Top Chicago How to Get Around - page 5

Discover one of Chicago’s most picturesque, historic neighborhoods—and learn all about the buildings that make it an architectural standout—on this small-group walking tour of Wicker Park. Meet your guide in the morning, and set off on foot: you’ll discover the 19th-century workers’ cottages that fill the neighborhood, will admire local landmarks like mansions and historic baths, and will learn all about the city’s architectural history.

Enjoy an immersive way to discover Chicago's more recent architectural heritage with this small-group walking tour. Led by your architectural expert guide, you'll discover many of the Windy City's modern, postmodern, and other newer structures, including works by architects like Mies van der Rohe, Bertrand Goldberg, and beyond. As you go, your guide will point out the buildings many visitors overlook, and share stories from their history you wouldn't otherwise hear.

Instead of sticking to land-based tour or only taking to the water, combine both to see more than you’d be able to with just one on this hop-on-hop-off bus tour and architecture cruise combo package. Explore at your own pace while snapping photos of the city from the open-top bus, and take in the city skyline from the Chicago River.

Considered Chicago’s original “Millionaire’s Row,” Prairie Avenue in the Near South Side is renowned for its Gilded Age mansions—and this tour makes exploring easy (and delightfully spooky). In the evening, meet your guide in front of the Glessner House, and set off with ghost-hunting gear to accompany you. In between spotting highlights including the Marshall Field Jr. Mansion and the Henry B. Clarke House, you’ll hunt for specters and hear ghost stories.

Leave behind Chicago’s buzz and see the Windy City as it used to be, some 150 years ago. The Oldtown Triangle—one of the most beloved ‘hoods in the city—survived the Great Chicago Fire of 1871, and it still stands today as a beacon to history. With your guide at the helm, you’ll witness fantastic architecture, national landmarks, and hear stories of the city’s often wild past.

Set sail on our flagship vessel, where style meets comfort in a Tiki Chic atmosphere. Your adventure begins on the iconic Chicago Riverwalk, where you’ll board a beautifully appointed boat featuring two climate-controlled decks, two full bars, two bathrooms, and both indoor and outdoor viewing areas—perfect for soaking in the sights no matter the weather. As you sip a refreshing beverage, enjoy the rare experience of transiting the historic Chicago Locks—a must-see for locals and visitors alike. Once you glide into the open waters of Lake Michigan, you’ll be treated to breathtaking views of Chicago’s world-famous skyline, framed by the gentle breeze and city lights. Looking to elevate your cruise? Upgrade to the exclusive Admiral’s Lounge, where you’ll enjoy top-shelf spirits, including selections from the Captain’s Private Reserve, all in a more intimate, upscale setting. This is more than just a boat ride—it’s a uniquely Chicago experience you won’t forget!

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.

Enjoy a fun and time-saving way to explore the best of Chicago on this small-group, guided Segway tour. Visit popular Grant Park and see Buckingham Fountain, plus optimal views of the Windy City skyline. Glide along the Lakefront Trail, taking in the Field Museum, Shedd Aquarium, Soldier Field, and beyond. Guided Segway training and helmets are included on this beginner-friendly outing.

Glide through Chicago by moonlight on a haunted Segway tour. Follow your costumed guide and small group as they show you the sites of some of the most gruesome murders and disasters in Chicago's history. See iconic landmarks lit up at night and hear about the mysterious, haunted history of this storied city.

Enjoy a uniquely adventurous way to explore Chicago with this zombie apocalypse-themed smartphone scavenger hunt game. Upon booking, download the app and set off at a time that works best for you, with help from your remote interactive guide. You’ll be given a list of challenges to solve and objects to find to beat the zombies, all while exploring some of Chicago’s most popular corners.

Don’t just explore Chicago’s best-known landmarks—put your problem-solving skills and competitive side to the test with this private scavenger hunt experience. The game will be conducted via your smartphone, with a live, remote guide to accompany and assist you. As you go, hunt for clues, discover unusual sights, take part in bonus challenges—and see where you team falls on the national leaderboard.

Get a chance to experience the Windy City from multiple vantage points during this two-hour, small-group boat tour in Chicago. Hop aboard a secure and reliable US Navy-built Rigid Inflatable Boat (RIB) for a unique sightseeing experience. Pass by iconic sights such as Navy Pier, Soldier Field, Fort Dearborn, Vietnam Memorial, Wolf Point, Shedd Aquarium, and more, all while comfortably seated in a group capped at only six people.

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.

Descend below street level to discover Chicago’s famed subterranean Pedway—and pair your adventure with stops at top landmarks and above-ground attractions. Meet your guide downtown, and head underground: stroll the Chicago Loop's Pedway and learn about its history, see the city’s famed Tiffany dome, visit the origin of Route 66, and finish at one of Chicago’s most iconic sculptures.

Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seats in town! Grab a cool drink from our full bar, relax, and enjoy a leisurely evening sail past the brilliant and beautiful Chicago nighttime skyline. Windy provides the accompanying sound track, over the ship sound system coordinated fireworks display, amazing show! Rain or Shine event. no umbrellas are allowed to be opened underway. Tall Ship Windy, located on Navy Pier, and we have a ticket booth and dock, in front of the Billy Goat Bar and Grill. Arrive early, as fireworks crowds are huge! expect travel delays.

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.

Bored of traditional walking tours? Try an experience that mixes sightseeing with an engaging game in this murder mystery tour through Chicago. Play as a detective and a suspect as you wander through various neighborhoods and see the city. Learn about the real legends and crimes of Chicago while you try to solve a murder.

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.

Set sail for a memorable experience on Lake Michigan with a Signature Chicago Brunch Cruise that is as scenic as it is delicious! You'll savor a chef-prepared buffet and bottomless mimosas while in our comfortable indoor areas. Marvel at unparalleled views of Chicago’s iconic landmarks, such as Willis Tower and Navy Pier from inside or enjoy fresh breezes on the open-air decks. This fun-filled brunch cruise experience for all ages is complete with lively DJ entertainment, dancing, games, and a fully stocked cash bar. Elevate your weekend plans with a one-of-a-kind brunch cruise on the water!

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.

Discover the creative side of Chicago beyond the city limits with this small-group tour of suburban hidden gems! Visit charming historic districts, offbeat local landmarks, striking public art, scenic waterfronts, and under-the-radar eateries as your expert guide shares insider stories you won’t find in guidebooks. With transport included and group size kept small, it’s a relaxed, camera-worthy way to explore unique neighborhoods, architectural treasures, and distinctive local culture. Ideal for repeat visitors, adventure seekers, or anyone curious to see more than the Magnificent Mile.

It isn’t a trip to Chicago without tasting deep-dish pizza—and this private tour for food lovers will introduce you to true Chicago-style pizza, plus other Windy City specialties. Meet your guide downtown, and be sure to come hungry: You’ll eat hot dogs, Italian beef sandwiches, pizza, donuts, and more. Along the way, see highlights like the Wrigley Building and Magnificent Mile, and learn more about the city’s history and culture.

Chicago’s “L,” or elevated train, is an icon of public transportation and a major feature of the Loop neighborhood. On this interactive tour, you’ll learn about the railway’s history while experiencing it as a rider. Meet your guide in the morning and set off with just a small group for company. As you ride between stops, you’ll also view Chicago icons like the Willis Tower, and will learn about the city’s architectural history.

There are many spots around Chicago where you can take in views of the city, but setting sail on Lake Michigan lets you take in the full scenic skyline. On this boat tour, hop aboard a traditional vessel and learn how to hoist a sail, or just relax on board at the fully stocked bar.