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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 7 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 to Mcghee Tyson Airport, drive

    best
    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 10m
    $100–575

  2. Fly to Asheville Regional Airport, drive

    cheapest
    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 36m
    $78–355

  3. Bus, drive (Greyhound)

    1. Take the bus from Chicago Bus Station to Lexington Bus Stopbus bus
    2. Take the bus from Lexington Bus Stop to Londonbus bus
    3. Drive from London to Middlesborocar car
    12h 51m
    $88–193

  4. Drive 480.7 mi

    1. Drive from Chicago to Middlesborocar car 480.7 mi
    8h 52m
    $88–127

  5. Fly 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 Middlesborocar car
    5h 29m
    $90–451

  6. Train, bus, drive

    1. Take the train from Chicago Union Station to Indianapolistrain train
    2. Take the bus from Indianapolis Union Station to Lexington Bus Stopbus bus
    3. Take the bus from Lexington Bus Stop to Londonbus bus
    4. Drive from London to Middlesborocar car
    13h 40m
    $108–213

  7. Bus, drive via Dayton

    1. Take the bus from Chicago to Dayton Trotwood Bus Stationbus bus
    2. Take the bus from Dayton Trotwood Bus Station to Londonbus bus
    3. Drive from London to Middlesborocar car
    14h 31m
    $78–184

Chicago O'Hare International Airport (ORD) to Mcghee Tyson Airport (TYS) flights

Calendar51Weekly Planes
Duration2h 33mAverage Duration
Ticket$89Cheapest Price
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Questions & Answers

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 O'Hare, walk to Chicago O'Hare International Airport (ORD) airport, fly to Mcghee Tyson Airport (TYS), then drive to Middlesboro. Alternatively, you can take a bus from Chicago Bus Station to Middlesboro via Lexington Bus Stop and London in around 12h 51m.

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