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

Find Transport to Winslow

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There are 5 ways to get from Chicago to Winslow by train, car, bus, 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. Train, drive

    best
    1. Take the train from Chicago OTC to Harvardtrain train Up-Nw
    2. Drive from Harvard to Winslowcar car
    3h 27m
    $19–27

  2. Bus, drive

    1. Take the bus from W Jackson Blvd, after S Clinton St to 3120 N Pontiac Dr - Van Galder Bus Terminalbus bus Van Galder
    2. Drive from 3120 N Pontiac Dr - Van Galder Bus Terminal to Winslowcar car
    4h 10m
    $29–56

  3. Drive 130.5 mi

    1. Drive from Chicago to Winslowcar car 130.5 mi
    2h 35m
    $24–35

  4. Fly, taxi

    1. Fly from Chicago O'Hare International Airport (ORD) to Dane County Regional Airport-Truax Field (MSN)plane plane ORD - MSN
    2. Take the taxi from W Verona at Nine Mound to Winslowtaxi taxi
    5h 30m
    $184–567

  5. Bus, taxi

    1. Take the bus from Chicago Bus Station to Madisonbus bus FlixBus 2548 / ...
    2. Take the taxi from W Verona at Nine Mound to Winslowtaxi taxi
    5h 56m
    $158–212

Chicago O'Hare International Airport (ORD) to Dane County Regional Airport-Truax Field (MSN) flights

Calendar91Weekly Planes
Duration1h 9mAverage Duration
Ticket$52Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Winslow.ExpandLaunch map view
  • Distance: 130.3 mi
  • Duration: 3h 27m

What companies run services between Chicago, IL, USA and Winslow, IL, USA?

There is no direct connection from Chicago to Winslow. However, you can take the train to Harvard then drive to Winslow. Alternatively, you can take a bus from W Jackson Blvd, after S Clinton St to Winslow via 3120 N Pontiac Dr - Van Galder Bus Terminal in around 4h 10m.

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