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

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There are 6 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
    2. Fly from Mcghee Tyson Airport (TYS) to Chicago O'Hare International Airport (ORD)planeTYS - ORD
    4h 28m
    $85–444

  2. Drive, bus via Dayton

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

  3. Drive, bus (Greyhound)

    1. Drive from Middlesboro to Londoncar
    2. Take the bus from London to Lexington Bus Stopbus
    3. Take the bus from Lexington Bus Stop to Chicago Bus Stationbus
    13h 41m
    $86–184

  4. Drive 483.4 mi

    1. Drive from Middlesboro to Chicagocar483.4 mi
    8h 43m
    $89–128

  5. Drive to Asheville Regional Airport, fly

    1. Drive from Middlesboro to Asheville-Airport-AVLcar
    2. Fly from Asheville Regional Airport (AVL) to Chicago O'Hare International Airport (ORD)planeAVL - ORD
    5h 43m
    $78–322

  6. Drive, bus, train

    1. Drive from Middlesboro to Londoncar
    2. Take the bus from London to Lexington Bus Stopbus
    3. Take the bus from Lexington Bus Stop to Indianapolis Union Stationbus
    4. Take the train from Indianapolis to Chicago Union Stationtrain
    14h 16m
    $111–449

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

Calendar58Weekly Planes
Duration2h 36mAverage 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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