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

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There are 7 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

    best
    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
    $85–464

  2. Drive to Tri-Cities Regional Tn/Va Airport, fly

    cheapest
    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 43m
    $64–310

  3. Drive, bus (Greyhound)

    1. Drive from Middlesboro to Londoncar car
    2. Take the bus from London to Lexington Bus Stopbus bus
    3. Take the bus from Lexington Bus Stop to Chicago Bus Stationbus bus
    13h 41m
    $96–204

  4. Drive 483.4 mi

    1. Drive from Middlesboro to Chicagocar car 483.4 mi
    8h 48m
    $89–128

  5. Drive to Asheville Regional Airport, fly

    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 47m
    $73–322

  6. Drive, bus via Dayton

    1. Drive from Middlesboro to Londoncar car
    2. Take the bus from London to Dayton Trotwood Bus Stationbus bus
    3. Take the bus from Dayton Trotwood Bus Station to Chicagobus bus
    14h 11m
    $77–184

  7. Drive, bus, train

    1. Drive from Middlesboro to Londoncar car
    2. Take the bus from London to Lexington Bus Stopbus bus
    3. Take the bus from Lexington Bus Stop to Indianapolis Union Stationbus bus
    4. Take the train from Indianapolis to Chicago Union Stationtrain train
    14h 16m
    $111–224

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

Calendar63Weekly Planes
Duration2h 58mAverage Duration
Ticket$73Cheapest Price
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Questions & Answers

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 O'Hare International Airport (ORD), walk to O'Hare, then take the subway to Jackson-Blue. Alternatively, you can take a vehicle from Middlesboro to Chicago Bus Station via London and Lexington Bus Stop in around 13h 41m.

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Need to know: Greyhound

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