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

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There are 5 ways to get from Siesta Key to Chicago by plane, bus (Flixbus, Greyhound), car, or train

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 to Chicago Midway International Airport

    best
    1. Fly from Sarasota–Bradenton International Airport (SRQ) to Chicago Midway International Airport (MDW)plane plane SRQ - MDW
    5h 4m
    $134–658

  2. Fly to Chicago O'Hare International Airport

    cheapest
    1. Fly from Sarasota–Bradenton International Airport (SRQ) to Chicago O'Hare International Airport (ORD)plane plane SRQ - ORD
    5h 38m
    $124–608

  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 54m
    $172–328

  4. Drive, train (Amtrak)

    1. Drive from Siesta Key to Tampacar car
    2. Take the train from Tampa to Chicago Union Stationtrain train Floridian
    42h 14m
    $501–1,115

  5. Drive 1,178.4 mi

    1. Drive from Siesta Key to Chicagocar car 1,178.4 mi
    21h
    $216–311

Siesta Key to Chicago by bus

Calendar7Weekly Buses
Duration29h 54mAverage Duration
Ticket$172Cheapest Price
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Questions & Answers

Map of how to get from Siesta Key to Chicago.ExpandLaunch map view
  • Distance: 1,061.8 mi
  • Duration: 5h 4m

What companies run services between Siesta 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 bus from Ocean Blvd @ Avenida Madera NB to Chicago Bus Station via Main St @ Lemon Ave, Downtown Transfer Station, Cattlemen Transit Station, Sarasota Cattlemen Transfer Center, Tampa Bus Station, and Atlanta Bus Station in around 29h 54m.

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