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

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There are 8 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 from Chicago O'Hare International Airport, taxi

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Sioux Falls (FSD)plane plane ORD - FSD
    2. Take the taxi from Sioux Falls (FSD) to Madisontaxi taxi
    4h 30m
    $178–485

  2. Drive 586.9 mi

    cheapest
    1. Drive from Chicago to Madisoncar car 586.9 mi
    10h 58m
    $108–155

  3. Bus, taxi via Omaha

    1. Take the bus from Chicago Bus Station to Omaha, NEbus bus
    2. Take the bus from Omaha to Sioux Fallsbus bus
    3. Take the taxi from Sioux Falls to Madisontaxi taxi
    15h 8m
    $279–375

  4. Train, bus, taxi via Albert Lea

    1. Take the train from Chicago Union Station to St. Paul-Minneapolistrain train
    2. Take the bus from St. Paul to Albert Leabus bus
    3. Take the bus from Albert Lea to Sioux Fallsbus bus
    4. Take the taxi from Sioux Falls to Madisontaxi taxi
    15h 34m
    $328–537

  5. Train, bus, taxi

    1. Take the train from Chicago Union Station to St. Paul-Minneapolistrain train
    2. Take the bus from Minneapolis-St. Paul to Pipestonebus bus
    3. Take the taxi from Pipestone to Madisontaxi taxi
    16h 17m
    $295–490

  6. Fly from Chicago Midway International Airport, taxi

    1. Fly from Chicago Midway International Airport (MDW) to Sioux Falls (FSD)plane plane MDW - FSD
    2. Take the taxi from Sioux Falls (FSD) to Madisontaxi taxi
    6h 4m
    $202–595

  7. Bus, taxi

    1. Take the bus from Chicago Bus Station to Saint Cloudbus bus
    2. Take the bus from St. Cloud to Pipestonebus bus
    3. Take the taxi from Pipestone to Madisontaxi taxi
    16h 51m
    $228–334

  8. Train, bus, taxi via Fargo

    1. Take the train from Chicago Union Station to Detroit Lakes Amtrak Stationtrain train
    2. Take the bus from Detroit Lakes to Fargobus bus
    3. Take the bus from Fargo to Brookingsbus bus
    4. Take the taxi from Brookings to Madisontaxi taxi
    19h 18m
    $372–638

Chicago O'Hare International Airport (ORD) to Sioux Falls (FSD) flights

Calendar69Weekly Planes
Duration2h 30mAverage Duration
Ticket$58Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Madison.ExpandLaunch map view
  • Distance: 528 mi
  • Duration: 4h 30m

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

There is no direct connection from Chicago to Madison. However, you can take the subway to O'Hare, walk to Chicago O'Hare International Airport (ORD) airport, fly to Sioux Falls (FSD), then take the taxi to Madison. Alternatively, you can take the bus to Omaha, NE, take the bus to Sioux Falls, then take the taxi to Madison.

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