Top Illinois Tours by Duration - page 2

Explore a new side of Chicago and the city's gangster past on this mafia tour in a coach vehicle. Drive around the Windy City to see where Al Capone, The Untouchables, Hymie Weiss, John Dillinger, and more famous figures hung out. There are ample chances to get out of the bus and pose for pictures in front of a historic courthouse, among other infamous sites.

Discover some of the Windy City’s spookiest ghost stories—and step back in time to the era of gangsters, bootleggers, jazz performers, and more—on this small-group walking tour. Meet your guide in Chicago’s Lincoln Park neighborhood, and set off after dark. You’ll visit supposedly haunted former burial grounds, pubs, theaters, and more—and will hear about macabre legends and unexplained happenings as you go.

Have only a short stay planned in Chicago? Make the most of your time in the Windy City, and see more of the city in less time, when you book a private driving tour of Chicago. Pick between several convenient tour times, and meet your guide and driver directly at your hotel. Over the course of your excursion, you’ll make stops at highlight attractions like the Lincoln Park Conservatory, Millennium Park, and Museum Campus. You’ll also learn about Chicago’s history and can spy other remarkable sights as you go.

Outside of Italy, few places in the world are as famous for their pizza as Chicago. Eat like a local as you travel off the beaten path to savor the city's best pizza, traveling by bus so you can cover more food hot spots in less time. Discover the science behind ingredient selection and baking as you sample slices from historic pizzerias, and take away plenty of tips to enhance your eating in Chicago.

See (and taste) the best of Chicago in just half a day on this bicycle tour of the Windy City’s most iconic sights and neighborhoods. Follow your guide along the Lakefront Trail, admire views of Millennium Park, and discover the Chicago Riverwalk. As you go, stop to sample culinary classics of Chicago, like deep-dish pizza, a true Chicago hot dog, and a tasty dessert for good measure.

Exploring Oak Park, Illinois, where Frank Lloyd Wright resided during the crucial early years of his career, offers a captivating journey through the evolution of his architectural vision. The neighborhood is renowned for hosting the largest collection of Wright's work. Built between 1892 and 1909, your stroll through the neighborhood takes you to several private homes and Wright’s studio providing a fascinating glimpse into his creative progression and the birth of the iconic Prairie style. View the exteriors of nearly a dozen of Wright’s structures. This one-hour walking tour covers nearly a dozen homes on Chicago and Forest avenues and on Elizabeth Court.

Tower above the Windy City’s world-famous skyline with pre-booked admission to 360 Chicago—a great way to avoid long ticket lines. Ascend one of the tallest buildings in North America aboard its lightning-fast elevator, and be rewarded with bird’s-eye views of Chicago and Lake Michigan. You can also upgrade to the Sip and View ticket, which includes one drink at the newly renovated CloudBar. Once onsite, you can purchase tickets to TILT, 360 Chicago's top attraction.

Get the most out of your trip to Chicago as you enjoy discount access to five of the city’s top attractions with the CityPASS®. This easy-to-use mobile ticket grants you free entry into top-tier sights including the Chicago's most famous aquarium and Skydeck Chicago, plus your choice of admission to three of the following attractions: Field Museum, Art Institute of Chicago, Museum of Science and Industry, 360 CHICAGO Observation Deck, Adler Planetarium, or Shoreline Sightseeing Architecture River Tour.

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.

Get to know the foodie Chicago neighborhood made famous by "The Bear"—and taste your way through some of the Windy City's best bites—on this small-group walking tour of River North. Visit locals-loved hotspots that represent the best of the city's dining scene, and Be sure to come hungry: You'll try everything from tacos and Italian beef sandwiches to deep-dish pizza, all while learning about the neighborhood's history and food culture.

Discover the dark side of the Windy City on this nighttime crime history bus tour of Chicago. Through your expert guide's rich storytelling, immerse yourself in tales of notorious mobsters like Al Capone, Frank Nitti, and Bugs Moran as you explore infamous crime scenes including the site of the St. Valentine’s Day Massacre.

Step aboard a boat for a comprehensive cruise that details the history of Chicago's architecture. Enjoy views of the Chicago skyline accompanied by architecture-focused commentary that points out each of the landmark buildings. As you cruise through Lake Michigan, snap photos of you and your party against the stretch of Chicago's 26-mile shoreline.

Calling all fans of the paranormal, this evening ghost bus tour of Chicago takes you into the city’s darkest recesses—and reveals a side of the city few others get to experience. Travel with ease between locations where hauntings are reported to have taken place and listen to chilling tales delivered by your guide. The City Cemetery, the site of the notorious St. Valentine’s Day massacre, and more are all included.

