Rome2Rio

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

Find Transport to Chicago

See all options

There are 8 ways to get from Sag Harbor to Chicago by bus, plane, train, bus (Flixbus), 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
    7h 2m
    $240–743

  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
    10h 7m
    $160–698

  3. 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
    $536–925

  4. 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 N2640 / ...
    24h 42m
    $190–329

  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 24m
    $170–643

  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 11m
    $173–900

  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
    27h 5m
    $206–340

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

Calendar67Weekly Planes
Duration2h 54mAverage Duration
Ticket$106Cheapest Price
See schedules

Comparing Your Travel Options

Map of how to get from Sag Harbor to Chicago.ExpandLaunch map view
  • Distance: 829.2 mi
  • Duration: 7h 2m

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 24h 42m.

Airlines
Train operators
Bus operators

Want to know more about travelling around United States

Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

Related travel guides

Need to know: Greyhound

Read the travel guideNeed to know: Greyhound

Booking & Getting There