Our Trolley Fleet

Find the right Second City Trolley for your wedding, celebration, corporate outing or special event.

Choose Your Trolley

Browse our fleet below. Select a trolley to view more information or start your reservation.

Molley trolley

Trolley Molley

36 passengers

$1,895 — up to 4 hours

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Iowa trolley

Trolley 504

36 passengers

$1,898 — up to 4 hours

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Molley 36 passenger trolley

Trolley Molley

36 passengers

$1,998 — up to 4 hours

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Dupont trolley

Trolley Dupont

Up to 36 passengers

$1,898 — up to 4 hours

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706 trolley

Trolley 706

36 passengers

$1,898 — up to 4 hours

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Boston trolley

Boston Trolley

36 passengers

$1,998 — up to 4 hours

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Planning a Chicago Event?

Tell us about your date, group size and event, and we’ll help you choose the right trolley.

Email Second City Trolley

Pricing and capacities shown here are carried over from the existing trolley gallery. Confirm current availability and pricing before booking.