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How to get fromRockland to Chicagoby bus, plane, bus (Flixbus), train, car, or bus (Greyhound, Amtrak)

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There are 9 ways to get from Rockland to Chicago by bus, plane, bus (Flixbus), train, car, or bus (Greyhound, Amtrak)

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

  1. Amtrak Thruway to Bangor, fly to Chicago O'Hare International Airport

    best
    1. Take the bus from Maine State Ferry Terminal - Rockland to Bangor, MEbus bus
    2. Fly from Bangor (BGR) to Chicago O'Hare International Airport (ORD)plane plane BGR - ORD
    7h 7m
    $138–649

  2. Fly Rockland to Chicago Midway International Airport

    cheapest
    1. Fly from Rockland (RKD) to Chicago Midway International Airport (MDW)plane plane RKD - MDW
    5h 43m
    $103–448

  3. Bus

    1. Take the bus from Maine State Ferry Terminal - Rockland to Boston South Busesbus bus
    2. Take the bus from Boston to New York Midtownbus bus
    3. Take the bus from New York Midtown to Chicago Bus Stationbus bus
    27h 16m
    $211–353

  4. Amtrak Thruway, train (Amtrak)

    1. Take the bus from Maine State Ferry Terminal - Rockland to South Stationbus bus Bangor
    2. Take the train from Boston to Chicago Union Stationtrain train Lake Shore Limited
    27h 57m
    $355–746

  5. Drive 1,113.6 mi

    1. Drive from Rockland to Chicagocar car 1,113.6 mi
    20h 55m
    $204–294

  6. Bus to Portland, fly to Chicago Midway International Airport

    1. Take the bus from Maine State Ferry Terminal - Rockland to Portland Transportation Centerbus bus
    2. Fly from Portland (PWM) to Chicago Midway International Airport (MDW)plane plane PWM - MDW
    7h 39m
    $123–556

  7. Bus to Portland, fly to Chicago O'Hare International Airport

    1. Take the bus from Maine State Ferry Terminal - Rockland to Portland Transportation Centerbus bus
    2. Fly from Portland (PWM) to Chicago O'Hare International Airport (ORD)plane plane PWM - ORD
    8h 10m
    $108–486

  8. Bus, bus to Boston Logan Airport, fly to Chicago Midway International Airport

    1. Take the bus from Maine State Ferry Terminal - Rockland to Portland Transportation Centerbus bus
    2. Take the bus from Portland, ME to Logan International Airportbus bus
    3. Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane plane BOS - MDW
    8h 53m
    $126–488

  9. Bus via Brook Park

    1. Take the bus from Maine State Ferry Terminal - Rockland to Boston South Busesbus bus
    2. Take the bus from Boston to Cleveland Bus Stationbus bus
    3. Take the bus from Cleveland Bus Station to Toledo Bus Stopbus bus
    4. Take the bus from Toledo to Chicago Union Stationbus bus
    27h 32m
    $236–403

Rockland to Chicago by bus

Calendar7Weekly Buses
Duration27h 16mAverage Duration
Ticket$211Cheapest Price
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Questions & Answers

Map of how to get from Rockland to Chicago.ExpandLaunch map view
  • Distance: 1,059 mi
  • Duration: 7h 7m

What companies run services between Rockland, ME, USA and Chicago, IL, USA?

You can take a bus from Maine State Ferry Terminal - Rockland to Chicago Bus Station via Boston South Buses, Boston, and New York Midtown in around 27h 16m. Alternatively, Cape Air and Southwest Airlines fly from Rockland (RKD) to Chicago Midway International Airport (MDW) once daily.

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