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

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There are 10 ways to get from Olean to Chicago by bus, plane, train, bus (Greyhound), 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 bus
    2. Fly from Buffalo Niagara International Airport (BUF) to Chicago Midway International Airport (MDW)plane plane BUF - MDW
    6h 34m
    $127–684

  2. Drive 536.3 mi

    cheapest
    1. Drive from Olean to Chicagocar car 536.3 mi
    9h 6m
    $98–142

  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
    13h 57m
    $208–416

  4. Bus

    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 5m
    $100–206

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

    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 2m
    $102–514

  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 44m
    $109–388

  7. 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 to Rochester Bus Stopbus bus
    3. Fly from Rochester (ROC) to Chicago O'Hare International Airport (ORD)plane plane ROC - ORD
    8h 22m
    $110–430

  8. 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 to Rochester Bus Stopbus bus
    3. Fly from Rochester (ROC) to Chicago Midway International Airport (MDW)plane plane ROC - MDW
    8h 9m
    $130–540

  9. Bus, train via Pittsburgh

    1. Take the bus from Olean to Pittsburgh, Pabus bus 530
    2. Take the train from Pittsburgh Amtrak Station to Chicago Union Stationtrain train Floridian
    16h 16m
    $181–461

  10. Bus via Pittsburgh

    1. Take the bus from Olean to Pittsburgh, Pabus bus 530
    2. Take the bus from Pittsburgh Intermodal Station to Chicagobus bus FlixBus N2640
    17h 52m
    $113–286

Olean to Chicago by bus, taxi, and train

Calendar14Weekly Services
Duration13h 57mAverage Duration
Ticket$208Cheapest Price
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Questions & Answers

Map of how to get from Olean to Chicago.ExpandLaunch map view
  • Distance: 573.3 mi
  • Duration: 6h 34m

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 5m.

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