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How to get fromChicago to Cuba Cityby train, bus, car, or plane

Find Transport to Cuba City

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There are 7 ways to get from Chicago to Cuba City by train, bus, car, or plane

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, bus, drive

    best
    1. Take the train from Chicago Union Station to Milwaukeetrain train
    2. Take the bus from Milwaukee, WI - Amtrak to Madison, WI-Lake St.bus bus
    3. Drive from Madison, WI-Lake St. to Cuba Citycar car
    5h 34m
    $53–101

  2. Drive 167.9 mi

    cheapest
    1. Drive from Chicago to Cuba Citycar car 167.9 mi
    3h 21m
    $31–45

  3. Fly to Dane County Regional Airport-Truax Field, drive

    1. Fly from Chicago O'Hare International Airport (ORD) to Dane County Regional Airport-Truax Field (MSN)plane plane ORD - MSN
    2. Drive from Madison-Airport-MSN to Cuba Citycar car
    4h 32m
    $68–407

  4. Bus, drive

    1. Take the bus from Chicago Bus Station to Madisonbus bus FlixBus 2548 / ...
    2. Drive from Northern Lights at Epic Staff C to Cuba Citycar car
    6h 22m
    $41–71

  5. Bus, drive via W Jackson Blvd, after S Clinton St

    1. Take the bus from W Jackson Blvd, after S Clinton St to 250 N. Lake St - Madison UW Campusbus bus Van Galder
    2. Drive from Northern Lights at Epic Staff C to Cuba Citycar car
    6h 27m
    $40–74

  6. Fly to Quad City International Airport, drive

    1. Fly from Chicago O'Hare International Airport (ORD) to Quad City International Airport (MLI)plane plane ORD - MLI
    2. Drive from Moline-Airport-MLI to Cuba Citycar car
    4h 42m
    $54–291

  7. Fly to The Eastern Iowa Airport, drive

    1. Fly from Chicago O'Hare International Airport (ORD) to The Eastern Iowa Airport (CID)plane plane ORD - CID
    2. Drive from Cedar-Rapids-Airport-CID to Cuba Citycar car
    4h 53m
    $60–301

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

Calendar114Weekly Planes
Duration1h 9mAverage Duration
Ticket$51Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Cuba City.ExpandLaunch map view
  • Distance: 239.3 mi
  • Duration: 5h 34m

What companies run services between Chicago, IL, USA and Cuba City, WI, USA?

There is no direct connection from Chicago to Cuba City. However, you can take the train to Milwaukee, walk to Milwaukee, WI - Amtrak, take the bus to Madison, WI-Lake St., then drive to Cuba City. Alternatively, you can drive from Chicago to Cuba City in around 3h 21m.

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