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How to get fromChicago to Lexingtonby plane, car, train, taxi, or bus

Find Transport to Lexington

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There are 6 ways to get from Chicago to Lexington by plane, car, train, taxi, or bus

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 Midway International Airport to Jackson/Vicksburg, drive

    best
    1. Fly from Chicago Midway International Airport (MDW) to Jackson/Vicksburg (JAN)plane plane MDW - JAN
    2. Drive from Jackson/Vicksburg (JAN) to Lexingtoncar car
    6h 46m
    $104–513

  2. Fly Chicago O'Hare International Airport to Jackson/Vicksburg, drive

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Jackson/Vicksburg (JAN)plane plane ORD - JAN
    2. Drive from Jackson/Vicksburg (JAN) to Lexingtoncar car
    7h 34m
    $84–393

  3. Train, taxi (Amtrak)

    1. Take the train from Chicago Union Station to Greenwood Amtrak Stationtrain train City of New Orleans
    2. Take the taxi from Greenwood Amtrak Station to Lexingtontaxi taxi
    14h 18m
    $490–722

  4. Bus, train, taxi

    1. Take the bus from Chicago Bus Station to Memphis Bus Stationbus bus
    2. Take the bus from Memphis Bus Station to Jacksonbus bus
    3. Take the train from Jackson to Yazoo City Amtrak Stationtrain train
    4. Take the taxi from Yazoo City Amtrak Station to Lexingtontaxi taxi
    17h 28m
    $274–405

  5. Drive  687.3 mi

    1. Drive from Chicago to Lexingtoncar car 687.3 mi
    11h 11m
    $126–182

  6. Fly Chicago Midway International Airport to Birmingham–Shuttlesworth International Airport, drive

    1. Fly from Chicago Midway International Airport (MDW) to Birmingham–Shuttlesworth International Airport (BHM)plane plane MDW - BHM
    2. Drive from Birmingham-Airport-BHM to Lexingtoncar car
    7h 44m
    $202–1,020

Chicago Midway International Airport (MDW) to Jackson/Vicksburg (JAN) flights

Calendar34Weekly Planes
Duration6h 14mAverage Duration
Ticket$92Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Lexington.ExpandLaunch map view
  • Distance: 744.6 mi
  • Duration: 6h 46m

What companies run services between Chicago, IL, USA and Lexington, MS, USA?

There is no direct connection from Chicago to Lexington. However, you can take the subway to Midway, walk to Chicago-Midway-Airport-MDW airport, fly to Jackson/Vicksburg (JAN), then drive to Lexington. Alternatively, you can take the train to Greenwood Amtrak Station then take the taxi to Lexington.

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