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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 9 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 O'Hare International Airport 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 17m
    $146–825

  2. Bus, drive

    cheapest
    1. Take the bus from Chicago Bus Station 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
    13h 16m
    $67–149

  3. Bus, drive via Cincinnati

    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 46m
    $73–157

  4. Drive 480.7 mi

    1. Drive from Chicago to Middlesborocar car 480.7 mi
    8h 53m
    $88–127

  5. Fly Chicago Midway International Airport to Mcghee Tyson Airport, drive

    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 45m
    $196–1,125

  6. 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 Middlesborocar car
    5h 27m
    $84–421

  7. 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
    6h 1m
    $116–640

  8. 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 42m
    $88–385

  9. Train, bus, drive

    1. Take the train from Chicago Union Station to Indianapolistrain train
    2. Take the bus from Indianapolis, IN to Greyhound Station Cincinnatibus bus
    3. Take the bus from Cincinnati Bus Station to Londonbus bus
    4. Drive from London to Middlesborocar car
    14h 35m
    $105–234

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

Calendar84Weekly Planes
Duration2h 20mAverage Duration
Ticket$133Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Middlesboro.ExpandLaunch map view
  • Distance: 566.6 mi
  • Duration: 5h 17m

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 University of Cincinnati, Arlington Heights, Cincinnati Bus Station, and London in around 12h 46m.

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