Weddings
Elegant group transportation for ceremonies, photos, receptions and hotel returns.
Wedding reservations →
Chicago & the suburbs
Your celebration.
Chicago style.
Classic trolleys with character for weddings, birthdays, bar hopping, corporate outings and every reason to bring your favorite people together.
- 25-36 passengers
- Climate controlled
- Professional drivers
Make the ride part of the memory
One trolley.
So many ways to celebrate.
Keep your group together, your plans moving and the energy high from the first pickup to the final stop.
Bar hopping
A social, safe and memorable way to move your entire party, day or night, around Chicago.
Book your event →Birthdays, Bachelorette/Bachelor Parties
Turn the city into your celebration with music, friends and the stops you choose.
Book your event →Corporate & special events
Distinctive transportation for outings, guests, celebrations and Chicago experiences.
Request a quote →Meet the fleet
Vintage charm.
Modern comfort.
Our trolleys bring the classic styling people love—with open social seating, sound systems, heating and air conditioning for Chicago weather.
25–36passenger options
3–4 hrpopular packages
The Second City experience
More than transportation.
Bring your playlist
Set the mood with an onboard sound system ready for your celebration.
Chicago-ready comfort
Heated and air-conditioned vehicles keep guests comfortable through every season.
Everyone together
Perimeter seating creates a friendly, social atmosphere from stop to stop.
Professional service
Helpful drivers keep your group moving so you can stay focused on the occasion.
“
One of the best nights we had ever had in Chicago. All of the stops were perfect—and we started planning the next trolley night right away.
Birthday celebration · Chicago
Dates fill quickly. Planning 2 to 4+ weeks ahead? Book with confidence - no need to check availability first!
Wedding reservations → CASUAL EVENTS →Ready to make your event unforgettable?
Tell us your date, group size and occasion. We’ll help match you with the right trolley.