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

Find Transport to Longboat Key

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There are 7 ways to get from Chicago to Longboat Key by plane, bus (Flixbus, Greyhound), 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 31m
    $182–810

  2. Bus

    cheapest
    1. Take the bus from Chicago Bus Station to Atlanta Bus Stationbus bus
    2. Take the bus from Atlanta - Civic Center MARTA Station to Gainesvillebus bus
    3. Take the bus from Gainesville - Commuter Lot Parking Garage @ Gale Lemerand to Bradenton/Sarasota - Mobil Gas Stationbus bus
    26h 27m
    $173–525

  3. 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 4m
    $313–781

  4. Drive 1,175.8 mi

    1. Drive from Chicago to Longboat Keycar car 1,175.8 mi
    20h 55m
    $215–310

  5. 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 10m
    $192–610

  6. Fly Chicago Midway International Airport to Tampa, taxi

    1. Fly from Chicago Midway International Airport (MDW) to Tampa (TPA)plane plane MDW - TPA
    2. Take the taxi from St Petersburg 7-11 to Longboat Keytaxi taxi
    6h 31m
    $218–815

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

    1. Fly from Chicago O'Hare International Airport (ORD) to Tampa (TPA)plane plane ORD - TPA
    2. Take the taxi from St Petersburg 7-11 to Longboat Keytaxi taxi
    6h 58m
    $218–565

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

Calendar53Weekly Planes
Duration4h 21mAverage Duration
Ticket$143Cheapest Price
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Questions & Answers

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, Garnett Station, Civic Center Station, Atlanta - Civic Center MARTA Station, Gainesville, Gainesville - Commuter Lot Parking Garage @ Gale Lemerand, and Bradenton/Sarasota - Mobil Gas Station in around 26h 27m.

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