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

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There are 9 ways to get from Lexington 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 Louisville International Airport, fly to Chicago Midway International Airport

    best
    1. Drive from Lexington to Louisville-Airport-SDFcar car
    2. Fly from Louisville International Airport (SDF) to Chicago Midway International Airport (MDW)plane plane SDF - MDW
    3h 23m
    $66–376

  2. Line 3 bus to Blue Grass Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the bus from Centre Parkway @ 1349 to Transit Centerbus bus
    2. Fly from Blue Grass Airport (LEX) to Chicago O'Hare International Airport (ORD)plane plane LEX - ORD
    5h 27m
    $59–357

  3. Drive, bus (Amtrak)

    1. Drive from Lexington to Middletown Station @ Targetcar car
    2. Take the bus from Louisville, KY to Chicago Union Stationbus bus
    9h 51m
    $64–83

  4. Drive 363.1 mi

    1. Drive from Lexington to Chicagocar car 363.1 mi
    6h 33m
    $67–96

  5. Drive to Covington, fly to Chicago Midway International Airport

    1. Drive from Lexington to Covington (CVG)car car
    2. Fly from Covington (CVG) to Chicago Midway International Airport (MDW)plane plane CVG - MDW
    3h 17m
    $67–387

  6. Drive to Covington, fly to Chicago O'Hare International Airport

    1. Drive from Lexington to Covington (CVG)car car
    2. Fly from Covington (CVG) to Chicago O'Hare International Airport (ORD)plane plane CVG - ORD
    3h 45m
    $62–337

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

    1. Drive from Lexington to Louisville-Airport-SDFcar car
    2. Fly from Louisville International Airport (SDF) to Chicago O'Hare International Airport (ORD)plane plane SDF - ORD
    3h 53m
    $61–326

  8. Drive, bus via Indianapolis

    1. Drive from Lexington to Middletown Station @ Targetcar car
    2. Take the bus from Louisville, KY to Indianapolis Union Stationbus bus
    3. Take the bus from Indianapolis Union Station to Chicago Bus Stationbus bus
    10h 46m
    $64–123

  9. Drive, bus, train (Amtrak)

    1. Drive from Lexington to Middletown Station @ Targetcar car
    2. Take the bus from Louisville, KY to Lafayette Amtrak Stationbus bus
    3. Take the train from Lafayette Amtrak Station to Chicago Union Stationtrain train
    12h 2m
    $79–153

Louisville International Airport (SDF) to Chicago Midway International Airport (MDW) flights

Calendar20Weekly Planes
Duration1h 15mAverage Duration
Ticket$53Cheapest Price
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Questions & Answers

Map of how to get from Lexington to Chicago.ExpandLaunch map view
  • Distance: 360.3 mi
  • Duration: 3h 23m

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

There is no direct connection from Lexington to Chicago. However, you can drive to Louisville-Airport-SDF 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 Lexington to Chicago Union Station via Middletown Station @ Target, S 5th @ W Jefferson, W Jefferson @ S 6th, W Broadway @ S 10th, and Louisville, KY in around 9h 51m.

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