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How to get fromGulf Shores to Chicagoby taxi, plane, bus, train, or car

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There are 8 ways to get from Gulf Shores to Chicago by taxi, plane, bus, 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. Taxi to Pensacola International Airport, fly to Chicago Midway International Airport

    best
    1. Take the taxi from Gulf Shores to Pensacola-Airport-PNStaxi taxi
    2. Fly from Pensacola International Airport (PNS) to Chicago Midway International Airport (MDW)plane plane PNS - MDW
    4h 1m
    $191–574

  2. Drive to Destin–Fort Walton Beach Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Drive from Gulf Shores to Destin–Fort Walton Beach Airport (VPS)car car
    2. Fly from Destin–Fort Walton Beach Airport (VPS) to Chicago O'Hare International Airport (ORD)plane plane VPS - ORD
    5h 28m
    $77–346

  3. Taxi, bus

    1. Take the taxi from Gulf Shores to Mobiletaxi taxi
    2. Take the bus from Mobile to La Grange Bus Stationbus bus
    3. Take the bus from La Grange Bus Station to Atlanta Bus Stationbus bus
    4. Take the bus from Atlanta Bus Station to Chicago Bus Stationbus bus
    23h 35m
    $263–393

  4. Taxi, train

    1. Take the taxi from Gulf Shores to Mobile, ALtaxi taxi
    2. Take the train from Mobile, AL to New Orleans, LA - Union Passenger Terminaltrain train
    3. Take the train from New Orleans Union Passenger Terminal to Chicago Union Stationtrain train
    25h 9m
    $658–1,072

  5. Drive  896.5 mi

    1. Drive from Gulf Shores to Chicagocar car 896.5 mi
    16h 19m
    $159–229

  6. Taxi to Pensacola International Airport, fly to Chicago O'Hare International Airport

    1. Take the taxi from Gulf Shores to Pensacola-Airport-PNStaxi taxi
    2. Fly from Pensacola International Airport (PNS) to Chicago O'Hare International Airport (ORD)plane plane PNS - ORD
    4h 29m
    $171–454

  7. Drive to Destin–Fort Walton Beach Airport, fly to Chicago Midway International Airport

    1. Drive from Gulf Shores to Destin–Fort Walton Beach Airport (VPS)car car
    2. Fly from Destin–Fort Walton Beach Airport (VPS) to Chicago Midway International Airport (MDW)plane plane VPS - MDW
    5h 1m
    $97–466

  8. Drive to Northwest Florida Beaches International Airport, fly to Chicago Midway International Airport

    1. Drive from Gulf Shores to Northwest Florida Beaches International Airport (ECP)car car
    2. Fly from Northwest Florida Beaches International Airport (ECP) to Chicago Midway International Airport (MDW)plane plane ECP - MDW
    6h 13m
    $105–479

Pensacola International Airport (PNS) to Chicago Midway International Airport (MDW) flights

Calendar38Weekly Planes
Duration4h 36mAverage Duration
Ticket$84Cheapest Price
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Comparing Your Travel Options

Map of how to get from Gulf Shores to Chicago.ExpandLaunch map view
  • Distance: 831.6 mi
  • Duration: 4h 1m

What companies run services between Gulf Shores, AL, USA and Chicago, IL, USA?

There is no direct connection from Gulf Shores to Chicago. However, you can take the taxi to Pensacola-Airport-PNS airport, fly to Chicago Midway International Airport (MDW), walk to Midway, then take the subway to Harold Washington Library. Alternatively, you can take the taxi to Mobile, take the bus to La Grange Bus Station, take the bus to Atlanta Bus Station, then take the bus to Chicago Bus Station.

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