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How to get fromLeavenworth to Chicagoby plane, bus, train, bus (Greyhound, Flixbus), or car

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There are 5 ways to get from Leavenworth to Chicago by plane, bus, train, bus (Greyhound, Flixbus), or car

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 to Chicago Midway International Airport

    best
    1. Fly from Kansas City (MCI) to Chicago Midway International Airport (MDW)plane plane MCI - MDW
    2h 28m
    $122–494

  2. Drive 512.5 mi

    cheapest
    1. Drive from Leavenworth to Chicagocar car 512.5 mi
    9h 4m
    $94–136

  3. Bus, train

    1. Take the bus from Leavenworth Bus Stop to Kansas City Bus Stationbus bus Greyhound US0180s
    2. Take the train from Kansas City to Chicago Union Stationtrain train Southwest Chief / ...
    10h 7m
    $145–300

  4. Bus

    1. Take the bus from Leavenworth Bus Stop to St Louis Bus Stationbus bus Greyhound US0180s
    2. Take the bus from St Louis Bus Station to Chicago Bus Stationbus bus FlixBus 2510 / ...
    12h 40m
    $96–170

  5. Fly to Chicago O'Hare International Airport

    1. Fly from Kansas City (MCI) to Chicago O'Hare International Airport (ORD)plane plane MCI - ORD
    2h 56m
    $402–814

Leavenworth to Chicago by bus, foot, and train

Calendar7Weekly Services
Duration10h 7mAverage Duration
Ticket$145Cheapest Price
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Questions & Answers

Map of how to get from Leavenworth to Chicago.ExpandLaunch map view
  • Distance: 431.8 mi
  • Duration: 2h 28m

What companies run services between Leavenworth, KS, USA and Chicago, IL, USA?

Southwest Airlines flies from Kansas City (MCI) to Chicago Midway International Airport (MDW) every 4 hours. Alternatively, you can take a bus from Leavenworth Bus Stop to Chicago Bus Station via St Louis Bus Station in around 12h 40m.

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