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How to get fromChicago to Pensacola Beachby plane, taxi, bus, car, or train

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There are 9 ways to get from Chicago to Pensacola Beach by plane, taxi, bus, car, or train

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 Destin–Fort Walton Beach Airport, taxi

    best
    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 Pensacola Beachtaxi taxi
    4h 58m
    $202–635

  2. Fly Chicago O'Hare International Airport to Pensacola International Airport, line 61 bus

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Pensacola International Airport (PNS)plane plane ORD - PNS
    2. Take the bus from ECAT Transfer Station to Pensacola Beach Visitors Info Centerbus bus
    6h 45m
    $76–369

  3. Bus, drive

    1. Take the bus from Chicago Bus Station to Indianapolis Union Stationbus bus
    2. Take the bus from Indianapolis Union Station to Montgomery Intermodal Centerbus bus
    3. Take the bus from Montgomery Intermodal Center to Mobile Bus Stationbus bus
    4. Drive from Mobile Bus Station to Pensacola Beachcar car
    22h 21m
    $163–318

  4. Train, drive (Amtrak)

    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 Mobile Amtrak Statrain train
    3. Drive from Mobile Amtrak Sta to Pensacola Beachcar car
    24h 39m
    $346–716

  5. Drive 876.5 mi

    1. Drive from Chicago to Pensacola Beachcar car 876.5 mi
    16h 21m
    $160–232

  6. 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 Pensacola Beachtaxi taxi
    5h 23m
    $182–535

  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 Pensacola Beachcar car
    5h 59m
    $120–580

  8. 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 Pensacola Beachcar car
    6h 37m
    $100–430

  9. 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
    8h 6m
    $96–469

Chicago Midway International Airport (MDW) to Destin–Fort Walton Beach Airport (VPS) flights

Calendar12Weekly Planes
Duration3h 44mAverage Duration
Ticket$102Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Pensacola Beach.ExpandLaunch map view
  • Distance: 835.5 mi
  • Duration: 4h 58m

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

Delta and Southwest Airlines fly from Chicago Midway International Airport (MDW) to Pensacola International Airport (PNS) every 4 hours.

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