The average bus between Chicago and Waterbury takes 24h 29m and the fastest bus takes 22h 46m. The bus service runs several times per day from Chicago to Waterbury. The journey time may be longer on weekends and holidays; use the search form on this page to search for a specific travel date.
Buses run twice daily between Chicago and Waterbury. The earliest departure is at 12:25 PM in the afternoon, and the last departure from Chicago is at 7:15 PM which arrives into Waterbury at 9:46 PM. All services require a transfer at New York Midtown and take an average of 24h 29m. The schedules shown below are for the next available departures.
Arrives next day


23h 55m • 2 changes
Arrives next day


26h 36m • 2 changes
Arrives next day


23h 55m • 2 changes
Arrives next day


26h 36m • 2 changes
Want to know about travelling from Chicago to Waterbury? We have put together a list of the most frequently asked questions from our users such as: What is the cheapest mode of transport? What is the quickest option? How much do tickets usually cost? and many more.
No, there is no direct bus from Chicago to Waterbury. However, there are services departing from Chicago station and arriving at Waterbury station via New York Midtown. The journey, including transfers, takes approximately 24h 29m.
Chicago to Waterbury bus services, operated by Flixbus USA, depart from Chicago Bus Station.
Chicago to Waterbury bus services, operated by Flixbus USA, arrive at Grand St @ State St station.
The distance between Chicago and Waterbury is 1,208.9 km. The road distance is 1,594 km.
You can take a bus from Chicago Bus Station to Grand St @ State St via New York Midtown, Port Authority Bus Terminal, New Haven Union Station, and Church St @ Chapel St in around 22h 7m.