Travel made simple with Trailways
Unbeatable Prices
One of the best inventories of bus tickets in one place - with exclusive fares you won't find elsewhere.
Proven Reliability
On-time travel services - trust our reputation for reliable bus transportation.
Comfort and Convenience
Numerous upgraded buses with large leather recliners, free wi-fi, and power outlets for each seat.
Overview
About buses from Annapolis, MD to Chicago, IL
Buses from Annapolis, MD to Chicago, IL travel the 0mi (0.00km) journey, taking approximately 1d, 2h, 41m. Usually, there are 4 buses operating per day. While the average ticket price for this journey is around $316.95, you can find the cheapest bus tickets for as low as $316.95.
- Average bus duration
- Average bus ticket price$316.95
- Trips per day4
- Top CarriersFlixBus
Bus Station Information for Chicago, IL
Chicago (95th & Dan Ryan)
Chicago, IL 60628
- Address
- 95th & Dan Ryan
Chicago, IL 60628
Phone Number
(800) 858-8555
Chicago (Cumberland Avenue)
Chicago, IL 60631
- Address
- 5800 N Cumberland Ave
Chicago, IL 60631
Phone Number
(800) 858-8555
Chicago (Bus Station)
Chicago, IL 60607
- Address
- 630 West Harrison Street
Chicago, IL 60607
Phone Number
(319) 753-2864/(800) 858-8555
Chicago (Amtrak Union Station)
Chicago, IL 60606
- Address
- 225 S. Canal St.
Chicago, IL 60606
Phone Number
(800) 858-8555
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.
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.
Frequently Asked Questions about the Bus Ride
Planning on taking the bus from Annapolis to Chicago? Book a trip to Chicago from Annapolis for as low as $316.95. We have 4 trip(s) departing daily. Take a convenient and affordable bus trip to Chicago today!How long does it take to get from Annapolis to Chicago?
How many buses are there from Annapolis to Chicago?
How early should I arrive at Annapolis?
What is the average cost of the trip?
What bus companies offer services?
How long does it take?
What if my question isn't listed?
