Rome2Rio

How to get fromOssining to Chicagoby train, plane, train (Amtrak), bus (Flixbus), car or bus

Find Transport to Chicago

See all options

There are 10 ways to get from Ossining to Chicago by train, plane, train (Amtrak), bus (Flixbus), 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. Train to Laguardia Airport, fly to Chicago O'Hare International Airport

    best
    1. Take the train from Ossining to 125th Street - Harlemtrain
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)planeLGA - ORD
    5h 51m
    $69–288

  2. Train (Amtrak)

    1. Take the train from Croton-Harmon Amtrak Station to Chicago Union StationtrainLake Shore Limited
    19h 55m
    $136–380

  3. Bus (Flixbus)

    1. Take the bus from New York Midtown to Chicago Bus StationbusFlixBus N2640
    24h 24m
    $108–245

  4. Drive 809.2 mi

    1. Drive from Ossining to Chicagocar809.2 mi
    13h 27m
    $148–214

  5. Train to Laguardia Airport, fly to Chicago Midway International Airport

    1. Take the train from Ossining to 125th Street - Harlemtrain
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)planeLGA - MDW
    5h 40m
    $94–448

  6. Train to John F. Kennedy International Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Ossining to Grand Central Terminaltrain
    2. Fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD)planeJFK - ORD
    6h 22m
    $826–1,039

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

    1. Take the train from Ossining to Grand Central Terminaltrain
    2. Take the bus from Bryant Park to Terminal Bbus
    3. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)planeEWR - ORD
    6h 46m

  8. Train, bus to Newark Liberty International Airport, fly to Chicago Midway International Airport

    1. Take the train from Ossining to Grand Central Terminaltrain
    2. Take the bus from Bryant Park to Terminal Bbus
    3. Fly from Newark Liberty International Airport (EWR) to Chicago Midway International Airport (MDW)planeEWR - MDW
    6h 35m

  9. Line 0019 bus, train to Westchester County Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Croton Ave @ S Highland Ave to Bedford Rd @ Wheeler Avebus
    2. Take the train from Pleasantville to White Plainstrain
    3. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)planeHPN - ORD
    7h 3m
    $80–383

  10. Train to Laguardia Airport, fly to General Mitchell International Airport, train

    1. Take the train from Ossining to 125th Street - Harlemtrain
    2. Fly from Laguardia Airport (LGA) to General Mitchell International Airport (MKE)planeLGA - MKE
    3. Take the train from Milwaukee to Chicago Union Stationtrain
    8h 13m
    $206–628

Ossining to Chicago by train (Amtrak)

Calendar7Weekly Trains
Duration19h 55mAverage Duration
Ticket$136Cheapest Price
See schedules

Questions & Answers

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

Amtrak operates a train from Croton-Harmon Amtrak Station to Chicago Union Station once daily. Tickets cost $130–370 and the journey takes 18h 46m. Alternatively, Flixbus USA operates a bus from New York Midtown to Chicago Bus Station once daily. Tickets cost $95–230 and the journey takes 20h 25m.

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

More Questions & Answers

Where to next?

Trips from Ossining

Trips to Chicago

Popular routes