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How to get fromMilwaukee to Westportby bus, plane, train (Amtrak), bus (Greyhound, Flixbus), car, or train

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There are 10 ways to get from Milwaukee to Westport by bus, plane, train (Amtrak), bus (Greyhound, Flixbus), car, or train

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 Chicago O'Hare International Airport, fly to Westchester County Airport

    best
    1. Take the bus from Milwaukee Intermodal/Amtrak Station to O'Hare International Airport - Terminal 2 Departuresbus bus
    2. Fly from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN)plane plane ORD - HPN
    5h 36m
    $188–586

  2. Fly General Mitchell International Airport to Laguardia Airport, train

    cheapest
    1. Fly from General Mitchell International Airport (MKE) to Laguardia Airport (LGA)plane plane MKE - LGA
    2. Take the train from 125th Street - Harlem to Darientrain train
    6h 48m
    $159–833

  3. Train

    1. Take the train from Milwaukee to Chicago Union Stationtrain train
    2. Take the train from Chicago Union Station to Croton-Harmon Amtrak Stationtrain train
    3. Take the train from Croton-Harmon to 125th Street - Harlemtrain train
    4. Take the train from 125th Street - Harlem to Westporttrain train
    24h 26m
    $282–647

  4. Bus

    1. Take the bus from Milwaukee Intermodal Station to Chicago Bus Stationbus bus
    2. Take the bus from Chicago Bus Station to New York Midtownbus bus
    3. Take the bus from Port Authority Bus Terminal to Bridgeport Bus Stopbus bus
    26h 58m
    $164–269

  5. Drive  919.2 mi

    1. Drive from Milwaukee to Westportcar car 919.2 mi
    15h 40m
    $168–243

  6. Fly General Mitchell International Airport to John F. Kennedy International Airport, train

    1. Fly from General Mitchell International Airport (MKE) to John F. Kennedy International Airport (JFK)plane plane MKE - JFK
    2. Take the train from Grand Central Terminal to Darientrain train
    7h 7m
    $681–994

  7. Bus to Chicago O'Hare International Airport, fly to Laguardia Airport, train

    1. Take the bus from Milwaukee Intermodal/Amtrak Station to O'Hare International Airport - Terminal 2 Departuresbus bus
    2. Fly from Chicago O'Hare International Airport (ORD) to Laguardia Airport (LGA)plane plane ORD - LGA
    3. Take the train from 125th Street - Harlem to Darientrain train
    8h 4m
    $185–622

  8. Fly General Mitchell International Airport to Newark Liberty International Airport, train

    1. Fly from General Mitchell International Airport (MKE) to Newark Liberty International Airport (EWR)plane plane MKE - EWR
    2. Take the train from Newark Liberty International Airport to Bridgeport Amtrak Stationtrain train
    7h 57m
    $571–849

  9. Train to Chicago Midway International Airport, fly to Laguardia Airport, train

    1. Take the train from Milwaukee to Chicago Union Stationtrain train
    2. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    3. Take the train from 125th Street - Harlem to Darientrain train
    8h 40m
    $240–735

  10. Bus, train

    1. Take the bus from Milwaukee Intermodal Station to Detroit Bus Stationbus bus
    2. Take the bus from Detroit Bus Station to Newark Penn Stationbus bus
    3. Take the train from Newark Penn Station to Stamford Amtrak Stationtrain train
    29h 3m
    $169–860

Milwaukee to Westport by bus and foot

Calendar7Weekly Services
Duration26h 58mAverage Duration
Ticket$164Cheapest Price
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Comparing Your Travel Options

Map of how to get from Milwaukee to Westport.ExpandLaunch map view
  • Distance: 840.2 mi
  • Duration: 5h 36m

What companies run services between Milwaukee, WI, USA and Westport, CT, USA?

You can take a train from Milwaukee to Westport via Chicago Union Station, Croton-Harmon, 125th Street - Harlem, and Westport in around 24h 26m. Alternatively, you can take a bus from Milwaukee Intermodal Station to Post Rd. West at Myrtle Ave. via Chicago Bus Station, New York Midtown, Port Authority Bus Terminal, and Bridgeport Transportation Center in around 26h 58m.

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