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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 47m
    $176–707

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

    cheapest
    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 34m
    $143–420

  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
    29h 31m
    $211–379

  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
    $649–1,376

  5. Drive 1,176.6 mi

    1. Drive from Longboat Key to Chicagocar car 1,176.6 mi
    20h 58m
    $215–311

  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 22m
    $156–607

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

    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
    $173–570

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

Calendar19Weekly Planes
Duration4h 35mAverage Duration
Ticket$134Cheapest Price
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Questions & Answers

Map of how to get from Longboat Key to Chicago.ExpandLaunch map view
  • Distance: 1,063.2 mi
  • Duration: 3h 47m

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

Southwest Airlines and Allegiant Air fly from Sarasota–Bradenton International Airport (SRQ) to Chicago Midway International Airport (MDW) 3 times a day. 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 29h 31m.

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