• Millennium Park - Millennium Park is a showcase of modern Chicago. During the Chicago Bike Tour, participants will glide into this renowned public space where striking architecture, public art, and skyline views converge. Savvy visitors look beyond Cloud Gate to appreciate how the park was constructed over active rail lines, transforming industrial space into one of the city’s most significant civic accomplishments.

On the Bicycle Tour in Chicago, participants will learn how Millennium Park became a global emblem of Chicago’s creativity and reinvention. From the sweeping steel design of the Jay Pritzker Pavilion to interactive art installations, it exemplifies urban innovation. Among the top attractions in Chicago, experiencing Millennium Park by bike allows participants to feel its scale, energy, and cultural impact in a dynamic and lively way.

• Buckingham Fountain - Buckingham Fountain epitomizes Chicago’s grandeur. On the Chicago Bike Tour, participants will roll into Grant Park to witness one of the world’s largest fountains set against a cinematic skyline. Savvy visitors time their visit near the top of the hour when the central jet soars skyward, creating a quintessential summer photo opportunity in the city.

During the Bicycle Tour in Chicago, participants will hear how this Beaux-Arts masterpiece symbolizes Lake Michigan and the city’s connection to the water. It’s not merely decorative—it’s civic pride in motion. As one of the most iconic attractions in Chicago, experiencing Buckingham Fountain by bike allows participants to appreciate its scale, symmetry, and skyline backdrop in an immersive and unforgettable way.

• Lakefront Trail - The Lakefront Bike Trail is more than just a path—it’s a front-row seat to Chicago’s greatest show. On the Chicago Bike Tour, participants will cruise along this iconic 18-mile stretch with Lake Michigan on one side and a world-class skyline on the other. Locals know this is where the city breathes: early-morning runners, beach volleyball, sailboats dotting the horizon, and the unmistakable lake breeze that makes summer in Chicago legendary.

On the Bicycle Tour in Chicago, participants won’t just ride it—they’ll understand it. Guides will share how the lakefront transformed from an industrial shoreline into one of the world’s most celebrated urban waterfronts. It’s undoubtedly one of the top attractions in Chicago, and there’s no better way to experience it than on two wheels, moving at the perfect pace to take it all in.

• Museum Campus - Museum Campus is where Chicago’s skyline, lakefront, and world-class institutions converge in one unforgettable setting. On the Chicago Bike Tour, participants will ride into this stunning peninsula surrounded by water and framed by the city’s most dramatic skyline views. Savvy visitors pause to look back toward downtown—this is one of the most breathtaking vantage points in the entire city.

During the Bicycle Tour in Chicago, participants will learn how this area evolved from rail yards and industrial land into a cultural powerhouse anchored by the Field Museum, Shedd Aquarium, and Adler Planetarium. It represents Chicago’s ambition, intellect, and reinvention. Among the top attractions in Chicago, exploring Museum Campus by bike offers open space, fresh lake air, and a panoramic perspective that most visitors never fully experience.

• Navy Pier - Navy Pier is where Chicago’s waterfront energy comes alive. On the Chicago Bike Tour, participants will ride along the lake and see the Centennial Wheel rise above the skyline, blending history, entertainment, and unbeatable views. Savvy visitors know the pier began as a shipping and training facility in 1916 before evolving into one of the city’s most visited destinations.

During the Bicycle Tour in Chicago, participants will hear how Navy Pier reflects Chicago’s ability to reinvent itself—transforming industrial space into a vibrant gathering place for locals and visitors alike. From lake breezes to skyline backdrops, it captures the spirit of the city in one sweeping view. Among the classic attractions in Chicago, experiencing Navy Pier by bike allows participants to feel the scale, movement, and excitement firsthand.

• Northerly Island - Northerly Island is one of Chicago’s best-kept secrets. On the Chicago Bike Tour, participants will ride out onto this peaceful peninsula where prairie landscape, skyline views, and Lake Michigan converge. Locals know this is where you escape the city without ever leaving it—wide open paths, migratory birds, and one of the most dramatic vantage points of downtown.

During the Bicycle Tour in Chicago, participants will learn how this former airfield was transformed into a nature preserve, symbolizing Chicago’s evolution from industry to sustainability. It’s a quiet contrast to the city’s towering architecture just minutes away. Among the most unique attractions in Chicago, exploring Northerly Island by bike offers space, perspective, and a refreshing insider experience few visitors ever discover.

• Soldier Field - Soldier Field is where Chicago’s grit and pride come together. On the Chicago Bike Tour, participants will roll past this historic stadium on Museum Campus, where generations have gathered for Bears games, championship moments, and unforgettable concerts. Savvy visitors notice the striking contrast between the original 1924 colonnades and the modern redesign—a bold architectural conversation that mirrors Chicago itself.

During the Bicycle Tour in Chicago, participants will hear how Soldier Field became a symbol of resilience and civic identity. Set against the lake and skyline, it’s more than a stadium—it’s a cultural landmark. As one of the classic attractions in Chicago, seeing it by bike gives participants space to appreciate its scale, history, and dramatic setting in a way most visitors never do.

