Rome2Rio

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

Find Transport to Wellfleet

See all options
QR code to download the Rome2Rio app

Download the Rome2Rio travel app

Scan QR code with your phone to download the app

Download on the App StoreGet it on Google Play

There are 10 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 57m
    $194–755

  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 34m
    $122–346

  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
    $575–886

  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
    $175–252

  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 17m
    $150–495

  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
    10h 55m
    $182–714

  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 7m
    $152–506

  9. 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 1m
    $262–1,079

  10. 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
    29h 56m
    $222–330

Chicago to Wellfleet by bus

Calendar7Weekly Buses
Duration26h 37mAverage Duration
Ticket$216Cheapest Price
See schedules

Comparing Your Travel Options

Map of how to get from Chicago to Wellfleet.ExpandLaunch map view
  • Distance: 944.7 mi
  • Duration: 8h 57m

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.

Airlines
Train operators
Bus operators
Ferry operators

Want to know more about travelling around United States

Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

Related travel guides

Need to know: Greyhound

Read the travel guideNeed to know: Greyhound

Booking & Getting There