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How to get fromChicago to Pensacola Beachby plane, taxi, bus, car, or train

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There are 8 ways to get from Chicago to Pensacola Beach by plane, taxi, bus, car, or train

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 Destin–Fort Walton Beach Airport, taxi

    best
    1. Fly from Chicago Midway International Airport (MDW) to Destin–Fort Walton Beach Airport (VPS)plane plane MDW - VPS
    2. Take the taxi from Destin–Fort Walton Beach Airport (VPS) to Pensacola Beachtaxi taxi
    4h 55m
    $198–635

  2. Fly Chicago O'Hare International Airport to Pensacola International Airport

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Pensacola International Airport (PNS)plane plane ORD - PNS
    6h 49m
    $52–269

  3. Bus, drive (Greyhound)

    1. Take the bus from Chicago Bus Station to Indianapolis Union Stationbus bus
    2. Take the bus from Indianapolis Union Station to Montgomery Intermodal Centerbus bus
    3. Take the bus from Montgomery Intermodal Center to Mobile Bus Stationbus bus
    4. Drive from Mobile Bus Station to Pensacola Beachcar car
    22h 21m
    $174–270

  4. Train, drive (Amtrak)

    1. Take the train from Chicago Union Station to New Orleans Union Passenger Terminaltrain train
    2. Take the train from New Orleans Union Passenger Terminal to Mobile Amtrak Statrain train
    3. Drive from Mobile Amtrak Sta to Pensacola Beachcar car
    24h 39m
    $558–930

  5. Drive  876.5 mi

    1. Drive from Chicago to Pensacola Beachcar car 876.5 mi
    16h 21m
    $160–232

  6. Fly Chicago Midway International Airport to Pensacola International Airport

    1. Fly from Chicago Midway International Airport (MDW) to Pensacola International Airport (PNS)plane plane MDW - PNS
    6h 24m
    $72–379

  7. Fly Chicago Midway International Airport to Northwest Florida Beaches International Airport, drive

    1. Fly from Chicago Midway International Airport (MDW) to Northwest Florida Beaches International Airport (ECP)plane plane MDW - ECP
    2. Drive from Northwest Florida Beaches International Airport (ECP) to Pensacola Beachcar car
    6h 4m
    $114–580

  8. Fly Chicago O'Hare International Airport to Northwest Florida Beaches International Airport, drive

    1. Fly from Chicago O'Hare International Airport (ORD) to Northwest Florida Beaches International Airport (ECP)plane plane ORD - ECP
    2. Drive from Northwest Florida Beaches International Airport (ECP) to Pensacola Beachcar car
    6h 37m
    $84–390

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

Calendar26Weekly Planes
Duration3h 53mAverage Duration
Ticket$95Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Pensacola Beach.ExpandLaunch map view
  • Distance: 835.5 mi
  • Duration: 4h 55m

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

Southwest Airlines and Delta fly from Chicago Midway International Airport (MDW) to Pensacola International Airport (PNS) every 4 hours.

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