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How to get fromOlean to Chicagoby bus, plane, bus (Greyhound), train, car or bus (Flixbus)

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There are 9 ways to get from Olean to Chicago by bus, plane, bus (Greyhound), train, car, 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. Bus to Buffalo Niagara International Airport, fly to Chicago Midway International Airport

    best
    1. Take the bus from Olean to Buffalobus
    2. Fly from Buffalo Niagara International Airport (BUF) to Chicago Midway International Airport (MDW)planeBUF - MDW
    6h 51m
    $126–744

  2. Bus

    cheapest
    1. Take the bus from Olean to Buffalobus
    2. Take the bus from Buffalo to Cleveland Bus Stationbus
    3. Take the bus from Cleveland Bus Station to Chicago Bus Stationbus
    15h 15m
    $76–209

  3. Bus, train

    1. Take the bus from Olean to BuffalobusFab510
    2. Take the train from Buffalo Depew Station to Chicago Union StationtrainLake Shore Limited
    16h 9m
    $109–263

  4. Drive 537 mi

    1. Drive from Olean to Chicagocar537 mi
    8h 58m
    $98–142

  5. Bus to Buffalo Niagara International Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Olean to Buffalobus
    2. Fly from Buffalo Niagara International Airport (BUF) to Chicago O'Hare International Airport (ORD)planeBUF - ORD
    7h 15m
    $101–574

  6. Bus, bus to Penn State University Park Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Olean to DuBoisbus
    2. Take the bus from DuBois to State Collegebus
    3. Fly from Penn State University Park Airport (SCE) to Chicago O'Hare International Airport (ORD)planeSCE - ORD
    8h 53m
    $131–381

  7. Bus, bus to Rochester, fly to Chicago O'Hare International Airport

    1. Take the bus from Olean to Buffalobus
    2. Take the bus from Buffalo, NY to Rochester, NYbus
    3. Fly from Rochester (ROC) to Chicago O'Hare International Airport (ORD)planeROC - ORD
    9h 22m
    $176–629

  8. Bus, bus to Rochester, fly to Chicago Midway International Airport

    1. Take the bus from Olean to Buffalobus
    2. Take the bus from Buffalo, NY to Rochester, NYbus
    3. Fly from Rochester (ROC) to Chicago Midway International Airport (MDW)planeROC - MDW
    9h 6m
    $131–669

  9. Bus via Pittsburgh

    1. Take the bus from Olean to PittsburghbusFab530
    2. Take the bus from Pittsburgh Intermodal Station to ChicagobusFlixBus N2640
    17h 51m
    $96–239

Olean to Chicago by bus

Calendar7Weekly Buses
Duration15h 15mAverage Duration
Ticket$76Cheapest Price
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Questions & Answers

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

You can take a bus from Olean to Chicago Bus Station via Buffalo and Cleveland Bus Station in around 15h 15m.

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