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How to get fromChicago to Middlesboroby plane, car, bus, or train

Find Transport to Middlesboro

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There are 10 ways to get from Chicago to Middlesboro by plane, car, bus, 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 Midway International Airport to Mcghee Tyson Airport, drive

    best
    1. Fly from Chicago Midway International Airport (MDW) to Mcghee Tyson Airport (TYS)plane plane MDW - TYS
    2. Drive from Mcghee Tyson Airport (TYS) to Middlesborocar car
    4h 48m
    $214–1,224

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

    cheapest
    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 Middlesborocar car
    5h 29m
    $64–319

  3. Bus, drive

    1. Take the bus from Chicago Bus Station to Cincinnatibus bus
    2. Take the bus from Cincinnati Bus Station to Londonbus bus
    3. Drive from London to Middlesborocar car
    12h 51m
    $86–162

  4. Drive  480.7 mi

    1. Drive from Chicago to Middlesborocar car 480.7 mi
    8h 53m
    $83–119

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

    1. Fly from Chicago O'Hare International Airport (ORD) to Mcghee Tyson Airport (TYS)plane plane ORD - TYS
    2. Drive from Mcghee Tyson Airport (TYS) to Middlesborocar car
    5h 13m
    $134–774

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

    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 Middlesborocar car
    5h 54m
    $64–310

  7. Fly Chicago O'Hare International Airport to Asheville Regional Airport, drive

    1. Fly from Chicago O'Hare International Airport (ORD) to Asheville Regional Airport (AVL)plane plane ORD - AVL
    2. Drive from Asheville-Airport-AVL to Middlesborocar car
    6h 33m
    $76–340

  8. 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 Middlesborocar car
    7h 1m
    $152–855

  9. Bus, drive via Indianapolis

    1. Take the bus from Chicago Bus Station to Indianapolis Union Stationbus bus
    2. Take the bus from Indianapolis to Cincinnatibus bus
    3. Take the bus from Cincinnati Bus Station to Londonbus bus
    4. Drive from London to Middlesborocar car
    12h 51m
    $84–162

  10. Train, bus, drive

    1. Take the train from Chicago Union Station to Indianapolistrain train
    2. Take the bus from Indianapolis to Cincinnatibus bus
    3. Take the bus from Cincinnati Bus Station to Londonbus bus
    4. Drive from London to Middlesborocar car
    14h 40m
    $159–279

Chicago Midway International Airport (MDW) to Mcghee Tyson Airport (TYS) flights

Calendar13Weekly Planes
Duration2h 48mAverage Duration
Ticket$204Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Middlesboro.ExpandLaunch map view
  • Distance: 544.4 mi
  • Duration: 4h 48m

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

There is no direct connection from Chicago to Middlesboro. However, you can take the subway to Midway, walk to Chicago-Midway-Airport-MDW airport, fly to Mcghee Tyson Airport (TYS), then drive to Middlesboro. Alternatively, you can take a bus from Chicago Bus Station to Middlesboro via Cincinnati, Cincinnati, Cincinnati Bus Station, and London in around 12h 51m.

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