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

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There are 10 ways to get from Hyannis to Chicago by bus, plane, train, bus (Greyhound, Flixbus), 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. Bus to Boston Logan Airport, fly to Chicago O'Hare International Airport

    best
    1. Take the bus from Hyannis Transportation Center to Logan International Airportbus bus
    2. Fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD)plane plane BOS - ORD
    7h 2m
    $140–441

  2. Bus, train to Theodore Francis Green State Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the bus from Hyannis Transportation Center to Boston South Stationbus bus
    2. Take the train from Boston to Providencetrain train
    3. Fly from Theodore Francis Green State Airport (PVD) to Chicago O'Hare International Airport (ORD)plane plane PVD - ORD
    8h 19m
    $69–913

  3. Bus, train

    1. Take the bus from Hyannis Transportation Center to Boston South Stationbus bus Hyannis
    2. Take the train from Boston to Chicago Union Stationtrain train Lake Shore Limited
    25h 2m
    $120–736

  4. Bus

    1. Take the bus from Hyannis Transportation Center to Boston South Busesbus bus
    2. Take the bus from Boston to Newark Penn Stationbus bus
    3. Take the bus from Newark Penn Station to Chicago Bus Stationbus bus
    28h 20m
    $152–330

  5. Drive 1,027.2 mi

    1. Drive from Hyannis to Chicagocar car 1,027.2 mi
    17h 54m
    $188–271

  6. Bus to Boston Logan Airport, fly to Chicago Midway International Airport

    1. Take the bus from Hyannis Transportation Center to Logan International Airportbus bus
    2. Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane plane BOS - MDW
    6h 46m
    $120–511

  7. Fly Barnstable Municipal Airport to Chicago Midway International Airport

    1. Fly from Barnstable Municipal Airport (HYA) to Chicago Midway International Airport (MDW)plane plane HYA - MDW
    5h 59m
    $97–487

  8. Bus, train to Theodore Francis Green State Airport, fly to Chicago Midway International Airport

    1. Take the bus from Hyannis Transportation Center to Boston South Stationbus bus
    2. Take the train from Boston to Providencetrain train
    3. Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)plane plane PVD - MDW
    7h 56m
    $89–1,033

  9. Bus, bus to Manchester Airport, fly to Chicago Midway International Airport

    1. Take the bus from Hyannis Transportation Center to Boston South Stationbus bus
    2. Take the bus from Boston to Boston Manchester Airportbus bus
    3. Fly from Manchester Airport (MHT) to Chicago Midway International Airport (MDW)plane plane MHT - MDW
    8h 6m
    $135–676

  10. Bus to Boston Logan Airport, fly to General Mitchell International Airport, train

    1. Take the bus from Hyannis Transportation Center to Logan International Airportbus bus
    2. Fly from Boston Logan Airport (BOS) to General Mitchell International Airport (MKE)plane plane BOS - MKE
    3. Take the train from Milwaukee to Chicago Union Stationtrain train
    8h 47m
    $332–756

Hyannis to Chicago by bus and train

Calendar7Weekly Services
Duration25h 2mAverage Duration
Ticket$120Cheapest Price
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Questions & Answers

What companies run services between Hyannis, MA, USA and Chicago, IL, USA?

You can take a bus from Hyannis Transportation Center to Chicago Bus Station via Boston, Bus Terminal South Station, Boston, and Newark Penn Station in around 28h 20m. Alternatively, American Airlines, Southwest Airlines, and Cape Air fly from Barnstable Municipal Airport (HYA) to Chicago Midway International Airport (MDW) 4 times a day.

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