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

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There are 11 ways to get from Chicago to Wellfleet by plane, ferry, train, car, 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. 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
    8h 56m
    $184–705

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

    cheapest
    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 37m
    $132–376

  3. Train, drive

    1. Take the train from Chicago Union Station to Bostontrain train
    2. Take the train from South Station to Kingstontrain train
    3. Drive from Kingston to Wellfleetcar car
    25h 30m
    $577–889

  4. Bus via Brook Park

    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 Buses to Hyannis Transportation Centerbus bus
    4. Take the bus from Hyannis to Wellfleetbus bus
    26h 37m
    $216–318

  5. Drive  1,056.6 mi

    1. Drive from Chicago to Wellfleetcar car 1,056.6 mi
    18h 36m
    $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 16m
    $624–1,105

  7. Fly Chicago Midway International Airport to Provincetown Municipal Airport

    1. Fly from Chicago Midway International Airport (MDW) to Provincetown Municipal Airport (PVC)plane plane MDW - PVC
    7h 5m
    $138–674

  8. 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
    10h 54m
    $182–664

  9. 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 6m
    $158–516

  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
    11h 55m
    $232–929

  11. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus
    2. Take the bus from New York Midtown to Bostonbus bus
    3. Take the bus from Boston South Buses to Hyannis Transportation Centerbus bus
    4. Take the bus from Hyannis to Wellfleetbus bus
    30h
    $222–329

Chicago to Wellfleet by bus

Calendar7Weekly Buses
Duration26h 37mAverage Duration
Ticket$216Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Wellfleet.ExpandLaunch map view
  • Distance: 944.7 mi
  • Duration: 8h 56m

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 Buses, and Hyannis in around 26h 37m. Alternatively, Southwest Airlines, Cape Air, and Delta fly from Chicago Midway International Airport (MDW) to Provincetown Municipal Airport (PVC) twice daily.

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