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How to get fromStaten Island to Chicagoby bus, subway, plane, train (Amtrak), bus (Flixbus), car, train or bus (Greyhound)

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There are 10 ways to get from Staten Island to Chicago by bus, subway, plane, train (Amtrak), bus (Flixbus), 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. Bus, subway to Laguardia Airport, fly to Chicago Midway International Airport

    best
    1. Take the bus from Hylan Blvd/Montreal Av to Church St/Fulton Stbus bus
    2. Take the subway from World Trade Center to Jackson Hts-Roosevelt Avsubway subway
    3. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    5h 57m
    $88–465

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

    cheapest
    1. Take the bus from Hylan Blvd/Montreal Av to Church St/Fulton Stbus bus
    2. Take the subway from World Trade Center to Jackson Hts-Roosevelt Avsubway subway
    3. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    6h 12m
    $58–295

  3. Train (Amtrak)

    1. Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain train Lake Shore Limited / ...
    22h 2m
    $123–487

  4. Bus (Flixbus)

    1. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2640
    23h 8m
    $95–224

  5. Drive 787.6 mi

    1. Drive from Staten Island to Chicagocar car 787.6 mi
    13h 23m
    $144–208

  6. Bus, train to Newark Liberty International Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Hylan Blvd/Montreal Av to Church St/Fulton Stbus bus
    2. Take the train from World Trade Center to Newark Penn Stationtrain train
    3. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)plane plane EWR - ORD
    6h 11m
    $76–340

  7. Bus, subway to John F. Kennedy International Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Hylan Blvd/Montreal Av to Church St/Fulton Stbus bus
    2. Take the subway from Chambers St to Howard Beach-JFK Airportsubway subway
    3. Fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD)plane plane JFK - ORD
    6h 31m
    $817–1,024

  8. Bus, line 4 subway, train to Westchester County Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Hylan Blvd/Montreal Av to Greenwich St/Battery Plbus bus
    2. Take the subway from Bowling Green to 125th Streetsubway subway
    3. Take the train from 125th Street - Harlem to White Plainstrain train
    4. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    8h 15m
    $84–382

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

    1. Take the train from Newark Penn Station to 30th Street Stationtrain train
    2. Fly from Philadelphia International Airport (PHL) to Chicago Midway International Airport (MDW)plane plane PHL - MDW
    7h 27m
    $104–1,075

  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
    25h 2m
    $108–262

Staten Island to Chicago by bus, foot, and train (Amtrak)

Calendar10Weekly Services
Duration22h 2mAverage Duration
Ticket$123Cheapest Price
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Questions & Answers

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

Amtrak operates a train from Ny Moynihan Train Hall At Penn Station to Chicago Union Station once daily. Tickets cost $120–480 and the journey takes 19h 32m. Alternatively, Flixbus USA operates a bus from New York Midtown to Chicago Bus Station once daily. Tickets cost $90–210 and the journey takes 20h 25m.

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