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

Find Transport to Gasparilla Island

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There are 8 ways to get from Chicago to Gasparilla Island by plane, car, bus, taxi, 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 Chicago Midway International Airport to Ft. Myers, drive

    best
    1. Fly from Chicago Midway International Airport (MDW) to Ft. Myers (RSW)plane plane MDW - RSW
    2. Drive from Ft-Myers-Airport-RSW to Gasparilla Islandcar car
    5h 41m
    $154–723

  2. Fly Chicago O'Hare International Airport to Ft. Myers, drive

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Ft. Myers (RSW)plane plane ORD - RSW
    2. Drive from Ft-Myers-Airport-RSW to Gasparilla Islandcar car
    6h 5m
    $114–523

  3. Bus, Amtrak Thruway, 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 Union Station to Port Charlottebus bus
    4. Take the taxi from Port Charlotte to Gasparilla Islandtaxi taxi
    30h 16m
    $267–415

  4. Train, bus, taxi

    1. Take the train from Chicago Union Station to Tampatrain train
    2. Take the bus from Tampa Bus Station to Sarasota Cattlemen Transfer Centerbus bus
    3. Take the taxi from Sarasota Cattlemen Transfer Center to Gasparilla Islandtaxi taxi
    44h 45m
    $562–1,191

  5. Drive  1,213.5 mi

    1. Drive from Chicago to Gasparilla Islandcar car 1,213.5 mi
    21h 38m
    $222–320

  6. Fly Chicago Midway International Airport to Sarasota–Bradenton International Airport, bus, taxi

    1. Fly from Chicago Midway International Airport (MDW) to Sarasota–Bradenton International Airport (SRQ)plane plane MDW - SRQ
    2. Take the bus from Downtown Transfer Station to Venice Train Depotbus bus
    3. Take the taxi from Venice Train Depot to Gasparilla Islandtaxi taxi
    6h 29m
    $264–1,094

  7. Fly Chicago O'Hare International Airport to Sarasota–Bradenton International Airport, bus, taxi

    1. Fly from Chicago O'Hare International Airport (ORD) to Sarasota–Bradenton International Airport (SRQ)plane plane ORD - SRQ
    2. Take the bus from Downtown Transfer Station to Venice Train Depotbus bus
    3. Take the taxi from Venice Train Depot to Gasparilla Islandtaxi taxi
    7h 6m
    $214–794

  8. Fly Chicago Midway International Airport to Tampa, Amtrak Thruway, taxi

    1. Fly from Chicago Midway International Airport (MDW) to Tampa (TPA)plane plane MDW - TPA
    2. Take the bus from Tampa Union Station to Port Charlottebus bus
    3. Take the taxi from Port Charlotte to Gasparilla Islandtaxi taxi
    10h 3m
    $198–536

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

Calendar63Weekly Planes
Duration4h 14mAverage Duration
Ticket$141Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Gasparilla Island.ExpandLaunch map view
  • Distance: 1,186.9 mi
  • Duration: 5h 41m

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

There is no direct connection from Chicago to Gasparilla Island. However, you can take the subway to Midway, walk to Chicago-Midway-Airport-MDW airport, fly to Ft. Myers (RSW), then drive to Gasparilla Island. Alternatively, you can take the bus to Atlanta Bus Station, take the bus to Tampa Bus Station, take the line 400 bus to Nebraska Av @ Twiggs St, walk to Tampa Union Station, take the bus to Port Charlotte, then take the taxi to Gasparilla Island.

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