Top Illinois Private Sightseeing Tours

On most tours of Chicago, you only see a small selection of the city’s highlights, but you can customize this flexible-duration private tour to suit your schedule and tastes. Choose to discover hidden gems that most tourists miss, snap photos of landmarks like the Willis Tower, explore the Windy City’s shopping scene, and much more.

Take in sweeping views of Chicago from the air during a scenic helicopter flight that offers a premier experience of the Windy City. This private 45-minute flight provides an aerial look at landmarks such as Millennium Park, Navy Park, and Wrigley Field. Ideal for a special occasion, this helicopter tour accommodates up to three people and includes the use of noise-cancelling headsets to hear the pilot clearly.

Discover the vibrant essence of Chicago with a self-guided tour through the Loop, the city’s historic downtown. This journey unveils a blend of striking skyscrapers and hidden architectural gems, allowing you to explore at your own pace. Uncover the rich history from the Great Fire of 1871 to the architectural masterpieces that define the skyline. Stroll past renowned theaters, museums, and captivating public art pieces that contribute to the city’s creative spirit. The Loop offers a unique perspective on Chicago's past and present, whether it's your first visit or a familiar stroll. — Self-guided exploration of Chicago’s historic Loop area — Learn about the city’s architectural innovations and history — Visit iconic landmarks like the Art Institute and Millennium Park — Perfect for first-time visitors or seasoned Chicagoans alike

Walk through Galena, an unusually intact nineteenth-century town carved into a steep river valley, with a self-guided audio tour that plays automatically as you go. Starting downtown, you’ll follow a scenic route past brick storefronts and terraced hillsides using an app with GPS playback. Along the way, you will pass historic landmarks like the DeSoto House Hotel, the bustling Main Street, and the scenic Galena River waterfront. You will uncover how a booming 1820s lead-mining rush built this city, and how fading industry inadvertently preserved it as an outdoor museum of the Victorian Midwest. Explore at your own pace—pause to browse Main Street's galleries, stop for a coffee, or admire the hillside views. The audio resumes whenever you're ready, so you can move freely without keeping up with a group. This is a self-guided experience (no in-person guide). Download the tour in advance and use it anytime—it works offline and follows your location along the route.

Discover the architectural gems of the Windy City from an ideal vantage point—and learn insider facts and stories about the city's top attractions—on this Chicago River cruise. Travel in comfort aboard a boat equipped with both indoor and outdoor seating areas. Covering more than 130 years of architectural history, this tour is the perfect opportunity to see a huge area of the city without the hassle of taxis and public transit.

The Art Institute of Chicago is home to over 300,000 works of art by local and international artists. With so much to explore, it’s easy to get overwhelmed by all of the options during a visit. Sit back and let an expert guide handle the planning as they take you through the museum’s major pieces. Learn about the history and context behind each piece in this culturally enriching experience.

This is your chance to tour the coolest of Chicago's 77 neighborhoods alongside a funny, knowledgeable local guide. You've done the Loop; now it's time to see a whole different side of the city. The tour has 2 options: Wicker Park and Bucktown - faster pace, 2.5 miles of walking. Wicker Park only - slower pace, 1.5 miles of walking

Discover Starved Rock’s canyons, bluffs and seasonal waterfalls on this 3-mile (round trip) guided hike. Listen as the guide tells stories of how Starved Rock got its name along with other legends of the area. Break for lunch at the halfway point. Lunch includes your choice of turkey, ham or veggie wrap, snacks and bottled water. Please wear appropriate clothing and footwear. Hike will vary upon group skill and trail conditions. *Boxed lunch and souvenir drawstring backpack included. Online bookings are subject to additional fees.

Explore historic Springfield and hear Lincoln's history and the stories behind the sites connected to Honest Abe. Go at your own pace and schedule. Advantages of this tour? Our app offers immersive location aware walking tours navigated by your smart phone. Go at your own pace, on your own schedule and on your own terms. It's like a real life tour guide. Best deal in town. We use professional narration, production and music to bring the history to life. Walk at your own pace and hear the stories of what you see. Stop anytime. The tour never expires. Listen remotely after taking the in person tour. You’ll see his old home, his church, his office, the buildings he frequented, murals of Abe and the places named in his honor. And I’ll share with you his coming-of-age story from a one room log cabin in Kentucky to becoming the 16th President of the United states.

Discover Pilsen, one of Chicago’s most vibrant neighborhoods, known for its colorful street art, rich Mexican heritage, historic architecture, and thriving local culture. This locally led Pilsen walking tour offers an authentic, insider experience beyond typical Chicago sightseeing. - Pilsen-based experts with 40+ years of combined experience - Explore iconic sites like 16th Street murals, Thalia Hall, and local cultural landmarks - Official Pilsen tour partner of the Chicago History Museum - Bilingual tours available in English and Spanish - Multiple routes and flexible options, including walking, running, or biking tours

Discover Chicago's soaring ambition and neighborhood soul with your self-guided audio tour, allowing you to explore America's most architecturally significant city at your own pace. Begin at Millennium Park where Anish Kapoor's Cloud Gate reflects the skyline that pioneered skyscraper design and continues to push architectural boundaries today. Wander along the Chicago Riverwalk where boat tours explain how the city reversed the river's flow and rebuilt in steel and stone after the Great Fire of 1871. Marvel at the ICAs world-class collection. Explore the Magnificent Mile's shopping and historic Water Tower, then discover the vibrant neighborhoods where Polish, Mexican, and African American communities have shaped Chicago's culture. Experience the blues at clubs where Muddy Waters and Buddy Guy defined a genre, then savor deep-dish pizza in the taverns that perfected this Chicago original.

