Chicago Holiday Package

Tourist Attractions to Add To Your Chicago Holiday Package

2-Hour Guided Segway Tour of Chicago

Dive into two exhilarating hours where your inner child takes the lead! Embark on our dynamic Segway exploration and witness the stunning allure of Chicago like never before. Navigate alongside an expert guide who’ll lead you to the city's hotspots. Marvel at the majestic Chicago skyline as you gently roll through the bustling downtown, absorb the grandeur of serene Grant Park, circle the iconic Buckingham Fountain, and meander by the insightful Museum Campus. Glide gracefully along the Lake Michigan waterfront with its alluring vistas. Alternatively, choose our captivating Riverwalk excursion to traverse the banks of the winding Chicago River. You'll encounter the splendor of Navy Pier, the architectural finesse of Chicago's emblematic bridges, experience the pulse of the historical Michigan Avenue, and whisk by the charming sights of Millennium Park. Each journey promises an unforgettable adventure etched into your memory forever, bringing to life the city's magic that will leave you in awe long after the tour ends.

Chicago Favorites Ultimate Food and Walking Tour

Experience the essence of Chicago with our expertly guided tour designed for visitors and food enthusiasts alike. Immerse yourself in a delightful journey that combines the exploration of Chicago's culinary delights with the discovery of the city's most celebrated sights. As you meander through bustling downtown streets, our seasoned guides will indulge your taste buds with quintessential Chicago fare, including savoring a hearty slice of deep-dish pizza, relishing a classic Chicago-style hot dog, enjoying succulent Italian beef, and indulging in scrumptious brownies. While you feast, you'll also witness the splendor of Millennium Park, the historic charm of State Street, the grandeur of the Chicago Theatre, the elegance of the Chicago Riverwalk, Michigan Avenue's Magnificent Mile, and the iconic Wrigley Building. Delight in the rich tapestry of stories that weave together the city's food heritage and architectural marvels. Each ticket purchased comes with an additional perk: a complimentary 2-hour bike or kayak rental to elevate your Chicago adventure. Cycle with ease along the scenic Lakefront Trail or paddle peacefully on the serene waters of Lake Michigan, and make your visit truly unforgettable.

Nitti's Supper Club Dinner and Show

Venture into the historic realm of Harry Caray's iconic establishment—an edifice with a notorious past linked to the infamous Chicago gangster Frank Nitti. Embark on a captivating evening that blends fine dining with a theatrical extravaganza, diving into the unsolved mystery surrounding the assassination of Eddie O'Hare, the legal maestro for none other than Al Capone and the father of the heroic aviator Butch O'Hare, the namesake of the famous airport. Engage in a theatrical escapade where fingers are pointed at a cast of potential culprits, from Frank Nitti and his spouse Annette to Al Capone among other notorious figures. Expect a night of historical tales, hearty laughter, interactive elements with the audience, and vivacious musical numbers that will keep your feet tapping long after the curtains close.

Bike Tour of Chicago's Lakefront Neighborhoods

Join in on the fun with Bobby's Bike Hike, a pioneering bike tour experience that catapulted Bobby into the spotlight. Celebrated by National Geographic, USA Today, The Associated Press, Conde Nast Traveler, and many more, Bobby's has grown to offer a vast selection of specialized tours. However, the classic Lakefront Neighborhoods tour remains the original gem. On this 3-hour adventure, let one of Bobby's seasoned guides lead you through Chicago's scenic North Side, exploring the towering urban oasis of Streeterville, the opulence of Gold Coast residences, the quaint charm of Old Town's artist enclave, and the picturesque expanse of Lincoln Park. The journey culminates with a breezy ride along the bustling Lakefront Trail, a beloved lakeside path. Get ready for an unforgettable, leisurely ride that promises to leave you with enduring memories. Your exploration sets off from 540 N. Lake Shore Drive, Chicago—where cityscapes meet nature and culture intertwines with urban life.

Chicago River 45-Minute Architecture Tour from Magnificent Mile

Discover the architectural marvels that have shaped Chicago's skyline and made it a living gallery of design innovation and skyscraper technology. Join us on an unforgettable journey through the city's storied past, narrated by our knowledgeable local guides who bring the stories of Chicago's architectural giants to life. Cruise along the river on our top-tier vessels, ideal for families and history enthusiasts alike, and immerse yourself in the visual feast of structural masterpieces that defines the Windy City's ever-evolving urban landscape. This condensed exploration draws from the comprehensive voyages offered by Wendella, presenting the essence of Chicago's architectural grandeur in a format accessible to all.

