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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 10 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 Midway International Airport to Buffalo Niagara International Airport, bus

    best
    1. Fly from Chicago Midway International Airport (MDW) to Buffalo Niagara International Airport (BUF)planeMDW - BUF
    2. Take the bus from Buffalo to Oleanbus
    7h 11m
    $196–1,145

  2. Bus via Cleveland

    cheapest
    1. Take the bus from Chicago Bus Station to Cleveland Bus Stationbus
    2. Take the bus from Cleveland, OH to Buffalo, NYbus
    3. Take the bus from Buffalo to Oleanbus
    14h 20m
    $72–223

  3. Train, bus

    1. Take the train from Chicago Union Station to Buffalo Depew StationtrainLake Shore Limited
    2. Take the bus from Buffalo to OleanbusFab530
    15h 27m
    $80–245

  4. Drive 537.1 mi

    1. Drive from Chicago to Oleancar537.1 mi
    8h 59m
    $98–142

  5. 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)planeORD - BUF
    2. Take the bus from Buffalo to Oleanbus
    7h 36m
    $166–995

  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)planeORD - SCE
    2. Take the bus from State College to DuBoisbus
    3. Take the bus from DuBois to Oleanbus
    10h 3m
    $110–416

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

    1. Fly from Chicago Midway International Airport (MDW) to Pittsburgh International Airport (PIT)planeMDW - PIT
    2. Take the bus from Pittsburgh to Oleanbus
    10h 58m
    $92–495

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

    1. Fly from Chicago O'Hare International Airport (ORD) to Rochester (ROC)planeORD - ROC
    2. Take the bus from Rochester, NY to Buffalo, NYbus
    3. Take the bus from Buffalo to Oleanbus
    9h 47m
    $156–660

  9. Fly Chicago Midway International Airport to Rochester, bus

    1. Fly from Chicago Midway International Airport (MDW) to Rochester (ROC)planeMDW - ROC
    2. Take the bus from Rochester, NY to Buffalo, NYbus
    3. Take the bus from Buffalo to Oleanbus
    9h 21m
    $136–700

  10. Bus

    1. Take the bus from Chicago Bus Station to Pittsburgh Intermodal StationbusGreyhound US0164
    2. Take the bus from Pittsburgh to OleanbusFab510
    16h 50m
    $91–268

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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