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How to get fromWinter Haven to Chicagoby bus, plane, bus (Greyhound, Flixbus), train (Amtrak), or car

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There are 7 ways to get from Winter Haven to Chicago by bus, plane, bus (Greyhound, Flixbus), train (Amtrak), 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. Bus to Tampa, fly to Chicago Midway International Airport

    best
    1. Take the bus from Winter Haven Transportation Center to Tampa Bus Stationbus bus
    2. Fly from Tampa (TPA) to Chicago Midway International Airport (MDW)plane plane TPA - MDW
    6h 47m
    $111–422

  2. Bus to Orlando, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the bus from Winter Haven Transportation Center to Orlando Bus Stationbus bus
    2. Fly from Orlando (MCO) to Chicago O'Hare International Airport (ORD)plane plane MCO - ORD
    7h 37m
    $82–431

  3. Bus

    1. Take the bus from Winter Haven Transportation Center to Orlando Bus Stationbus bus
    2. Take the bus from Orlando Bus Station to Atlanta Bus Stationbus bus
    3. Take the bus from Atlanta Bus Station to Chicago Bus Stationbus bus
    26h 25m
    $166–322

  4. Train (Amtrak)

    1. Take the train from Lakeland Amtrak Station to Chicago Union Stationtrain train Floridian
    42h 5m
    $472–1,102

  5. Drive 1,123.5 mi

    1. Drive from Winter Haven to Chicagocar car 1,123.5 mi
    20h 12m
    $205–297

  6. Bus to Tampa, fly to Chicago O'Hare International Airport

    1. Take the bus from Winter Haven Transportation Center to Tampa Bus Stationbus bus
    2. Fly from Tampa (TPA) to Chicago O'Hare International Airport (ORD)plane plane TPA - ORD
    7h 19m
    $161–572

  7. Bus to Orlando, fly to Chicago Midway International Airport

    1. Take the bus from Winter Haven Transportation Center to Orlando Bus Stationbus bus
    2. Fly from Orlando (MCO) to Chicago Midway International Airport (MDW)plane plane MCO - MDW
    7h 13m
    $202–501

Winter Haven to Chicago by bus

Calendar7Weekly Buses
Duration26h 25mAverage Duration
Ticket$166Cheapest Price
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Questions & Answers

Map of how to get from Winter Haven to Chicago.ExpandLaunch map view
  • Distance: 1,071.5 mi
  • Duration: 6h 47m

What companies run services between Winter Haven, FL, USA and Chicago, IL, USA?

You can take a bus from Winter Haven Transportation Center to Chicago Bus Station via Orlando Bus Station and Atlanta Bus Station in around 26h 25m. Alternatively, Amtrak operates a train from Lakeland Amtrak Station to Chicago Union Station once daily. Tickets cost $470–1,100 and the journey takes 40h 20m.

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