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.
Chicago Trolley Rentals for Weddings, Dinners, Corporate Events & Group Shuttles
Reliable Trolley Rentals for Events in Chicago.
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.
Why Choose a Rent a Trolley for Transportation in Chicago?
Renting a trolley in Chicago is the smart way to simplify event logistics and ensure guests arrive on time together, and in style.
Stylish Vehicles
Elegant trolleys perfect for weddings, corporate events, and group outings across Chicago, from the Loop to Wicker Park!
Trusted and Reliable Service
Travel with confidence thanks to our experienced chauffeurs and on-time, secure transportation service.
Expert Planning Support
Our Chicago team helps you build efficient routes and coordinate pickup logistics.
Custom Routes Across Chicago
Personalized trolley routes tailored to your Chicago event ideal for multiple stops or round-trip service.
Customer Support
Quick, friendly support to help streamline your booking experience and keep your group moving smoothly.
Multiple Options
RentATrolley have multi option From vintage to modern, choose from our Chicago trolley fleet to match your event style, size, and vibe.
Trolley rentals in Chicago for weddings, events & group outings
Explore our local Chicago fleet of modern and vintage-style trolleys perfect for lakefront weddings, downtown events, and private group transportation.
Classic Trolley – 28 Passengers
Another white classic in our fleet with its timeless look and smooth ride, it’s perfect for downtown weddings, city tours.
Red & Green Trolley - 30 Passengers
A bold, vintage-inspired trolley with wood bench seating and a vibrant exterior, great for laid-back celebrations or standout arrivals.
White Classic Trolley – 30 Passengers
Most popular for Gold Coast weddings and luxury transfers wood interior, classic white design, and elegant presence.
White Classic Trolley – 28 Passengers
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?
What’s Included with Your Chicago Trolley Rental.
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.
We know Chicago. Every block of it.
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.
Gold Coast
Luxury hotels, historic mansions, and upscale venues.
Lincoln Park
Charming estates and garden-style event spaces.
The Loop
Iconic ballrooms, museums, and urban event venues.
River North
Trendy lofts, galleries, and rooftop event spaces.
West Loop
Industrial-chic venues and modern event spaces.
Wicker Park
Eclectic venues with artistic and vintage charm.
Lakeview
Lakeside venues and intimate event spaces.
Hyde Park
Historic venues and cultural event spaces.
Trusted by Top Venues in Chicago
From historic ballrooms to modern lofts, our trolleys serve the most sought-after venues in Chicago for weddings, galas, and private events.
Salvatore’s
A romantic Lincoln Park venue with elegant interiors, perfect for intimate weddings with trolley shuttles from downtown hotels.
Chicago, IL
The Drake Hotel
An iconic Gold Coast hotel with grand ballrooms, ideal for luxury weddings and seamless trolley transfers for guests.
Chicago, IL
Chicago Cultural Center
A historic Loop venue with stunning Tiffany glass domes, perfect for grand weddings with trolley service from nearby hotels.
Chicago, IL
Stan Mansion
A historic Logan Square mansion with opulent interiors, ideal for elegant weddings with trolley transport for guests.
Chicago, IL
Loft on Lake
An industrial-chic West Loop venue with exposed brick and skylights, perfect for modern weddings with trolley shuttles.
Chicago, IL
Café Brauer
A charming Lincoln Park venue with views of the South Pond, ideal for romantic weddings with trolley service for guests.
Chicago, IL
The Ivy Room at Tree Studios
A sophisticated River North venue with a private courtyard and elegant interiors, perfect for weddings with trolley transfers.
Chicago, IL
Adler Planetarium
A unique South Loop venue with stunning lakefront views and modern spaces, ideal for galas and weddings with trolley service.
Chicago, IL
Morgan Manufacturing
A modern industrial venue in West Loop with customizable spaces, perfect for chic weddings and events with trolley shuttles.
Chicago, IL
What Our Riders Say
Real stories from happy customers who made memories on wheels with RentATrolley Chicago.
Fast and Effortless Booking!
"Booked my Chicago trolley ride within minutes. Loved the live seat map and instant confirmation perfect for exploring Chicago’s vibrant neighborhoods smoothly!"
Affordable and Convenient
"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."
Perfect for Family Trips
"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!"
GoogleGamechanger for Daily Commute
"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."
Ideal for Tourists
"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!"
GoogleTop-notch Experience
"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."
FAQs About Renting a Trolley in Chicago
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.
Make your arrival
unforgettable
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.