Windy City Trolley is Chicagoland’s premier trolley company for event transportation.  Our modern, stylized trolleys are the perfect compliment to all of your event needs.  Whether your outing is a corporate function, the wedding of your dreams, or just a night out with friends, Windy City Trolley will be a wonderful extension to your vision.  Be amazed as your guests and passers-by look with glee and excitement.  The adoration that encompasses trolley transportation is something that brings a smile to everyone’s face and warmth to their hearts; something Windy City Trolley pride’s itself on and looks forward to sharing with you.  The Windy City Trolley team consists of experienced event specialists who will ensure that your wishes are met and no detail will go untouched. 
We look forward to providing you with transportation for:
  • Corporate Events
  • Conventions/Trade Shows
  • Weddings
  • Reunions
  • Bachelor/Bachelorette Parties
  • Charity functions
  • Sporting events
  • And anything in between
Our Trolleys:
  • Freshly painted with chic design
  • 32 passenger
  • Open air windows (seasonal)
  • Hard windows for cooler months
  • Oak bench seating
  • PA system
  • Our trolleys offer radio with CD player and ipod hook-up


You name the occasion and we’ll be there with bells on... “Ding, Ding Goes the Trolley.”

Announcing $500 Fridays for up to 5 hours of charter service. *
Need a trolley on a Sunday? 
Contact us for our special discounted rates.
*Restrictions Apply

Contact Information




  Windy City Trolley, Inc                                                                                               ©Copyright  2006