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

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There are 6 ways to get from Winter Haven to Milwaukee by bus, plane, bus (Greyhound, Flixbus), train (Amtrak), car, or train

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 General Mitchell International Airport

    best
    1. Take the bus from Winter Haven Transportation Center to Tampa Bus Stationbus bus
    2. Fly from Tampa (TPA) to General Mitchell International Airport (MKE)plane plane TPA - MKE
    7h 2m
    $665–1,120

  2. Bus to Tampa, fly to Chicago Midway International Airport, train

    cheapest
    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
    3. Take the train from Chicago Union Station to Milwaukeetrain train
    9h 31m
    $159–497

  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
    4. Take the bus from Chicago Bus Station to Milwaukee Intermodal Stationbus bus
    28h 35m
    $197–357

  4. Train (Amtrak)

    1. Take the train from Lakeland Amtrak Station to Chicago Union Stationtrain train Floridian
    2. Take the train from Chicago Union Station to Milwaukeetrain train Hiawatha Service / ...
    44h 34m
    $996–1,576

  5. Drive  1,211.3 mi

    1. Drive from Winter Haven to Milwaukeecar car 1,211.3 mi
    21h 55m
    $207–299

  6. Bus to Orlando, fly to General Mitchell International Airport

    1. Take the bus from Winter Haven Transportation Center to Orlando Bus Stationbus bus
    2. Fly from Orlando (MCO) to General Mitchell International Airport (MKE)plane plane MCO - MKE
    7h 22m
    $424–1,119

Winter Haven to Milwaukee by bus

Calendar14Weekly Buses
Duration28h 35mAverage Duration
Ticket$197Cheapest Price
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Comparing Your Travel Options

Map of how to get from Winter Haven to Milwaukee.ExpandLaunch map view
  • Distance: 1,146 mi
  • Duration: 7h 2m

What companies run services between Winter Haven, FL, USA and Milwaukee, WI, USA?

You can take a bus from Winter Haven Transportation Center to Milwaukee Intermodal Station via Orlando Bus Station, Atlanta Bus Station, and Chicago Bus Station in around 28h 35m. Alternatively, you can take a bus from Winter Haven Terminal to Milwaukee via 600 E. Main St., Lakeland Amtrak Station, and Chicago Union Station in around 44h 34m.

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