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

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There are 8 ways to get from Chicago to Diamondhead by plane, train, taxi, bus (Flixbus, Greyhound), car, 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 Gulfport-Biloxi Regional Airport

    best
    1. Fly from Chicago Midway International Airport (MDW) to Gulfport-Biloxi Regional Airport (GPT)plane plane MDW - GPT
    6h 8m
    $188–825

  2. Fly Chicago O'Hare International Airport to Gulfport-Biloxi Regional Airport

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Gulfport-Biloxi Regional Airport (GPT)plane plane ORD - GPT
    6h 36m
    $152–575

  3. Train, taxi (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 Picayune Amtrak Stationtrain train
    3. Take the taxi from Picayune Amtrak Station to Diamondheadtaxi taxi
    22h 45m
    $352–705

  4. Bus via Newnan

    1. Take the bus from Chicago Bus Station to Atlanta Bus Stationbus bus
    2. Take the bus from Washington St at MLK Jr Dr to Newnan Park and Ridebus bus 453
    3. Take the bus from Newnan Park and Ride to Gulfportbus bus
    23h 13m
    $229–413

  5. Drive 900.3 mi

    1. Drive from Chicago to Diamondheadcar car 900.3 mi
    15h 8m
    $165–238

  6. Fly Chicago Midway International Airport to Louis Armstrong New Orleans International Airport, train, taxi

    1. Fly from Chicago Midway International Airport (MDW) to Louis Armstrong New Orleans International Airport (MSY)plane plane MDW - MSY
    2. Take the train from New Orleans Union Passenger Terminal to Picayune Amtrak Stationtrain train
    3. Take the taxi from Picayune Amtrak Station to Diamondheadtaxi taxi
    8h 14m
    $170–584

  7. Fly Chicago O'Hare International Airport to Louis Armstrong New Orleans International Airport, train, taxi

    1. Fly from Chicago O'Hare International Airport (ORD) to Louis Armstrong New Orleans International Airport (MSY)plane plane ORD - MSY
    2. Take the train from New Orleans Union Passenger Terminal to Picayune Amtrak Stationtrain train
    3. Take the taxi from Picayune Amtrak Station to Diamondheadtaxi taxi
    8h 34m
    $170–454

  8. Bus (Greyhound)

    1. Take the bus from Chicago Train Station to Atlanta Bus Stationbus bus Greyhound US0100
    2. Take the bus from Atlanta Bus Station to Biloxi Transit Centerbus bus Greyhound US0602
    28h 30m
    $259–460

Chicago Midway International Airport (MDW) to Gulfport-Biloxi Regional Airport (GPT) flights

Calendar35Weekly Planes
Duration5h 32mAverage Duration
Ticket$136Cheapest Price
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Questions & Answers

What companies run services between Chicago, IL, USA and Diamondhead, MS, USA?

Delta, Southwest Airlines, and Breeze Airways fly from Chicago Midway International Airport (MDW) to Gulfport-Biloxi Regional Airport (GPT) 5 times a day. Alternatively, you can take a bus from Chicago Bus Station to Diamondhead via Atlanta Bus Station, Washington St at MLK Jr Dr, Newnan Park and Ride, and Gulfport in around 23h 13m.

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