Halloween in Chicago isn’t just about haunted houses and pumpkin patches — it’s about making memories with your favorite ghouls, and there’s no better way to do it than aboard one of Pontarelli’s legendary vintage trolleys!
This Halloween season, trade your broomstick for a ride on Pontarelli’s American Heritage trolley buses. Our trolleys aren’t just transportation — they’re rolling pieces of history, decked out for the season and ready to deliver a hauntingly good time. Whether you’re planning a ghostly night out, a spooky sightseeing adventure, or a private party with friends and family, Pontarelli’s trolleys set the perfect stage for all things eerie and fun.
Ghost Tours & Haunted Hot Spots: Cruise through Chicago’s most infamous haunted locations, or let us take you straight to the scariest haunted houses in town.
Autumn City Sights: Enjoy the golden glow of the city’s fall foliage and festive lights — all from the comfort (and safety!) of your private trolley.
Good Company & Great Vibes: Gather your best-dressed monsters, sip on pumpkin-spiced brews, and snap photos you’ll want to share all season long.
Our vintage trolleys are perfect for larger parties, but if you’re planning something more intimate, Pontarelli also offers a full fleet of luxury vehicles for smaller groups. From sleek sedans and SUVs to cozy mini coaches, you can still enjoy a stylish, comfortable, and spooky ride through the city — no matter your group size.
Don your spookiest, silliest, or most creative costume — our rides are the perfect place to show off your Halloween spirit! Costumes are encouraged, screams are optional, and fun is absolutely guaranteed.
Spots for Pontarelli’s Halloween Trolley Tours are limited and will vanish into the night before you know it. Ready to claim your seat on the spookiest ride in Chicago?
Reserve your Halloween Trolley Tour or private vehicle today!
Call 312-361-4111 or visit pontarelliischicago.com
Modified on Oct 24th 2025 by Pontarelli Chicago Limousine Service
