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How to get fromMiddlesboro to Chicagoby car, plane, bus, or train

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There are 9 ways to get from Middlesboro to Chicago by car, plane, 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. Drive to Mcghee Tyson Airport, fly to Chicago Midway International Airport

    best
    1. Drive from Middlesboro to Mcghee Tyson Airport (TYS)car car
    2. Fly from Mcghee Tyson Airport (TYS) to Chicago Midway International Airport (MDW)plane plane TYS - MDW
    3h 58m
    $90–474

  2. Drive to Blue Grass Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Drive from Middlesboro to Lexington-Airport-LEXcar car
    2. Fly from Blue Grass Airport (LEX) to Chicago O'Hare International Airport (ORD)plane plane LEX - ORD
    5h 14m
    $61–290

  3. Drive, bus

    1. Drive from Middlesboro to Londoncar car
    2. Take the bus from London to Cincinnati Bus Stationbus bus
    3. Take the bus from Cincinnati to Chicago Bus Stationbus bus
    12h 46m
    $84–159

  4. Drive  482.2 mi

    1. Drive from Middlesboro to Chicagocar car 482.2 mi
    8h 53m
    $88–128

  5. Drive to Mcghee Tyson Airport, fly to Chicago O'Hare International Airport

    1. Drive from Middlesboro to Mcghee Tyson Airport (TYS)car car
    2. Fly from Mcghee Tyson Airport (TYS) to Chicago O'Hare International Airport (ORD)plane plane TYS - ORD
    4h 27m
    $70–374

  6. Drive to Tri-Cities Regional Tn/Va Airport, fly to Chicago O'Hare International Airport

    1. Drive from Middlesboro to Tri-Cities-Regional-Airport-TRIcar car
    2. Fly from Tri-Cities Regional Tn/Va Airport (TRI) to Chicago O'Hare International Airport (ORD)plane plane TRI - ORD
    4h 51m
    $64–310

  7. Drive to Asheville Regional Airport, fly to Chicago O'Hare International Airport

    1. Drive from Middlesboro to Asheville-Airport-AVLcar car
    2. Fly from Asheville Regional Airport (AVL) to Chicago O'Hare International Airport (ORD)plane plane AVL - ORD
    5h 53m
    $73–322

  8. Drive, bus via Lafayette

    1. Drive from Middlesboro to Londoncar car
    2. Take the bus from London to Cincinnati Bus Stationbus bus
    3. Take the bus from Cincinnati to Indianapolisbus bus
    4. Take the bus from Indianapolis Union Station to Lafayette Amtrak Stationbus bus
    5. Take the bus from Lafayette Amtrak Station to Chicago Union Stationbus bus
    14h 6m
    $89–199

  9. Drive, bus, train

    1. Drive from Middlesboro to Londoncar car
    2. Take the bus from London to Cincinnati Bus Stationbus bus
    3. Take the bus from Cincinnati to Indianapolisbus bus
    4. Take the train from Indianapolis to Chicago Union Stationtrain train
    14h 26m
    $151–279

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

Calendar13Weekly Planes
Duration2h 38mAverage Duration
Ticket$75Cheapest Price
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Comparing Your Travel Options

Map of how to get from Middlesboro to Chicago.ExpandLaunch map view
  • Distance: 543.9 mi
  • Duration: 3h 58m

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

There is no direct connection from Middlesboro to Chicago. However, you can drive to Mcghee Tyson Airport (TYS) airport, fly to Chicago Midway International Airport (MDW), walk to Midway, then take the subway to Harold Washington Library. Alternatively, you can take a vehicle from Middlesboro to Chicago Bus Station via London, Cincinnati Bus Station, Cincinnati, and Cincinnati in around 12h 46m.

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