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

Find Transport to Pensacola

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There are 10 ways to get from Chicago to Pensacola by plane, bus (Greyhound, Flixbus), train, bus, car, taxi, or bus (Greyhound)

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
    $94–477

  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
    5h 24m
    $60–297

  3. 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
    $232–354

  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
    24h 50m
    $599–914

  5. Drive  873.1 mi

    1. Drive from Chicago to Pensacolacar car 873.1 mi
    15h 57m
    $155–223

  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 55m
    $222–705

  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 20m
    $182–495

  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
    6h 5m
    $120–581

  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 31m
    $84–371

  10. Bus via Opelika

    1. Take the bus from Chicago Train Station to Atlanta Bus Stationbus bus
    2. Take the bus from Atlanta Bus Station to Opelika 4th Street Stationbus bus
    3. Take the bus from Opelika 4th Street Station to Mobilebus bus
    4. Take the bus from Loxley to Pensacolabus bus
    25h 22m
    $258–371

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

Calendar28Weekly Planes
Duration4h 12mAverage Duration
Ticket$90Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Pensacola.ExpandLaunch map view
  • Distance: 797.8 mi
  • Duration: 5h

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

Southwest Airlines and Delta fly from Chicago Midway International Airport (MDW) to Pensacola International Airport (PNS) 4 times a day. 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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