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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 8 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)planeMDW - SRQ
    4h 36m
    $172–710

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

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Sarasota–Bradenton International Airport (SRQ)planeORD - SRQ
    5h 10m
    $152–610

  3. Bus

    1. Take the bus from Chicago Bus Station to Atlanta Bus Stationbus
    2. Take the bus from Atlanta - Civic Center MARTA Station to Gainesvillebus
    3. Take the bus from Gainesville - Commuter Lot Parking Garage @ Gale Lemerand to Bradenton/Sarasota - Mobil Gas Stationbus
    26h 26m
    $177–443

  4. Train, taxi

    1. Take the train from Chicago Union Station to TampatrainFloridian
    2. Take the taxi from Tampa to Longboat Keytaxi
    42h 4m
    $396–848

  5. Drive 1,175.8 mi

    1. Drive from Chicago to Longboat Keycar1,175.8 mi
    20h 43m
    $215–310

  6. Train to South Bend, fly to Sarasota–Bradenton International Airport

    1. Take the train from Van Buren St. to South Bend Airporttrain
    2. Fly from South Bend (SBN) to Sarasota–Bradenton International Airport (SRQ)planeSBN - SRQ
    5h 59m
    $233–969

  7. Fly Chicago Midway International Airport to Tampa, taxi

    1. Fly from Chicago Midway International Airport (MDW) to Tampa (TPA)planeMDW - TPA
    2. Take the taxi from St Petersburg 7-11 to Longboat Keytaxi
    6h 31m
    $194–635

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

    1. Fly from Chicago O'Hare International Airport (ORD) to Tampa (TPA)planeORD - TPA
    2. Take the taxi from St Petersburg 7-11 to Longboat Keytaxi
    6h 52m
    $198–485

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

Calendar35Weekly Planes
Duration4h 25mAverage Duration
Ticket$132Cheapest 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) 5 times a day. 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 26m.

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