must-visit for burger enthusiasts and dessert lovers alike.

Eat$$$4.1/5

STACKED

STACKED in Crestwood offers a unique dining experience with its innovative menu featuring mouthwatering stacked burgers and creative comfort food, making it a must-visit destination for food enthusiasts seeking bold flavors and a lively atmosphere.

Eat4.3/5

In The Game Hollywood Park

Step into the lively world of In The Game Hollywood Park in Crestwood, IL! Packed with thrilling arcade games, laser tag, and bowling, it's a wonderland for all ages. Grab some tasty bites at the café, and unleash your inner kiddo! Perfect for family outings or a fun night with friends—this is the ultimate entertainment hotspot!

Eat$$$4/5

At The Office Sports Bar & Grill

Cafe$$$4/5

Dulce Mami Cafe Crestwood

Eat4/5

Dunkin'

Eat$$4.7/5

Nutrition Lab

Things To Do
Provided by

5/5

4 h

Private Chicago Guided Tour with Hotel Pickup

One of the best ways to explore a city is with a private tour. This tour isn't any different. Have your driver and separate tour guide take you around the most important sites and locations of Chicago. Being a private tour, stop whenver you want to take pictures and also explore by foot specific locations. Pick up is included from your hotel or place of choice inside the city and downtown Chicago. Please include this information as well as a contact number when booking. This private tour will give you a great experience to get to know Chicago. This is a 4 hour private tour with driver and separate tour guide. During this tour, you will explore great locations in Chicago like the Richard J. Daley Center. There will also be a photo stop at the Lakefront Trail and South Michigan Avenue. Don't miss the Grant Park, Cloud Gate and of course the Downtown / The Loop. This private tour will finish off at your hotel in Chicago.

$765.90

5/5

Private City Tour 6-10ppl

PRICE IS PER VEHICLE AND YOU MAY BRING UP TO 10 PASSENGERS TOTAL. Thank you for contacting Chicago Private Tours! We would love to help your group discover Chicago. Our services include pick up from your downtown Chicago hotel, a 3-4 hour private City Tour in a chauffeured vehicle, and the services of one of our knowledgeable guides. This means you will have two people working with you the entire time, allowing you to get out of the vehicle with your guide at several stops. These stops include, but are not limited to Millennium Park, Lincoln Park Conservatory, Museum Campus, and more. The tour will be interactive and entertaining, covering history, architecture and culture. We share stories to bring Chicago's rich history to life. Once the tour concludes, we will drop your group off at your preferred, downtown Chicago location.

$770.00

5/5

9 h

Iconic Action Film and Movie Locations 1 Day Tour in Chicago

From the Gotham chaos in The Dark Knight to the explosive battles of Transformers, Chicago’s skyline has played a starring role in countless blockbusters. On today’s Chicago Film and Television Tour, you'll explore the city through the lens of movie magic. Begin at one of Chicago’s most iconic theaters, seen in The Blues Brothers and Transformers. Stroll through downtown streets flanked by skyscrapers featured in the Joker’s money truck chase scene in The Dark Knight. At Union Station, relive the dramatic staircase sequence from The Untouchables, where Kevin Costner’s character battles criminals as a baby carriage tumbles down. Visit the University of Chicago, whose Gothic architecture and academic prestige have made it a popular filming location. Along the way, admire Chicago’s rare mechanical lift bridges and architectural wonders that make the city a perfect backdrop for filmmakers. In Chicago, every corner holds a scene, and every street tells a story—waiting for you to explore.

