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How to get fromAnnapolis to Chicagoby bus, plane, bus (Flixbus, Greyhound), train, car, subway, or bus (Greyhound, Flixbus)

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

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

  1. Bus to Ronald Reagan Washington National Airport, fly to Chicago Midway International Airport

    best
    1. Take the bus from Annapolis to Washington Union Stationbus bus
    2. Fly from Ronald Reagan Washington National Airport (DCA) to Chicago Midway International Airport (MDW)plane plane DCA - MDW
    4h 46m
    $120–669

  2. Line 70 bus to Baltimore-Washington International Airport, fly to Chicago Midway International Airport

    cheapest
    1. Take the bus from COLLEGE AVE & BLADEN ST eb to Cromwell Light Rail Station Bay 1bus bus
    2. Fly from Baltimore-Washington International Airport (BWI) to Chicago Midway International Airport (MDW)plane plane BWI - MDW
    5h 23m
    $88–445

  3. Bus

    1. Take the bus from Annapolis to Washington Union Stationbus bus FlixBus 2601 / ...
    2. Take the bus from Washington Union Station to Chicago Bus Stationbus bus Greyhound US0164
    18h 55m
    $104–207

  4. Bus, train via Rockville

    1. Take the bus from Annapolis to Washington Union Stationbus bus FlixBus 2601 / ...
    2. Take the train from Rockville Amtrak to Chicago Union Stationtrain train Floridian
    19h 47m
    $246–503

  5. Drive 709.9 mi

    1. Drive from Annapolis to Chicagocar car 709.9 mi
    12h 17m
    $130–188

  6. Bus to Ronald Reagan Washington National Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Annapolis to Washington Union Stationbus bus
    2. Fly from Ronald Reagan Washington National Airport (DCA) to Chicago O'Hare International Airport (ORD)plane plane DCA - ORD
    5h 8m
    $100–509

  7. Line 70 bus to Baltimore-Washington International Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from COLLEGE AVE & BLADEN ST eb to Cromwell Light Rail Station Bay 1bus bus
    2. Fly from Baltimore-Washington International Airport (BWI) to Chicago O'Hare International Airport (ORD)plane plane BWI - ORD
    5h 41m
    $318–765

  8. Bus, subway to Washington Dulles International Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Annapolis to Washington Union Stationbus bus
    2. Take the subway from Farragut West, Blue/Orange/Silver Line Track 2 Platform to Washington Dulles International Airport, Silver Line Center Platformsubway subway
    3. Fly from Washington Dulles International Airport (IAD) to Chicago O'Hare International Airport (ORD)plane plane IAD - ORD
    5h 42m
    $430–924

  9. Bus, subway to Washington Dulles International Airport, fly to South Bend, train

    1. Take the bus from Annapolis to Washington Union Stationbus bus
    2. Take the subway from Farragut West, Blue/Orange/Silver Line Track 2 Platform to Washington Dulles International Airport, Silver Line Center Platformsubway subway
    3. Fly from Washington Dulles International Airport (IAD) to South Bend (SBN)plane plane IAD - SBN
    4. Take the train from South Bend Airport to Van Buren St.train train
    7h 38m
    $111–684

  10. Bus via Harrisburg

    1. Take the bus from West St & Church Cir to Patapsco Light Rail Station Bay 3bus bus 70
    2. Take the bus from Baltimore Downtown Bus Station to Harrisburg Bus Stationbus bus
    3. Take the bus from Harrisburg Bus Station to Chicago Bus Stationbus bus
    22h 15m
    $125–216

  11. Bus, train

    1. Take the bus from West St & Church Cir to Patapsco Light Rail Station Bay 3bus bus 70
    2. Take the train from Baltimore Penn Station to Chicago Union Stationtrain train Cardinal
    28h 46m
    $314–658

Annapolis to Chicago by bus

Calendar10Weekly Buses
Duration18h 55mAverage Duration
Ticket$104Cheapest Price
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Questions & Answers

Map of how to get from Annapolis to Chicago.ExpandLaunch map view
  • Distance: 646.1 mi
  • Duration: 4h 46m

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

You can take a bus from Annapolis to Chicago Bus Station via Washington Union Station in around 18h 55m.

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