Chicago Walking Tour of Highlights with Free Bike or Kayak Rental

What's Included

Meeting and pickup

Itinerary

• 1
  Millennium Park

  Millennium Park is one of the city’s most captivating stops on our Chicago Walking Tour, a centerpiece of your Walking Tour of Chicago designed to showcase the city’s most iconic Top Attractions and unforgettable Highlights. Your guide shares insider stories about how this award-winning public space transformed from industrial rail yards into one of the world’s most visited urban parks. Discover why Cloud Gate’s mirrored surface was once debated, how its flawless reflection was engineered, and the exact spot for the best skyline photo. Learn the acoustic secrets behind the Jay Pritzker Pavilion and why its sweeping trellis was created to deliver concert-quality sound outdoors. From hidden garden pathways to surprising public art details many visitors miss, Millennium Park offers beauty, design, and storytelling that inspire guests to turn curiosity into a must-book experience.

  15 minutes • Admission ticket free
• 2
  The Magnificent Mile

  The Magnificent Mile is one of the most iconic stretches you’ll explore on our Chicago Walking Tour, a vibrant stop on any Walking Tour of Chicago showcasing the city's most impressive Top Attractions and urban Highlights. As you stroll this world-famous avenue, your guide shares insider stories about how Michigan Avenue transformed from a quiet boulevard into a premier shopping and architectural corridor known around the globe. Learn which skyscraper first gave the Mile its name, why luxury brands flocked here, and how hidden design features on historic buildings reveal Chicago’s evolution over the last century. Discover little-known facts about the Tribune Tower’s embedded world artifacts, the Wrigley Building’s original purpose, and the engineering breakthroughs that shaped the skyline. With its blend of history, culture, and sweeping views, the Magnificent Mile offers an energetic, must-see moment that turns lookers into bookers eager to explore more of the city.

  10 minutes • Admission ticket free
• 3
  Chicago Riverwalk

  The Chicago Riverwalk is a standout stop on our Chicago Walking Tour, an essential moment on any Walking Tour of Chicago that highlights the city’s most scenic Top Attractions and memorable Highlights. As you stroll along the waterfront, your guide shares insider stories about how this vibrant promenade transformed a once-industrial channel into one of Chicago’s most celebrated public spaces. Learn how the river was famously reversed—an engineering feat that shaped modern city planning—and how the Riverwalk was constructed in stages, each with its own architectural and cultural theme. Discover hidden art installations, ecological efforts that support fish and bird life, and distinctive design details visible only from the river’s edge. Your guide also points out ideal photo spots, peaceful alcoves, and unique perspectives that most visitors overlook. With sweeping views and a rich, evolving history, the Chicago Riverwalk offers a fresh and inspiring way to experience the city.

  15 minutes • Admission ticket free
• 4
  Crown Fountain

  Crown Fountain is one of the most captivating stops on our Chicago Walking Tour, a guest favorite on any Walking Tour of Chicago featuring the city’s most innovative Top Attractions and memorable Highlights. Your guide reveals insider stories about how this groundbreaking art installation by Jaume Plensa blends technology, architecture, and community in a way no other fountain in the world does. Learn why over 1,000 Chicago residents were filmed for the digital faces that appear on the 50-foot towers, how the “spitting” water effect was engineered, and the unexpected symbolism behind the ever-changing expressions. Discover the hidden design elements built into the black granite reflecting pool, the surprising maintenance challenges, and why the fountain was considered bold and controversial at its debut. With its mix of playfulness, public art, and cultural meaning, Crown Fountain offers a moment that transforms lookers into bookers eager to explore even more of Chicago.

  5 minutes • Admission ticket free
• 5
  The Chicago Theatre

  The Chicago Theatre is a showstopping highlight on our Chicago Walking Tour, a must-see stop on any Walking Tour of Chicago featuring the city’s most iconic Top Attractions and cultural Highlights. Standing beneath its glowing marquee, your guide shares insider stories about how this 1921 French Baroque masterpiece became the crown jewel of Chicago entertainment. Learn why the theatre’s grand lobby was modeled after the Palace of Versailles, how its seven-story marquee became one of the most photographed signs in the world, and the surprising celebrities who once performed here before they were famous. Discover the hidden symbolism in the auditorium’s architecture, the secrets behind the theater’s massive renovation, and how this landmark helped revive the entire theatre district. With its rich history, breathtaking design, and legendary stories, the Chicago Theatre becomes a moment that transforms curious lookers into excited bookers eager to explore more of the city.

