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How to get fromChicago to Wellfleetby plane, ferry, bus (Greyhound), train, car, or bus

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There are 10 ways to get from Chicago to Wellfleet by plane, ferry, bus (Greyhound), train, car, or bus

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Fly Chicago Midway International Airport to Boston Logan Airport, ferry

    best
    1. Fly from Chicago Midway International Airport (MDW) to Boston Logan Airport (BOS)plane plane MDW - BOS
    2. Take the ferry from World Trade Center Pier, Boston, MA to MacMillan Pier, Provincetown, MAferry ferry
    9h 1m
    $178–680

  2. Fly Chicago Midway International Airport to Provincetown Municipal Airport

    cheapest
    1. Fly from Chicago Midway International Airport (MDW) to Provincetown Municipal Airport (PVC)plane plane MDW - PVC
    8h 28m
    $138–711

  3. Bus

    1. Take the bus from Chicago Bus Station to Cleveland Bus Stationbus bus
    2. Take the bus from Cleveland Bus Station to Bostonbus bus
    3. Take the bus from Boston South Station to Hyannis Transportation Centerbus bus
    4. Take the bus from Hyannis Transportation Center to Wellfleetbus bus
    26h 40m
    $174–343

  4. Train, ferry

    1. Take the train from Chicago Union Station to Bostontrain train Lake Shore Limited
    2. Take the ferry from World Trade Center Pier, Boston, MA to MacMillan Pier, Provincetown, MAferry ferry Fast Ferry
    26h 53m
    $403–747

  5. Drive 1,056.6 mi

    1. Drive from Chicago to Wellfleetcar car 1,056.6 mi
    18h 32m
    $193–279

  6. Fly Chicago O'Hare International Airport to Boston Logan Airport, ferry

    1. Fly from Chicago O'Hare International Airport (ORD) to Boston Logan Airport (BOS)plane plane ORD - BOS
    2. Take the ferry from World Trade Center Pier, Boston, MA to MacMillan Pier, Provincetown, MAferry ferry
    9h 26m
    $238–680

  7. Fly Chicago Midway International Airport to Manchester Airport, bus, ferry

    1. Fly from Chicago Midway International Airport (MDW) to Manchester Airport (MHT)plane plane MDW - MHT
    2. Take the bus from Boston Manchester Airport to Bostonbus bus
    3. Take the ferry from World Trade Center Pier, Boston, MA to MacMillan Pier, Provincetown, MAferry ferry
    11h
    $204–768

  8. Fly Chicago Midway International Airport to Theodore Francis Green State Airport, train, ferry

    1. Fly from Chicago Midway International Airport (MDW) to Theodore Francis Green State Airport (PVD)plane plane MDW - PVD
    2. Take the train from TF Green Airport to South Stationtrain train
    3. Take the ferry from World Trade Center Pier, Boston, MA to MacMillan Pier, Provincetown, MAferry ferry
    11h 17m
    $166–539

  9. Fly Chicago O'Hare International Airport to Theodore Francis Green State Airport, train, ferry

    1. Fly from Chicago O'Hare International Airport (ORD) to Theodore Francis Green State Airport (PVD)plane plane ORD - PVD
    2. Take the train from TF Green Airport to South Stationtrain train
    3. Take the ferry from World Trade Center Pier, Boston, MA to MacMillan Pier, Provincetown, MAferry ferry
    11h 47m
    $146–429

  10. Fly Chicago Midway International Airport to Bradley International Airport, bus, ferry

    1. Fly from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL)plane plane MDW - BDL
    2. Take the bus from Hartford Union Station to Bostonbus bus
    3. Take the ferry from World Trade Center Pier, Boston, MA to MacMillan Pier, Provincetown, MAferry ferry
    12h 4m
    $192–685

Chicago to Wellfleet by bus

Calendar7Weekly Buses
Duration26h 40mAverage Duration
Ticket$174Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Wellfleet.ExpandLaunch map view
  • Distance: 944.7 mi
  • Duration: 9h 1m

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

You can take a bus from Chicago Bus Station to Wellfleet via Cleveland Bus Station, Boston, Boston South Station, and Hyannis Transportation Center in around 26h 40m. Alternatively, Southwest Airlines, Cape Air, and two other airlines fly from Chicago Midway International Airport (MDW) to Provincetown Municipal Airport (PVC) 3 times a day.

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