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Bus from Chicago, IL to Annapolis, MD

More travel options

You now can select from more schedules across U.S., Mexico and Canada with Greyhound and FlixBus.

Enjoy free onboard Wi-Fi

We offer free Wi-Fi and power outlets to keep you connected and powered up during your trip.

Reserve a Seat

Reserve your favorite seat when you book your ticket.

Need to make a change?

Easily change your ticket or add bags with Manage My Booking.

On this page

Bus stations and stops in Chicago, IL

Please note: your ticket will contain the most up-to-date address information.
wifi
Free WiFi
Stay connected throughout your journey
socket
Power Outlets
Keep your devices charged on the go
seat
Comfortable seats
Relax with extra legroom and reclining seats
luggage
Luggage storage
Space to safely stow your belongings
toilet
Toilets
Conveniently available on every FlixBus
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Frequently asked questions

The journey by Greyhound bus from Chicago to Annapolis covers approximately 849 miles. The quickest trip takes 22 hours 50 minutes.
To track your bus from Chicago to Annapolis, use Greyhound’s bus tracker. This tool provides live updates on the bus’s location and expected arrival times.
When traveling from Chicago to Annapolis with Greyhound, you can bring one carry-on bag (up to 25 lbs, 16x12x7 inches) for free. Additionally, one checked bag is included, with a second bag free for Flexible fare passengers. Extra or oversized baggage can be added during booking or later through the "Manage My Booking" section. Some locations also allow in-person payment for additional luggage. Full details are available on our baggage policy page.
Opting for Greyhound to travel from Chicago to Annapolis is an environmentally responsible choice, reducing traffic and lowering emissions compared to car travel.
Onboard amenities on Greyhound buses from Chicago to Annapolis include free Wi-Fi, personal power outlets, reclining seats with extra legroom, overhead storage, and an onboard restroom.
The first Greyhound bus from Chicago to Annapolis departs at 9:40 am.
The last Greyhound bus from Chicago to Annapolis leaves at 10:00 pm.
Yes, you can book both Greyhound and FlixBus tickets for travel from Chicago to Annapolis through our website. After selecting your cities and travel dates, you can compare the schedules and prices of both services.
Greyhound operates up to 3 trips daily from Chicago to Annapolis. You can find the schedule by entering your departure date in the search box above.
Greyhound buses are equipped with wheelchair lifts and have space for two passengers using wheelchairs or mobility scooters. We recommend booking your trip from Chicago to Annapolis in advance to secure the necessary accommodations. Service animals are also welcome on all Greyhound buses. For more details, visit our accessibility page.
You can find the Greyhound bus stops in both Chicago and Annapolis by checking the map on this page, which shows the addresses and locations of all stops.

Planning Your Greyhound Bus Trip from Chicago to Annapolis?

How to Book Your Bus Ticket to Annapolis from Chicago

With Greyhound, reserving a ticket for your bus trip is a breeze. You can easily complete your booking on this website or through the free Greyhound App, all within a few simple clicks. You will have a variety of rides to choose from, as on many of our routes you will be offered both Greyhound and FlixBus bus rides, so you can choose the option that best fits your schedule. When booking your ticket from Chicago to Annapolis, you have a range of secure online payment options at your disposal, including both debit and credit cards. If you prefer, cash payments are also accepted at various sales points. If you're on the hunt for a cheap ticket to Annapolis, remember to book early. Traveling on weekdays or during non-peak hours can also lead you to some of the most budget-friendly fares available!

Onboard services are subject to availability