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How to get fromChicago to Legoland Floridaby plane, bus, bus (Greyhound, Flixbus), train (Amtrak), or car

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There are 10 ways to get from Chicago to Legoland Florida 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
    9h 14m
    $144–424

  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
    9h 53m
    $84–524

  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
    28h 37m
    $180–347

  4. Train (Amtrak)

    1. Take the train from Chicago Union Station to Winter Haventrain train Floridian
    42h 5m
    $600–1,231

  5. Drive 1,127.9 mi

    1. Drive from Chicago to Legoland Floridacar car 1,127.9 mi
    20h 17m
    $206–298

  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
    9h 27m
    $214–514

  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
    9h 43m
    $174–574

  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
    12h
    $182–842

  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
    12h 34m
    $152–692

  10. Fly Chicago Midway International Airport to Jacksonville, bus

    1. Fly from Chicago Midway International Airport (MDW) to Jacksonville (JAX)plane plane MDW - JAX
    2. Take the bus from Jacksonville to Orlando Bus Stationbus bus
    3. Take the bus from Orlando Bus Station to Winter Haven Transportation Centerbus bus
    12h 45m
    $182–608

Chicago Midway International Airport (MDW) to Tampa (TPA) flights

Calendar39Weekly Planes
Duration2h 59mAverage Duration
Ticket$117Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Legoland Florida.ExpandLaunch map view
  • Distance: 1,077.7 mi
  • Duration: 9h 14m

What companies run services between Chicago, IL, USA and Legoland Florida, FL, USA?

You can take a bus from Chicago Bus Station to Legoland Florida via Atlanta Bus Station, Orlando Bus Station, Winter Haven Terminal, and Register Rd. S.E. & Cypress Gardens Blvd. in around 28h 37m. Alternatively, Amtrak operates a train from Chicago Union Station to Winter Haven once daily. Tickets cost $550–1,200 and the journey takes 41h 59m.

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