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How to get fromOrland Park to Pensacolaby plane, bus (Flixbus, Greyhound), train, bus, car, or taxi

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There are 9 ways to get from Orland Park to Pensacola by plane, bus (Flixbus, Greyhound), train, bus, car, or taxi

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
    7h 14m
    $89–455

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

    cheapest
    1. Take the train from Orland Park 143rd to Chicago Union Stationtrain train
    2. Fly from Chicago O'Hare International Airport (ORD) to Pensacola International Airport (PNS)plane plane ORD - PNS
    6h 28m
    $79–363

  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
    25h 46m
    $227–371

  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 40m
    $366–766

  5. Drive 869.6 mi

    1. Drive from Orland Park to Pensacolacar car 869.6 mi
    15h 50m
    $159–230

  6. 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
    5h 29m
    $217–653

  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 Pensacolacar car
    6h 31m
    $120–530

  8. Fly Chicago O'Hare International Airport to Destin–Fort Walton Beach Airport, taxi

    1. Fly from Chicago O'Hare International Airport (ORD) to Destin–Fort Walton Beach Airport (VPS)plane plane ORD - VPS
    2. Take the taxi from Destin–Fort Walton Beach Airport (VPS) to Pensacolataxi taxi
    6h 31m
    $202–561

  9. 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 Pensacolacar car
    7h 45m
    $105–438

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

Calendar46Weekly Planes
Duration5h 36mAverage Duration
Ticket$89Cheapest Price
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Questions & Answers

Map of how to get from Orland Park to Pensacola.ExpandLaunch map view
  • Distance: 804.8 mi
  • Duration: 7h 14m

What companies run services between Orland Park, IL, 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 La Grange Rd & 143rd St to Pensacola via Moraine Valley Community College, Chicago, Atlanta Bus Station, La Grange Bus Station, and Loxley in around 25h 46m.

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