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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
    2. Fly from Ronald Reagan Washington National Airport (DCA) to Chicago Midway International Airport (MDW)planeDCA - MDW
    4h 52m
    $148–780

  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
    2. Fly from Baltimore-Washington International Airport (BWI) to Chicago Midway International Airport (MDW)planeBWI - MDW
    5h 34m
    $78–425

  3. Bus

    1. Take the bus from Annapolis to Washington Union StationbusFlixBus 2601 / ...
    2. Take the bus from Washington Union Station to Chicago Bus StationbusGreyhound US0164
    19h 10m
    $82–208

  4. Bus, train via Rockville

    1. Take the bus from Annapolis to Washington Union StationbusFlixBus 2601 / ...
    2. Take the train from Rockville Amtrak to Chicago Union StationtrainFloridian
    19h 39m
    $104–294

  5. Drive 709.9 mi

    1. Drive from Annapolis to Chicagocar709.9 mi
    12h 8m
    $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
    2. Fly from Ronald Reagan Washington National Airport (DCA) to Chicago O'Hare International Airport (ORD)planeDCA - ORD
    5h 12m
    $118–580

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

    1. Take the bus from Annapolis to Washington Union Stationbus
    2. Take the subway from Farragut West, Blue/Orange/Silver Line Track 2 Platform to Washington Dulles International Airport, Silver Line Center Platformsubway
    3. Fly from Washington Dulles International Airport (IAD) to Chicago O'Hare International Airport (ORD)planeIAD - ORD
    5h 48m
    $168–785

  8. 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
    2. Fly from Baltimore-Washington International Airport (BWI) to Chicago O'Hare International Airport (ORD)planeBWI - ORD
    5h 53m
    $88–355

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

    1. Take the bus from Annapolis to Washington Union Stationbus
    2. Take the subway from Farragut West, Blue/Orange/Silver Line Track 2 Platform to Washington Dulles International Airport, Silver Line Center Platformsubway
    3. Fly from Washington Dulles International Airport (IAD) to South Bend (SBN)planeIAD - SBN
    4. Take the train from South Bend Airport to Van Buren St.train
    7h 48m
    $104–495

  10. Bus via Harrisburg

    1. Take the bus from West St & Church Cir to Patapsco Light Rail Station Bay 3bus70
    2. Take the bus from Baltimore Downtown Bus Station to Harrisburg Bus Stationbus
    3. Take the bus from Harrisburg Bus Station to Chicago Bus Stationbus
    22h 11m
    $116–289

  11. Bus, train

    1. Take the bus from West St & Church Cir to Patapsco Light Rail Station Bay 3bus70
    2. Take the train from Baltimore Penn Station to Chicago Union StationtrainCardinal
    28h 27m
    $124–608

Annapolis to Chicago by bus

Calendar7Weekly Buses
Duration19h 10mAverage Duration
Ticket$82Cheapest Price
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Questions & Answers

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 19h 10m.

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