Rome2Rio

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

Find Transport to Gasparilla Island

See all options

There are 7 ways to get from Chicago to Gasparilla Island by plane, car, bus, train, or taxi

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
    $154–673

  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
    $124–513

  3. Bus, drive

    1. Take the bus from Chicago Bus Station to Atlanta Bus Stationbus bus
    2. Take the bus from Atlanta Bus Station to University of South Floridabus bus
    3. Take the bus from Tampa USF to Fort Myersbus bus
    4. Drive from Fort Myers to Gasparilla Islandcar car
    27h 39m
    $225–416

  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 9m
    $707–1,340

  5. Drive 1,215 mi

    1. Drive from Chicago to Gasparilla Islandcar car 1,215 mi
    21h 38m
    $222–321

  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 58m
    $244–894

  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 32m
    $204–744

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

Calendar51Weekly Planes
Duration3h 58mAverage Duration
Ticket$140Cheapest Price
See schedules

Questions & Answers

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 a bus from Chicago Bus Station to Gasparilla Island via Atlanta Bus Station, Tampa USF, and Fort Myers in around 27h 39m.

Airlines
Train operators
Bus operators
Other operators

Want to know more about travelling around United States

Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

Related travel guides

Need to know: Greyhound

Read the travel guideNeed to know: Greyhound