Chicago Trolley Co

What Chicago Trolley Co does

Chicago Trolley & Double Decker Co. (Chicago Trolley Co.) was founded in 1994 by three friends and operates as the largest tourism transportation company in the Midwest, providing hop-on-hop-off sightseeing tours and charter rentals exclusively within the Chicago metropolitan area. The company runs a fleet of 40 classic San Francisco-style trolleys custom-built in Maine, 27 open-top double decker buses, and 8 motor coaches, supported by more than 150 tour guides and drivers. Its operating technology centers on a GPS vehicle tracking system for real-time location, multi-lingual iOS and Android mobile applications offering narrated tours, and an online ticketing platform with both direct consumer and IATA-registered travel agent booking channels.

The business generates revenue through per-person hop-on-hop-off tickets ($42-$44 adult, $18-$19 child), private charter rentals priced by vehicle type and duration (e.g., $950 for 4 hours on a trolley, approximately $5,200/day for a motor coach), group discounts (15+ at $44 per person, 20% off), and bundled cross-promotional packages with anchor attractions. Customer segments include leisure tourists, wedding parties, corporate clients, school groups (notably Chicago Public Schools), pub crawl and social events, and parade/event organizers. Marquee accounts include the Chicago Cubs 2016 World Series Parade (5M+ attendees), Blackhawks Stanley Cup parades, White Sox transportation, Oprah Winfrey's production company, and President Obama's 2008 and 2012 election nights, alongside institutional relationships with the Clinton Global Initiative. The company is a privately held subsidiary of Coach USA L.L.C., a New Jersey-based diversified transportation conglomerate, with corporate functions including payment processing routed through the parent's Paramus, NJ office.

Publicly listed partners include Mercury Cruises, Lincoln Park Zoo, 360 Chicago, Skydeck, and Broadway in Chicago. Recognition includes repeated Trip Advisor "Best Hop On Hop Off" awards and Concierge Preferred Winner 2017-18. The company's operating data indicates a notice of cessation of operations after December 31, 2019, signaling the wind-down of the business at the close of its 25th anniversary year.

Name

Chicago Trolley Co

Legal name

Coach USA, LLC

Website

https://chicagotrolley.com

Company type

Private

Founded year

1994

Operating status

Closed

Headcount range

11–50 employees

Short description

Chicago Trolley & Double Decker Co. is the largest tourism transportation company in the Midwest, operating 75 trolleys, open-top double deckers, and motor coaches for hop-on-hop-off sightseeing and private charters in Chicago. It is a privately held subsidiary of Coach USA.

Ownership category

akta.pro rank

Product category

Tourism Transportation Services

NAICS

Scenic and Sightseeing Transportation, Land (487110), Charter Bus Industry (48551)

SIC

Services-Amusement & Recreation Services (7900)

akta.pro primary industry

Tour & Sightseeing Coach Charters (THAIAIAB)

akta.pro secondary industry

Convention, Conference & Trade Show Charters (THAIAIAG)

Keywords

• Hop on hop off tours
• Sightseeing transportation
• Trolley rentals
• City tour services
• Private charter buses

Headquarters

HQ city

Chicago, Illinois

HQ country

United States

HQ region

North America

Offices2 records

Markets served

GTM type

B2B and B2C

Offering type

Services

Cost components

Personnel, Operations, Marketing or Sales, Technology or R&D, Supply Chain

Revenue model

1. Hop On Hop Off Tour Tickets: Per-person ticket sales for downtown tours with options for single day, multi-day, and package deals. Adults $42-$44, Children $18-$19. Includes free second day with purchase.
2. Private Trolley/Charter Rentals: Hourly and block rental of trolleys, double deckers, and motor coaches for events including weddings, pub crawls, corporate events. Rates vary by vehicle type and duration.
3. Travel Agent Commissions: Commission payments to travel agents who book sightseeing tours through their website using IATA numbers
4. Vehicle Advertising: Vinyl wraps and advertising placements on trolleys and double decker buses targeting pedestrians, motorists and passengers in downtown Chicago area

Pricing tiers

Go-to-market motion4 records

Distribution channels5 records

Marketing channels8 records

Core offering

Chicago Trolley & Double Decker Co. sold hop-on-hop-off sightseeing tours of downtown Chicago across 12 stops via a fleet of 40 custom San Francisco-style trolleys, 27 open-top double decker buses, and 8 motorcoaches. The company also offered private charter rentals of those vehicles for weddings, corporate events, school field trips, pub crawls, and parades, with quote-based pricing and bundled packages combining trolley tours with boat cruises and observation deck tickets.

