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Trailways Bus Tickets
from Chicago, IL to Annapolis, MD

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Overview

About buses from Chicago, IL to Annapolis, MD

Buses from Chicago, IL to Annapolis, MD travel the 628mi (1010.67km) journey, taking approximately 22h, 5m. Usually, there are 3 buses operating per day. While the average ticket price for this journey is around $243.62, you can find the cheapest bus tickets for as low as $167.54.

  • Distance
    628mi (1010.67km)
  • Average trip duration
  • Average bus ticket price
    $243.62
  • Trips per day
    3
  • Top Carriers
    FlixBus

Bus Station Information for Annapolis, MD

Annapolis

Curbside Stop, use arrow keys or tab to explore more about this bus station

Annapolis, MD 021401

Curbside Stop
Address
80 West Street 
Annapolis, MD 021401
Phone Number
(858) 800-8898
More Detailsabout Annapolis Curbside Stop

City InformationforChicago, IL

There’s so much to see in the Windy City, you’ll be booking your next bus to Chicago before your trip is over. No matter the season, there’s plenty to do, from lounging on lakeside beaches in the summer to ice skating in Millennium Park.

Chicago’s famous for its dogs and its deep dish, if you’re looking for eats. Museums dot the map, including The Art Institute of Chicago, Field Museum, and Griffin Museum of Science and Industry. Catch a game if your sport’s in season – Bulls or Bears, Cubs or White Sox.

If you ask a local – which we always do – an Architecture Tour is on the don’t miss list. And if you’re on a budget, just go for a stroll on the Riverwalk, Navy Pier, or by “the bean” - Millennium Park’s famed Cloud Gate sculpture.

Whatever mood strikes you, Chi-town's got something to keep you busy.

Scenic photo of Chicago, ILScenic photo of Chicago, ILScenic photo of Chicago, IL
Scenic photo of Chicago, IL
Scenic photo of Chicago, IL
Scenic photo of Chicago, IL

City InformationforAnnapolis, MD

Set sail for Annapolis, MD, where the charm of maritime history is alive and well! Not just a port town, Annapolis is a treasure trove of experiences waiting on the other end of your bus to Annapolis, MD. Start your adventure by wandering through the cobblestone streets of its charming Historic District. Here, colonial buildings and navy pride blend beautifully with local art galleries and quirky shops.

At the United States Naval Academy, you can immerse yourself in naval grandeur and learn a bit about those budding admirals. If you're more inclined toward the arts, the city offers venues like the Maryland Hall for the Creative Arts, perfect for catching a live performance or enjoying an exhibit. On a sunny day, hop on one of the many boat tours for an unforgettable Bay view – don’t forget your captain’s hat!

End your day sampling some crabcakes at a local eatery, savoring Chesapeake Bay flavors that truly capture the town's spirit. So grab your itinerary, hop on a bus, and let the sea breezes guide your journey in Annapolis.

Frequently Asked Questions about the Bus Ride

Planning on taking the bus from Chicago to Annapolis? If you want a fast and cheap way to get to Annapolis, or need an alternative to rail or airfare, Trailways helps you get there. Get your bus ticket to Annapolis now!

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