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How to get fromChicago to Rocklandby plane, bus (Flixbus), train, bus, or car

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There are 7 ways to get from Chicago to Rockland by plane, bus (Flixbus), train, bus, or car

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 O'Hare International Airport to Rockland

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Rockland (RKD)plane plane ORD - RKD
    6h 37m
    $78–328

  2. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus
    2. Take the bus from New York Midtown to Bostonbus bus
    3. Take the bus from Boston South Buses to Maine State Ferry Terminal - Rocklandbus bus
    27h 6m
    $212–348

  3. Train, Amtrak Thruway (Amtrak)

    1. Take the train from Chicago Union Station to Bostontrain train Lake Shore Limited
    2. Take the bus from South Station to Maine State Ferry Terminal - Rocklandbus bus Boston
    27h 17m
    $359–717

  4. Drive 1,112.1 mi

    1. Drive from Chicago to Rocklandcar car 1,112.1 mi
    20h 55m
    $203–294

  5. Fly Chicago O'Hare International Airport to Bangor, Amtrak Thruway

    1. Fly from Chicago O'Hare International Airport (ORD) to Bangor (BGR)plane plane ORD - BGR
    2. Take the bus from Bangor, ME to Maine State Ferry Terminal - Rocklandbus bus
    8h 8m
    $138–652

  6. Fly Chicago Midway International Airport to Portland, Amtrak Thruway

    1. Fly from Chicago Midway International Airport (MDW) to Portland (PWM)plane plane MDW - PWM
    2. Take the bus from Portland, ME to Maine State Ferry Terminal - Rocklandbus bus
    8h 29m
    $142–658

  7. Fly Chicago O'Hare International Airport to Portland, Amtrak Thruway

    1. Fly from Chicago O'Hare International Airport (ORD) to Portland (PWM)plane plane ORD - PWM
    2. Take the bus from Portland, ME to Maine State Ferry Terminal - Rocklandbus bus
    8h 55m
    $118–528

Chicago to Rockland by bus

Calendar7Weekly Buses
Duration27h 6mAverage Duration
Ticket$212Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Rockland.ExpandLaunch map view
  • Distance: 980.2 mi
  • Duration: 6h 37m

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

JetBlue Airways, Cape Air, and three other airlines fly from Chicago O'Hare International Airport (ORD) to Rockland (RKD) every 4 hours. Alternatively, you can take a bus from Chicago Bus Station to Maine State Ferry Terminal - Rockland via New York Midtown, Boston, and Boston South Buses in around 27h 6m.

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