Our tour will take you through Millennium Park, starting at the Millennium Park Welcome Center. We’ll wander past shining sculptures, playful fountains, and peaceful gardens, all while soaking in the city’s energy, ending at Queen’s Landing, where the city meets the lake, and the skyline stretches as far as you can see. You'll learn the history of the city, see the sites, learn about what you are seeing and be guided step by step by our walking tour app.

Have only a limited amount of time to explore the Windy City? Leave the planning to someone else with this convenient SUV transfer service. Meet your private driver at a time and place that work best for you, and set off: You’ll be dropped off directly at top Chicago landmarks like Navy Pier, Wrigley Field, Michigan Avenue, and Millennium Park, with time for solo sightseeing at each stop.

Discover the wild heart of Chicago on our guided walking tour through Lincoln Park, where nature and history meet in one unforgettable experience. What sets our tour apart is the seamless blend of three iconic destinations—the Peggy Notebaert Nature Museum, the lush Lincoln Park Conservatory, and the vibrant Lincoln Park Zoo—curated into one dynamic, story-filled journey led by a knowledgeable local guide. You'll marvel at the butterflies in flight, wander through exotic gardens under glass, and encounter wildlife from around the world—all while uncovering the hidden history and surprising beauty of this beloved urban oasis. Whether you're a first-time visitor or a lifelong Chicagoan, this tour offers fresh insights, natural wonders, and photo-worthy moments at every turn. Book now and see why Lincoln Park is one of Chicago’s most treasured gems!

See the best of the Windy City, all in just half a day—and learn the stories behind its best-known sights—on this private tour. In the morning, meet your driver at your Downtown hotel, hop aboard your private vehicle, and set off with a tour guide in tow. You can look forward to seeing sights like Grant Park, Navy Pier, and Buckingham Fountain—and stopping for photo opportunities along the way.

Explore the sights and skyscrapers of Chicago’s spectacular Riverwalk on this private, self-led smartphone walking tour. Upon booking, download the app and receive a password to access your tour; once it’s on your phone, it is valid for an entire year. Set off at a time that works best for you: see highlights like the Merchandise Mart, Wrigley Building, Vietnam Veterans Memorial, and much more.

Discover many of Chicago's best-known landmarks—and explore without breaking a sweat—on this private electric bike tour. Meet your guide right at the Buckingham Fountain, grab your e-bike and helmet, and get ready to explore. You'll view Lakefront landmarks like the Field Museum and Adler Planetarium, will zip right along the waters of Lake Michigan, and will stop to soak up picture-perfect views of the Chicago skyline.

Explore haunted Chicago at your own pace and schedule. Go anytime. Why take this tour? -It's like an in person tour guide, only it's on your phone. -Tour at your own pace and schedule -Professionally produced, narrated and musically edited immersive experience -Guided by technology. Put your phone in your pocket as the smart phone tour guided you with voice turn by turn. -Great deal -See and learn about Chicago's haunted spots, tragic events, fires, and the spirits that stayed behind. -Listen again after taking the tour. -The tour never expires, go or listen (after the on location tour) anytime. This haunted adventure is a smart phone guided on location tour. You go to the first stop, open the tour, enter your experience code and press play. From there you are guided turn by turn through Huntsville. The app knows your location and seamlessly guides you each step of the way.

Channel your inner detective on this immersive, self-guided scavenger hunt through Chicago’s Loop! Step back to 1923 as you gather clues, solve a murder mystery, and unlock secrets of Prohibition-era Chicago. Your group receives a mystery kit, then follows a story-driven trail at your own pace—no app required. Observe real landmarks and hidden clues as you work together, making this ideal for friends, families, and groups seeking a hands-on, flexible adventure. The perfect blend of history, teamwork, and local intrigue in the heart of Chicago.

Experience Chicago’s glowing skyline and scenic lakefront on a private, fully personalized night tour. Travel in comfort with your English-speaking driver, who shares stories and insights about the city’s architecture, neighborhoods, and history as the skyline comes alive after sunset. Begin along the Magnificent Mile, where illuminated skyscrapers and elegant streets create a stunning urban scene. Continue to the Chicago River for reflections of iconic buildings, then visit Navy Pier with its sparkling Ferris wheel and waterfront views. Drive along Lake Shore Drive to admire the dramatic skyline over Lake Michigan, and finish at Adler Planetarium for one of the city’s most spectacular panoramic night views. This flexible, door-to-door private tour offers a relaxed, immersive way to enjoy Chicago’s landmarks and lakefront illuminated under the night sky.

See Abraham Lincoln as you’ve never seen him before with this self-guided walking tour of historic Springfield. Stroll through the 16th president’s old neighborhood, see the home where he lived before heading to the White House, and stop by his old law office! As you explore these historic sites, your audio guide will reveal the man behind the myth. So get your top hat ready and embark on a picturesque stroll worthy of the history books! After booking, check your email/text to download the separate Audio Tour Guide App by Action while connected to WiFi or mobile data. Enter the password, download the tour, and enjoy it offline. Follow the audio instructions and route from the designated starting point. New, Lifetime access, no expiry. Use it anytime, on any trip, as many times as you want. This isn't an entrance ticket. Check opening hours before your visit.

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.

We create custom walking tours for groups of all sizes and interests, blending delicious food experiences with rich historical storytelling. From downtown explorations for high school students, to tavern tours tracing Chicago’s beer history, to local neighborhood food tours, every tour is crafted to be engaging, flavorful, and unforgettable.