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How to get fromMadison to Chicagoby taxi, plane, bus, train, or car

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There are 8 ways to get from Madison to Chicago by taxi, plane, 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. Taxi to Louisville International Airport, fly to Chicago Midway International Airport

    best
    1. Take the taxi from Madison to Louisville-Airport-SDFtaxi taxi
    2. Fly from Louisville International Airport (SDF) to Chicago Midway International Airport (MDW)plane plane SDF - MDW
    3h 9m
    $196–563

  2. Drive  270.4 mi

    cheapest
    1. Drive from Madison to Chicagocar car 270.4 mi
    5h 5m
    $50–72

  3. Taxi, bus

    1. Take the taxi from Madison to TA Travel Center - Seymourtaxi taxi
    2. Take the bus from TA Travel Center - Seymour to Indianapolisbus bus
    3. Take the bus from Indianapolis Union Station to Chicago Bus Stationbus bus
    7h 55m
    $144–202

  4. Taxi, bus, train

    1. Take the taxi from Madison to TA Travel Center - Seymourtaxi taxi
    2. Take the bus from TA Travel Center - Seymour to Indianapolisbus bus
    3. Take the train from Indianapolis to Chicago Union Stationtrain train
    9h 20m
    $214–322

  5. Taxi to Louisville International Airport, fly to Chicago O'Hare International Airport

    1. Take the taxi from Madison to Louisville-Airport-SDFtaxi taxi
    2. Fly from Louisville International Airport (SDF) to Chicago O'Hare International Airport (ORD)plane plane SDF - ORD
    3h 33m
    $181–493

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

    1. Drive from Madison to Covington (CVG)car car
    2. Fly from Covington (CVG) to Chicago O'Hare International Airport (ORD)plane plane CVG - ORD
    3h 35m
    $164–822

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

    1. Drive from Madison to Covington (CVG)car car
    2. Fly from Covington (CVG) to Chicago Midway International Airport (MDW)plane plane CVG - MDW
    3h 10m
    $164–382

  8. Taxi, bus via Chicago Union Station

    1. Take the taxi from Madison to TA Travel Center - Seymourtaxi taxi
    2. Take the bus from TA Travel Center - Seymour to Indianapolisbus bus
    3. Take the bus from Indianapolis Union Station to Chicago Union Stationbus bus
    8h
    $144–202

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

Calendar20Weekly Planes
Duration1h 15mAverage Duration
Ticket$60Cheapest Price
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Comparing Your Travel Options

Map of how to get from Madison to Chicago.ExpandLaunch map view
  • Distance: 332.6 mi
  • Duration: 3h 9m

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

There is no direct connection from Madison to Chicago. However, you can take the taxi 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 the taxi to TA Travel Center - Seymour, take the bus to Indianapolis, walk to Lafayette Rd & Office Plaza Blvd, take the line 37 bus to Ctc-R, walk to Indianapolis Union Station, then take the bus to Chicago Bus Station.

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