The average bus between Annapolis and Chicago takes 25h 50m and the fastest bus takes 21h 20m. There is at least one bus per day from Annapolis 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 once daily between Annapolis and Chicago. The earliest departure is at 1:40 PM in the afternoon, and the last departure from Annapolis is at 5:00 PM which arrives into Chicago at 8:05 PM. All services require a transfer, and take on average 25h 50m. The schedules shown below are for the next available departures.
Arrives next day

20h 20m • 1 change
Arrives next day

27h 5m • 1 change
Arrives next day

20h 20m • 1 change
Arrives next day

27h 5m • 1 change
Want to know about travelling from Annapolis 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 Annapolis to Chicago. However, there are services departing from Annapolis station and arriving at Chicago station via Washington Union Station station. The journey, including transfers, takes approximately 25h 50m.
Annapolis to Chicago bus services, operated by Flixbus USA, depart from Annapolis station.
Annapolis to Chicago bus services, operated by Flixbus USA, arrive at Chicago Bus Station.
Book your Annapolis to Chicago bus tickets online with Flixbus USA and Greyhound USA.
The distance between Annapolis and Chicago is 995.2 km. The road distance is 1,194 km.
You can take a bus from Annapolis to Chicago Bus Station via Washington Union Station in around 19h 5m.