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

Find Transport to Siesta Key

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There are 5 ways to get from Chicago to Siesta Key by plane, bus (Flixbus, Greyhound), train, bus, 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 from Chicago Midway International Airport

    best
    1. Fly from Chicago Midway International Airport (MDW) to Sarasota–Bradenton International Airport (SRQ)planeMDW - SRQ
    5h 13m
    $134–709

  2. Fly from Chicago O'Hare International Airport

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Sarasota–Bradenton International Airport (SRQ)planeORD - SRQ
    5h 41m
    $104–559

  3. Bus

    1. Take the bus from Chicago Bus Station to Atlanta Bus Stationbus
    2. Take the bus from Atlanta Bus Station to Orlando Bus Stationbus
    3. Take the bus from Orlando Bus Station to Sarasota Cattlemen Transfer Centerbus
    29h 31m
    $150–328

  4. Train, bus

    1. Take the train from Chicago Union Station to TampatrainFloridian
    2. Take the bus from Tampa Bus Station to Sarasota Cattlemen Transfer CenterbusFlixBus 2421
    44h 55m
    $233–483

  5. Drive 1,178.7 mi

    1. Drive from Chicago to Siesta Keycar1,178.7 mi
    20h 46m
    $216–311

Chicago to Siesta Key by bus

Calendar32Weekly Buses
Duration29h 31mAverage Duration
Ticket$150Cheapest Price
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Questions & Answers

What companies run services between Chicago, IL, USA and Siesta 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 Ocean Blvd @ Avenida Madera via Atlanta Bus Station, Orlando Bus Station, Sarasota Cattlemen Transfer Center, and Cattlemen Transit Station in around 29h 31m.

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