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How to get fromChicago to Winter Havenby plane, bus, bus (Greyhound, Flixbus), train (Amtrak), or car

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There are 9 ways to get from Chicago to Winter Haven by plane, bus, 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. Fly Chicago Midway International Airport to Tampa, bus

    best
    1. Fly from Chicago Midway International Airport (MDW) to Tampa (TPA)plane plane MDW - TPA
    2. Take the bus from Tampa Bus Station to Winter Haven Transportation Centerbus bus
    7h 38m
    $172–623

  2. Fly Chicago O'Hare International Airport to Orlando, bus

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Orlando (MCO)plane plane ORD - MCO
    2. Take the bus from Orlando Bus Station to Winter Haven Transportation Centerbus bus
    8h 16m
    $84–623

  3. Bus

    1. Take the bus from Chicago Bus Station to Atlanta Bus Stationbus bus
    2. Take the bus from Atlanta Bus Station to Orlando Bus Stationbus bus
    3. Take the bus from Orlando Bus Station to Winter Haven Transportation Centerbus bus
    27h
    $192–369

  4. Train (Amtrak)

    1. Take the train from Chicago Union Station to Lakeland Amtrak Stationtrain train Floridian
    41h 41m
    $581–1,162

  5. Drive 1,123.7 mi

    1. Drive from Chicago to Winter Havencar car 1,123.7 mi
    20h 12m
    $206–297

  6. Fly Chicago Midway International Airport to Orlando, bus

    1. Fly from Chicago Midway International Airport (MDW) to Orlando (MCO)plane plane MDW - MCO
    2. Take the bus from Orlando Bus Station to Winter Haven Transportation Centerbus bus
    7h 50m
    $214–513

  7. Fly Chicago O'Hare International Airport to Tampa, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Tampa (TPA)plane plane ORD - TPA
    2. Take the bus from Tampa Bus Station to Winter Haven Transportation Centerbus bus
    8h 7m
    $172–573

  8. Fly Chicago Midway International Airport to Sarasota–Bradenton International Airport, bus

    1. Fly from Chicago Midway International Airport (MDW) to Sarasota–Bradenton International Airport (SRQ)plane plane MDW - SRQ
    2. Take the bus from Sarasota Cattlemen Transfer Center to Tampa Bus Stationbus bus
    3. Take the bus from Tampa Bus Station to Winter Haven Transportation Centerbus bus
    10h 23m
    $192–842

  9. Fly Chicago O'Hare International Airport to Sarasota–Bradenton International Airport, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Sarasota–Bradenton International Airport (SRQ)plane plane ORD - SRQ
    2. Take the bus from Sarasota Cattlemen Transfer Center to Tampa Bus Stationbus bus
    3. Take the bus from Tampa Bus Station to Winter Haven Transportation Centerbus bus
    10h 57m
    $152–692

Chicago to Winter Haven by bus

Calendar7Weekly Buses
Duration27hAverage Duration
Ticket$192Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Winter Haven.ExpandLaunch map view
  • Distance: 1,070.7 mi
  • Duration: 7h 38m

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

You can take a bus from Chicago Bus Station to Winter Haven Transportation Center via Atlanta Bus Station and Orlando Bus Station in around 27h. Alternatively, Amtrak operates a train from Chicago Union Station to Lakeland Amtrak Station once daily. Tickets cost $550–1,200 and the journey takes 39h 58m.

Airlines
Train operators
Bus operators

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