The average bus between Chicago and Annapolis takes 24h 36m and the fastest bus takes 21h 10m. There is at least one bus per day from Chicago to Annapolis. 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 once daily between Chicago and Annapolis. 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 Annapolis at 4:10 PM. All services require a transfer, and take on average 24h 36m. The schedules shown below are for the next available departures.
Arrives next day

27h 20m • 1 change
Arrives next day

22h 10m • 1 change
Arrives next day

27h 20m • 1 change
Arrives next day

22h 10m • 1 change
Want to know about travelling from Chicago to Annapolis? 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 Annapolis. However, there are services departing from Chicago station and arriving at Annapolis station via Washington Union Station station. The journey, including transfers, takes approximately 24h 36m.
Chicago to Annapolis bus services, operated by Greyhound USA, depart from Chicago Bus Station.
Chicago to Annapolis bus services, operated by Greyhound USA, arrive at Annapolis station.
Book your Chicago to Annapolis bus tickets online with Greyhound USA and Flixbus USA.
The distance between Chicago and Annapolis is 995.2 km. The road distance is 1,211 km.
You can take a bus from Chicago Bus Station to Annapolis via Washington Union Station in around 18h 15m.