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How to get fromChicago to Westportby plane, taxi, bus (Flixbus), train, bus, or car

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There are 7 ways to get from Chicago to Westport by plane, taxi, bus (Flixbus), train, bus, 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. Fly Chicago Midway International Airport to Theodore Francis Green State Airport, taxi

    best
    1. Fly from Chicago Midway International Airport (MDW) to Theodore Francis Green State Airport (PVD)plane plane MDW - PVD
    2. Take the taxi from Theodore Francis Green State Airport (PVD) to Westporttaxi taxi
    4h 22m
    $168–485

  2. Fly Chicago Midway International Airport to Boston Logan Airport, bus

    cheapest
    1. Fly from Chicago Midway International Airport (MDW) to Boston Logan Airport (BOS)plane plane MDW - BOS
    2. Take the bus from Boston South Buses to UMass Dartmouthbus bus
    6h 37m
    $130–544

  3. 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 UMass Dartmouthbus bus
    24h 14m
    $199–329

  4. Train, bus

    1. Take the train from Chicago Union Station to Bostontrain train Lake Shore Limited
    2. Take the bus from Boston South Buses to UMass Dartmouthbus bus Boston Commuter
    24h 24m
    $351–703

  5. Drive 975.8 mi

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

  6. Fly Chicago O'Hare International Airport to Theodore Francis Green State Airport, taxi

    1. Fly from Chicago O'Hare International Airport (ORD) to Theodore Francis Green State Airport (PVD)plane plane ORD - PVD
    2. Take the taxi from Theodore Francis Green State Airport (PVD) to Westporttaxi taxi
    4h 52m
    $152–415

  7. Fly Chicago O'Hare International Airport to Boston Logan Airport, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Boston Logan Airport (BOS)plane plane ORD - BOS
    2. Take the bus from Boston South Buses to UMass Dartmouthbus bus
    6h 55m
    $630–1,044

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

Calendar37Weekly Planes
Duration3h 36mAverage Duration
Ticket$76Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Westport.ExpandLaunch map view
  • Distance: 880.9 mi
  • Duration: 4h 22m

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

You can take a bus from Chicago Bus Station to Westport via New York Midtown, Boston, Boston South Buses, and UMass Dartmouth in around 24h 14m.

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