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Bus from Chicago, IL to Annapolis, MD

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Bus stations and stops in Chicago, IL

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Frequently asked questions

The journey by Greyhound bus from Chicago to Annapolis covers approximately 807 miles. The quickest trip duration is 21 hours 15 minutes, .
Bus tickets from Chicago to Annapolis start at $217.99. For the best rates, it is recommended to book in advance via our app or website. You can pay online using debit or credit cards, or choose to pay in person with cash at selected locations.
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 6:20 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 4 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?

The journey from Chicago to Annapolis can take as little as 21 hours 15 minutes and starts from as little as $217.99. The earliest bus leaves at 6:20 am and the last bus leaves at 10:00 pm. Greyhound schedules 4 buses per day from Chicago to Annapolis. Travel with Greyhound and enjoy complimentary Wifi, access to power sockets, and a comfortable seat throughout your trip. Don't miss any updates on your bus trip: stay informed with our real-time bus tracker and check the status of your ride to Annapolis in seconds.

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