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

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There are 10 ways to get from Manhattan to Chicago by plane, bus (Flixbus), train (Amtrak), car, 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. Fly Laguardia Airport to Chicago Midway International Airport

    best
    1. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    4h 43m
    $90–472

  2. Fly Laguardia Airport to Chicago O'Hare International Airport

    cheapest
    1. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    4h 58m
    $55–262

  3. Bus (Flixbus)

    1. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2640
    20h 25m
    $90–220

  4. Train (Amtrak)

    1. Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain train Lake Shore Limited / ...
    21h 4m
    $123–487

  5. Drive 792.2 mi

    1. Drive from Manhattan to Chicagocar car 792.2 mi
    13h 13m
    $145–209

  6. Fly Newark Liberty International Airport to Chicago O'Hare International Airport

    1. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)plane plane EWR - ORD
    4h 56m
    $72–332

  7. Fly John F. Kennedy International Airport to Chicago O'Hare International Airport

    1. Fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD)plane plane JFK - ORD
    5h 11m
    $816–1,023

  8. Train to Westchester County Airport, fly to Chicago O'Hare International Airport

    1. Take the train from 125th Street - Harlem to White Plainstrain train
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    6h 49m
    $74–362

  9. Train to Philadelphia International Airport, fly to Chicago Midway International Airport

    1. Take the train from Ny Moynihan Train Hall At Penn Station to 30th Street Stationtrain train
    2. Fly from Philadelphia International Airport (PHL) to Chicago Midway International Airport (MDW)plane plane PHL - MDW
    6h 4m
    $100–1,081

  10. Bus via Baltimore

    1. Take the bus from Port Authority Bus Terminal to Baltimore Downtown Bus Stationbus bus Greyhound US0670 / ...
    2. Take the bus from Baltimore Downtown Bus Station to Chicago Bus Stationbus bus Greyhound US0164
    22h 55m
    $107–261

Manhattan to Chicago by bus (Flixbus)

Calendar7Weekly Buses
Duration20h 25mAverage Duration
Ticket$90Cheapest Price
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Questions & Answers

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

Southwest Airlines and Delta fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW) every 3 hours. Alternatively, Flixbus USA operates a bus from New York Midtown to Chicago Bus Station once daily. Tickets cost $90–220 and the journey takes 20h 25m.

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