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How to get fromWaukegan to Winonaby bus, train, car, plane, or taxi

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There are 5 ways to get from Waukegan to Winona by bus, train, car, plane, or taxi

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Bus, train

    best
    1. Take the bus from Tornado Bus Co - Waukegan to Water & Chicago - Circle Kbus bus Milwaukee
    2. Take the train from Milwaukee to Winonatrain train Empire Builder / ...
    5h 57m
    $106–275

  2. Drive 268.2 mi

    cheapest
    1. Drive from Waukegan to Winonacar car 268.2 mi
    4h 46m
    $49–71

  3. Bus

    1. Take the bus from Tornado Bus Co - Waukegan to Water & Chicago - Circle Kbus bus Milwaukee
    2. Take the bus from Milwaukee to Winona State Univ.bus bus Jefferson 966 / ...
    6h 53m
    $96–210

  4. Train, fly to La Crosse, taxi

    1. Take the train from Waukegan to Clybourntrain train
    2. Fly from Chicago O'Hare International Airport (ORD) to La Crosse (LSE)plane plane ORD - LSE
    3. Take the taxi from La-Crosse-Airport-LSE to Winonataxi taxi
    5h 3m
    $113–372

  5. Train, fly to Chippewa Valley Regional Airport, drive

    1. Take the train from Waukegan to Clybourntrain train
    2. Fly from Chicago O'Hare International Airport (ORD) to Chippewa Valley Regional Airport (EAU)plane plane ORD - EAU
    3. Drive from Eau-Claire-Airport-EAU to Winonacar car
    6h 12m
    $66–321

Chicago O'Hare International Airport (ORD) to La Crosse (LSE) flights

Calendar28Weekly Planes
Duration1h 22mAverage Duration
Ticket$41Cheapest Price
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Questions & Answers

Map of how to get from Waukegan to Winona.ExpandLaunch map view
  • Distance: 273.4 mi
  • Duration: 5h 57m

What companies run services between Waukegan, IL, USA and Winona, MN, USA?

You can take a bus from Tornado Bus Co - Waukegan to Winona State Univ. via Water & Chicago - Circle K and Milwaukee in around 6h 53m.

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