MDW - GPT

$238 Find Cheap Flights from Chicago Midway Airport to Gulfport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Gulfport departing on 5/26. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Gulfport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Gulfport, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Gulfport, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$291
Delta
Tue 6/2Tue 6/9
MDW - GPT • 1 stop
Cheapest one-way
$238
Delta
Tue 5/26
MDW - GPT • 1 stop
Nonstop flights
Not available
There are currently no direct flights between Midway and Gulfport. You'll need at least 1 connection.
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Top layover airports
Dallas (DFW)
Cheapest • Avg $278 (round-trip)
Atlanta (ATL)
Shortest trip • 4h 58m (one-way)
Insights
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Avoid delays
Sun Country Air
Most punctual • 50% on-time
Afternoon flights
Best time • Fewest delays
Insights
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Gulfport!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Midway to Gulfport (MDW-GPT)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Gulfport that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Gulfport

Tue, Jun 2 - Tue, Jun 9
Delta Logo
5:15 pm - 9:51 pm
MDW
-
GPT
4h 36m
1 stop
Delta Logo
5:56 pm - 10:17 pm
GPT
-
MDW
4h 21m
1 stop
$291Delta
Mon, Aug 17 - Sat, Aug 22
Delta Logo
6:05 am - 1:03 pm
MDW
-
GPT
6h 58m
1 stop
Delta Logo
4:00 pm - 10:36 pm
GPT
-
MDW
6h 36m
1 stop
$300Delta
Tue, May 19 - Sat, May 23
Delta Logo
5:10 pm - 9:51 pm
MDW
-
GPT
4h 41m
1 stop
Delta Logo
3:00 pm - 9:09 pm
GPT
-
MDW
6h 09m
1 stop
$339Delta
Fri, Jul 31 - Mon, Aug 3
Delta Logo
5:10 pm - 10:14 pm
MDW
-
GPT
5h 04m
1 stop
Delta Logo
6:00 pm - 10:15 pm
GPT
-
MDW
4h 15m
1 stop
$344Delta
Thu, Jun 11 - Mon, Jun 15
Delta Logo
6:00 am - 1:07 pm
MDW
-
GPT
7h 07m
1 stop
Delta Logo
5:56 pm - 10:17 pm
GPT
-
MDW
4h 21m
1 stop
$364Delta
Thu, May 28 - Sun, May 31
Delta Logo
5:10 pm - 9:51 pm
MDW
-
GPT
4h 41m
1 stop
Delta Logo
6:32 am - 11:56 am
GPT
-
MDW
5h 24m
1 stop
$435Delta
Sat, May 23 - Sun, Aug 2
Delta Logo
5:10 pm - 9:51 pm
MDW
-
GPT
4h 41m
1 stop
Delta Logo
6:00 pm - 10:15 pm
GPT
-
MDW
4h 15m
1 stop
$489Delta
Fri, Jun 5 - Sun, Jun 7
Delta Logo
5:08 pm - 9:51 pm
MDW
-
GPT
4h 43m
1 stop
Delta Logo
10:06 am - 4:16 pm
GPT
-
MDW
6h 10m
1 stop
$499Delta
Tue, Jun 2 - Tue, Jun 9
Delta Logo
5:15 pm - 9:51 pm
MDW
-
GPT
4h 36m
1 stop
Delta Logo
5:56 pm - 10:17 pm
GPT
-
MDW
4h 21m
1 stop
$526Delta
Thu, Jul 16 - Sun, Jul 19
Delta Logo
6:00 am - 1:05 pm
MDW
-
GPT
7h 05m
1 stop
Delta Logo
6:00 pm - 10:15 pm
GPT
-
MDW
4h 15m
1 stop
$528Delta
Booking Insights

KAYAK's insights & trends for Midway to Gulfport flights

Get data-powered insights and trends into flights from Midway to Gulfport to help you find the cheapest flights, the best time to fly and much more.

How often are flights from Chicago to Gulfport delayed?

Weekly flights between Chicago and Gulfport historically see delays in approximately 44% of cases, with the average delay over the past year being 123 minutes.

What is the most punctual flight time for Chicago to Gulfport flights?

Typically, flights leaving in the early afternoon tend to face fewer delays, whereas flights in the evening have historically encountered delays more often.

What day of the week experiences the fewest flight delays on this route?

Statistically, Wednesday is the day of the week with the fewest delays on this flight route, while Tuesday has typically experienced more delays than other days.

Which airline has the best punctuality record on Chicago to Gulfport flights?

Based on our data, Sun Country Air have experienced the fewest delays on this route in the past 12 months, with only about 50% of their flights encountering any delays.

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Good to know

Cheapest flight$238
Flight from Chicago Midway Airport to Gulfport

When to book flights from Midway to Gulfport

Are your dates flexible? Find out the best times to travel from Midway to Gulfport based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to Gulfport flights

  • What is the cheapest flight from Chicago Midway Airport to Gulfport?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Gulfport was $238 for a one-way ticket and $291 for a round-trip.

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

    A passport is not required to fly from Chicago Midway Airport to Gulfport.

  • Which airports will I be using when flying from Chicago Midway Airport to Gulfport?

    On your way to Gulfport, you’ll fly out from Chicago Midway. You’ll be landing at Gulfport Biloxi Regional.

  • Which aircraft models fly most regularly from Chicago Midway Airport to Gulfport?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago Midway Airport to Gulfport?

    SkyTeam is the only airline alliance operating flights between Chicago Midway Airport and Gulfport.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Gulfport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to Gulfport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Gulfport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Gulfport from Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to Gulfport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Gulfport with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and GPT can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Gulfport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Gulfport from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Midway to Gulfport

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Gulfport. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to Gulfport? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
DeltaOverall score based on 8459 reviews
7.8Entertainment
8.1Boarding
8.5Crew
7.9Comfort
7.2Food
Airline reviews

Seats in Delta Main are unbelievably close to the seat in front of. Hard to get a backpack under the seat.

8.0 ExcellentMatthew, May 2026
OKC - ATL
Read more Delta reviews

Seats in Delta Main are unbelievably close to the seat in front of. Hard to get a backpack under the seat.

The agent at check in and at the gate were less than thrilled to be at work. I'm not a fan of Kayak's placement on the plane. I got put in the middle seat and none of my preferences were used.

In ATL they have two sets of departure screens. Follow what is on your airline's departure board - the ATL Airport Authority departure board had completely incorrect details about the gate assignment for my flight, which would have made me miss boarding.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

The flight was very good and the staff was very friendly and helpful!

The only thing I would say is we tried to get on a standby earlier flight, but with our fair we couldn’t. That seems senseless to leave with open seats..

Very easy to use and convenient, you can perform any action within the same portal

In a world of delays, Delta was on time both ways! Boarding was fast and efficient. Staff was friendly. AND wifi worked.

WiFi didn’t work. Flight delayed 3 hours Crew members were illiterate Seat lean back did not work.

Flight was delayed, we could have been notified earlier and in a consistent manner. App was not refreshing for another passenger to get the latest flight status. We could have stayed and waited at the hotel instead of waiting at the airport had we known the flight was going to delayed for more than 5 hours. The toilet is too tight, and needs to be cleaned more frequently (every hour). The entertainment screen froze, the touch screen not responding to touch. We were upgraded to comfort, it is more comfortable than regular economy seats.

Everything you need to know for your flight from Midway to Gulfport

Information on your arrival and departure airports

Chicago Midway Airport (MDW)
Gulfport (GPT)