$158.00

5/5

168 h

Chicago and All MidWest Self Guided AI Audio Tours for 7 Days

With this AI app, you're no longer restricted to crowded group tours or rigid scripts. Explore iconic Chicago sites like Millennium Park and the Magnificent Mile—or dive deep into 1920s mobster hangouts and hidden Prairie Style masterpieces. Ask about literally anything that catches your eye—from a Gilded Age historic district to a secret jazz club or a towering steel-and-glass skyscraper. The Windy City's deepest secrets are entirely yours to uncover. Point & Discover: Snap a photo of any monument or museum masterpiece to instantly receive a captivating and accurate story. It’s like having a historian in your pocket! Ultimate Freedom: Navigate seamlessly with interactive map-based audio tours. Your schedule, your pace, your rules. Choose Your Vibe: Select a narrator persona that matches your style—from a deep-diving scholar to a fun companion for the kids. Get Started: 7 Days of Premium Access available instantly for iPhone and Android.

$11.46

5/5

4 h

Fun Chicago Bike Tour with Pizza, Hot Dogs, Cupcakes and Beer

Take an adventurous half-day journey through the most interesting Chicago neighborhoods with a friendly private guide and see the city from a new perspective riding a bike. Dive into the atmosphere of the city’s movement and combine it with tasting the most delicious and iconic treats of the Chi after whetting your appetite, absorbing the unique beauty of the city. Discover more sights in a shorter time using a bike Get a true taste of the City by the Lake following the tips of a local guide Discover iconic neighborhoods and be entertained with historical insights. Learn about the peculiarities of local cuisine and its origins.

$179.00

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

5/5

4 h

Chicago Private Neighborhoods Tour to Lincoln and Hyde Park

Discover the vibrant neighborhoods and cultural districts of Chicago on a private, fully personalized tour. Travel in comfort with your English-speaking driver, who shares local stories, historical insights, and highlights the architecture and communities that shape the city’s unique character. Begin in the Gold Coast Historic District with its elegant mansions and tree-lined streets, then explore Lincoln Park with its scenic paths, gardens, and historic zoo. Visit Wrigley Field to experience Chicago’s sports culture, followed by Hyde Park and the University of Chicago, known for its stunning architecture and intellectual heritage. Conclude in Chinatown, a lively cultural district with colorful streets, markets, and traditional restaurants. With a flexible, door-to-door itinerary, this private tour offers a relaxed, immersive way to experience Chicago’s history, culture, and diverse neighborhoods.

$217.89

4.9/5

4 h

Chicago's West Side Foodie Ride Bike Tour

Take a detour off the beaten path, and explore the flavors of Chicago’s delicious West Side with Bobbys's Bike Hike & Food Tours, America's longest running city bike tour company, who recently ranked as Top 20 Food Tours in the World by TripAdvisor and Top 10 Food Tours in America by USA Today! This 4-hour guided food and bike tour is the perfect way to learn more about Chicago's immigrant neighboroods and taste authentic Chicago culinary dishes along the way. You’ll explore the cultural cuisines of historic Fulton Market district, Ukrainian Village, Wicker Park, and Lincoln Park. The Chicago Bike and Food tour finishes with a chocolate tasting in Old Town. You’ll learn the history of these beautiful neighborhoods and the tradition behind each of the dishes we sample. Ride through Chicago's gorgeous and unique neighborhoods, plus our legendary Lakefront Trail! There is no better way to explore Chicago than by bike! All equipment is included on this food and bicycle tour of Chicago.

$99.00

4.9/5

4 h 30 mins

Chicago Bike & Classic Food Tour: Bikes, Bites & Views - Adults

Taste all of Chicago’s classic eats on this 4 1/2 hr Adults-only guided food & bicycle tour! Join the expert guides of Bobby’s Bike Hike, America’s first city bike tour company, on this exciting & informative adventure which recently ranked Top 20 Food Tours in the World by TripAdvisor. The journey is a leisurely paced 13mi & includes deep dish pizza, Chicago-style hot dog, Italian Beef, & dessert. Upgrade to sample local craft beer! On the DAY version of bike tour, you’ll drink in the sights of Chicago’s beautiful northside neighborhoods, including the Lakefront and Wrigleyville, home to our Chicago Cubs baseball team. On the NIGHT bike tour, you'll ride through the major downtown attractions & see the lights of Buckingham Fountain, Millennium Park and the glorious skyline. Cruise the Lakefront Trail, one of the most popular waterfront bike paths in the country. Don’t miss out on this fun tour! You’ll leave with a profound understanding of Chicago, even if you only came for the food.

