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

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There are 9 ways to get from Chicago to Valparaiso 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 Midway International Airport to Destin–Fort Walton Beach Airport

    best
    1. Fly from Chicago Midway International Airport (MDW) to Destin–Fort Walton Beach Airport (VPS)plane plane MDW - VPS
    3h 53m
    $112–523

  2. Fly Chicago O'Hare International Airport to Destin–Fort Walton Beach Airport

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Destin–Fort Walton Beach Airport (VPS)plane plane ORD - VPS
    4h 20m
    $92–423

  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 Crestviewbus bus
    25h 33m
    $278–433

  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 Crestviewbus bus
    26h 4m
    $423–798

  5. Drive 867.2 mi

    1. Drive from Chicago to Valparaisocar car 867.2 mi
    15h 59m
    $159–229

  6. 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 Valparaisocar car
    4h 55m
    $112–521

  7. 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 Valparaisocar car
    5h 33m
    $92–421

  8. Fly Chicago O'Hare International Airport to Pensacola International Airport, taxi

    1. Fly from Chicago O'Hare International Airport (ORD) to Pensacola International Airport (PNS)plane plane ORD - PNS
    2. Take the taxi from Pensacola-Airport-PNS to Valparaisotaxi taxi
    5h 31m
    $212–525

  9. Fly Chicago Midway International Airport to Pensacola International Airport, taxi

    1. Fly from Chicago Midway International Airport (MDW) to Pensacola International Airport (PNS)plane plane MDW - PNS
    2. Take the taxi from Pensacola-Airport-PNS to Valparaisotaxi taxi
    6h 53m
    $228–625

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

Calendar11Weekly Planes
Duration3h 43mAverage Duration
Ticket$99Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Valparaiso.ExpandLaunch map view
  • Distance: 797.4 mi
  • Duration: 3h 53m

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

Allegiant Air and Southwest Airlines fly from Chicago Midway International Airport (MDW) to Destin–Fort Walton Beach Airport (VPS) twice daily. Alternatively, you can take a bus from Chicago Bus Station to Valparaiso via Atlanta Bus Station, La Grange Bus Station, Loxley, and Crestview in around 25h 33m.

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