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How to get fromChicago Midway Airport (MDW) to Pensacolaby plane, subway, bus (Flixbus, Greyhound), train, bus, taxi, or car

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There are 7 ways to get from Chicago Midway Airport (MDW) to Pensacola by plane, subway, bus (Flixbus, Greyhound), train, bus, taxi, 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 Chicago Midway International Airport to Pensacola International Airport

    best
    1. Fly from Chicago Midway International Airport (MDW) to Pensacola International Airport (PNS)plane plane MDW - PNS
    5h 8m
    $82–408

  2. Subway to Chicago O'Hare International Airport, fly to Pensacola International Airport

    cheapest
    1. Take the subway from Midway to Clark/Lakesubway subway
    2. Fly from Chicago O'Hare International Airport (ORD) to Pensacola International Airport (PNS)plane plane ORD - PNS
    5h 52m
    $72–352

  3. Bus

    1. Take the bus from Chicago to Atlanta Bus Stationbus bus
    2. Take the bus from Atlanta Bus Station to La Grange Bus Stationbus bus
    3. Take the bus from La Grange Bus Station to Mobilebus bus
    4. Take the bus from Loxley to Pensacolabus bus
    24h 51m
    $220–374

  4. Train, bus

    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 Gulfport Amtrak Statrain train
    3. Take the bus from Gulfport to Pensacolabus bus
    26h 29m
    $356–718

  5. Fly Chicago Midway International Airport to Destin–Fort Walton Beach Airport, taxi

    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 Pensacolataxi taxi
    3h 23m
    $213–624

  6. 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 Pensacolacar car
    4h 25m
    $112–504

  7. Drive 874.2 mi

    1. Drive from Chicago Midway Airport (MDW) to Pensacolacar car 874.2 mi
    15h 56m
    $160–231

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

Calendar45Weekly Planes
Duration5h 35mAverage Duration
Ticket$79Cheapest Price
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Questions & Answers

Map of how to get from Chicago Midway Airport (MDW) to Pensacola.ExpandLaunch map view
  • Distance: 786.7 mi
  • Duration: 5h 8m

What companies run services between Chicago Midway Airport (MDW), USA and Pensacola, FL, USA?

Delta and Southwest Airlines fly from Chicago Midway International Airport (MDW) to Pensacola International Airport (PNS) every 4 hours. Alternatively, you can take a bus from Midway Orange Line Station to Pensacola via Ashland & 59th Street, 95th Red Line Station, Chicago, Atlanta Bus Station, La Grange Bus Station, and Loxley in around 24h 51m.

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