• Christkindlmarket - Bypass the queues and enjoy VIP access to Christkindlmarket. Delight in the festive spirit of Christmas in Chicago as the Chicago Walking Tour guides lead you through the heart of Christkindlmarket Chicago—one of the most cherished Christmas activities in the city. Stroll past illuminated wooden stalls, relish the aroma of roasted nuts and warm cider, and discover insider tales about how this Old World tradition became a beloved part of Chicago’s holiday celebrations. Along the way, the local guide reveals hidden details about vendors, festive treats, and cultural traditions that are not easily found on your own. This delightful stop combines European charm with Chicago’s essence, creating an unforgettable holiday experience. Ideal for culture enthusiasts, food adventurers, and anyone looking for a little extra sparkle this season.
• Chicago Christmas Tree - Be amazed by one of the most iconic Christmas activities in Chicago as the Chicago Walking Tour takes you to the magnificent Chicago Christmas Tree, proudly glowing in Millennium Park. This towering symbol of Christmas in Chicago shines with thousands of twinkling lights, handcrafted ornaments, and a history that spans generations. The guide shares insider stories about how the tree is selected, the families behind past donations, and the quiet traditions locals cherish during the holidays. Surrounded by joyful music, crisp winter air, and the warm buzz of the season, this festive stop becomes more than just a photo opportunity—it becomes a moment of wonder. Perfect for culture seekers who want to experience the city’s holiday heartbeat up close.
• Millennium Park Ice Rink - Discover one of the most joyful Christmas activities in Chicago as the Chicago Walking Tour brings you to the Millennium Park Ice Rink, sparkling with festive lights during the holiday season. Skaters glide beneath the skyline, music floats through the crisp air, and the entire scene captures the classic charm of the holidays. The guide shares insider tips about the rink’s traditions, the best times to visit, and how this beloved winter spot became a seasonal must-do for locals and visitors alike. With Cloud Gate reflecting the twinkle of holiday décor just steps away, this stop surrounds culture lovers with pure Chicago magic—perfect for anyone seeking iconic winter memories in the heart of the city.
• Cloud Gate - Experience one of the most iconic Christmas activities in Chicago as the Chicago Walking Tour leads you to Cloud Gate—“The Bean”—shimmering beneath the winter lights. During the holiday season, this mirrored monument becomes a festive masterpiece, reflecting the skyline, twinkling decorations, and joyful crowds celebrating the holidays. The guide shares insider stories about the sculpture’s creation, its surprising engineering secrets, and how it became a global magnet for holiday photos. As you step beneath its arch, the polished steel captures every sparkle of the season, creating a magical moment only Chicago can offer. Perfect for culture lovers seeking an unforgettable blend of art, architecture, and holiday spirit in the heart of Millennium Park.
• Macy’s on State Street - Step into one of the most beloved Christmas activities in Chicago as the Chicago Walking Tour brings you to the enchanting Macy’s on State Street Holiday Display. During the holiday season, the windows come alive with handcrafted scenes, nostalgic animations, and storybook artistry that has captivated Chicagoans for generations. The guide shares insider details about how these magical displays are designed, the decades-old traditions behind them, and the cultural moments that shaped their themes throughout the holidays. As twinkling lights glow against the historic building and holiday music fills the air, this stop becomes a warm, whimsical celebration of Chicago’s creative spirit—perfect for culture lovers seeking a deeper connection to the city’s seasonal magic.
• The Magnificent Mile - Witness one of the most dazzling Christmas activities in Chicago as the Chicago Walking Tour guides you beneath the shimmering Magnificent Mile Lights. During the holiday season, this famous stretch glows with millions of twinkling bulbs draped across trees and towering storefronts, turning Michigan Avenue into a glowing holiday corridor. The guide shares insider stories about how the lights are installed, the traditions behind the lighting procession, and the hidden gems along the avenue that locals love during the holidays. With festive window displays, street musicians, and the sparkle of the skyline all around, this stop immerses culture lovers in the radiant heart of Chicago’s holiday spirit.
• Millennium Park - Experience one of the most iconic Christmas activities in Chicago as the Chicago Walking Tour guides you through the festive heart of Millennium Park. During the holiday season, the park transforms into a glowing winter wonderland filled with shimmering lights, holiday art installations, and joyful crowds celebrating the holidays. The guide shares insider stories about the park’s creation, surprising design secrets, and how its landmarks—like Cloud Gate, the Great Lawn, and towering evergreens—take on new magic in the winter season. With music drifting through the air and the skyline shining in every direction, this stop immerses culture lovers in the very essence of Chicago’s holiday spirit.
• Michigan Avenue Bridge - Take in one of the most enchanting Christmas activities in Chicago as the Chicago Walking Tour brings you onto the historic Michigan Avenue Bridge, glowing with festive lights during the holiday season. From this iconic spot, the riverfront sparkles with reflections of holiday décor, towering trees, and the warm glow from nearby landmarks. The guide shares insider stories about the bridge’s engineering marvels, its role in shaping Chicago’s skyline, and why locals consider this overlook a secret favorite during the holidays. With twinkling lights above, shimmering water below, and the city’s seasonal energy all around, this stop invites culture lovers to soak in the true magic of Chicago’s winter beauty.
• Daley Bicentennial Plaza - Discover a quieter gem among the Christmas activities in Chicago as the Chicago Walking Tour leads you through Daley Bicentennial Plaza, where peaceful pathways and skyline views take on a warm glow during the holiday season. This serene corner of Grant Park becomes a winter hideaway filled with twinkling trees, festive décor, and a gentle calm that contrasts beautifully with the bustle just steps away. The guide shares insider history about the park’s transformation, its hidden connections to Millennium Park, and why locals treasure this spot during the holidays. Wrapped in crisp air and holiday charm, this stop offers culture lovers a reflective moment surrounded by Chicago’s seasonal beauty.
• Jay Pritzker Pavilion - Experience a cultural highlight of the season as the Chicago Walking Tour brings you to the Jay Pritzker Pavilion, one of the most breathtaking Christmas activities in Chicago. During the holiday season, Gehry’s sweeping steel ribbons shimmer with festive reflections, creating a dramatic winter backdrop unlike anything else in the city. The guide shares insider details about the pavilion’s world-class acoustics, its role in Chicago’s music scene, and how this architectural marvel comes alive during the holidays with lights, performances, and seasonal energy. Standing beneath its iconic trellis, you’ll feel the heartbeat of Chicago’s artistic soul wrapped in pure holiday magic—perfect for culture lovers seeking an unforgettable winter moment.
• The Chicago Theatre - Experience one of the most photogenic Christmas activities in Chicago as the Chicago Walking Tour brings you to the legendary Chicago Theatre marquee, glowing brilliantly during the holiday season. Its neon lights shine even brighter against the crisp winter air, creating a cinematic holiday moment you can’t find anywhere else. The guide shares insider stories about the theatre’s century of showbiz history, secret architectural gems hidden behind the marquee, and how this iconic sign became a symbol of the city’s holidays. Surrounded by festive crowds, shimmering decorations, and the hum of State Street’s seasonal energy, this stop immerses culture lovers in Chicago’s theatrical heart—illuminated with pure holiday magic.
• Palmer House Hilton Historic Lobby - Step inside one of the grandest Christmas activities in Chicago as the Chicago Walking Tour brings you into the richly decorated lobby of the historic Palmer House. During the holiday season, this legendary hotel transforms into a glowing holiday escape filled with sparkling garlands, towering wreaths, and the warm scent of chocolate from the original brownie recipe born right here. The guide shares insider stories about the hotel’s famous guests, hidden design details, and the traditions that make this spot a beloved treasure during the holidays. With its gilded ceilings and festive décor, the Palmer House becomes a breathtaking pause in the city’s winter bustle—an unforgettable moment for culture lovers seeking the true magic of Chicago’s holiday season.
• State Street - Experience one of the most festive Christmas activities in Chicago as the Chicago Walking Tour guides you through State Street Holiday Shopping, where the storefronts glow with dazzling décor during the holiday season. This legendary shopping district comes alive with sparkling lights, nostalgic displays, and the joyful bustle of locals preparing for the holidays. The guide shares insider stories about historic department stores, decades-old traditions, and the hidden architectural touches you might miss on your own. From enchanting window scenes to seasonal pop-ups tucked between iconic buildings, this stop offers culture lovers a vibrant blend of history, style, and Christmas charm—capturing the very heartbeat of Chicago’s winter season.

