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How to get fromChicago to Southamptonby plane, train, bus (Flixbus), train (Amtrak), car, or bus

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There are 8 ways to get from Chicago to Southampton by plane, train, bus (Flixbus), train (Amtrak), car, or bus

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 Laguardia Airport, train

    best
    1. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    2. Take the train from Jamaica to Southamptontrain train
    7h 19m
    $224–603

  2. Fly Chicago O'Hare International Airport to Westchester County Airport, train

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN)plane plane ORD - HPN
    2. Take the train from Jamaica to Southamptontrain train
    10h 5m
    $130–577

  3. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2641 / ...
    2. Take the bus from 40th & Lex to Southamptonbus bus Montauk-Eastbound / ...
    20h 9m
    $175–316

  4. Train

    1. Take the train from Chicago Union Station to Ny Moynihan Train Hall At Penn Stationtrain train Lake Shore Limited / ...
    2. Take the train from Jamaica to Southamptontrain train Montauk Branch
    23h 37m
    $326–684

  5. Drive 879.5 mi

    1. Drive from Chicago to Southamptoncar car 879.5 mi
    15h
    $161–232

  6. Fly Chicago O'Hare International Airport to John F. Kennedy International Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to John F. Kennedy International Airport (JFK)plane plane ORD - JFK
    2. Take the train from Jamaica to Southamptontrain train
    7h 19m
    $340–909

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

    1. Fly from Chicago O'Hare International Airport (ORD) to Laguardia Airport (LGA)plane plane ORD - LGA
    2. Take the train from Jamaica to Southamptontrain train
    7h 39m
    $234–703

  8. Bus, train

    1. Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus bus
    2. Take the bus from Baltimore Downtown Bus Station to Port Authority Bus Terminalbus bus
    3. Take the train from Jamaica to Southamptontrain train
    25h 5m
    $182–394

Chicago to Southampton by train

Calendar10Weekly Trains
Duration23h 37mAverage Duration
Ticket$326Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Southampton.ExpandLaunch map view
  • Distance: 821.9 mi
  • Duration: 7h 19m

What companies run services between Chicago, IL, USA and Southampton, NY, USA?

You can take a bus from Chicago Bus Station to Southampton via New York Midtown, W 34 St/7 Av, E 34 St/3 Av, and 40th & Lex in around 20h 9m. Alternatively, you can take a train from Chicago Union Station to Southampton via Ny Moynihan Train Hall At Penn Station, New York Penn Station, and Jamaica in around 23h 37m.

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