Chicago’s Friday Night Pirates Pub Sail Aboard a Tall Ship

Embark on a timeless maritime adventure with Chicago's iconic Pirates Pub Sail. Set sail on the 148-foot Tall Ship Windy, your Friday night voyage commences at 8:45pm directly from Navy Pier. Spanning a duration of two hours, you'll be welcomed back to the pier at 10:45pm, hearts full of new tales to tell. As the majestic Chicago skyline unfolds before your eyes, you'll partake in the festive atmosphere reminiscent of a pirate's life, complemented by the tranquil waters of Lake Michigan. Join in the hearty choruses of sea shanties and pirate ditties, creating an unforgettable backdrop to an evening of panoramic urban views and joyous revelry. Set sail with us for an experience that captures the essence of Chicago and the thrill of the high seas all in one.

Field Museum of Natural History All-Access Pass

Immerse yourself in a treasure trove of biological and anthropological wonders with the all-encompassing Field Museum All Access Pass in Chicago. Your ticket opens the door to every special exhibit on offer. Dedicate as much time as you desire to a collection that encapsulates over 26 million pieces spanning the breadth of history and science. Familiarize yourself with SUE, the colossal T. Rex that reigns supreme in the dinosaur world, and wander amid the lustrous splendor of the Hall of Gems. Navigate through an epic narrative spanning 13 millennia across the Western Hemisphere, traversing the epoch of glaciation to the architectural feats of the ancient Inca and Aztec civilizations. Engage with the museum's knowledgeable docents on complimentary daily tours that will enrich your understanding of the exhibits. And be sure to encounter Maximo, the towering titanosaur that casts an impressive shadow at over two stories high, a testament to the gargantuan wonders of the past.

2-Hour Chicago Lakefront and Museum Campus Segway Tour

Embark on a captivating journey through Chicago's urban landscapes with our expertly led Segway excursions. Covering a distance of 6-8 miles, you'll effortlessly cruise through the lush trails of Grant Park and be treated to the awe-inspiring Buckingham Fountain. Feel the city's energy as you glide along the stunning lakefront, taking in panoramic views and visiting must-see landmarks including the Museum Campus. With the Shedd Aquarium, Field Museum, and Soldier Field within reach, our tours are not only scenic but also filled with cultural highlights. Perfect for both Chicago residents and visitors, this guided Segway experience is an innovative way to discover the Windy City's renowned sights, combining leisure and adventure for a truly memorable outing.

Private Evening Sail in Chicago Ending with Navy Pier Fireworks

Immerse yourself in the magic of Chicago with a bespoke sailboat journey, complete with your own private viewing of the Navy Pier’s dazzling fireworks display. Glide along the picturesque lakefront for two enthralling hours as you behold the city’s magnificent skyline from a fresh perspective. This voyage is entirely yours to personalize—from selecting the sailing path to curating your playlist and tailoring the invite list. Charter a private sail for up to six guests and revel in the tranquility of Chicago’s waterfront. Let our US Coast Guard certified captain be your guide as you indulge in breathtaking panoramas of the urban oasis. This sailing sojourn offers you the liberty to craft an outing that reflects your own style, whether through the ambiance, route, or company. The spectacle of Navy Pier’s fireworks bursting above you is a memory you’ll carry long after the cruise concludes. Available on select Saturday evenings, this sailing escapade is a smoke-free experience, ensuring a pristine environment as you create cherished memories.

Chicago's West Side Foodie Ride Bike Tour

Embark on a culturally enriching cycling journey with Bobby's Bike Hike, the pioneers of urban bicycle tours in the U.S., recently acclaimed among the Top 20 Global Food Tours by TripAdvisor and listed in the Top 10 Food Tours in America by USA Today. This 4-hour culinary cycling adventure offers an unparalleled opportunity to delve into Chicago’s West Side neighborhoods, immersing you in the diverse local flavors and rich history of the area. You'll savor a variety of quintessential Chicago tastes as you pedal through the storied streets of the vibrant Fulton Market district, the heritage-rich Ukrainian Village, the trendy corridors of Wicker Park, and the quaint ambiance of Lincoln Park with stops for artisanal toffee and gourmet ice cream. The excursion culminates with a decadent chocolate sampling in the historical Old Town. Uncover the tales of these neighborhoods and the origins of the delicacies you enjoy. Traverse the iconic Lakefront Trail and immerse yourself in Chicago's distinctive neighborhoods—there's truly no more intimate way to experience the city's charm than by bicycle.