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

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There are 10 ways to get from Chicago to Olean by plane, bus, train, car, or bus (Greyhound, 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. Fly Chicago O'Hare International Airport to Buffalo Niagara International Airport, bus

    best
    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 39m
    $198–388

  2. Bus

    cheapest
    1. Take the bus from Chicago to Clevelandbus bus
    2. Take the bus from Cleveland to Buffalobus bus
    3. Take the bus from Buffalo to Oleanbus bus
    14h 5m
    $72–194

  3. Train, bus

    1. Take the train from Chicago Union Station to Buffalo Depew Stationtrain train Lake Shore Limited
    2. Take the bus from Buffalo to Oleanbus bus Fab530
    15h 27m
    $315–506

  4. Drive  536.5 mi

    1. Drive from Chicago to Oleancar car 536.5 mi
    9h 9m
    $98–142

  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 19m
    $188–458

  6. 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 4m
    $90–430

  7. 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 Bus Stop to Buffalobus bus
    3. Take the bus from Buffalo to Oleanbus bus
    9h 12m
    $152–752

  8. 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 Bus Stop to Buffalobus bus
    3. Take the bus from Buffalo to Oleanbus bus
    8h 53m
    $202–1,052

  9. Fly Chicago Midway International Airport to Pittsburgh International Airport, bus

    1. Fly from Chicago Midway International Airport (MDW) to Pittsburgh International Airport (PIT)plane plane MDW - PIT
    2. Take the bus from Pittsburgh to Oleanbus bus
    11h 7m
    $132–685

  10. Bus via Pittsburgh

    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 5m
    $109–266

Chicago to Olean by bus

Calendar7Weekly Buses
Duration14h 5mAverage Duration
Ticket$72Cheapest Price
See schedules

Comparing Your Travel Options

Map of how to get from Chicago to Olean.ExpandLaunch map view
  • Distance: 584.7 mi
  • Duration: 7h 39m

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

You can take a bus from Chicago to Olean via Cleveland and Buffalo in around 14h 5m.

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