The average bus between Waterbury and Chicago takes 27h 25m and the fastest bus takes 22h 15m. The bus service runs several times per day from Waterbury to Chicago. 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 Waterbury and Chicago. The earliest departure is at 5:40 AM in the morning, and the last departure from Waterbury is at 11:40 PM which arrives into Chicago at 6:10 AM. All services require a transfer at Asylum St @ Bushnell Park and take an average of 27h 25m. The schedules shown below are for the next available departures.
Arrives next day


22h 8m • 2 changes
Arrives +2 days


36h 33m • 2 changes
Arrives next day


22h 8m • 2 changes
Arrives +2 days


36h 33m • 2 changes
Want to know about travelling from Waterbury to Chicago? 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 Waterbury to Chicago. However, there are services departing from Waterbury station and arriving at Chicago station via Asylum St @ Bushnell Park. The journey, including transfers, takes approximately 27h 25m.
Waterbury to Chicago bus services, operated by CT Transit, depart from W Main St @ Leavenworth St station.
Waterbury to Chicago bus services, operated by CT Transit, arrive at Chicago Bus Station.
The distance between Waterbury and Chicago is 1,208.9 km. The road distance is 1,662 km.
You can take a bus from W Main St @ Leavenworth St to Chicago Bus Station via Asylum St @ Bushnell Park, Hartford Union Station, Port Authority Bus Terminal, and New York Midtown in around 22h 41m.