$89.00

4.9/5

Chicago Private Custom City Tour with Hotel Pick Up

PRICE IS PER VEHICLE AND YOU MAY BRING UP TO 5 PASSENGERS. Thank you for contacting Chicago Private Tours! We would love to help your group discover Chicago. Our services include pick up from your downtown Chicago hotel, a 3-4 hour private City Tour in a chauffeured vehicle, and the services of one of our knowledgeable guides. This means you will have two people working with you the entire time, allowing you to get out of the vehicle with your guide at several stops. These stops include, but are not limited to Millennium Park, Lincoln Park Conservatory, Museum Campus, and more. The tour will be interactive and entertaining, covering history, architecture and culture. We share stories to bring Chicago's rich history to life. Once the tour concludes, we will drop your group off at your preferred, downtown Chicago location.

$539.00

4.9/5

3 h

Chicago's Ultimate City Bike Tour of Top Downtown Attractions

Get acquainted with Chicago’s most iconic landmarks on this riotous guided Chicago bicycle tour! Join the expert guides of Bobby’s Bike Hike, America’s longest-running city bicycle tour company, on this exciting and informative adventure. Over the course of a 3-hour bike ride (traversed at a nice leisurely pace), you’ll get up close and personal with Chicago’s legendary Museum Campus, Grant Park, Chicago Riverwalk, Lakefront and Millennium Park. You’ll become intimately familiar with Soldier Field, The Adler Planetarium, Buckingham Fountain, The Pritzker Pavilion, and Cloud Gate (the formal name of Chicago’s dearly-beloved “Bean”). This tour is perfect for first time visitors looking to see all of the classic hotspots, and for returning guests looking to understand more about the landmarks they know and love. Hop on two wheels, and come make memories that are sure to last a lifetime! All equipment included on this Bicycle Tour of Chicago.

$59.00

4.9/5

3 h

Bike Tour of Chicago's Lakefront Neighborhoods

This is the tour that made Bobby famous! Bobby’s Bike Hike is America’s longest-running city bicycle tour company, and has been repeatedly recognized for excellence by National Geographic, USA Today, The Associated Press, Conde Nast Traveler, and more! Bobby’s now offers over a dozen specialized tours, but The Lakefront Neighborhoods Chicago Bike Tour is what started it all. Join one of Bobby’s expert guides on this 3-hour bicycle tour through Chicago’s beautiful North Side Lakefront neighborhoods. See the ever-rising skyscrapers of Streeterville, the deluxe residential mansions of the Gold Coast, the cozy artists’ village of Old Town, and the rolling greenery of Lincoln Park. You’ll finish off with a cruise down the world-famous Lakefront Bike Trail, one of the most popular waterfront bike paths in the nation. This leisure-paced journey is sure to make memories that’ll last a lifetime! This Bicycle Tour of Chicago is kid-friendly and all equipment (bikes, helmets) is included.

$59.00

4.8/5

4 h

Chicago Family Food and Bike Tour with Top Attractions

This Chicago Food & Bike tour is perfect for the entire family, put on by Bobby’s Bike Hike, whose food tours in just the past year have ranked as Top 10 in America by USA Today and Top 20 in the world by Tripadvisor. Biking is easy in Chicago because of it's miles of bike trails, flat terrain and easy connections between attractions. We’ll be sampling from each of Chicago’s well known and unique foods -- deep dish pizza, a true Chicago hot dog, and a dessert for good measure. You’ll learn the history behind the foods and also get a taste for some of Chicago’s most popular downtown districts as we cruise through the Gold Coast, Chicago Riverwalk, Millennium Park, Buckingham Fountain, Museum Campus, Navy Pier and along the Lakefront. Whether day or night, you'll get fantastic views of the skyline and feel the city's vibrant energy. Veggie options available. Bikes, Helmets and all Child Equipment included on this engaging bicycle tour of Chicago.

