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

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There are 11 ways to get from Chicago to Wellfleet by plane, ferry, train, bus, bus (Greyhound), 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. 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 Logan Airport Ferry Terminal to Seaport/Fan Pierferry ferry
    3. Take the ferry from World Trade Center Pier, Boston, MA to MacMillan Pier, Provincetown, MAferry ferry
    9h 41m
    $198–717

  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
    $148–761

  3. Train, bus

    1. Take the train from Chicago Union Station to Bostontrain train
    2. Take the bus from Boston South Buses to Hyannis Transportation Centerbus bus
    3. Take the bus from Hyannis Transportation Center to Wellfleetbus bus
    26h 34m
    $333–673

  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 Station to Hyannis Transportation Centerbus bus
    4. Take the bus from Hyannis Transportation Center to Wellfleetbus bus
    26h 40m
    $173–350

  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 Logan Airport Ferry Terminal to Seaport/Fan Pierferry ferry
    3. Take the ferry from World Trade Center Pier, Boston, MA to MacMillan Pier, Provincetown, MAferry ferry
    10h 7m
    $208–717

  7. 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 35m
    $176–579

  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
    11h 44m
    $214–818

  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
    12h 26m
    $150–449

  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 43m
    $200–737

  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 Transportation Center to Wellfleetbus bus
    29h 50m
    $189–312

Chicago to Wellfleet by train and bus

Calendar7Weekly Services
Duration26h 34mAverage Duration
Ticket$333Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Wellfleet.ExpandLaunch map view
  • Distance: 940.9 mi
  • Duration: 9h 41m

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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