• Chicago Riverwalk - The Chicago Riverwalk is where the city’s architectural story unfolds at eye level. On the Chicago Bike Tour, participants will ride above the river while looking down at historic bridges, boat tours, and some of the most celebrated skyscrapers in the world. Savvy visitors know this stretch was once purely industrial—today it’s a vibrant waterfront that showcases Chicago’s remarkable reinvention.

During the Bicycle Tour in Chicago, participants will hear how the reversal of the river changed the course of the city and helped shape modern engineering history. It’s more than scenery—it’s innovation in motion. Among the must-see attractions in Chicago, experiencing the Riverwalk by bike gives participants perspective, movement, and context that transforms a simple view into a powerful story of ambition and design.

• The Chicago Theatre - The Chicago Theatre is where the city’s glamour still shines bright. On the Chicago Bike Tour, participants will ride into the heart of The Loop and see its iconic marquee glowing above State Street—one of the most photographed signs in America. Savvy visitors know this 1921 landmark helped define Chicago as an entertainment capital long before Broadway tours arrived.

During the Bicycle Tour in Chicago, participants will hear how the theatre survived changing eras, near demolition, and revival to become a symbol of downtown’s resilience. It’s more than a venue—it’s a piece of living history wrapped in neon. Among the classic attractions in Chicago, seeing the Chicago Theatre by bike allows participants to feel the energy of the street, the architecture, and the story all at once.

• Shedd Aquarium - Shedd Aquarium is where Chicago’s love of discovery meets the lakefront. On the Chicago Bike Tour, participants will glide into Museum Campus and see this stunning Beaux-Arts landmark set against one of the most breathtaking skyline backdrops in the city. Locals know that from the steps near Shedd, you get a panoramic view that perfectly captures Chicago’s bold architecture rising from the water.

During the Bicycle Tour in Chicago, participants will hear how Shedd became one of the world’s premier aquariums and a symbol of Chicago’s commitment to science and education. It’s not just a photo stop—it’s a cultural cornerstone. As one of the essential attractions in Chicago, seeing Shedd by bike connects participants to the city’s history, innovation, and unbeatable lakefront energy in one unforgettable ride.

• Grant Park - Grant Park is Chicago’s front yard—and locals treat it that way. On the Chicago Bike Tour, participants will ride through this expansive green space known as “the city’s backyard,” framed by skyline views and lakefront breezes. Savvy visitors know this is where Chicago gathers for festivals, concerts, and historic moments—from Lollapalooza to championship celebrations.

During the Bicycle Tour in Chicago, participants will hear how Daniel Burnham fought to keep this land “forever open, clear, and free,” preserving it for public use. That vision still shapes the city today. Among the essential attractions in Chicago, exploring Grant Park by bike gives participants the perfect balance of culture, history, and open space—allowing them to experience downtown the way Chicagoans actually do.

• Field Museum - The Field Museum isn’t just a stop—it’s a statement about Chicago’s global ambition. On the Chicago Bike Tour, participants will roll up to this neoclassical giant on Museum Campus, where world exploration, science, and culture converge against a breathtaking skyline backdrop. Locals know this area offers one of the most underrated views of downtown—especially when you glance back toward the city from the lake.

During the Bicycle Tour in Chicago, participants will hear the insider story of how this museum became a symbol of Chicago’s rise after the 1893 World’s Fair. It’s more than architecture; it’s legacy. Among the top attractions in Chicago, seeing Museum Campus by bike gives participants space, perspective, and context—far beyond what they’d get on foot or from a bus window.

• 12th Street Beach - 12th Street Beach is one of those hidden-in-plain-sight gems locals quietly love. On the Chicago Bike Tour, participants will cruise past this relaxed stretch of sand tucked beside Museum Campus, where calm waters, sailboats, and skyline views create a peaceful contrast to downtown’s buzz. Savvy visitors know it’s one of the best spots to see the city framed against Lake Michigan without the crowds of larger beaches.

During the Bicycle Tour in Chicago, participants will learn how the lakefront was intentionally preserved for public use—giving everyone access to this incredible shoreline. It’s a reminder that Chicago’s greatest asset isn’t just its architecture, but its waterfront. Among the most refreshing attractions in Chicago, experiencing 12th Street Beach by bike offers perspective, space, and a true local vibe.

• Cloud Gate - Cloud Gate—better known as “The Bean”—is more than a selfie spot. On the Chicago Bike Tour, participants will roll into Millennium Park and see this mirrored sculpture reflect the skyline in a way that feels almost surreal. Savvy visitors walk beneath it and look up—the warped reflections of the city create a perspective most visitors miss.

