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.

Chicago Trolley Rentals

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.

Exterior view of Green & Tan Trolley – 32 Passengers
Interior view of Green & Tan Trolley – 32 Passengers

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.

Exterior view of Classic Trolley – 28 Passengers
Interior view of Classic Trolley – 28 Passengers

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.

Exterior view of Red & Green Trolley - 30 Passengers
Interior view of Red & Green Trolley - 30 Passengers

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.

Exterior view of White Classic Trolley – 30 Passengers
Interior view of White Classic Trolley – 30 Passengers

White Classic Trolley – 30 Passengers

Most popular for Gold Coast weddings and luxury transfers wood interior, classic white design, and elegant presence.

Exterior view of White Classic Trolley – 28 Passengers
Interior view of White Classic Trolley – 28 Passengers

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.

Wedding party inside trolley

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

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

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

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

Stan Mansion

A historic Logan Square mansion with opulent interiors, ideal for elegant weddings with trolley transport for guests.

Chicago, IL

Loft on Lake

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

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

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

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

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!"

Trustpilot
Sarah Thompson

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."

Trustpilot
Smith Johnson

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!"

GoogleGoogle
Maria Lopez

Gamechanger 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."

Trustpilot
Mr Wanes

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!"

GoogleGoogle
Emily Zhang

Top-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."

Trustpilot
Usman Raza

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.

Luxury wedding trolley

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.