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How to get fromChicago to Cubaby train, car, bus (Greyhound, Flixbus), plane, bus, or bus (Flixbus)

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There are 11 ways to get from Chicago to Cuba by train, car, bus (Greyhound, Flixbus), plane, bus, or bus (Flixbus)

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, drive (Amtrak)

    best
    1. Take the train from Chicago Union Station to Buffalo Depew Stationtrain train Lake Shore Limited
    2. Drive from Buffalo Depew Station to Cubacar car
    11h 58m
    $181–364

  2. Fly Chicago O'Hare International Airport to Erie International Airport, bus, drive

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Erie International Airport (ERI)plane plane ORD - ERI
    2. Take the bus from Erie, PA to Buffalo, NYbus bus
    3. Drive from Buffalo, NY to Cubacar car
    9h 8m
    $82–374

  3. Bus

    1. Take the bus from Chicago Bus Station to Pittsburgh Intermodal Stationbus bus Greyhound US0164
    2. Take the bus from Pittsburgh, Pa to Oleanbus bus 510
    17h 21m
    $117–290

  4. Drive 549.2 mi

    1. Drive from Chicago to Cubacar car 549.2 mi
    9h 19m
    $101–145

  5. Fly Chicago Midway International Airport to Buffalo Niagara International Airport, bus

    1. Fly from Chicago Midway International Airport (MDW) to Buffalo Niagara International Airport (BUF)plane plane MDW - BUF
    2. Take the bus from Buffalo to Oleanbus bus
    7h 11m
    $194–470

  6. Train, bus

    1. Take the train from Chicago Union Station to Pittsburgh Amtrak Stationtrain train Floridian
    2. Take the bus from Pittsburgh, Pa to Oleanbus bus 510
    16h 21m
    $198–465

  7. Bus via Chicago

    1. Take the bus from Chicago to Pittsburgh Intermodal Stationbus bus FlixBus N2640
    2. Take the bus from Pittsburgh, Pa to Oleanbus bus 510
    18h 55m
    $132–306

  8. Fly Chicago O'Hare International Airport to Buffalo Niagara International Airport, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Buffalo Niagara International Airport (BUF)plane plane ORD - BUF
    2. Take the bus from Buffalo to Oleanbus bus
    7h 36m
    $204–400

  9. Fly Chicago Midway International Airport to Rochester, bus

    1. Fly from Chicago Midway International Airport (MDW) to Rochester (ROC)plane plane MDW - ROC
    2. Take the bus from Rochester to Hornellbus bus
    7h 58m
    $240–910

  10. Fly Chicago O'Hare International Airport to Rochester, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Rochester (ROC)plane plane ORD - ROC
    2. Take the bus from Rochester to Hornellbus bus
    8h 23m
    $210–760

  11. Fly Chicago O'Hare International Airport to Penn State University Park Airport, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Penn State University Park Airport (SCE)plane plane ORD - SCE
    2. Take the bus from State College to DuBoisbus bus
    3. Take the bus from DuBois to Oleanbus bus
    10h 25m
    $116–461

Chicago Midway International Airport (MDW) to Buffalo Niagara International Airport (BUF) flights

Calendar27Weekly Planes
Duration1h 45mAverage Duration
Ticket$110Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Cuba.ExpandLaunch map view
  • Distance: 589.1 mi
  • Duration: 11h 58m

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

You can take a bus from Chicago Bus Station to Cuba via Pittsburgh, Pa and Olean in around 17h 21m.

Airlines
Train operators
Bus operators

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