The average bus between Chicago Union Station and Waterbury takes 24h 53m and the fastest bus takes 22h 55m. The bus service runs several times per day from Chicago Union Station 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 Union Station and Waterbury. The earliest departure is at 7:00 AM in the morning, and the last departure from Chicago Union Station is at 7:15 PM which arrives into Waterbury at 9:51 PM. All services require a transfer at Chicago Bus Station and take an average of 24h 53m. The schedules shown below are for the next available departures.
Arrives next day



24h 17m • 3 changes
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26h 31m • 3 changes
Arrives next day



23h 55m • 3 changes
Arrives next day



26h 36m • 3 changes
Want to know about travelling from Chicago Union Station 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 Union Station to Waterbury. However, there are services departing from Chicago Union Station station and arriving at Waterbury station via New York Midtown. The journey, including transfers, takes approximately 24h 53m.
Chicago Union Station to Waterbury bus services, operated by Flixbus USA, depart from Chicago Bus Station.
Chicago Union Station to Waterbury bus services, operated by Flixbus USA, arrive at Grand St @ State St station.
The distance between Chicago Union Station and Waterbury is 1,209.8 km. The road distance is 1,601 km.
You can take a vehicle from Chicago Union Station to Grand St @ State St via Chicago Bus Station, New York Midtown, 8 Av/W 31 St, 8 Av/W 41 St, New York, New Haven, and Church St @ Chapel St in around 22h 17m.