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

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There are 9 ways to get from Chicago to Pensacola by plane, bus (Greyhound, Flixbus), 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 O'Hare International Airport to Pensacola International Airport

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Pensacola International Airport (PNS)plane plane ORD - PNS
    5h 21m
    $74–367

  2. Bus

    1. Take the bus from Chicago Bus Station 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 19m
    $229–372

  3. 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
    24h 50m
    $378–725

  4. Drive 873.1 mi

    1. Drive from Chicago to Pensacolacar car 873.1 mi
    15h 57m
    $160–231

  5. 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 42m
    $94–467

  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
    4h 58m
    $222–655

  7. 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
    5h 24m
    $202–555

  8. 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
    5h 59m
    $120–582

  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
    6h 37m
    $100–432

Chicago O'Hare International Airport (ORD) to Pensacola International Airport (PNS) flights

Calendar46Weekly Planes
Duration4h 22mAverage Duration
Ticket$73Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Pensacola.ExpandLaunch map view
  • Distance: 818 mi
  • Duration: 5h 21m

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

American Airlines, United Airlines, and Delta fly from Chicago O'Hare International Airport (ORD) to Pensacola International Airport (PNS) every 4 hours. Alternatively, you can take a bus from Chicago Bus Station to Pensacola via Atlanta Bus Station, La Grange Bus Station, and Loxley in around 24h 19m.

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