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

Find Transport to Winona

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There are 7 ways to get from Chicago to Winona by plane, car, bus, train, 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. Fly Chicago Midway International Airport to Birmingham–Shuttlesworth International Airport, drive

    best
    1. Fly from Chicago Midway International Airport (MDW) to Birmingham–Shuttlesworth International Airport (BHM)plane plane MDW - BHM
    2. Drive from Birmingham-Airport-BHM to Winonacar car
    6h 52m
    $198–1,010

  2. Bus, drive

    cheapest
    1. Take the bus from Chicago Bus Station to Memphis Bus Stationbus bus
    2. Take the bus from Memphis Bus Station to Batesville(Terza One Stop Shop)bus bus
    3. Drive from Batesville(Terza One Stop Shop) to Winonacar car
    12h 50m
    $107–177

  3. Train, taxi (Amtrak)

    1. Take the train from Chicago Union Station to Greenwood Amtrak Stationtrain train City of New Orleans
    2. Take the taxi from Greenwood Amtrak Station to Winonataxi taxi
    13h 56m
    $459–681

  4. Drive  651.7 mi

    1. Drive from Chicago to Winonacar car 651.7 mi
    10h 34m
    $119–172

  5. Fly Chicago O'Hare International Airport to Birmingham–Shuttlesworth International Airport, drive

    1. Fly from Chicago O'Hare International Airport (ORD) to Birmingham–Shuttlesworth International Airport (BHM)plane plane ORD - BHM
    2. Drive from Birmingham-Airport-BHM to Winonacar car
    7h 20m
    $148–710

  6. Fly Chicago O'Hare International Airport to Memphis, bus, drive

    1. Fly from Chicago O'Hare International Airport (ORD) to Memphis (MEM)plane plane ORD - MEM
    2. Take the bus from Memphis Bus Station to Batesville(Terza One Stop Shop)bus bus
    3. Drive from Batesville(Terza One Stop Shop) to Winonacar car
    8h 10m
    $124–640

  7. Fly Chicago Midway International Airport to Memphis, bus, drive

    1. Fly from Chicago Midway International Airport (MDW) to Memphis (MEM)plane plane MDW - MEM
    2. Take the bus from Memphis Bus Station to Batesville(Terza One Stop Shop)bus bus
    3. Drive from Batesville(Terza One Stop Shop) to Winonacar car
    7h 43m
    $164–890

Chicago Midway International Airport (MDW) to Birmingham–Shuttlesworth International Airport (BHM) flights

Calendar38Weekly Planes
Duration2h 47mAverage Duration
Ticket$165Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Winona.ExpandLaunch map view
  • Distance: 782.4 mi
  • Duration: 6h 52m

What companies run services between Chicago, IL, USA and Winona, MS, USA?

There is no direct connection from Chicago to Winona. However, you can take the subway to Midway, walk to Chicago-Midway-Airport-MDW airport, fly to Birmingham–Shuttlesworth International Airport (BHM), then drive to Winona. Alternatively, you can take a bus from Chicago Bus Station to Winona via Memphis Bus Station and Batesville(Terza One Stop Shop) in around 12h 50m.

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