GPT - MDW

$170 Find Cheap Flights from Gulfport to Chicago Midway Airport - Compare and Save

1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$271
Typical prices: $268-$343
Multiple Airlines
Mon 2/19Tue 2/27
GPT - MDW • 2 stops
Cheapest one-way
$170
Typical prices: $168-$260
Multiple Airlines
Tue 12/11
GPT - MDW • 3 stops
Nonstop flights
There are currently no direct flights between Gulfport and Chicago Midway Airport. You'll need to take a connecting flight to reach the destination.
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When to travel
Cheapest • 17% price drop
Most popular
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Flight Deals

Cheap Flights from Gulfport to Midway (GPT-MDW)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Gulfport to Midway

Fri, Feb 19 - Sat, Feb 27
Multiple Airlines Logo
6:46 pm - 11:46 pmGPT  Gulfport Biloxi Regional-MDW Chicago Midway
29h 00m2 stops Tampa Atlanta Hartsfield-Jackson
Multiple Airlines Logo
8:47 pm - 7:10 pmMDW  Chicago Midway-GPT Gulfport Biloxi Regional
22h 23m1 stop Orlando
$271Multiple Airlines
Fri, Dec 11 - Fri, Dec 18
Delta Logo
6:09 pm - 10:54 pmGPT  Gulfport Biloxi Regional-MDW Chicago Midway
4h 45m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:00 am - 1:06 pmMDW  Chicago Midway-GPT Gulfport Biloxi Regional
7h 06m1 stop Atlanta Hartsfield-Jackson
$339Delta
Fri, Nov 13 - Mon, Nov 16
Delta Logo
10:04 am - 4:18 pmGPT  Gulfport Biloxi Regional-MDW Chicago Midway
6h 14m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:13 pm - 9:52 pmMDW  Chicago Midway-GPT Gulfport Biloxi Regional
4h 39m1 stop Atlanta Hartsfield-Jackson
$354Delta
Thu, Nov 12 - Mon, Nov 16
Delta Logo
6:04 pm - 10:54 pmGPT  Gulfport Biloxi Regional-MDW Chicago Midway
4h 50m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:13 pm - 9:52 pmMDW  Chicago Midway-GPT Gulfport Biloxi Regional
4h 39m1 stop Atlanta Hartsfield-Jackson
$354Delta
Fri, Nov 13 - Mon, Nov 16
Delta Logo
6:04 pm - 10:54 pmGPT  Gulfport Biloxi Regional-MDW Chicago Midway
4h 50m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:13 pm - 9:52 pmMDW  Chicago Midway-GPT Gulfport Biloxi Regional
4h 39m1 stop Atlanta Hartsfield-Jackson
$354Delta
Thu, Nov 12 - Mon, Nov 16
Delta Logo
10:04 am - 4:18 pmGPT  Gulfport Biloxi Regional-MDW Chicago Midway
6h 14m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:13 pm - 9:52 pmMDW  Chicago Midway-GPT Gulfport Biloxi Regional
4h 39m1 stop Atlanta Hartsfield-Jackson
$354Delta
Fri, Nov 13 - Mon, Nov 16
Delta Logo
10:04 am - 6:04 pmGPT  Gulfport Biloxi Regional-MDW Chicago Midway
8h 00m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
Delta Logo
5:13 pm - 9:52 pmMDW  Chicago Midway-GPT Gulfport Biloxi Regional
4h 39m1 stop Atlanta Hartsfield-Jackson
$359Delta
Thu, Nov 12 - Mon, Nov 16
Delta Logo
10:04 am - 4:18 pmGPT  Gulfport Biloxi Regional-MDW Chicago Midway
6h 14m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:31 pm - 9:52 pmMDW  Chicago Midway-GPT Gulfport Biloxi Regional
8h 21m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
$359Delta
Booking Insights

Price, demand and travel trends for Gulfport to Chicago Midway Airport flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

Which airline is the cheapest to fly from Gulfport to Chicago Midway Airport?

Delta ($339) offered the cheapest round-trip ticket from Gulfport to Chicago Midway Airport in the last 5 days.

Key details for Gulfport to Chicago Midway Airport flights

Low season

August

Cheapest flight

$170
Beat the crowds with an average 73% drop in travelers.
The most popular month to fly with an average 7% increase in travelers.
One-way flight from Gulfport to Chicago Midway Airport

When to book flights from Gulfport to Midway

Are your dates flexible? Find out the best times to travel from Gulfport to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Gulfport to Chicago Midway Airport flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What cabin classes can I book on flights from Gulfport to Chicago Midway Airport?

    Only Economy Class is available on flights from Gulfport to Chicago Midway Airport.

  • How long is a flight from Gulfport to Chicago Midway Airport?

    A nonstop flight from Gulfport to Chicago Midway Airport takes 00m, covering 789 miles.

  • Do I need a passport to fly from Gulfport to Chicago Midway Airport?

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

  • How much should I expect to pay for a Gulfport to Chicago Midway Airport flight?

    Round-trip flights from Gulfport to Chicago Midway Airport range from $268 to $343, with an average of $299 over the past 12 months. Anything below $268 counts as a good deal.

  • Have flight prices from Gulfport to Chicago Midway Airport changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $271 to $1,899. That means the highest observed fare was about 7x higher than the lowest one.

  • How are flight prices from Gulfport to Chicago Midway Airport looking right now?

    One-way fares from Gulfport to Chicago Midway Airport are currently in line with typical prices for this route. Average one-way fares are about $230.

  • What car rental options are available at Chicago Midway Airport (MDW)?

    Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates averaging $84 for economy cars. Top options include:

    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

  • Which airports can I use when flying from Gulfport to Chicago Midway Airport?

    Flights from Gulfport to Chicago Midway Airport usually depart from Gulfport Biloxi Regional (GPT) and arrive at Chicago Midway (MDW).

  • Which airports do connecting flights from Gulfport to Chicago Midway Airport pass through?

    Most connecting flights from Gulfport to Chicago Midway Airport pass through Atlanta Hartsfield-Jackson (ATL), which handles 100% of one-stop traffic on this route.

  • Can I save money by using flexible dates for flights from Gulfport to Chicago Midway Airport?

    Yes. Flexible dates can save you up to 75% on flights from Gulfport to Chicago Midway Airport. Wednesday is the cheapest departure day at $248 round-trip on average, while Monday is the most expensive at $966, a difference of $718.

    KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • What popular places can I visit in Chicago Midway Airport?

    Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, Grant Park and Soldier Field. These are among the most viewed places in Chicago Midway Airport on KAYAK.

Your guide to booking Gulfport to Chicago Midway Airport flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Wednesday departure and avoid flying on Monday. On this route, Wednesday flights average $248, about $718 less than Monday fares (74% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Gulfport to Chicago Midway Airport trip for November. Fares historically average $248 round-trip in that month - typically $718 less than the most expensive month, which is April (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.

    • DoubleTree by Hilton Chicago Midway Airport
    • Holiday Inn Chicago - Midway Airport S by IHG
    • Skylark Motel Chicago Midway Airport

More options for your flight from Gulfport to Midway

Complete your trip to Chicago with a hotel stay or car rental