Rome2Rio

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

Find Transport to Olean

See all options

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)plane plane MDW - BUF
    2. Take the bus from Buffalo to Oleanbus bus
    7h 11m
    $228–1,388

  2. Bus via Cleveland

    cheapest
    1. Take the bus from Chicago Bus Station to Cleveland Bus Stationbus bus
    2. Take the bus from Cleveland, OH to Buffalo, NYbus bus
    3. Take the bus from Buffalo to Oleanbus bus
    14h 20m
    $84–194

  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
    15h 28m
    $150–341

  4. Drive 537.1 mi

    1. Drive from Chicago to Oleancar car 537.1 mi
    9h 5m
    $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 41m
    $158–888

  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 26m
    $168–854

  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 57m
    $248–564

  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 3m
    $90–400

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

    1. Fly from Chicago Midway International Airport (MDW) to Pittsburgh International Airport (PIT)plane plane MDW - PIT
    2. Take the bus from Pittsburgh to Oleanbus bus
    11h 13m
    $112–685

  10. Bus

    1. Take the bus from Chicago Bus Station to Pittsburgh Intermodal Stationbus bus Greyhound US0164
    2. Take the bus from Pittsburgh to Oleanbus bus Fab510
    17h 5m
    $88–276

Chicago to Olean by bus

Calendar14Weekly Buses
Duration14h 20mAverage Duration
Ticket$84Cheapest Price
See schedules

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.

Airlines
Train operators
Bus operators

Want to know more about travelling around United States

Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

Related travel guides

Need to know: Greyhound

Read the travel guideNeed to know: Greyhound

More Questions & Answers

Trips from Chicago

Trips to Olean

Popular routes