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How to get fromWestport to Chicagoby taxi, plane, bus (Flixbus), bus, train, or car

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There are 6 ways to get from Westport to Chicago by taxi, plane, bus (Flixbus), bus, train, or car

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

  1. Taxi to Theodore Francis Green State Airport, fly to Chicago Midway International Airport

    best
    1. Take the taxi from Westport to Theodore Francis Green State Airport (PVD)taxi taxi
    2. Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)plane plane PVD - MDW
    3h 47m
    $172–508

  2. Bus to Boston Logan Airport, fly to Chicago Midway International Airport

    cheapest
    1. Take the bus from UMass Dartmouth to Boston South Busesbus bus
    2. Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane plane BOS - MDW
    6h 23m
    $116–453

  3. Bus

    1. Take the bus from UMass Dartmouth to Boston South Busesbus 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
    24h 4m
    $198–335

  4. Bus, train

    1. Take the bus from UMass Dartmouth to Boston South Busesbus bus Boston Commuter
    2. Take the train from Boston to Chicago Union Stationtrain train Lake Shore Limited
    24h 44m
    $348–735

  5. Drive 975.8 mi

    1. Drive from Westport to Chicagocar car 975.8 mi
    17h 3m
    $179–258

  6. Taxi to Theodore Francis Green State Airport, fly to Chicago O'Hare International Airport

    1. Take the taxi from Westport to Theodore Francis Green State Airport (PVD)taxi taxi
    2. Fly from Theodore Francis Green State Airport (PVD) to Chicago O'Hare International Airport (ORD)plane plane PVD - ORD
    4h 17m
    $162–448

Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW) flights

Calendar41Weekly Planes
Duration3h 33mAverage Duration
Ticket$79Cheapest Price
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Questions & Answers

Map of how to get from Westport to Chicago.ExpandLaunch map view
  • Distance: 881.9 mi
  • Duration: 3h 47m

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

You can take a vehicle from Westport to Chicago Bus Station via UMass Dartmouth, Boston, South Station, Boston, and New York Midtown in around 24h 4m.

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