Chicago Seasonal Stroll Walking Tour of Holiday Attractions

By Bobby's Bike, Hike & Food Tours - Chicago

Exceptional

Free cancellation available

See tickets

Features

Free cancellation available
2h
Mobile voucher
Instant confirmation

Overview

There’s nothing more magical than Christmas in Chicago, & this 2hr guided Chicago Walking Tour takes you straight into the heart of it. Journey through the Chicago Loop, Millennium Park, & the Magnificent Mile with an internationally recognized tour company proudly headquartered right here in Chicago. Our entertaining guides will spark your holiday spirit with fun facts, cultural insights, & the very best seasonal décor—like the surprising fact that Rudolph the Red-Nosed Reindeer was created in Chicago! Along the way, you’ll marvel at the iconic Christmas window displays of the original Marshall Field’s store, admire Chicago’s official Christmas tree, Mag Mile lights, and take in the festive Millennium Park ice skating rink. You’ll even enjoy VIP access—no waiting in line—to the legendary Christkindlmarket, the city’s beloved German holiday market. If you’re searching for Things to do in Chicago during the holidays, this experience is a perfect fit. Note: This is a walking tour only.

Activity location

Christkindlemarket
- 50 W Washington St
- 60602-1305, Chicago, Illinois, United States

Meeting/Redemption Point

Petterinos
- 150 North Dearborn Street
- 60601, Chicago, Illinois, United States

Check availability

Chicago's Seasonal Stroll

2h
English

Travelers

Language options: English

Starting time: 3:30pm

Price details

$44.99 x 1 Adult$44.99

Total

Until Thu, Nov 27

What's included, what's not

Walk beneath millions of glittering lights as the Magnificent Mile glows for the season.
Skip the Lines—enjoy festive, VIP front-of-line access to Christkindlmarket’s holiday magic.
Stroll through Millennium Park as it sparkles with lights and joyful holiday energy.
Watch skaters glide under the skyline as Millennium Park transforms into a holiday wonder.
Experience State Street’s festive shops bursting with lights, décor, and holiday cheer.
See Chicago’s soaring Christmas tree glowing with festive lights—pure holiday magic.
See the Wrigley Building glow with festive lights—an elegant icon shining bright for Christmas.
Join a lively local guide who brings Chicago’s holiday spirit to life with every story.
Marvel at Macy’s iconic holiday windows—sparkling scenes that capture pure Christmas joy.
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

Know before you book

Service animals allowed
Public transportation options are available nearby
Infants and small children can ride in a pram or stroller
All areas and surfaces are wheelchair accessible
Transportation options are wheelchair accessible
Wheelchair accessible
Suitable for all physical fitness levels
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.

Activity itinerary

Christkindlemarket

Skip the long lines and get VIP entry into Christkindlemarket. Experience the magic of Christmas in Chicago Christmas as our Chicago Walking Tour guides you through the heart of the Christkindlmarket Chicago — one of the most beloved Things to do at Christmas in Chicago. Wander past glowing wooden stalls, savor the scent of roasted nuts and warm cider, and learn insider stories about how this Old World tradition became a cherished part of Chicago’s Holidays. Along the way, your local guide shares hidden details about vendors, festive treats, and cultural traditions you won’t find on your own. This joyful stop blends European charm with Chicago soul, creating an unforgettable holiday moment. Perfect for culture lovers, food explorers, and anyone seeking a little extra sparkle this season.

Chicago Christmas Tree

Marvel at one of the most iconic Things to do at Christmas in Chicago as our Chicago Walking Tour leads you to the dazzling Chicago Christmas Tree, glowing proudly in Millennium Park. This towering symbol of Christmas in Chicago Christmas shines with thousands of twinkling lights, handcrafted ornaments, and a history that stretches back generations. Your guide shares insider stories about how the tree is chosen, 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 a photo op—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 Things to do at Christmas in Chicago as our Chicago Walking Tour brings you to the Millennium Park Ice Rink, sparkling with festive lights during Christmas in Chicago. Skaters glide beneath the skyline, music floats through the crisp air, and the entire scene captures the classic charm of the Holidays. Your 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 Things to do at Christmas in Chicago as our Chicago Walking Tour leads you to Cloud Gate—“The Bean”—shimmering beneath the winter lights. During Christmas in Chicago, this mirrored monument becomes a festive masterpiece, reflecting the skyline, twinkling decorations, and joyful crowds celebrating the Holidays. Your 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 Things to do at Christmas in Chicago as our Chicago Walking Tour brings you to the enchanting Macy’s on State Street Holiday Display. During Christmas in Chicago, the windows come alive with handcrafted scenes, nostalgic animations, and storybook artistry that has captivated Chicagoans for generations. Your 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 Things to do at Christmas in Chicago as our Chicago Walking Tour guides you beneath the shimmering Magnificent Mile Lights. During Christmas in Chicago, this famous stretch glows with millions of twinkling bulbs draped across trees and towering storefronts, turning Michigan Avenue into a glowing holiday corridor. Your 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 Things to do at Christmas in Chicago as our Chicago Walking Tour guides you through the festive heart of Millennium Park. During Christmas in Chicago, the park transforms into a glowing winter wonderland filled with shimmering lights, holiday art installations, and joyful crowds celebrating the Holidays. Your 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 Things to do at Christmas in Chicago as our Chicago Walking Tour brings you onto the historic Michigan Avenue Bridge, glowing with festive lights during Christmas in Chicago. From this iconic spot, the riverfront sparkles with reflections of holiday décor, towering trees, and the warm glow from nearby landmarks. Your 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 Things to do at Christmas in Chicago as our Chicago Walking Tour leads you through Daley Bicentennial Plaza, where peaceful pathways and skyline views take on a warm glow during Christmas in Chicago. 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. Your 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 our Chicago Walking Tour brings you to the Jay Pritzker Pavilion, one of the most breathtaking Things to do at Christmas in Chicago. During Christmas in Chicago, Gehry’s sweeping steel ribbons shimmer with festive reflections, creating a dramatic winter backdrop unlike anything else in the city. Your 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

5m
Admission ticket not included

Experience one of the most photogenic Things to do at Christmas in Chicago as our Chicago Walking Tour brings you to the legendary Chicago Theatre marquee, glowing brilliantly during Christmas in Chicago. Its neon lights shine even brighter against the crisp winter air, creating a cinematic holiday moment you can’t find anywhere else. Your 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 Things to do at Christmas in Chicago as our Chicago Walking Tour brings you into the richly decorated lobby of the historic Palmer House. During Christmas in Chicago, 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. Your 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 Things to do at Christmas in Chicago as our Chicago Walking Tour guides you through State Street Holiday Shopping, where the storefronts glow with dazzling décor during Christmas in Chicago. This legendary shopping district comes alive with sparkling lights, nostalgic displays, and the joyful bustle of locals preparing for the Holidays. Your 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.

Location

Activity location

Christkindlemarket
- 50 W Washington St
- 60602-1305, Chicago, Illinois, United States

Meeting/Redemption Point

Petterinos
- 150 North Dearborn Street
- 60601, Chicago, Illinois, United States

Best Deals on Things to Do

Experience the wonders of the world up close with great deals on things to do near and far. Expedia offers one-of-a-kind activities that allow you to explore Chicago your way. Whether you love nature, culture, food, or a bit of adventure, we have the perfect activity for you.

Top Experiences in Chicago

With so many things to do in Chicago, planning the perfect day out may seem like a daunting task. Expedia is here to take the hassle out of finding the best attractions, tours, and activities in Chicago. Families, couples, and business travelers can all find the perfect activity in Chicago to create life-long memories with the help of Expedia.