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How to get fromChicago to Longboat Keyby plane, bus (Greyhound, Flixbus), train, taxi, or car

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There are 7 ways to get from Chicago to Longboat Key by plane, bus (Greyhound, Flixbus), train, taxi, 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 Sarasota–Bradenton International Airport

    best
    1. Fly from Chicago Midway International Airport (MDW) to Sarasota–Bradenton International Airport (SRQ)plane plane MDW - SRQ
    4h 34m
    $162–710

  2. Fly Chicago Midway International Airport to Tampa, drive

    cheapest
    1. Fly from Chicago Midway International Airport (MDW) to Tampa (TPA)plane plane MDW - TPA
    2. Drive from Tampa-Airport-TPA to Longboat Keycar car
    5h 18m
    $106–319

  3. Bus

    1. Take the bus from Chicago Bus Station to Atlanta Bus Stationbus bus
    2. Take the bus from Atlanta Bus Station to Tampa Bus Stationbus bus
    3. Take the bus from Tampa Bus Station to Sarasota Cattlemen Transfer Centerbus bus
    29h 35m
    $240–381

  4. Train, taxi

    1. Take the train from Chicago Union Station to Tampatrain train Floridian
    2. Take the taxi from Tampa to Longboat Keytaxi taxi
    42h 2m
    $1,138–1,696

  5. Drive  1,174.2 mi

    1. Drive from Chicago to Longboat Keycar car 1,174.2 mi
    20h 57m
    $194–281

  6. Fly Chicago O'Hare International Airport to Sarasota–Bradenton International Airport

    1. Fly from Chicago O'Hare International Airport (ORD) to Sarasota–Bradenton International Airport (SRQ)plane plane ORD - SRQ
    5h 2m
    $118–430

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

    1. Fly from Chicago O'Hare International Airport (ORD) to Tampa (TPA)plane plane ORD - TPA
    2. Drive from Tampa-Airport-TPA to Longboat Keycar car
    5h 39m
    $122–389

Chicago Midway International Airport (MDW) to Sarasota–Bradenton International Airport (SRQ) flights

Calendar48Weekly Planes
Duration4h 30mAverage Duration
Ticket$125Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Longboat Key.ExpandLaunch map view
  • Distance: 1,063.1 mi
  • Duration: 4h 34m

What companies run services between Chicago, IL, USA and Longboat Key, FL, USA?

Southwest Airlines and Delta fly from Chicago Midway International Airport (MDW) to Sarasota–Bradenton International Airport (SRQ) every 4 hours. Alternatively, you can take a bus from Chicago Bus Station to Longboat Key via Atlanta Bus Station, Tampa Bus Station, Sarasota Cattlemen Transfer Center, Cattlemen Transit Station, and Downtown Transfer Station in around 29h 35m.

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