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

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There are 11 ways to get from Wellfleet to Chicago by ferry, plane, car, train, bus (Greyhound), bus, 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. Ferry to Boston Logan Airport, fly to Chicago Midway International Airport

    best
    1. Take the ferry from MacMillan Pier, Provincetown, MA to World Trade Center Pier, Boston, MAferry ferry
    2. Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane plane BOS - MDW
    8h 53m
    $160–535

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

    cheapest
    1. Take the bus from Wellfleet to Hyannisbus bus
    2. Take the bus from Hyannis Transportation Center to Boston South Busesbus bus
    3. Take the train from South Station to TF Green Airporttrain train
    4. Fly from Theodore Francis Green State Airport (PVD) to Chicago O'Hare International Airport (ORD)plane plane PVD - ORD
    10h 14m
    $111–421

  3. Drive, train

    1. Drive from Wellfleet to Kingstoncar car
    2. Take the train from Kingston to South Stationtrain train
    3. Take the train from Boston to Chicago Union Stationtrain train
    25h 50m
    $278–630

  4. Bus via Brook Park

    1. Take the bus from Wellfleet to Hyannisbus bus
    2. Take the bus from Hyannis Transportation Center to Boston South Busesbus bus
    3. Take the bus from Boston to Cleveland Bus Stationbus bus
    4. Take the bus from Cleveland Bus Station to Chicago Bus Stationbus bus
    26h 22m
    $185–350

  5. Drive  1,058 mi

    1. Drive from Wellfleet to Chicagocar car 1,058 mi
    18h 36m
    $194–279

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

    1. Take the bus from Wellfleet to Hyannisbus bus
    2. Take the bus from Hyannis Transportation Center to Boston South Busesbus bus
    3. Take the bus from Boston to Boston Manchester Airportbus bus
    4. Fly from Manchester Airport (MHT) to Chicago Midway International Airport (MDW)plane plane MHT - MDW
    9h 14m
    $144–620

  7. Ferry to Boston Logan Airport, fly to Chicago O'Hare International Airport

    1. Take the ferry from MacMillan Pier, Provincetown, MA to World Trade Center Pier, Boston, MAferry ferry
    2. Fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD)plane plane BOS - ORD
    9h 14m
    $675–1,005

  8. Fly Provincetown Municipal Airport to Chicago Midway International Airport

    1. Fly from Provincetown Municipal Airport (PVC) to Chicago Midway International Airport (MDW)plane plane PVC - MDW
    6h 27m
    $137–674

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

    1. Take the bus from Wellfleet to Hyannisbus bus
    2. Take the bus from Hyannis Transportation Center to Boston South Busesbus bus
    3. Take the train from South Station to TF Green Airporttrain train
    4. Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)plane plane PVD - MDW
    9h 51m
    $121–481

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

    1. Take the ferry from MacMillan Pier, Provincetown, MA to World Trade Center Pier, Boston, MAferry ferry
    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
    11h 23m
    $747–2,064

  11. Bus

    1. Take the bus from Wellfleet to Hyannisbus bus
    2. Take the bus from Hyannis Transportation Center to Boston South Busesbus bus
    3. Take the bus from Boston to New York Midtownbus bus
    4. Take the bus from New York Midtown to Chicago Bus Stationbus bus
    29h 52m
    $205–340

Wellfleet to Chicago by bus

Calendar7Weekly Buses
Duration26h 22mAverage Duration
Ticket$185Cheapest Price
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Questions & Answers

Map of how to get from Wellfleet to Chicago.ExpandLaunch map view
  • Distance: 939 mi
  • Duration: 8h 53m

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

You can take a bus from Wellfleet to Chicago Bus Station via Hyannis Transportation Center, Boston, South Station, Boston, and Cleveland Bus Station in around 26h 22m. Alternatively, Cape Air, Southwest Airlines, and JetBlue Airways fly from Provincetown Municipal Airport (PVC) to Chicago Midway International Airport (MDW) twice daily.

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