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

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There are 11 ways to get from Cape Cod to Chicago by bus, plane, bus (Flixbus), train, car, or bus (Greyhound)

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
    7h 13m
    $100–468

  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
    9h 59m
    $94–389

  3. Bus

    1. Take the bus from Hyannis Transportation Center 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
    25h 57m
    $190–313

  4. 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
    26h 11m
    $330–688

  5. Drive 1,031.1 mi

    1. Drive from Cape Cod to Chicagocar car 1,031.1 mi
    17h 57m
    $189–272

  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
    7h 38m
    $620–1,048

  7. 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
    8h 50m
    $122–558

  8. 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
    9h 28m
    $104–449

  9. 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
    7h 13m
    $101–479

  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
    9h 42m
    $695–2,012

  11. Bus via Brook Park

    1. Take the bus from Hyannis Transportation Center 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 Chicago Bus Stationbus bus
    26h 4m
    $180–328

Cape Cod to Chicago by bus

Calendar15Weekly Buses
Duration25h 57mAverage Duration
Ticket$190Cheapest Price
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Questions & Answers

Map of how to get from Cape Cod to Chicago.ExpandLaunch map view
  • Distance: 949 mi
  • Duration: 7h 13m

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

You can take a bus from Town Hall Lawton Bus Shelter to Chicago Bus Station via Hyannis Transportation Center, Boston, South Station, Boston, and New York Midtown in around 25h 57m. Alternatively, Cape Air, Southwest Airlines, and American Airlines fly from Barnstable Municipal Airport (HYA) to Chicago Midway International Airport (MDW) 3 times a day.

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