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

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There are 11 ways to get from Chicago to Olean by plane, bus, bus (Greyhound), 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 42m
    $176–1,045

  2. Bus via Cleveland

    cheapest
    1. Take the bus from Chicago Bus Station to Cleveland Bus Stationbus bus
    2. Take the bus from Cleveland, OH to Buffalo, NYbus bus
    3. Take the bus from Buffalo to Oleanbus bus
    14h 20m
    $72–200

  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
    $82–264

  4. Drive 537.1 mi

    1. Drive from Chicago to Oleancar car 537.1 mi
    9h 4m
    $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 11m
    $216–1,245

  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 9m
    $116–426

  7. 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 11m
    $98–545

  8. 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, NY to Buffalo, NYbus bus
    3. Take the bus from Buffalo to Oleanbus bus
    9h 50m
    $156–750

  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, NY to Buffalo, NYbus bus
    3. Take the bus from Buffalo to Oleanbus bus
    9h 21m
    $146–800

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

    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. Take the bus from Buffalo to Oleanbus bus
    10h 12m
    $84–439

  11. Bus

    1. Take the bus from Chicago Bus Station to Pittsburgh Intermodal Stationbus bus Greyhound US0164
    2. Take the bus from Pittsburgh to Oleanbus bus Fab510
    16h 50m
    $84–237

Chicago to Olean by bus

Calendar14Weekly Buses
Duration14h 20mAverage Duration
Ticket$72Cheapest Price
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Questions & Answers

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

You can take a bus from Chicago Bus Station to Olean via Cleveland Bus Station, Cleveland, OH, Buffalo, NY, and Buffalo in around 14h 20m.

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