Make Spirits Bright with a Corporate Holiday Outing Everyone Will Love

Treat your team to a uniquely festive experience aboard Pontarelli’s Holiday Trolley Lights Tour

Skip the awkward office party and treat your team to something truly memorable this holiday season—a private Holiday Trolley Lights Tour through Chicago’s most iconic and dazzling holiday displays, brought to you by Pontarelli.

Whether you’re rewarding your employees, celebrating with clients, or simply looking for a festive way to wrap up the year, our trolley tours are a one-of-a-kind way to bring people together—no ugly sweaters or karaoke required (unless you want them).

 

Why It Works for Teams

✔️ It’s a fresh take on the company holiday party

✔️ Zero stress—we handle all the driving, parking, and logistics

✔️ Great for bonding—laugh, sing, sip cocoa, and enjoy the season together

✔️ Customizable—add character appearances like Santa’s Elf, The Grinch, or Mrs. Claus for extra cheer

✔️ Accommodates groups of all sizes—choose from luxury coaches, sedans, or nostalgic trolleys

 

What You’ll See

Your private group will cruise past some of Chicago’s most iconic holiday hotspots:

✨ Millennium Park – Snap a group photo in front of the city’s glittering Christmas tree

✨ Macy’s Window Displays – A Chicago tradition full of whimsy and nostalgia

✨ The Magnificent Mile – Lit up from end to end, offering breathtaking city views

Or go beyond downtown and explore our North Shore Holiday Lights Tour, where homes in Winnetka, Glencoe, and Highland Park are transformed into festive works of art. These snow-dusted neighborhoods offer a quieter but equally magical escape.

 

Add a Dash of Holiday Character

Want to make the night even more fun? Choose to include appearances from beloved holiday characters to bring laughter and photo ops to your tour:

The Grinch – Always a crowd-pleaser with just the right amount of mischief

Mrs. Claus – Warm, friendly, and great at spreading cheer

Santa’s Elves – Perfect for breaking the ice and engaging your group

These characters bring energy and holiday magic that make the evening unforgettable—no matter your industry.

 

Book Now—Before We Sell Out

End-of-year celebrations are better with a little sparkle—and Pontarelli’s Holiday Trolley Lights Tours are already filling up fast.

Book your corporate holiday outing now at ChicagoTrolleyBuses.com

Questions or custom requests? Let our team help you plan the perfect event.

Because the best gift you can give your team… is a night they’ll actually want to attend.