The average bus between Chicago and Chesapeake takes 25h 28m and the fastest bus takes 24h 10m. 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 6:30 AM in the morning, and the last departure from Chicago is at 6:00 PM which arrives into Chesapeake at 7:14 PM. All services require a transfer at Washington Union Station and take an average of 25h 28m. The schedules shown below are for the next available departures.
Arrives next day


27h 42m • 2 changes
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25h 10m • 2 changes
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27h 44m • 2 changes
Arrives next day


25h 14m • 2 changes
Arrives next day


27h 44m • 2 changes
Arrives next day


25h 14m • 2 changes
Arrives next day


27h 44m • 2 changes
Arrives next day


25h 14m • 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 25h 28m.
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 1,500 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 43m.