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How to get fromChicago to Annapolisby plane, bus, bus (Greyhound, Flixbus), train, car, subway or bus (Flixbus, Greyhound)

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There are 11 ways to get from Chicago to Annapolis by plane, bus, bus (Greyhound, Flixbus), train, car, subway, or bus (Flixbus, Greyhound)

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Fly Chicago Midway International Airport to Baltimore-Washington International Airport, bus

    best
    1. Fly from Chicago Midway International Airport (MDW) to Baltimore-Washington International Airport (BWI)plane plane MDW - BWI
    2. Take the bus from Cromwell Light Rail Station Bay 2 to West St & Church Cirbus bus
    5h 42m
    $88–503

  2. Bus

    cheapest
    1. Take the bus from Chicago Bus Station to Washington Union Stationbus bus Greyhound US0164
    2. Take the bus from Washington Union Station to Annapolisbus bus FlixBus 2601 / ...
    18h 20m
    $82–160

  3. Train, bus via Rockville

    1. Take the train from Chicago Union Station to Rockville Amtraktrain train Floridian
    2. Take the bus from Washington Union Station to Annapolisbus bus FlixBus 2601 / ...
    18h 57m
    $146–240

  4. Drive 712.6 mi

    1. Drive from Chicago to Annapoliscar car 712.6 mi
    12h 14m
    $131–188

  5. Fly Chicago Midway International Airport to Ronald Reagan Washington National Airport, bus

    1. Fly from Chicago Midway International Airport (MDW) to Ronald Reagan Washington National Airport (DCA)plane plane MDW - DCA
    2. Take the bus from Washington Union Station to Annapolisbus bus
    5h 25m
    $216–1,227

  6. Fly Chicago O'Hare International Airport to Ronald Reagan Washington National Airport, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Ronald Reagan Washington National Airport (DCA)plane plane ORD - DCA
    2. Take the bus from Washington Union Station to Annapolisbus bus
    5h 47m
    $156–827

  7. Fly Chicago O'Hare International Airport to Baltimore-Washington International Airport, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Baltimore-Washington International Airport (BWI)plane plane ORD - BWI
    2. Take the bus from Cromwell Light Rail Station Bay 2 to West St & Church Cirbus bus
    6h 10m
    $88–373

  8. Fly Chicago O'Hare International Airport to Washington Dulles International Airport, subway, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Washington Dulles International Airport (IAD)plane plane ORD - IAD
    2. Take the subway from Washington Dulles International Airport, Silver Line Center Platform to Farragut West, Blue/Orange/Silver Line Track 1 Platformsubway subway
    3. Take the bus from Washington Union Station to Annapolisbus bus
    6h 31m
    $126–492

  9. Train to General Mitchell International Airport, fly to Baltimore-Washington International Airport, bus

    1. Take the train from Chicago Union Station to Milwaukeetrain train
    2. Fly from General Mitchell International Airport (MKE) to Baltimore-Washington International Airport (BWI)plane plane MKE - BWI
    3. Take the bus from Cromwell Light Rail Station Bay 2 to West St & Church Cirbus bus
    7h 13m
    $160–614

  10. Bus via Harrisburg

    1. Take the bus from Chicago Bus Station to Harrisburg Bus Stationbus bus
    2. Take the bus from Harrisburg Bus Station to Baltimore Downtown Bus Stationbus bus
    3. Take the bus from Patapsco Light Rail Station Bay 3 to West St & Church Cirbus bus 70
    21h 28m
    $107–157

  11. Train, bus

    1. Take the train from Chicago Union Station to Baltimore Penn Stationtrain train Cardinal
    2. Take the bus from Patapsco Light Rail Station Bay 3 to West St & Church Cirbus bus 70
    27h 26m
    $123–288

Chicago to Annapolis by bus

Calendar10Weekly Buses
Duration18h 20mAverage Duration
Ticket$82Cheapest Price
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Questions & Answers

What companies run services between Chicago, IL, USA and Annapolis, MD, USA?

You can take a bus from Chicago Bus Station to Annapolis via Washington Union Station in around 18h 20m.

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