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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 8 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 52m
    $113–422

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

    cheapest
    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 20m
    $103–322

  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
    $183–332

  4. Train (Amtrak)

    1. Take the train from Lakeland Amtrak Station to Chicago Union Stationtrain train Floridian
    42h 5m
    $952–1,502

  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 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 22m
    $204–481

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

    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 44m
    $109–421

  8. Amtrak Thruway to Sarasota–Bradenton International Airport, fly to Chicago Midway International Airport

    1. Take the bus from Lakeland to Sarasota Amtrak Bus Stopbus bus
    2. Fly from Sarasota–Bradenton International Airport (SRQ) to Chicago Midway International Airport (MDW)plane plane SRQ - MDW
    10h 12m

Winter Haven to Chicago by bus

Calendar7Weekly Buses
Duration26h 25mAverage Duration
Ticket$183Cheapest Price
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Comparing Your Travel Options

Map of how to get from Winter Haven to Chicago.ExpandLaunch map view
  • Distance: 1,071.5 mi
  • Duration: 6h 52m

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 $950–1,500 and the journey takes 40h 20m.

Airlines
Train operators
Bus operators

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