Chicago Holiday Lights Trolley Tour
The Most Magical Way to See Chicago at Christmas
Climb aboard a warm, luxury trolley and cruise through Chicago's most spectacular holiday light displays. A uniquely magical experience for families, corporate parties, date nights, and holiday groups — available November through January.
Book Your Chicago Holiday Lights Trolley
Tell us your preferred date and we'll respond within 15 minutes with availability and details.
Chicago's Most Magical Holiday Lights Experience
There's no better way to experience Chicago's spectacular holiday lights than from inside a warm, luxury trolley. My Chicago Trolley's holiday lights trolley tours take you through the city's most famous Christmas displays — the Magnificent Mile lights, Lincoln Park Zoo Lights, Millennium Park's Crown Fountain, Fulton Market's festive installations, and Chicago's beautifully decorated residential neighborhoods — all from the comfort of a heated, vintage-style trolley with your favorite holiday music playing and drinks in hand.
Available from late November through early January, our Chicago holiday trolley tours are fully customizable — choose your neighborhoods, set your pace, and make the evening entirely your own. Whether you're planning a magical family outing, a unique corporate holiday party, a romantic date night, or a fun group celebration, the holiday lights trolley is an experience your group will talk about for years.
Who Is the Chicago Holiday Lights Trolley For?
Create unforgettable holiday memories with your family. Kids and adults alike are amazed by Chicago's lights from inside a cozy, festive trolley. A tradition worth starting.
A completely unique alternative to the standard restaurant holiday party. Treat your team to a private Chicago Christmas trolley experience they'll remember all year.
Gather your crew for a festive BYOB trolley tour through the city lights. Hot chocolate, holiday cocktails, great company — and Chicago at its most beautiful.
A romantic and unique holiday date night. Book a private trolley experience for just the two of you or a small group for an intimate, magical evening through the city.
Safe, supervised, and memorable holiday outings for schools, churches, scout troops, and community organizations of all sizes.
Looking for a truly unique gift? A Chicago holiday lights trolley tour is a gift of experience — something no one expects and everyone loves.
Chicago Holiday Light Displays We Visit
Every tour is customized based on your preferences and the season's best displays. Here are the most popular stops our holiday trolley tours include:
Choose Your Chicago Holiday Lights Vehicle
What's Included in Your Chicago Holiday Lights Trolley Tour
Why Choose My Chicago Trolley for Your Holiday Lights Tour
- 20+ years of Chicago holiday tour experience — we know the best routes and timing
- Fully heated vehicles — you stay warm and comfortable all evening
- BYOB-friendly — bring your holiday drinks, hot chocolate, and festive snacks
- Customizable route — we tailor every tour to your preferred neighborhoods and displays
- Professional drivers who know every display location and optimal viewing spot
- Flexible duration — from a quick 2-hour highlights tour to a full evening experience
- Serving all Chicago neighborhoods and Chicagoland suburbs
- Corporate invoicing available for company holiday party bookings
How to Book Your Chicago Holiday Lights Trolley
Fill out the form above with your preferred date and group size. We respond within 15 minutes. December weekends go fast — the earlier you book, the better your selection of dates and vehicles.
We'll work with you to build the perfect holiday lights route based on your favorite neighborhoods, the season's best displays, and your preferred start time. Every tour is unique.
Your driver arrives early, vehicle warm and ready. Load your drinks, start the holiday playlist, and let Chicago's lights do the rest. Pure magic from start to finish.