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

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

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 18m
    $101–481

  2. Fly Barnstable Municipal Airport to Chicago Midway International Airport

    cheapest
    1. Fly from Barnstable Municipal Airport (HYA) to Chicago Midway International Airport (MDW)plane plane HYA - MDW
    7h 35m
    $93–476

  3. 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
    $192–295

  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
    $577–935

  5. Drive  1,031 mi

    1. Drive from Cape Cod to Chicagocar car 1,031 mi
    17h 58m
    $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 40m
    $616–1,031

  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 55m
    $144–693

  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 38m
    $110–506

  9. Bus, train to Theodore Francis Green State Airport, fly to Chicago O'Hare 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 O'Hare International Airport (ORD)plane plane PVD - ORD
    9h 56m
    $95–416

  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 39m
    $711–2,015

  11. 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
    29h 31m
    $197–315

Cape Cod to Chicago by bus

Calendar7Weekly Buses
Duration26h 4mAverage Duration
Ticket$192Cheapest Price
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Comparing Your Travel Options

Map of how to get from Cape Cod to Chicago.ExpandLaunch map view
  • Distance: 949 mi
  • Duration: 7h 18m

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 Cleveland Bus Station in around 26h 4m. 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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