Product overview

Chicago Trolley & Double Decker Co. operates a multi-product tour and transportation service portfolio built around hop-on-hop-off city sightseeing. The core offering is the Downtown Tour featuring 12 stops across Chicago's most popular attractions, supplemented by specialty routes (Wrigley Field/Lincoln Park Zoo, Night Tour, Museum of Science & Industry/Chinatown), premium package tours combining land, water, and sky experiences (Land & Sky Tour, Land/Lake/River Tour, Land/Lake/River & Sky Tour), and seasonal offerings (Holiday Lights Tour, Haunted Tours, O Christmas Tree Jingle Bus). The company also offers private trolley, double decker, and motorcoach rentals for weddings, school trips, company shuttles, pub crawls, and parade services. Technology features include GPS real-time bus tracking and a multi-lingual mobile app. The fleet comprises 40 classic trolleys, 27 open-top double deckers, and 8 motorcoaches, with business services for travel agents and group bookings. The company was founded 25 years ago and is the largest tourism transportation company in the Midwest, operated under parent company Coach USA.

Differentiator

Problem solved

Functional benefit

Products and services

• Hop On Hop Off Downtown Tour Flagship hop-on-hop-off sightseeing tour with 12 stops covering Chicago's most popular attractions including Magnificent Mile, Navy Pier, Art Institute, and Museum Campus. Allows unlimited boarding and reboarding at designated stops.
• Wrigley Field / Lincoln Park Zoo Route North-side tour route featuring stops at 360 Chicago, Chicago History Museum, Lincoln Park Zoo, and Wrigley Field with narration about quirky neighborhoods and baseball history.
• Night Tour Evening tour showcasing Chicago's illuminated skyline, Loop architecture, Grant Park, Buckingham Fountain, and Navy Pier under twilight conditions. Not a hop-on-hop-off format; approximately 2 hours.
• Deluxe Motorcoach Tour Year-round comprehensive city highlights tour via 55-seat motorcoach with hotel pickups, photo stops at Wrigley Field and Museum Campus, and narration through neighborhoods including Chinatown and Greektown.
• Land, Lake, River & Sky Tour Premium four-in-one package combining Hop On Hop Off Downtown Tour, Mercury Urban Adventure boat cruise on Chicago River and Lake Michigan, and choice of 360 Chicago or Skydeck observation deck tickets. Includes second day free for the trolley portion.
• Land, Lake & River Tour Combined package pairing Hop On Hop Off Downtown Tour with Mercury Urban Adventure Cruise on Chicago River and Lake Michigan, including second day free for the trolley portion.
• Land & Sky Tour Package combining Hop On Hop Off Downtown Tour with either 360 Chicago or Skydeck at Willis Tower ticket, including second day free for the trolley portion.
• Holiday Lights Tour Seasonal winter tour showcasing Chicago's holiday light displays at John Hancock Center, Christkindlmarket, Lincoln Park ZooLights, Magnificent Mile, and surrounding areas, in partnership with Lincoln Park Zoo.
• Haunted Trolley Tours Private haunted group tours exploring paranormal and mysterious stories of Chicago's history, including Haunted Death Alley, Resurrection Mary, and Graceland Cemetery. Available daily with 20-person minimum at $32 per person.
• O Christmas Tree Jingle Bus Coach bus tour visiting Chicago's iconic holiday trees, Museum of Science & Industry Christmas Around the World exhibit, and Millennium Park City Tree. Includes Museum admission and Garrett Popcorn.
• Home for the Holidays Tour 4-hour trolley tour of Lincoln Square and Andersonville neighborhoods with German and Swedish heritage, featuring local shop stops and holiday decorations.
• Hamilton Exhibition Shuttle Shuttle service connecting Soldier Field north parking lot and Adler Planetarium to the Hamilton Exhibition, running one hour before opening until one hour after closing, in partnership with Broadway in Chicago.
• Wedding Trolley Rentals Private trolley and double decker charters for wedding party transportation, photo excursions, rehearsal dinners, and bachelor/bachelorette parties. Food, drinks, and decorations welcome onboard.
• School Trip Trolley Rentals Private trolley and double decker charters for educational field trips to Chicago museums, historical sites, and parks, customized to school curriculum with school-location pickup. Approved Chicago Public Schools vendor #26481.
• Company Shuttle Rentals Corporate transportation for company outings, scavenger hunts, pub crawls, and city tours designed for staff team-building events with capacity for thousands of guests.
• Pub Crawl Trolley Rentals Party trolley service for bar crawls, birthday parties, and group celebrations with cooler storage, iPod hookup, and pickup from any location. Chicago Trolley claims to have invented the pub crawl market in Chicago, running over 1,000 pub crawls per year.
• Parade Services Trolley and double decker participation in parades including Independence Day, Memorial Day, Pride, Bud Billiken, Festival of Lights, St Patrick's Day, and World Series/Stanley Cup victory parades with exterior decoration options. Has served Cubs, Blackhawks, White Sox, President Obama, and Clinton Global Initiative.
• Tour Packages Bundled ticket packages offering savings on combinations of Downtown Tour, Night Tour, Wrigley Field Route, Land/Lake/River Tours, and observation deck tickets.

