The average bus between Chicago and Chesapeake takes 26h 45m and the fastest bus takes 26h 14m. The bus service runs several times per day from Chicago to Chesapeake. 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 Chesapeake. The earliest departure is at 7:00 AM in the morning, and the last departure from Chicago is at 6:00 PM which arrives into Chesapeake at 10:11 PM. All services require a transfer at Washington Union Station and take an average of 26h 45m. The schedules shown below are for the next available departures.
Arrives next day


27h 15m • 2 changes
Arrives next day


28h 11m • 2 changes
Arrives next day


27h 15m • 2 changes
Arrives next day


28h 11m • 2 changes
Want to know about travelling from Chicago to Chesapeake? 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 Chesapeake. However, there are services departing from Chicago station and arriving at Chesapeake station via Washington Union Station station. The journey, including transfers, takes approximately 26h 45m.
Chicago to Chesapeake bus services, operated by Greyhound USA, depart from Chicago Bus Station.
Chicago to Chesapeake bus services, operated by Greyhound USA, arrive at Norfolk station.
The distance between Chicago and Chesapeake is 1,125.2 km. The road distance is 1,501 km.
You can take a bus from Chicago Bus Station to Robert Hall & Military via Washington Union Station, Norfolk, and Military & Poplar Hall in around 22h 48m.