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How to get fromPensacola to Chicagoby plane, taxi, bus, train, bus (Greyhound, Flixbus), car, or bus (Flixbus, Greyhound)

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

    best
    1. Fly from Pensacola International Airport (PNS) to Chicago Midway International Airport (MDW)plane plane PNS - MDW
    5h 22m
    $71–369

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

    cheapest
    1. Fly from Pensacola International Airport (PNS) to Chicago O'Hare International Airport (ORD)plane plane PNS - ORD
    5h 49m
    $56–299

  3. Taxi, bus, train

    1. Take the taxi from Pensacola to Mobiletaxi taxi
    2. Take the bus from Mobile to Gulfportbus bus
    3. Take the train from Gulfport, MS to New Orleans, LA - Union Passenger Terminaltrain train
    4. Take the train from New Orleans Union Passenger Terminal to Chicago Union Stationtrain train
    25h 20m
    $425–892

  4. Bus

    1. Take the bus from Pensacola to Tallahasseebus bus
    2. Take the bus from Tallahassee to Nashville Bus Stationbus bus
    3. Take the bus from Nashville Bus Station to Chicago Bus Stationbus bus
    25h 47m
    $210–325

  5. Drive  872.7 mi

    1. Drive from Pensacola to Chicagocar car 872.7 mi
    15h 57m
    $160–231

  6. Bus to Destin–Fort Walton Beach Airport, fly to Chicago Midway International Airport

    1. Take the bus from Pensacola to Crestviewbus bus
    2. Fly from Destin–Fort Walton Beach Airport (VPS) to Chicago Midway International Airport (MDW)plane plane VPS - MDW
    5h 14m
    $169–523

  7. Drive to Northwest Florida Beaches International Airport, fly to Chicago Midway International Airport

    1. Drive from Pensacola to Northwest Florida Beaches International Airport (ECP)car car
    2. Fly from Northwest Florida Beaches International Airport (ECP) to Chicago Midway International Airport (MDW)plane plane ECP - MDW
    5h 22m
    $95–431

  8. Bus to Destin–Fort Walton Beach Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Pensacola to Crestviewbus bus
    2. Fly from Destin–Fort Walton Beach Airport (VPS) to Chicago O'Hare International Airport (ORD)plane plane VPS - ORD
    5h 39m
    $154–443

  9. Drive to Northwest Florida Beaches International Airport, fly to Chicago O'Hare International Airport

    1. Drive from Pensacola to Northwest Florida Beaches International Airport (ECP)car car
    2. Fly from Northwest Florida Beaches International Airport (ECP) to Chicago O'Hare International Airport (ORD)plane plane ECP - ORD
    5h 47m
    $80–351

  10. Bus via Atlanta

    1. Take the bus from Pensacola to Tallahasseebus bus
    2. Take the bus from Tallahassee to Atlanta Bus Stationbus bus
    3. Take the bus from Atlanta Bus Station to Chicago Bus Stationbus bus
    27h 42m
    $200–340

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

Calendar40Weekly Planes
Duration4h 42mAverage Duration
Ticket$67Cheapest Price
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Comparing Your Travel Options

Map of how to get from Pensacola to Chicago.ExpandLaunch map view
  • Distance: 798.3 mi
  • Duration: 5h 22m

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

Southwest Airlines and Delta fly from Pensacola International Airport (PNS) to Chicago Midway International Airport (MDW) every 4 hours. Alternatively, you can take a bus from Pensacola to Chicago Bus Station via Tallahassee, N Monroe Street and Silver Slipper Lane, Tallahassee, and Nashville Bus Station in around 25h 47m.

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