Rome2Rio

How to get fromChicago to Prestonsburgby plane, car, bus, taxi, or train

Find Transport to Prestonsburg

See all options

There are 11 ways to get from Chicago to Prestonsburg by plane, car, bus, taxi, or train

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 O'Hare International Airport to Blue Grass Airport, drive

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Blue Grass Airport (LEX)plane plane ORD - LEX
    2. Drive from Lexington-Airport-LEX to Prestonsburgcar car
    5h 20m
    $64–310

  2. Bus, taxi

    1. Take the bus from Chicago Bus Station to Washington Union Stationbus bus
    2. Take the bus from Washington Union Station to Bristol Exit 5 Park & Ride Lotbus bus
    3. Take the taxi from Bristol Exit 5 Park & Ride Lot to Southwest Virginia Community Collegetaxi taxi
    4. Take the bus from Southwest Virginia Community College to Centennial Heights Apartmentsbus bus
    5. Take the taxi from Centennial Heights Apartments to Prestonsburgtaxi taxi
    30h 21m

  3. Train, bus, taxi

    1. Take the train from Chicago Union Station to Washington Union Stationtrain train
    2. Take the bus from Washington Union Station to Bristol Exit 5 Park & Ride Lotbus bus
    3. Take the taxi from Bristol Exit 5 Park & Ride Lot to Southwest Virginia Community Collegetaxi taxi
    4. Take the bus from Southwest Virginia Community College to Centennial Heights Apartmentsbus bus
    5. Take the taxi from Centennial Heights Apartments to Prestonsburgtaxi taxi
    31h 16m

  4. Drive  466.5 mi

    1. Drive from Chicago to Prestonsburgcar car 466.5 mi
    8h 18m
    $86–123

  5. Fly Chicago O'Hare International Airport to Yeager Airport, drive

    1. Fly from Chicago O'Hare International Airport (ORD) to Yeager Airport (CRW)plane plane ORD - CRW
    2. Drive from Yeager Airport (CRW) to Prestonsburgcar car
    6h 8m
    $70–330

  6. Fly Chicago O'Hare International Airport to Covington, drive

    1. Fly from Chicago O'Hare International Airport (ORD) to Covington (CVG)plane plane ORD - CVG
    2. Drive from Covington (CVG) to Prestonsburgcar car
    6h 21m
    $182–805

  7. Fly Chicago Midway International Airport to Louisville International Airport, drive

    1. Fly from Chicago Midway International Airport (MDW) to Louisville International Airport (SDF)plane plane MDW - SDF
    2. Drive from Louisville-Airport-SDF to Prestonsburgcar car
    6h 3m
    $132–805

  8. Fly Chicago Midway International Airport to Covington, drive

    1. Fly from Chicago Midway International Airport (MDW) to Covington (CVG)plane plane MDW - CVG
    2. Drive from Covington (CVG) to Prestonsburgcar car
    5h 59m
    $192–355

  9. Fly Chicago O'Hare International Airport to Tri-Cities Regional Tn/Va Airport, drive

    1. Fly from Chicago O'Hare International Airport (ORD) to Tri-Cities Regional Tn/Va Airport (TRI)plane plane ORD - TRI
    2. Drive from Tri-Cities-Regional-Airport-TRI to Prestonsburgcar car
    6h 48m
    $70–340

  10. Fly Chicago Midway International Airport to John Glenn Columbus International Airport, drive

    1. Fly from Chicago Midway International Airport (MDW) to John Glenn Columbus International Airport (CMH)plane plane MDW - CMH
    2. Drive from Columbus-Airport-CMH to Prestonsburgcar car
    6h 49m
    $118–610

  11. Train, drive, bus, taxi

    1. Take the train from Chicago Union Station to Charlottesvilletrain train
    2. Drive from Charlottesville to Goodwin Transit Centercar car
    3. Take the bus from Goodwin Transit Center to Bristol Exit 5 Park & Ride Lotbus bus
    4. Take the taxi from Bristol Exit 5 Park & Ride Lot to Southwest Virginia Community Collegetaxi taxi
    5. Take the bus from Southwest Virginia Community College to Buchanan Funeral Homebus bus
    6. Take the taxi from Buchanan Funeral Home to Prestonsburgtaxi taxi
    31h 48m

Chicago O'Hare International Airport (ORD) to Blue Grass Airport (LEX) flights

Calendar78Weekly Planes
Duration1h 35mAverage Duration
Ticket$41Cheapest Price
See schedules

Comparing Your Travel Options

Map of how to get from Chicago to Prestonsburg.ExpandLaunch map view
  • Distance: 463 mi
  • Duration: 5h 20m

What companies run services between Chicago, IL, USA and Prestonsburg, KY, USA?

There is no direct connection from Chicago to Prestonsburg. However, you can take the subway to O'Hare, walk to Chicago O'Hare International Airport (ORD) airport, fly to Blue Grass Airport (LEX), then drive to Prestonsburg. Alternatively, you can take the bus to Washington Union Station, take the bus to Bristol Exit 5 Park & Ride Lot, take the taxi to Southwest Virginia Community College, take the bus to Centennial Heights Apartments, then take the taxi to Prestonsburg.

Airlines
Train operators
Bus operators
Other 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