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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 11 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 O'Hare International Airport

    best
    1. Take the bus from Olean to Buffalobus bus
    2. Fly from Buffalo Niagara International Airport (BUF) to Chicago O'Hare International Airport (ORD)plane plane BUF - ORD
    7h 17m
    $101–603

  2. Bus

    cheapest
    1. Take the bus from Olean to Buffalobus bus
    2. Take the bus from Buffalo to Cleveland Bus Stationbus bus
    3. Take the bus from Cleveland Bus Station to Chicago Bus Stationbus bus
    15h 15m
    $76–193

  3. Bus, train

    1. Take the bus from Olean to Buffalobus bus Fab510
    2. Take the train from Buffalo Depew Station to Chicago Union Stationtrain train Lake Shore Limited
    16h 9m
    $99–262

  4. Drive 537 mi

    1. Drive from Olean to Chicagocar car 537 mi
    9h 3m
    $98–142

  5. Bus to Buffalo Niagara International Airport, fly to Chicago Midway International Airport

    1. Take the bus from Olean to Buffalobus bus
    2. Fly from Buffalo Niagara International Airport (BUF) to Chicago Midway International Airport (MDW)plane plane BUF - MDW
    7h 6m
    $136–843

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

    1. Take the bus from Olean to DuBoisbus bus
    2. Take the bus from DuBois to State Collegebus bus
    3. Fly from Penn State University Park Airport (SCE) to Chicago O'Hare International Airport (ORD)plane plane SCE - ORD
    8h 59m
    $131–391

  7. Bus to Pittsburgh International Airport, fly to Chicago Midway International Airport

    1. Take the bus from Olean to Pittsburghbus bus
    2. Fly from Pittsburgh International Airport (PIT) to Chicago Midway International Airport (MDW)plane plane PIT - MDW
    10h 24m
    $101–549

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

    1. Take the bus from Olean to Buffalobus bus
    2. Take the bus from Buffalo, NY to Rochester, NYbus bus
    3. Fly from Rochester (ROC) to Chicago O'Hare International Airport (ORD)plane plane ROC - ORD
    9h 41m
    $176–688

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

    1. Take the bus from Olean to Buffalobus bus
    2. Take the bus from Buffalo, NY to Rochester, NYbus bus
    3. Fly from Rochester (ROC) to Chicago Midway International Airport (MDW)plane plane ROC - MDW
    9h 26m
    $136–748

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

    1. Take the bus from Olean to Buffalobus bus
    2. Take the bus from Buffalo to Eriebus bus
    3. Fly from Erie International Airport (ERI) to Chicago O'Hare International Airport (ORD)plane plane ERI - ORD
    10h 35m
    $84–372

  11. Bus via Pittsburgh

    1. Take the bus from Olean to Pittsburghbus bus Fab530
    2. Take the bus from Pittsburgh Intermodal Station to Chicagobus bus FlixBus 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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