About Us

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Started by three friends twenty-five years ago, Chicago Trolley & Double Decker is the largest tourism transportation company in the Midwest. We invented and perfected the hop on hop off tour here. There is no question everyone else is simply imitating our style though we’re always a few miles ahead. We’re committed to providing authentic experiences. We have forty trolleys in our fleet. No other city’s trolley company has this large of a fleet. We have twenty-seven open-top double decker buses and eight motor coaches. We employ over one hundred fifty tour guides and drivers. We sell more tour tickets and do more weddings, city tours, customized tours, pub crawls, corporate outings, shuttles, and parades than any company in Chicago. Chicago is our only location and certainly our specialty.

Our tour guides and drivers are natural performers and trained guides. They’re teachers, writers, stand-up and improv comics from Second City Theater and iO Theater. They’re musicians, dramatic actors, and “real world” people who decided not to work in a traditional office setting. They’re charismatic, personable, and safety conscious. They have one thing in common: a passion for all things Chicago.

We were the only vehicles in the 2016 Chicago Cubs World Series Parade. With over five million people in the streets, this was the largest gathering in American history. We had twenty-one double deckers and twenty-three trolleys carrying the players, coaches, and staff. We managed the parade from initial design to its operational end. This was the largest and most successful event in Chicago transportation history.

President Obama’s staff rented twenty-five trolleys from us for both of his election nights in 2008 and 2012. President Clinton and the Clinton Global Initiative rented sixteen trolleys for their Field Museum event in 2013. Mayor Richard M. Daley and his entire family rode in one of our trolleys every year in the St. Patrick’s Day Parade.

The Blackhawks used twenty trolleys and ten double deckers for the Stanley Cup Parades in 2010, 2013, and 2015. Mayor Emanuel and two governors rode with us in those Stanley Cup Parades. Mayor Emanuel also rode with us in the Little League World Series Parade. We were the only vehicles in the White Sox World Series Parade. And we’ve driven many events for the Bears and Bulls.

Oprah Winfrey broadcast her show on top of one of our double deckers when she famously shut down the entire Magnificent Mile for a day. On another episode, she had the Olympic medalists from the U.S.A. ride with us on top of the bus. We have recently been on Windy City Live, The Steve Harvey Show, The Onion A.V. Club, Bravo, WGN, WCIU, ABC, NBC, CBS, and VH1. We win Trip Advisor’s best hop on hop off tour year after year. In 2017-18, we were the Concierge Preferred Winner for Best Service and Best Culture and Attraction. Considering that almost a thousand concierges voted, this means so much to us.

We’re proud to provide classic and festive transportation for both travelers and locals. We were born and raised in Chicago and we’re never leaving. We at Chicago Trolley & Double Decker are thrilled to have the opportunity to be a part of your vacation or big event. Thank you.


  • 32 passenger capacity
  • Forward-facing oak benches
  • Open sides with roll-down flaps in warm months
  • Fully-heated with closable windows in cold months
  • PA system with microphone
  • iPod hookup and CD player
  • Wheelchair lifts and ADA compliant
  • Side rails for signs up to 16 ft. in length
  • Environmentally-friendly biodiesel
  • Uniform style and features custom-built for us in Maine
  • 55 seats on top, 16 on lower level
  • Open on top, enclosed on bottom with full windows
  • On-board PA system with microphone on top
  • Able to have banners and signs attached to the exterior
  • Environmentally-friendly biodiesel