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

Find Transport to Anna Maria

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There are 7 ways to get from Chicago to Anna Maria by plane, car, bus, taxi, train, or subway

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 Tampa, drive

    best
    1. Fly from Chicago Midway International Airport (MDW) to Tampa (TPA)plane plane MDW - TPA
    2. Drive from Tampa-Airport-TPA to Anna Mariacar car
    5h 18m
    $142–420

  2. Fly Chicago O'Hare International Airport to Sarasota–Bradenton 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
    7h 21m
    $134–662

  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 50Th Ave S + 34Th St S to Anna Mariataxi taxi
    29h 5m
    $269–440

  4. Train, taxi

    1. Take the train from Chicago Union Station to Tampatrain train Floridian
    2. Take the taxi from Tampa to Anna Mariataxi taxi
    42h 1m
    $705–1,349

  5. Drive 1,172.5 mi

    1. Drive from Chicago to Anna Mariacar car 1,172.5 mi
    20h 55m
    $214–310

  6. Fly Chicago O'Hare International Airport to Tampa, drive

    1. Fly from Chicago O'Hare International Airport (ORD) to Tampa (TPA)plane plane ORD - TPA
    2. Drive from Tampa-Airport-TPA to Anna Mariacar car
    5h 46m
    $172–570

  7. Subway to Chicago Midway International Airport, fly to Sarasota–Bradenton International Airport, line 304 bus

    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 48m
    $164–812

Chicago Midway International Airport (MDW) to Tampa (TPA) flights

Calendar39Weekly Planes
Duration2h 59mAverage Duration
Ticket$124Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Anna Maria.ExpandLaunch map view
  • Distance: 1,064.7 mi
  • Duration: 5h 18m

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

There is no direct connection from Chicago to Anna Maria. However, you can take the subway to Midway, walk to Chicago-Midway-Airport-MDW airport, fly to Tampa (TPA), then drive to Anna Maria. Alternatively, you can take the bus to Atlanta Bus Station, take the bus to Tampa Bus Station, walk to Marion Transit Parking Lot, take the line 100 bus to Gateway Mall - Shelter - 1, take the line 4 bus to 50Th Ave S + 34Th St S, then take the taxi to Anna Maria.

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