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.


$100 OFF

Receive $100 of your trolley when you book a “Day-of-Wedding” coordinator with WC EVENT GROUP.



$599 evening only charter. Excludes wedding service. Excludes Saturday evenings. Travel surcharges & taxes may apply. Does not include driver gratuity. Cannot be combined with any other offer. Limited promotional trolley’s available. First come, first served.

Just wanted to say Thank you for a wonderful trip. Richard was wonderful! Everyone had such a great time. Will certainly pass the word along about you guys.
Dan Slutsky