  10 minutes • Admission ticket free
• 6
  Historic Water Tower

  The Historic Water Tower is a defining stop on our Chicago Walking Tour, an essential feature of any Walking Tour of Chicago highlighting the city’s most enduring Top Attractions and architectural Highlights. As one of the few structures to survive the Great Chicago Fire of 1871, this limestone landmark stands as a symbol of resilience & rebirth. Your guide shares insider stories about how the tower once housed a powerful pumping system that helped modernize the city, why its castle-like design sparked debate among early critics, & how its survival shaped Chicago’s identity. Learn about the nearby pumping station’s role in supplying clean water, the engineering innovations hidden within its walls, & the reason artists & preservationists fought to protect it from demolition in the 20th century. Surrounded by skyscrapers on the Magnificent Mile, the Historic Water Tower offers a striking contrast between old Chicago & new—revealing the city’s history in a single, unforgettable landmark.

  10 minutes • Admission ticket free
• 7
  Cloud Gate

  Cloud Gate, affectionately known as “The Bean,” is one of the most iconic stops on our Chicago Walking Tour, a marquee moment on any Walking Tour of Chicago featuring the city’s most celebrated Top Attractions and unforgettable Highlights. Your guide shares insider stories about how artist Anish Kapoor designed this sculpture to capture Chicago’s skyline in a single perfect reflection, and why its creation sparked years of debate before becoming a global symbol of the city. Learn how its seamless mirror finish was engineered from 168 stainless steel plates, the surprising techniques used to polish it to perfection, and the exact locations for the most striking photos—spots even locals don’t know. Discover hidden details beneath the archway, the way sound behaves inside the “omphalos,” and how Cloud Gate helped redefine Millennium Park as a world-class cultural destination. This stop blends art, architecture, and insider insight, turning curiosity into a must-book experience.

  10 minutes • Admission ticket free
• 8
  The Art Institute of Chicago

  Experience the world-renowned Art Institute of Chicago on our Chicago Walking Tour, a centerpiece of your Walking Tour of Chicago designed to showcase the city’s most iconic Top Attractions and cultural Highlights. As you approach the museum’s grand entrance, you’ll be greeted by the famous bronze lions—symbols of Chicago’s artistic spirit—whose poses and names come with insider stories your guide will share. Learn how the museum’s massive collection grew from a small academy to one of the globe’s leading art institutions, housing masterpieces like American Gothic, Nighthawks, & unparalleled Impressionist collection. Your guide reveals surprising details, such as the hidden symbolism in the building’s Beaux-Arts design, why the Impressionists found an unexpected home in Chicago, & how the museum became a cornerstone of the 1893 World’s Fair. This stop blends art, architecture, & storytelling—an inspiring moment that transforms casual interest into the desire to book and explore more.

  10 minutes • Admission ticket free
• 9
  Holy Name Cathedral

  Holy Name Cathedral is an inspiring stop on our Chicago Walking Tour, a meaningful addition to any Walking Tour of Chicago showcasing some of the city’s most memorable Top Attractions and architectural Highlights. As you approach its striking Gothic Revival façade, your guide shares insider stories about the cathedral’s early history and its importance in Chicago’s cultural landscape. Step inside to see the dramatic ceiling shaped like an upturned ship’s hull, symbolizing shelter and strength. Learn how the bronze doors were designed, why the Resurrection Crucifix appears to float above the altar, and how the building was restored after the 2009 fire. Your guide also points out the exquisite woodwork, modern stained glass, and the cathedral’s connections to significant figures in the city’s past. With its peaceful atmosphere and intricate craftsmanship, Holy Name Cathedral reveals a quieter, deeper side of Chicago.

