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How to get fromSag Harbor to Chicagoby bus, plane, bus (Flixbus), train, car, or bus (Greyhound)

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There are 8 ways to get from Sag Harbor to Chicago by bus, plane, bus (Flixbus), train, car, 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 Sag Harbor Westbound to JFK Airport Connection - WBbus bus
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    6h 59m
    $190–643

  2. Bus to Westchester County Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the bus from Sag Harbor Westbound to 86 St & Central Park Westbus bus
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    9h 58m
    $135–538

  3. Bus

    1. Take the bus from Sag Harbor Westbound to JFK Airport Connection - WBbus bus Sag Harbor-Westbound / ...
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2641 / ...
    21h 14m
    $170–319

  4. Bus, train

    1. Take the bus from Sag Harbor Westbound to 79th St & Broadwaybus bus Sag Harbor-Westbound / ...
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain train Lake Shore Limited / ...
    23h 25m
    $346–725

  5. Drive 888.8 mi

    1. Drive from Sag Harbor to Chicagocar car 888.8 mi
    15h 14m
    $163–235

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

    1. Take the bus from Sag Harbor Westbound to JFK Airport Connection - WBbus bus
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    7h 20m
    $240–743

  7. Bus, bus to Newark Liberty International Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Sag Harbor Westbound to 86 St & Central Park Westbus bus
    2. Take the bus from Port Authority Bus Terminal to Terminal Bbus bus
    3. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)plane plane EWR - ORD
    8h 3m
    $213–1,505

  8. Bus via Baltimore

    1. Take the bus from Sag Harbor Westbound to 86 St & Central Park Westbus 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
    26h 14m
    $191–425

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

Calendar67Weekly Planes
Duration2h 44mAverage Duration
Ticket$89Cheapest Price
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Questions & Answers

Map of how to get from Sag Harbor to Chicago.ExpandLaunch map view
  • Distance: 829.2 mi
  • Duration: 6h 59m

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

You can take a bus from Sag Harbor Westbound to Chicago Bus Station via Main St/60 Av, Main St/Kissena Blvd, Flushing Main Street, Penn Station, and New York Midtown in around 21h 14m.

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