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How to get fromChicago to Captiva Islandby plane, taxi, bus, train, or car

Find Transport to Captiva Island

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There are 5 ways to get from Chicago to Captiva Island by plane, taxi, bus, 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 from Chicago Midway International Airport, taxi

    best
    1. Fly from Chicago Midway International Airport (MDW) to Ft. Myers (RSW)plane plane MDW - RSW
    2. Take the taxi from Ft-Myers-Airport-RSW to Captiva Islandtaxi taxi
    5h 18m
    $242–835

  2. Fly from Chicago O'Hare International Airport, taxi

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Ft. Myers (RSW)plane plane ORD - RSW
    2. Take the taxi from Ft-Myers-Airport-RSW to Captiva Islandtaxi taxi
    5h 42m
    $202–635

  3. Bus, taxi

    1. Take the bus from Chicago Bus Station to Atlanta Bus Stationbus bus
    2. Take the bus from Atlanta Bus Station to Tampa Bus Stationbus bus
    3. Take the bus from Tampa Bus Station to Fort Myers Bus Stopbus bus
    4. Take the taxi from Fort Myers Bus Stop to Captiva Islandtaxi taxi
    30h 29m
    $283–427

  4. Train, bus, taxi

    1. Take the train from Chicago Union Station to Tampatrain train
    2. Take the bus from Tampa to Fort Myers Amtrak Bus Stopbus bus
    3. Take the taxi from Fort Myers Amtrak Bus Stop to Captiva Islandtaxi taxi
    46h 26m
    $579–1,208

  5. Drive  1,252.6 mi

    1. Drive from Chicago to Captiva Islandcar car 1,252.6 mi
    23h 13m
    $229–331

Chicago Midway International Airport (MDW) to Ft. Myers (RSW) flights

Calendar67Weekly Planes
Duration4h 27mAverage Duration
Ticket$141Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Captiva Island.ExpandLaunch map view
  • Distance: 1,156.1 mi
  • Duration: 5h 18m

What companies run services between Chicago, IL, USA and Captiva Island, FL, USA?

There is no direct connection from Chicago to Captiva Island. However, you can take the subway to Midway, walk to Chicago-Midway-Airport-MDW airport, fly to Ft. Myers (RSW), then take the taxi to Captiva Island. Alternatively, you can take the bus to Atlanta Bus Station, take the bus to Tampa Bus Station, take the bus to Fort Myers Bus Stop, then take the taxi to Captiva Island.

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