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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 Midway International Airport

    best
    1. Take the bus from Hyannis to Bostonbus bus
    2. Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane plane BOS - MDW
    5h 59m
    $99–458

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

    cheapest
    1. Take the bus from Hyannis to Bostonbus bus
    2. Take the train from South Station to TF Green Airporttrain train
    3. Fly from Theodore Francis Green State Airport (PVD) to Chicago O'Hare International Airport (ORD)plane plane PVD - ORD
    8h 46m
    $92–402

  3. Bus, train

    1. Take the bus from Hyannis Transportation Center to Boston South Busesbus bus Hyannis - South Shore to Logan Airport
    2. Take the train from Boston to Chicago Union Stationtrain train Lake Shore Limited
    25h 12m
    $297–635

  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
    25h 30m
    $172–295

  5. Drive 1,027.2 mi

    1. Drive from Hyannis to Chicagocar car 1,027.2 mi
    17h 55m
    $188–271

  6. Bus to Boston Logan Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Hyannis to Bostonbus bus
    2. Fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD)plane plane BOS - ORD
    6h 22m
    $619–1,038

  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 1m
    $96–463

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

    1. Take the bus from Hyannis to Bostonbus 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
    7h 36m
    $125–600

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

    1. Take the bus from Hyannis to Bostonbus bus
    2. Take the train from South Station to TF Green Airporttrain train
    3. Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)plane plane PVD - MDW
    8h 19m
    $102–452

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

    1. Take the bus from Hyannis to Bostonbus 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 30m
    $691–2,002

Hyannis to Chicago by bus and train

Calendar7Weekly Services
Duration25h 12mAverage Duration
Ticket$297Cheapest Price
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Questions & Answers

Map of how to get from Hyannis to Chicago.ExpandLaunch map view
  • Distance: 943.2 mi
  • Duration: 5h 59m

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, South Station, Boston, and Newark Penn Station in around 25h 30m. Alternatively, Cape Air and Southwest Airlines fly from Barnstable Municipal Airport (HYA) to Chicago Midway International Airport (MDW) 3 times a day.

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