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

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There are 9 ways to get from Chicago to Madison by plane, taxi, bus, train, 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 Chicago Midway International Airport to Louisville International Airport, taxi

    best
    1. Fly from Chicago Midway International Airport (MDW) to Louisville International Airport (SDF)plane plane MDW - SDF
    2. Take the taxi from Louisville-Airport-SDF to Madisontaxi taxi
    3h 56m
    $228–815

  2. Drive  270.2 mi

    cheapest
    1. Drive from Chicago to Madisoncar car 270.2 mi
    5h 6m
    $50–72

  3. Bus, taxi via Speedway

    1. Take the bus from Chicago Bus Station to Indianapolis Union Stationbus bus
    2. Take the bus from Indianapolis to TA Travel Center - Seymourbus bus
    3. Take the taxi from TA Travel Center - Seymour to Madisontaxi taxi
    7h 30m
    $141–202

  4. Train, bus, taxi

    1. Take the train from Chicago Union Station to Indianapolistrain train
    2. Take the bus from Indianapolis to TA Travel Center - Seymourbus bus
    3. Take the taxi from TA Travel Center - Seymour to Madisontaxi taxi
    9h 19m
    $166–293

  5. Fly Chicago O'Hare International Airport to Covington, drive

    1. Fly from Chicago O'Hare International Airport (ORD) to Covington (CVG)plane plane ORD - CVG
    2. Drive from Covington (CVG) to Madisoncar car
    4h 21m
    $164–823

  6. Fly Chicago O'Hare International Airport to Louisville International Airport, taxi

    1. Fly from Chicago O'Hare International Airport (ORD) to Louisville International Airport (SDF)plane plane ORD - SDF
    2. Take the taxi from Louisville-Airport-SDF to Madisontaxi taxi
    4h 27m
    $202–625

  7. Fly Chicago Midway International Airport to Covington, drive

    1. Fly from Chicago Midway International Airport (MDW) to Covington (CVG)plane plane MDW - CVG
    2. Drive from Covington (CVG) to Madisoncar car
    4h 2m
    $164–383

  8. Fly Chicago O'Hare International Airport to Blue Grass Airport, drive

    1. Fly from Chicago O'Hare International Airport (ORD) to Blue Grass Airport (LEX)plane plane ORD - LEX
    2. Drive from Lexington-Airport-LEX to Madisoncar car
    5h 17m
    $56–307

  9. Bus, taxi

    1. Take the bus from Chicago Union Station to Louisville, KYbus bus Chicago
    2. Take the taxi from River Ridge Amazon to Madisontaxi taxi
    9h 37m
    $141–180

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

Calendar20Weekly Planes
Duration1h 14mAverage Duration
Ticket$98Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Madison.ExpandLaunch map view
  • Distance: 333.2 mi
  • Duration: 3h 56m

What companies run services between Chicago, IL, USA and Madison, IN, USA?

There is no direct connection from Chicago to Madison. However, you can take the subway to Midway, walk to Chicago-Midway-Airport-MDW airport, fly to Louisville International Airport (SDF), then take the taxi to Madison. Alternatively, you can take the bus to Indianapolis Union Station, walk to Ctc-R, take the line 37 bus to Lafayette Rd & Georgetown Rd, walk to Indianapolis, take the bus to TA Travel Center - Seymour, then take the taxi to Madison.

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