  10 minutes • Admission ticket free
• 10
  Jay Pritzker Pavilion

  The Jay Pritzker Pavilion is a standout stop on our Chicago Walking Tour, a highlight of any Walking Tour of Chicago featuring the city’s most impressive Top Attractions and cultural Highlights. Your guide shares insider stories about how architect Frank Gehry designed its flowing steel ribbons to merge sculpture, architecture, and performance into one striking structure. Learn how the sweeping trellis creates one of the world’s most advanced outdoor sound systems, delivering concert-quality audio across the entire Great Lawn. Hear little-known details about the pavilion’s engineering challenges, its influential donors, and how it helped redefine Millennium Park as a global arts destination. With its bold design, immersive acoustics, and rich backstory, this stop turns casual curiosity into a must-book Chicago experience.

  5 minutes • Admission ticket free
• 11

  Daley Bicentennial Plaza is a peaceful yet fascinating stop on our Chicago Walking Tour, an often-overlooked gem on any Walking Tour of Chicago featuring the city's most inviting Top Attractions and scenic Highlights. Your guide shares insider stories about how this quiet corner of Grant Park once served as the gateway to the old police headquarters and skating rink before its dramatic transformation. Learn how the reconstruction of nearby Millennium Park reshaped the entire landscape, why the plaza’s elevation hides a massive parking structure beneath your feet, & how this area is connected to Chicago’s bold plan to create more green space above active rail lines. Discover the best overlooks for skyline photos, the secret pathways locals use, and the role this plaza plays in the city’s larger park system. With its blend of history, calm, & surprising design choices, Daley Bicentennial Plaza offers a reflective moment that turns lookers into bookers seeking a deeper Chicago experience.

  10 minutes • Admission ticket free
• 12
  Palmer House Hilton Historic Lobby

  xperience the elegance of the Palmer House’s historic lobby on our Chicago Walking Tour, a signature stop on your Walking Tour of Chicago that reveals the city’s Top Attractions through rich stories and unforgettable Highlights. Step beneath the shimmering Tiffany-designed ceiling—one of the largest of its kind in the world—and feel the energy of a space that has hosted presidents, legendary performers, and generations of travelers. Your guide shares insider details you won’t hear elsewhere, like how the world-famous brownie was invented right here for the 1893 World’s Fair, and why the lobby’s French-inspired murals were nearly lost to time. You’ll discover hidden design features, secret restoration stories, and the surprising role this landmark played in shaping Chicago’s cultural identity. This stop blends history, luxury, and timeless charm, offering a must-see moment that turns curious lookers into confident bookers ready to explore even more of the city.

  10 minutes • Admission ticket free
• Bobby's Bike Hike - Chicago Bike, Walking & Food Tours (Pass by)

  FREE 2 HOUR BIKE or KAYAK RENTAL INFO: As an additional perk for booking this particular Chicago Walking tour, you will get a FREE 2-hour bike or kayak rental (to be used within (+/-) 3 days of your tour booking. Terms below: To be used within +/- 3 days of your tour booking. Bike rentals take place at Bobby’s Bike Hike World Headquarters, 540 N. Lake Shore Drive, Chicago, IL60611. Bike shop is open year-round (excluding Thanksgiving & Christmas). Explore the 20 mile Lakefront Bike Trail, named Best Things to Do in Chicago. Kayak rentals take place at Ohio Street Beach, Bobby’s Kayak, 550 E. Grand Avenue, Chicago, IL 60611. Kayak shop open mid-May to mid-October, weather dependent. Offer excludes Saturday Bike/Kayak rentals between Memorial Day (end of May) Weekend to Labor Day (early September). Kayaking only available from June-September). Kayak on Lake Michigan. No discounts for not using this activity or issues due to weather restrictions.

  Admission ticket free

Additional info

• Wheelchair accessible
• Infants and small children can ride in a pram or stroller
• Service animals allowed
• Public transportation options are available nearby
• Transportation options are wheelchair accessible
• All areas and surfaces are wheelchair accessible

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