Quantifiable outcome

• Over 5 million people transported during 2016 Cubs World Series Parade - largest gathering in American history
• +2 more outcomes

Named customers7 records

Segments6 records

Ideal customer profiles5 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Feature3 records

Partnerships

Six partnerships are on record, tiered core and minor.

• Mercury CruisescoreStrategic or Co-development PartnerLong-time partnership for combined land and water tour packages. Chicago Trolley provides hop on hop off bus tours while Mercury provides Urban Adventure cruises on Chicago River and Lake Michigan. Passengers book cruise tickets directly with Mercury (312-332-1366). This is their most popular package combination.
• Lincoln Park ZoocoreStrategic or Co-development PartnerOfficial Trolley and Double Decker of Lincoln Park ZooLights. Chicago Trolley provides transportation to ZooLights as part of Holiday Lights Tour, with complimentary ZooLights 3D glasses provided to riders.
• Broadway in ChicagominorGTM or Marketing PartnerContact for Hamilton Exhibition groups of 10 or more. Chicago Trolley provides shuttle service from Soldier Field north parking lot and Adler Planetarium to the exhibition.
• 360 Chicago (John Hancock Center)coreStrategic or Co-development PartnerStarting point for multiple tours including Land & Sky Tour package. 360 Chicago observation deck included as optional add-on in tour packages, located 1000 feet above Magnificent Mile.
• Skydeck at Willis TowercoreStrategic or Co-development PartnerIncluded in Land & Sky Tour package alongside hop on hop off tour. Skydeck at Willis Tower (103rd floor) offers panoramic views and The Ledge experience.
• Coach USAcoreOthersParent company providing corporate infrastructure including payment processing (charges appear as 'CoachUSA/Megabus' on credit cards), privacy policy, and administrative support. Corporate office at 160 S. Route 17 North, Paramus, NJ.

Scale indicators10 records

Recent moves6 records

Expansion highlights3 records

Direct peers

• City Sightseeing Worldwide: Global hop-on-hop-off sightseeing tour operator with presence in 100+ cities. Operates branded red buses on multi-stop sightseeing routes with similar ticket/pass structures and attraction partnerships as Chicago Trolley.
• Old Town Trolley Tours: US-based sightseeing trolley tour operator (Historic Tours of America) running hop-on-hop-off services in cities including Washington DC, Boston, San Diego, St Augustine, and Key West. Closest analog on vintage-trolley fleet positioning and city sightseeing model.
• Gray Line: Long-established sightseeing tour brand historically affiliated with Coach USA. Offers hop-on-hop-off, charter, and packaged tours in major US cities using a similar fleet composition of trolleys, double deckers, and motor coaches.
• Big Bus Tours: Largest global hop-on-hop-off sightseeing bus operator with active operations in major US cities including Chicago. Closest direct comparable on business model: branded open-top double decker buses, multi-stop routes, attraction partnerships, and pass-based ticketing.
• TopView Sightseeing: New York-based sightseeing operator offering hop-on-hop-off bus tours plus harbor cruises and helicopter packages. Comparable in product extensions (multi-modal tour bundles), premium pricing tiers, and experience-led differentiation.

Regional players

• Shoreline Sightseeing: Chicago-based water sightseeing operator offering architecture cruises, river tours, and lake excursions. Directly comparable in geography and Chicago visitor demographic, but operates boats rather than land vehicles.
• Wendella Boats: Family-owned Chicago water tour operator running architecture cruises and sightseeing on the Chicago River. Competes with Mercury's water offering and overlaps with Chicago Trolley on the same Chicago visitor demographic, especially around downtown sightseeing packages.
• Mercury Cruises: Chicago water tour operator explicitly referenced in the company data as a long-time Land/Lake/River & Sky package partner, providing Urban Adventure cruises on Chicago River and Lake Michigan. Competes for the same tourist spend pool with a complementary water-based experience.

Others

• Megabus: Coach USA sister brand providing low-cost intercity scheduled bus service across North America. Same corporate parent and shared infrastructure, but a different value proposition (point-to-point transit rather than sightseeing) - useful peer for parent-company economics.

Emerging players

• Chicago Architecture Center: Chicago nonprofit offering architecture-focused walking tours, river cruises, and bus tours. Directly competes with Chicago Trolley's downtown sightseeing routes for architecture-curious visitors, though smaller and more niche in product offering.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat5 records

Key risks6 records

Key highlights7 records

Customer concentration

• LinkedInlinkedin.com/company/chicago-trolley-co

Revenue estimate

Valuation estimate

Number of profiles

Funding overview

Funding rounds

Investors

Funding detail is available on the Subscription and Enterprise plan.Contact sales →

M&A

Investments

M&A and investment is available on the Subscription and Enterprise plan.Contact sales →

Frequently asked questions about Chicago Trolley Co