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How to get fromLongboat Key to Chicagoby plane, bus (Flixbus, Greyhound), taxi, train, or car

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

    best
    1. Fly from Sarasota–Bradenton International Airport (SRQ) to Chicago Midway International Airport (MDW)plane plane SRQ - MDW
    3h 52m
    $141–527

  2. Drive to Tampa, fly to Chicago O'Hare International Airport

    cheapest
    1. Drive from Longboat Key to Tampa-Airport-TPAcar car
    2. Fly from Tampa (TPA) to Chicago O'Hare International Airport (ORD)plane plane TPA - ORD
    5h 6m
    $103–320

  3. Bus

    1. Take the bus from Sarasota Cattlemen Transfer Center to Tampa Bus Stationbus bus
    2. Take the bus from Tampa Bus Station to Atlanta Bus Stationbus bus
    3. Take the bus from Atlanta Bus Station to Chicago Bus Stationbus bus
    30h 41m
    $237–379

  4. Taxi, train

    1. Take the taxi from Longboat Key to Tampataxi taxi
    2. Take the train from Tampa to Chicago Union Stationtrain train Floridian
    42h 13m
    $1,099–1,776

  5. Drive  1,175.2 mi

    1. Drive from Longboat Key to Chicagocar car 1,175.2 mi
    20h 59m
    $215–310

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

    1. Fly from Sarasota–Bradenton International Airport (SRQ) to Chicago O'Hare International Airport (ORD)plane plane SRQ - ORD
    4h 25m
    $116–417

  7. Drive to Tampa, fly to Chicago Midway International Airport

    1. Drive from Longboat Key to Tampa-Airport-TPAcar car
    2. Fly from Tampa (TPA) to Chicago Midway International Airport (MDW)plane plane TPA - MDW
    4h 39m
    $113–420

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

Calendar41Weekly Planes
Duration4h 15mAverage Duration
Ticket$96Cheapest Price
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Comparing Your Travel Options

Map of how to get from Longboat Key to Chicago.ExpandLaunch map view
  • Distance: 1,063.2 mi
  • Duration: 3h 52m

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

Southwest Airlines flies from Sarasota–Bradenton International Airport (SRQ) to Chicago Midway International Airport (MDW) every 4 hours. Alternatively, you can take a vehicle from Longboat Key to Chicago Bus Station via Downtown Transfer Station, Cattlemen Transit Station, Sarasota Cattlemen Transfer Center, Tampa Bus Station, and Atlanta Bus Station in around 30h 41m.

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