During the Bicycle Tour in Chicago, participants will hear how artist Anish Kapoor designed Cloud Gate to capture Chicago’s architectural boldness and ever-changing sky. It’s playful, artistic, and deeply symbolic of the city’s modern identity. As one of the must-see attractions in Chicago, experiencing it by bike means participants arrive energized, see it from multiple angles, and understand why locals still love it years after its debut.

• Jay Pritzker Pavilion - Jay Pritzker Pavilion is Chicago’s architectural showpiece in Millennium Park. On the Chicago Bike Tour, participants will ride past Frank Gehry’s sweeping stainless-steel design that looks like music frozen in motion. Savvy visitors look up at the crisscrossing trellis overhead—it’s engineered to deliver concert-quality sound across the entire Great Lawn.

During the Bicycle Tour in Chicago, participants will hear how this pavilion transformed downtown into a world-class outdoor performance space, hosting everything from classical symphonies to summer festivals. It’s bold, modern, and unmistakably Chicago. Among the essential attractions in Chicago, experiencing Pritzker Pavilion by bike allows participants to appreciate its scale, artistry, and cultural impact in a dynamic, up-close way.

• Crown Fountain - Crown Fountain is one of Chicago’s most playful and meaningful works of public art. On the Chicago Bike Tour, participants will roll into Millennium Park and see the twin glass towers project the faces of everyday Chicagoans—then suddenly “spit” water into the reflecting pool below. Savvy visitors know this isn’t just interactive fun; it’s a tribute to the diversity and spirit of the city itself.

During the Bicycle Tour in Chicago, participants will hear how artist Jaume Plensa designed the fountain to celebrate community and invite people to engage with art, not just observe it. Kids splash, adults laugh, and the skyline rises behind it all. Among the most unique attractions in Chicago, seeing Crown Fountain by bike allows participants to experience the city’s creativity, humor, and inclusivity in motion.

• Adler Planetarium - Adler Planetarium is where Chicago reaches for the stars—literally. On the Chicago Bike Tour, participants will ride to the edge of Museum Campus, where Adler sits like a crown at the tip of the peninsula. Savvy visitors know this is the single best skyline photo angle in the city—look back toward downtown and you’ll see the entire skyline rise dramatically over Lake Michigan.

During the Bicycle Tour in Chicago, participants will hear how Adler became America’s first planetarium and a symbol of Chicago’s forward-thinking spirit. It’s not just about astronomy—it’s about ambition and big ideas. Among the top attractions in Chicago, experiencing Adler by bike gives participants open space, fresh air, and a cinematic perspective you simply can’t get from inside a car or bus.

• Daley Bicentennial Plaza - Daley Plaza is where Chicago’s power and public life intersect. On the Chicago Bike Tour, participants will ride into this civic hub beneath towering modernist architecture and the famous Picasso sculpture that still sparks debate decades later. Savvy visitors know the plaza reflects Chicago’s bold, no-nonsense personality—art, government, and daily city life all sharing the same space.

During the Bicycle Tour in Chicago, participants will hear how this plaza became a stage for protests, celebrations, farmers markets, and winter holiday traditions. It’s where the city gathers when something important happens. Among the essential attractions in Chicago, seeing Daley Plaza by bike gives participants context—not just a photo, but a deeper understanding of Chicago’s political heartbeat and cultural confidence.

• Bicycle rental included
• Complimentary helmet provided
• Experienced tour guide accompanies the group

• $10 per person suggested guide gratuity. (via Cash, Venmo and PayPal)
• Food and drinks

Explore Chicago’s most famous landmarks on this lively guided bicycle tour! Join the knowledgeable guides from Bobby’s Bike Hike, the longest-running city bicycle tour company in the U.S., for an exciting and educational journey. During this 3-hour bike ride, taken at a comfortable pace, you’ll get an up-close look at Chicago’s renowned Museum Campus, Grant Park, Chicago Riverwalk, Lakefront, and Millennium Park. You’ll gain a deeper understanding of Soldier Field, The Adler Planetarium, Buckingham Fountain, The Pritzker Pavilion, and Cloud Gate (commonly known as “The Bean”). This tour is ideal for first-time visitors eager to see all the classic attractions, as well as returning guests wanting to learn more about the landmarks they cherish. Hop on a bike and create unforgettable memories! All equipment is provided for this Chicago Bicycle Tour.

• This Chicago Bike Tour is appropriate for most ages and fitness levels. Professional guides blend quality information, group interaction, and most of all, fun, to create an unforgettable Chicago experience. Bikes are provided
• TripAdvisor rated Bobby’s Bike Hike its highest-level Traveler’s Choice Award each year since 2002.
• Operates rain or shine, please dress appropriately. If extreme weather forces cancellation there will be options to change tours or refund.
• Minimum numbers apply. There is a possibility of cancellation after confirmation if there are not enough guests to meet requirements. In the event of this occurring, you will be offered an alternative or full refund.
• Please note: children must be strong, capable riders and be able to bike for 9 miles
• All equipment included: Bicycles, Helmets, and Child Equipment

For a full refund, cancel at least 24 hours before the scheduled departure time.