On this small-group Windy City bike tour, you won't just pedal past the lakefront neighborhoods of Chicago's North Side—you'll see more of the city than you could if exploring on your own. Follow a local guide along quiet streets, city parks, and scenic beaches, starting at Lake Shore Drive and continuing along Rush Street and the Magnificent Mile. As you go, glimpse offbeat attractions like the Playboy Mansion, Oprah’s penthouse, and the Victorian houses of Old Town.

Get an insider’s introduction to one of Chicago’s most distinctive neighborhoods during this half-day private tour of the South Side. Learn about Hyde Park’s blue-collar history and rich African American heritage. See where the atomic bomb was developed on the University of Chicago’s campus. You’ll also pass through Mexican communities in Pilsen, as well as Little Italy and Greektown.

Experience the ultimate Private Shameless TV Location Tour with the convenience of hotel pick and drop-off, allowing you to sit back, relax and enjoy the ride while exploring Chicago's iconic filming locations. Tour Highlights: - Visit the exterior of Gallagher House (Private Residence) - Visit the exterior of Sheila's House (Private Residence) - Visit the exterior of Kelvin & Veronica's House (Private Residence) - Explore Millennium Park and take a photo in front of the famous "Bean" Sculpture, a popular Chicago Landmark. - Explore the Chicago Cultural Center renowned for its stunning architecture, including the world's largest Tiffany stained-glass dome. This tour offers a unique blend of Shameless fandom and Chicago exploration, while prioritizing respect for private residences and local communities.

Learn about the history and legends surrounding the 1893 Chicago World's Fair and notorious criminal H.H.Holmes on a half-day tour inspired by the popular book ‘The Devil in the White City.’ Explore important locations such as the Prairie Avenue Historic District, Jackson Park, Midway Plaisance Park, and the ‘Murder Castle’ of H.H. Holmes as you learn more about the World's Columbian Exposition and Victorian Chicago.

See the towers, piers and iconic landmarks along the Chicago River on an architectural cruise through the heart of the city. Enjoy complimentary refreshments on deck as you cruise down the historic waterway, while listening to fun stories and facts throughout the tour. Spot gargoyles that keep watch high above the city, and buildings that range from Neoclassical to Art Deco. Take in over fifty sites from Lake Point Tower to the Navy Pier, and see the Second City from the water.

See Chicago your way with flexible hop-on hop-off tickets designed to suit every sightseeing style. Explore the Windy City at your own pace, hopping off to visit top attractions such as Millennium Park, Navy Pier, the Magnificent Mile, and the Chicago Riverwalk while enjoying onboard commentary that adds context to what you see. Perfect for first-time visitors or those short on time, this tour offers flexibility and ensures you don’t miss any of Chicago’s highlights. You can also upgrade your experience to enjoy extra sightseeing time and a panoramic sunset tour for unforgettable skyline views.

Zoom along the shoreline of Lake Michigan, zipping past famous landmarks as you go, during this exhilarating speedboat ride in Chicago. Climb aboard your 2,000-horsepower speed boat at Navy Pier, then hang on for the ride of a lifetime, as you zip past famous attractions like the Willis Tower, Grant Park, and Buckingham Fountain, pausing to learn a little about the history and architecture of the Windy City along the way.

Admire the ornamental facades and intricate interiors of the Windy City's art deco buildings during this in-depth walking tour of the vibrant Loop. This small-group tour will introduce you to some of the city's highlight architectural landmarks and its rich history, all in a single excursion. As you go, get an up-close look at landmarks that many other tours overlook—and learn insider stories from your architecture-expert guide.

Experience Chicago like never before—and see more of the sights in less time—on this immersive bicycle tour. Ride the walking- and cycling-only Chicago Lakefront Trail to and through the city’s beautiful beaches, parks and lagoons. See the coast of Lake Michigan and the one-of-a-kind Chicago skyline, plus bustling Navy Pier, popular North Avenue Beach, the 35-acre Lincoln Park Zoo and Conservatory, and much more. The use of a bike and helmet is included.

Arrange for a stress-free ride to O'Hare International Airport (ORD) or Midway Airport (MDW) with this private transfer service. Meet your professional chauffeur at your hotel in downtown Chicago (or other Chicagoland destinations), and relax on the journey to the airport in a private sedan or minivan. You can leave the navigation to someone else, and reach the airport relaxed and in time for your flight.

Taste food from around the world—and immerse yourself in some of the Windy City's most characterful, locally beloved neighborhoods—on this half-day biking and tasting tour of Chicago. With just a small group for company, you'll follow your guide through the city streets, stopping for views of Chicago’s famous architecture and seeing more than you could if traveling on foot. In between, stop for bites like Polish pierogis, locally made chocolates, and Mexican tacos.