$79.00

4.7/5

2 h

2 Hour Chicago Landmarks & Lakefront E-Bike Tour

Discover the unique flavor of our Absolutely Chicago E-Bike Tour. Experience the city's rich history, stunning architecture, and breathtaking views as you pedal along on our state-of-the-art electric bikes. From iconic landmarks to hidden gems, this unforgettable adventure combines adventure, warmth, and loads of fun. Immerse yourself in the vibrant atmosphere of Milton Olive Park, the wonder of Soldier Field, and capture unforgettable photos at the majestic Buckingham Fountain. With flexible routes and a focus on hidden treasures, our tour offers a truly unique and memorable experience through the heart of Chicago.

$72.15

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

4.6/5

1 h 30 mins

Lakefront Segway Tour in Chicago

Segways are amazingly fun, and Chicago's lakefront, parks, and skyline are absolutely gorgeous! Add our smart, entertaining tour guides to the mix, and you have the experience of a lifetime!

$59.50

4.5/5

3 h

The Devil in the White City: A Haunting History Tour

We are Chicago's first and best Devil in the White City tour, offering the history, legends and lore surrounding H.H.Holmes, the World's Fair and Victorian Chicago. We visit Prairie Avenue, Chicago's Victorian "Easy Street" and site of the Fort Dearborn Massacre, travel to the World's Fairgrounds and the Midway Plaisance at the University of Chicago, and make the notorious trek to the site of Holmes' "Murder Castle."

$74.99

4.4/5

216 h

Chicago CityPASS®

Experience 5 top attractions and save up to 50% with Chicago CityPASS® tickets. One simple purchase removes the stress of planning, so you can relax and enjoy your memories in the making. With 9 days to use your tickets, you’ll have plenty of time to explore the best sights. Chicago CityPASS® bundles one-time admission to 5 attractions. Includes: • Chicago's Famous Aquarium • Skydeck Chicago Plus choose 3 more attractions. • Shoreline Sightseeing Architecture River Tour • Field Museum • 360 CHICAGO Observation Deck • Griffin Museum of Science and Industry • Art Institute of Chicago • Adler Planetarium

$144.00

4.4/5

5 h

Frank Lloyd Wright Oak Park Architecture Tour from Chicago

Explore the architectural genius of Frank Lloyd Wright on a private, fully personalized tour in Chicago, home to the world’s largest collection of his buildings. Travel in comfort with your English-speaking driver, who shares insights into Wright’s life, ideas, and influence on modern architecture. Begin at the Frank Lloyd Wright Home & Studio, where he lived and developed many revolutionary designs. Continue through the Oak Park to admire beautifully preserved Prairie School homes and early residential works. Visit Unity Temple, one of Wright’s most celebrated modern religious buildings, then return toward Chicago to see The Rookery Building with its grand lobby and intricate design. Conclude at Robie House, a masterpiece of Prairie School architecture showcasing Wright’s signature horizontal lines and integration with the landscape. This flexible experience offers architecture enthusiasts a relaxed way to explore Wright’s legacy and the evolution of modern American design.

$217.89

4.4/5

Chicago Helicopter Tour: City to Shoreline

Your journey begins with a southeast departure from the Vertiport, offering early views of the city’s iconic skyline. Flying east, you’ll head toward the lakefront and cruise south along the shoreline, passing Soldier Field, the Museum Campus, and continuing down to the historic Museum of Science and Industry in Hyde Park. From there, the route turns north, following Lake Michigan’s edge past Navy Pier, the John Hancock Center, and up to Montrose Harbor; a favorite city escape with marinas and beaches. You’ll then loop south once more, enjoying a sweeping view of Chicago’s lakefront before heading west to return to the Vertiport. It’s a dynamic tour showcasing both downtown and the scenic south shore in one unforgettable flight.