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

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There are 8 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 26m
    $75–394

  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 45m
    $69–350

  3. Drive, bus via Cincinnati

    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
    $73–164

  4. Drive 482.2 mi

    1. Drive from Middlesboro to Chicagocar car 482.2 mi
    8h 52m
    $88–128

  5. Drive to Blue Grass Airport, fly

    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
    $81–430

  6. 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 55m
    $78–342

  7. Drive, bus

    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 Chicago Bus Stationbus bus
    13h 21m
    $72–154

  8. 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 Greyhound Station Cincinnati to Indianapolis, INbus bus
    4. Take the train from Indianapolis to Chicago Union Stationtrain train
    14h 26m
    $100–239

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

Calendar84Weekly Planes
Duration2h 29mAverage Duration
Ticket$61Cheapest 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, Cincinnati Bus Station, Arlington Heights, and Cincinnati in around 12h 46m.

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