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How to get fromThe Hamptons to Chicagoby bus, plane, bus (Flixbus), train (Amtrak), car, car ferry, train, or bus (Greyhound)

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There are 9 ways to get from The Hamptons to Chicago by bus, plane, bus (Flixbus), train (Amtrak), car, car ferry, train, 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 Laguardia Airport, fly to Chicago Midway International Airport

    best
    1. Take the bus from Water Mill to JFK Airport Connection - WBbus bus
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    7h 39m
    $240–648

  2. Bus, car ferry, train to Theodore Francis Green State Airport, fly to Chicago Midway International Airport

    cheapest
    1. Take the bus from North Rd/Old Canoe Place Rd to Orient Point Ferry Dockbus bus
    2. Take the carferry from Orient Point to New Londoncarferry car ferry
    3. Take the train from New London to Providencetrain train
    4. Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)plane plane PVD - MDW
    11h 24m
    $119–539

  3. Bus

    1. Take the bus from Water Mill to 86th St & Broadwaybus bus Sag Harbor-Westbound / ...
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2641 / ...
    21h 34m
    $175–320

  4. Train

    1. Take the train from Hampton Bays to Jamaicatrain train
    2. Take the train from Grand Central Terminal to Croton-Harmontrain train
    3. Take the train from Croton-Harmon Amtrak Station to Chicago Union Stationtrain train
    23h 11m
    $346–749

  5. Drive 873.2 mi

    1. Drive from The Hamptons to Chicagocar car 873.2 mi
    14h 48m
    $160–231

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

    1. Take the bus from Water Mill to JFK Airport Connection - WBbus bus
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    8h
    $250–748

  7. Drive, car ferry to Tweed-New Haven Airport, fly to Chicago O'Hare International Airport

    1. Drive from The Hamptons to Port Jeffersoncar car
    2. Take the carferry from Port Jefferson to Bridgeportcarferry car ferry
    3. Fly from Tweed-New Haven Airport (HVN) to Chicago O'Hare International Airport (ORD)plane plane HVN - ORD
    7h 14m
    $204–580

  8. Bus, car ferry, train, train to Bradley International Airport, fly to Chicago Midway International Airport

    1. Take the bus from North Rd/Old Canoe Place Rd to Orient Point Ferry Dockbus bus
    2. Take the carferry from Orient Point to New Londoncarferry car ferry
    3. Take the train from New London to New Haventrain train
    4. Take the train from New Haven to Windsor Lockstrain train
    5. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane plane BDL - MDW
    11h 47m
    $123–546

  9. Bus via Baltimore

    1. Take the bus from Aquebogue to Boerum Hill-Atlantic & 4 Avbus bus
    2. Take the bus from Port Authority Bus Terminal to Baltimore Downtown Bus Stationbus bus
    3. Take the bus from Baltimore Downtown Bus Station to Chicago Bus Stationbus bus
    28h 22m
    $190–430

Laguardia Airport (LGA) to Chicago Midway International Airport (MDW) flights

Calendar67Weekly Planes
Duration2h 44mAverage Duration
Ticket$93Cheapest Price
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Questions & Answers

Map of how to get from The Hamptons to Chicago.ExpandLaunch map view
  • Distance: 834.9 mi
  • Duration: 7h 39m

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

You can take a vehicle from The Hamptons to Chicago Bus Station via North Rd/Old Canoe Place Rd, Montauk Hwy/Station Rd, Water Mill, 86th St & Broadway, 86 St, 34 St-Penn Station, and New York Midtown in around 21h 34m. Alternatively, you can take a vehicle from The Hamptons to Chicago Union Station via Hampton Bays, Jamaica, Grand Central Terminal, and Croton-Harmon Amtrak Station in around 23h 11m.

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