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

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There are 10 ways to get from Chatham 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 to Boston Logan Airport, fly to Chicago Midway International Airport

    best
    1. Take the bus from Hyannis Transportation Center to Logan International Airportbus bus
    2. Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane plane BOS - MDW
    7h 41m
    $113–448

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

    cheapest
    1. Take the bus from Hyannis Transportation Center to South Station Transp. Ctrbus bus
    2. Take the train from South Station to TF Green Airporttrain train
    3. Fly from Theodore Francis Green State Airport (PVD) to Chicago O'Hare International Airport (ORD)plane plane PVD - ORD
    10h 34m
    $106–379

  3. Bus

    1. Take the bus from Hyannis Transportation Center to South Station Transp. Ctrbus bus
    2. Take the bus from Boston to New York Midtownbus bus
    3. Take the bus from New York Midtown to Chicago Bus Stationbus bus
    25h 58m
    $200–338

  4. Bus, train

    1. Take the bus from Hyannis Transportation Center to South Station Transp. Ctrbus bus Hyannis - South Shore to Logan Airport
    2. Take the train from Boston to Chicago Union Stationtrain train Lake Shore Limited
    26h 36m
    $360–738

  5. Drive 1,044 mi

    1. Drive from Chatham to Chicagocar car 1,044 mi
    18h 15m
    $191–276

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

    1. Take the bus from Hyannis Transportation Center to Logan International Airportbus bus
    2. Fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD)plane plane BOS - ORD
    8h 6m
    $633–948

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

    1. Take the bus from Hyannis Transportation Center to South Station Transp. Ctrbus bus
    2. Take the bus from Boston to Boston Manchester Airportbus bus
    3. Fly from Manchester Airport (MHT) to Chicago Midway International Airport (MDW)plane plane MHT - MDW
    9h 21m
    $130–509

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

    1. Take the bus from Hyannis Transportation Center to South Station Transp. Ctrbus bus
    2. Take the train from South Station to TF Green Airporttrain train
    3. Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)plane plane PVD - MDW
    10h 4m
    $116–439

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

    1. Take the bus from Hyannis Transportation Center to Logan International Airportbus bus
    2. Fly from Boston Logan Airport (BOS) to General Mitchell International Airport (MKE)plane plane BOS - MKE
    3. Take the train from Milwaukee to Chicago Union Stationtrain train
    10h 8m
    $710–3,417

  10. Bus via Brook Park

    1. Take the bus from Hyannis Transportation Center to South Station Transp. Ctrbus bus
    2. Take the bus from Boston to Cleveland Bus Stationbus bus
    3. Take the bus from Cleveland Bus Station to Chicago Bus Stationbus bus
    26h 29m
    $180–358

Chatham to Chicago by bus

Calendar22Weekly Buses
Duration25h 58mAverage Duration
Ticket$200Cheapest Price
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Questions & Answers

Map of how to get from Chatham to Chicago.ExpandLaunch map view
  • Distance: 969.3 mi
  • Duration: 7h 41m

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

You can take a bus from Veterans Field Rd to Chicago Bus Station via Hyannis Transportation Center, South Station Transp. Ctr, Boston, and New York Midtown in around 25h 58m.

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Train operators
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