• Holiday attractions
• Local tour guide

• Optional gratuity: $6 per person (or more) suggested guide gratuity (via Cash, Venmo and PayPal)
• Hotel pickup and drop-off
• This is purely a walking tour, no food or drink offered on this tour

Experience the enchantment of Christmas in Chicago with a 2-hour guided walking tour that immerses you in the city’s festive spirit. Explore the Chicago Loop, Millennium Park, and the Magnificent Mile with a renowned tour company based in Chicago. Our lively guides will ignite your holiday cheer with intriguing facts, cultural insights, and the finest seasonal decorations—did you know Rudolph the Red-Nosed Reindeer was created in Chicago? Along the route, you’ll be captivated by the iconic Christmas window displays at the original Marshall Field’s store, admire the official Christmas tree, the dazzling Mag Mile lights, and enjoy the festive atmosphere at the Millennium Park ice skating rink. Plus, benefit from VIP access—skip the lines—at the famous Christkindlmarket, Chicago’s cherished German holiday market. For those seeking holiday activities in Chicago, this tour is an ideal choice. Please note: This is a walking tour only.

• All of our walking tours at the present moment do allow for ADA compliant and wheelchair accessible.
• Operates in all weather conditions, please dress appropriately
• TripAdvisor rated Bobby’s Bike Hike its highest-level Traveler’s Choice Award each year since 2002.
• 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.
• Our groups have exclusive VIP access to locations we visit, including VIP access to Christkindlmarket.

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