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How to get fromChicago to Anna Maria Islandby subway, plane, bus, taxi, train, or car

Find Transport to Anna Maria Island

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There are 5 ways to get from Chicago to Anna Maria Island by subway, plane, bus, taxi, 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. Subway to Chicago Midway International Airport, fly, line 304 bus

    best
    1. Take the subway from Adams/Wabash to Midwaysubway subway
    2. Fly from Chicago Midway International Airport (MDW) to Sarasota–Bradenton International Airport (SRQ)plane plane MDW - SRQ
    3. Take the bus from Downtown Station to Gulf Dr/42Nd Stbus bus
    6h 21m
    $174–810

  2. Fly from Chicago O'Hare International Airport, line 304 bus

    cheapest
    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 Station to Gulf Dr/42Nd Stbus bus
    6h 55m
    $134–660

  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 taxi from Idaho St @ O'Brien St to Anna Maria Islandtaxi taxi
    28h 18m
    $329–509

  4. Train, taxi

    1. Take the train from Chicago Union Station to Tampatrain train Floridian
    2. Take the taxi from Tampa to Anna Maria Islandtaxi taxi
    41h 56m
    $719–1,350

  5. Drive 1,170.7 mi

    1. Drive from Chicago to Anna Maria Islandcar car 1,170.7 mi
    20h 50m
    $214–309

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

Calendar35Weekly Planes
Duration4h 24mAverage Duration
Ticket$172Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Anna Maria Island.ExpandLaunch map view
  • Distance: 1,069.4 mi
  • Duration: 6h 21m

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

There is no direct connection from Chicago to Anna Maria Island. However, you can take the subway to Midway, walk to Chicago-Midway-Airport-MDW airport, fly to Sarasota–Bradenton International Airport (SRQ), walk to Airport Cir @ Bradenton Connector Ns, take the line 99 bus to 13Th St W @ 6Th Ave W Ns, then take the line 304 bus to Gulf Dr/42Nd St. Alternatively, you can take the bus to Atlanta Bus Station, take the bus to Tampa Bus Station, walk to Marion Transit Center, take the line 19 bus to Idaho St @ O'Brien St, then take the taxi to Anna Maria Island.

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