Rome2Rio

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

Find Transport to Chicago

See all options

There are 11 ways to get from Wellfleet to Chicago by bus, plane, bus (Flixbus), train, car, or bus (Greyhound)

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

  1. Bus, bus to Boston Logan Airport, fly to Chicago Midway International Airport

    best
    1. Take the bus from Wellfleet to Hyannis Transportation Centerbus bus
    2. Take the bus from Hyannis Transportation Center to Logan International Airportbus bus
    3. Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane plane BOS - MDW
    8h 2m
    $118–483

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

    cheapest
    1. Take the bus from Wellfleet to Hyannis Transportation Centerbus bus
    2. Take the bus from Hyannis Transportation Center to Boston South Stationbus 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 49m
    $89–369

  3. Bus

    1. Take the bus from Wellfleet to Hyannis Transportation Centerbus 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
    26h 38m
    $185–323

  4. Bus, train

    1. Take the bus from Wellfleet to Hyannis Transportation Centerbus bus
    2. Take the bus from Hyannis Transportation Center to Boston South Busesbus bus
    3. Take the train from Boston to Chicago Union Stationtrain train
    26h 52m
    $365–703

  5. Drive 1,058 mi

    1. Drive from Wellfleet to Chicagocar car 1,058 mi
    18h 35m
    $194–279

  6. Bus, bus to Boston Logan Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Wellfleet to Hyannis Transportation Centerbus bus
    2. Take the bus from Hyannis Transportation Center to Logan International Airportbus bus
    3. Fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD)plane plane BOS - ORD
    8h 23m
    $248–613

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

    1. Take the bus from Wellfleet to Hyannis Transportation Centerbus bus
    2. Take the bus from Hyannis Transportation Center to Boston South Stationbus 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 41m
    $127–557

  8. Bus, bus to Boston Logan Airport, fly to General Mitchell International Airport, train

    1. Take the bus from Wellfleet to Hyannis Transportation Centerbus bus
    2. Take the bus from Hyannis Transportation Center to Logan International Airportbus bus
    3. Fly from Boston Logan Airport (BOS) to General Mitchell International Airport (MKE)plane plane BOS - MKE
    4. Take the train from Milwaukee to Chicago Union Stationtrain train
    10h 26m
    $186–777

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

    1. Take the bus from Wellfleet to Hyannis Transportation Centerbus bus
    2. Take the bus from Hyannis Transportation Center to Boston South Stationbus 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
    10h 19m
    $104–449

  10. 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
    8h 19m
    $108–561

  11. Bus via Brook Park

    1. Take the bus from Wellfleet to Hyannis Transportation Centerbus 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 45m
    $185–338

Wellfleet to Chicago by bus

Calendar15Weekly Buses
Duration26h 38mAverage Duration
Ticket$185Cheapest Price
See schedules

Questions & Answers

Map of how to get from Wellfleet to Chicago.ExpandLaunch map view
  • Distance: 979.4 mi
  • Duration: 8h 2m

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, Bus Terminal South Station, Boston, and New York Midtown in around 26h 38m. Alternatively, Cape Air and Southwest Airlines fly from Provincetown Municipal Airport (PVC) to Chicago Midway International Airport (MDW) once daily.

Airlines
Train operators
Bus 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

More Questions & Answers