Rome2Rio

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

Find Transport to Longboat Key

See all options

There are 7 ways to get from Chicago to Longboat Key by plane, bus (Greyhound, Flixbus), train, taxi, 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 Chicago Midway International Airport to Sarasota–Bradenton International Airport

    best
    1. Fly from Chicago Midway International Airport (MDW) to Sarasota–Bradenton International Airport (SRQ)plane plane MDW - SRQ
    4h 39m
    $202–860

  2. Fly Chicago O'Hare International Airport to Sarasota–Bradenton International Airport

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Sarasota–Bradenton International Airport (SRQ)plane plane ORD - SRQ
    5h 8m
    $152–610

  3. Bus

    1. Take the bus from Chicago Bus Station to Nashville Bus Stationbus bus
    2. Take the bus from Nashville Bus Station to Tallahasseebus bus
    3. Take the bus from Tallahassee to Bradentonbus bus
    28h 13m
    $248–434

  4. Train, taxi

    1. Take the train from Chicago Union Station to Tampatrain train Floridian
    2. Take the taxi from Tampa to Longboat Keytaxi taxi
    42h 2m
    $678–1,278

  5. Drive 1,175.7 mi

    1. Drive from Chicago to Longboat Keycar car 1,175.7 mi
    20h 57m
    $215–310

  6. Fly Chicago Midway International Airport to Tampa, taxi

    1. Fly from Chicago Midway International Airport (MDW) to Tampa (TPA)plane plane MDW - TPA
    2. Take the taxi from St Petersburg 7-11 to Longboat Keytaxi taxi
    6h 24m
    $222–736

  7. Fly Chicago O'Hare International Airport to Tampa, taxi

    1. Fly from Chicago O'Hare International Airport (ORD) to Tampa (TPA)plane plane ORD - TPA
    2. Take the taxi from St Petersburg 7-11 to Longboat Keytaxi taxi
    6h 53m
    $222–886

Chicago Midway International Airport (MDW) to Sarasota–Bradenton International Airport (SRQ) flights

Calendar42Weekly Planes
Duration4h 8mAverage Duration
Ticket$165Cheapest Price
See schedules

Questions & Answers

Map of how to get from Chicago to Longboat Key.ExpandLaunch map view
  • Distance: 1,063.1 mi
  • Duration: 4h 39m

What companies run services between Chicago, IL, USA and Longboat Key, FL, USA?

Southwest Airlines and Delta fly from Chicago Midway International Airport (MDW) to Sarasota–Bradenton International Airport (SRQ) every 4 hours. Alternatively, you can take a bus from Chicago Bus Station to Longboat Key via Nashville Bus Station, C.K. Steele Plaza Gate 16, N Monroe Street and John Knox Road, Tallahassee, and Bradenton in around 28h 13m.

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