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How to get fromDestin to Chicagoby plane, taxi, bus, or car

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There are 8 ways to get from Destin to Chicago by plane, taxi, bus, 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 Destin–Fort Walton Beach Airport to Chicago Midway International Airport

    best
    1. Fly from Destin–Fort Walton Beach Airport (VPS) to Chicago Midway International Airport (MDW)plane plane VPS - MDW
    3h 28m
    $120–455

  2. Taxi, bus

    1. Take the taxi from Destin to Crestviewtaxi taxi
    2. Take the bus from Crestview to Tallahasseebus bus
    3. Take the bus from Tallahassee to Nashville Bus Stationbus bus
    4. Take the bus from Nashville Bus Station to Chicago Bus Stationbus bus
    25h 42m
    $271–442

  3. Drive 882.1 mi

    1. Drive from Destin to Chicagocar car 882.1 mi
    16h 22m
    $161–233

  4. Taxi to Northwest Florida Beaches International Airport, fly to Chicago Midway International Airport

    1. Take the taxi from Destin to Northwest Florida Beaches International Airport (ECP)taxi taxi
    2. Fly from Northwest Florida Beaches International Airport (ECP) to Chicago Midway International Airport (MDW)plane plane ECP - MDW
    4h
    $224–578

  5. Taxi to Northwest Florida Beaches International Airport, fly to Chicago O'Hare International Airport

    1. Take the taxi from Destin to Northwest Florida Beaches International Airport (ECP)taxi taxi
    2. Fly from Northwest Florida Beaches International Airport (ECP) to Chicago O'Hare International Airport (ORD)plane plane ECP - ORD
    4h 36m
    $219–538

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

    1. Take the taxi from Destin to Pensacola-Airport-PNStaxi taxi
    2. Fly from Pensacola International Airport (PNS) to Chicago O'Hare International Airport (ORD)plane plane PNS - ORD
    4h 45m
    $190–467

  7. Taxi to Pensacola International Airport, fly to Chicago Midway International Airport

    1. Take the taxi from Destin to Pensacola-Airport-PNStaxi taxi
    2. Fly from Pensacola International Airport (PNS) to Chicago Midway International Airport (MDW)plane plane PNS - MDW
    5h 44m
    $195–497

  8. Taxi, bus via Atlanta

    1. Take the taxi from Destin to Crestviewtaxi taxi
    2. Take the bus from Crestview to Tallahasseebus bus
    3. Take the bus from Tallahassee to Atlanta Bus Stationbus bus
    4. Take the bus from Atlanta Bus Station to Chicago Bus Stationbus bus
    27h 42m
    $276–452

Destin–Fort Walton Beach Airport (VPS) to Chicago Midway International Airport (MDW) flights

Calendar13Weekly Planes
Duration4h 18mAverage Duration
Ticket$78Cheapest Price
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Questions & Answers

Map of how to get from Destin to Chicago.ExpandLaunch map view
  • Distance: 809.8 mi
  • Duration: 3h 28m

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

Allegiant Air and Southwest Airlines fly from Destin–Fort Walton Beach Airport (VPS) to Chicago Midway International Airport (MDW) twice daily.

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