

Green & Tan Trolley – 32 Passengers
Vintage-style trolley with warm wood tones & larger capacity, perfect for elegant events or stylish group travel across Cook County.
Elevate your Chicago event with premium trolley rentals designed for weddings, corporate functions, private dinners, and group outings. From the Loop to Lincoln Park, our stylish trolley rentals provide convenient, comfortable, and unforgettable group transportation. Enjoy flexible hourly or full-day rentals. Whether you're planning a luxury wedding in Gold Coast or a conference in Downtown Chicago, RentATrolley helps you move your group with ease and style.
Renting a trolley in Chicago is the smart way to simplify event logistics and ensure guests arrive on time together, and in style.
Elegant trolleys perfect for weddings, corporate events, and group outings across Chicago, from the Loop to Wicker Park!
Travel with confidence thanks to our experienced chauffeurs and on-time, secure transportation service.
Our Chicago team helps you build efficient routes and coordinate pickup logistics.
Personalized trolley routes tailored to your Chicago event ideal for multiple stops or round-trip service.
Quick, friendly support to help streamline your booking experience and keep your group moving smoothly.
RentATrolley have multi option From vintage to modern, choose from our Chicago trolley fleet to match your event style, size, and vibe.
Explore our local Chicago fleet of modern and vintage-style trolleys perfect for lakefront weddings, downtown events, and private group transportation.
Vintage-style trolley with warm wood tones & larger capacity, perfect for elegant events or stylish group travel across Cook County.
Another white classic in our fleet with its timeless look and smooth ride, it’s perfect for downtown weddings, city tours.
A bold, vintage-inspired trolley with wood bench seating and a vibrant exterior, great for laid-back celebrations or standout arrivals.
Most popular for Gold Coast weddings and luxury transfers wood interior, classic white design, and elegant presence.
Great for Gold Coast and Lincoln Park weddings features wooden accents, onboard music, and photo-ready style.
From the Loop to Lincoln Park and beyond, our Chicago trolleys include a chauffeur, onboard sound and flexible routing for weddings, events, and private tours
Ready to book a trolley bus in Chicago?
Our trolley rentals include a professional chauffeur trained for weddings, events, and private charters, plus your choice of classic or modern models with charming interiors. With RentATrolley, you can rent a trolley in Chicago by the hour or for the full day, enjoy BYOB-friendly service with a cooler and ice, and plan flexible routes with multiple stops. No hidden fees fuel, setup, and cleanup are included. Whether you're looking to rent a trolley in Chicago or anywhere in the USA, our team ensures a smooth, photo-worthy trolley rental from first pickup to final dropoff.
From elegant weddings in Gold Coast to modern ceremonies in the West Loop, our trolleys are trusted for stylish, reliable transportation in Chicago, including Lincoln Park, River North, and beyond.
Luxury hotels, historic mansions, and upscale venues.
Charming estates and garden-style event spaces.
Iconic ballrooms, museums, and urban event venues.
Trendy lofts, galleries, and rooftop event spaces.
Industrial-chic venues and modern event spaces.
Eclectic venues with artistic and vintage charm.
Lakeside venues and intimate event spaces.
Historic venues and cultural event spaces.
From historic ballrooms to modern lofts, our trolleys serve the most sought-after venues in Chicago for weddings, galas, and private events.
A romantic Lincoln Park venue with elegant interiors, perfect for intimate weddings with trolley shuttles from downtown hotels.
Chicago, IL
An iconic Gold Coast hotel with grand ballrooms, ideal for luxury weddings and seamless trolley transfers for guests.
Chicago, IL
A historic Loop venue with stunning Tiffany glass domes, perfect for grand weddings with trolley service from nearby hotels.
Chicago, IL
A historic Logan Square mansion with opulent interiors, ideal for elegant weddings with trolley transport for guests.
Chicago, IL
An industrial-chic West Loop venue with exposed brick and skylights, perfect for modern weddings with trolley shuttles.
Chicago, IL
A charming Lincoln Park venue with views of the South Pond, ideal for romantic weddings with trolley service for guests.
Chicago, IL
A sophisticated River North venue with a private courtyard and elegant interiors, perfect for weddings with trolley transfers.
Chicago, IL
A unique South Loop venue with stunning lakefront views and modern spaces, ideal for galas and weddings with trolley service.
Chicago, IL
A modern industrial venue in West Loop with customizable spaces, perfect for chic weddings and events with trolley shuttles.
Chicago, IL
Real stories from happy customers who made memories on wheels with RentATrolley Chicago.
"Booked my Chicago trolley ride within minutes. Loved the live seat map and instant confirmation perfect for exploring Chicago’s vibrant neighborhoods smoothly!"
"No more long lines! Got my trolley rental pass instantly with a great Chicago student discount. RentATrolley saved me time and hassle on my trip here."
"Booked seats for my whole family on a Chicago trolley easily. Real-time availability made planning simple and stress-free. Definitely using RentATrolley again for our next outing!"
"As a Chicago local commuter, quick trolley booking and delay alerts are lifesavers. I save favorite routes for easy access. RentATrolley makes Chicago travel convenient and reliable."
"Planned my entire Chicago vacation from Canada, booked all trolley rides ahead with RentATrolley. Support helped with a last-minute change. Highly recommend for hassle-free travel!"
"Smooth UI, fast loading, and secure payments RentATrolley’s platform nails Chicago trolley rentals. Saving frequent trips is a great feature for locals and visitors alike."
We recommend booking at least 4–6 weeks before your event especially during peak season (March–June and December).
Yes, all enclosed trolleys are equipped with air-conditioning to ensure a comfortable ride, even in Chicago's warm weather.
Yes, roundtrip transportation is available for all bookings. Our team will coordinate timing and routes with you in advance.
Yes, with certain restrictions and proper permits. Please inform us in advance so we can guide you through the process.
Trolley wedding transportation in Chicago brings timeless charm to your big day. From historic mansions in Gold Coast to modern venues in the West Loop, our classic trolleys add style, comfort, and a touch of magic to every celebration.