Weddings
Keep the wedding party together between hotels, photo locations, the ceremony and the reception.
Chicago Trolley Rental for Weddings & Events
Private trolley service for celebrations and coordinated group travel throughout Chicago and Chicagoland.
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Choose Your Trolley
Choose a trolley for every celebration
Compare traditional forward-facing rows, a social circular layout or our festive Christmas trolley for a private holiday lights tour.
Forward-Facing Seating
White Classic Trolley
Traditional forward-facing rows for a familiar, orderly ride.
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Circular Limo-Style Seating
White Limo Trolley
Circular perimeter seating that keeps the group facing one another.
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Private Holiday Lights Tours
Christmas Trolley
A heated, festively decorated trolley for private Christmas lights tours.
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What clients remember about ChiTown Trolley
Private Trolley Transportation
Private trolley service for the moments between destinations
From wedding parties and milestone celebrations to organized group outings, ChiTown Trolley keeps everyone together between stops. Share your route, timing and group size, and we will help match your plans with the right vehicle for private service throughout Chicago and Chicagoland.
Private Events
Keep guests together for birthdays, anniversaries, family celebrations and other private occasions.
Group Travel
Coordinate hotel pickups, venue transfers and multiple stops with one clear itinerary.
Local Service
Work with an owner-operated, licensed and insured, WBENC-certified Women Owned company.
Common Questions
Questions before you book
We recommend booking as early as you can — popular Saturdays in wedding season (May through October) and December holiday dates often fill six to twelve months out. That said, it never hurts to ask about a last-minute date; we’ll always check availability for you.
ChiTown Trolley provides private trolley service throughout Chicago and many surrounding Chicagoland suburbs. Availability depends on your event date, pickup location, itinerary and vehicle needs. Share your starting address and planned stops when requesting a quote, and we will confirm whether we can serve your route.
Yes — guests 21 and over are welcome to bring beverages aboard for private charters, provided everyone drinking is of legal age. We just ask that you let us know in advance so your chauffeur can have the cabin ready.
Our Classic White Trolley seats 30–36 passengers, the Limo Vans seat up to 14, and the Super Coach Bus holds up to 57. For larger parties, ask about pairing a trolley for the wedding party with a coach for the rest of your guests.
A deposit is required to hold your date, with the balance due before the event. Requesting a quote or reservation online places no charge and carries no obligation — we confirm availability first, then walk you through every detail.
It happens, and we plan for it. If the day’s schedule allows, additional time can often be added on the spot at an hourly rate. We’ll always confirm with you before extending, so there are never any surprises.
The Journal
Trolley and group transportation guides
Practical resources for planning routes, timing, vehicles and group travel throughout Chicago and Chicagoland.
Guides
How Many Guests Fit in a Trolley? A Wedding Transportation Sizing Guide
Capacity breakdowns for trolleys, coach buses, and limo vans — plus how to estimate your real guest count needs before you book.
Guides
Wedding Day Shuttle Logistics: A Timeline Guide for Guest Transportation
How to build a transportation timeline that actually holds up on the day — hotel pickups, ceremony-to-reception shuttles, and return trips guests won't stand around waiting for.
Guides
Chicago's Most Trolley-Friendly Wedding Venues
What actually makes a venue easy to arrive at by trolley — driveway clearance, drop-off zones, and photo backdrops — plus where around Chicagoland to look.