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

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There are 9 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 Midway International Airport to Buffalo Niagara International Airport, bus

    best
    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
    6h 52m
    $184–459

  2. Bus

    cheapest
    1. Take the bus from Chicago to Clevelandbus bus
    2. Take the bus from Cleveland, OH to Buffalo, NYbus 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
    13h 37m
    $214–435

  4. Drive 536.5 mi

    1. Drive from Chicago to Oleancar car 536.5 mi
    9h 6m
    $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)plane plane ORD - BUF
    2. Take the bus from Buffalo to Oleanbus bus
    7h 18m
    $194–389

  6. 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 17m
    $182–853

  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
    8h 42m
    $152–703

  8. 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
    $108–450

  9. 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
    $107–276

Chicago to Olean by train, taxi, and bus

Calendar14Weekly Services
Duration13h 37mAverage Duration
Ticket$214Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Olean.ExpandLaunch map view
  • Distance: 576.9 mi
  • Duration: 6h 52m

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

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

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