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 4/21. 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
$295
Multiple Airlines
Wed 4/29Sun 5/3
MDW - GPT • 2 stops
Cheapest one-way
$238
Delta
Tue 4/21
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 • 5h 16m (one-way)
Insights
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Avoid delays
Sun Country Air
Most punctual • 52% 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

Wed, Apr 29 - Sun, May 3
Multiple Airlines Logo
2:15 pm - 6:40 pm
MDW
-
GPT
28h 25m
2 stops
Multiple Airlines Logo
7:20 pm - 7:46 am
GPT
-
MDW
12h 26m
1 stop
$295Multiple Airlines
Sun, Apr 12 - Sun, Apr 19
Multiple Airlines Logo
5:05 am - 6:40 pm
MDW
-
GPT
13h 35m
1 stop
Multiple Airlines Logo
7:20 pm - 7:31 pm
GPT
-
MDW
48h 11m
2 stops
$326Multiple Airlines
Tue, Apr 14 - Tue, Apr 21
Delta Logo
12:52 pm - 5:08 pm
MDW
-
GPT
4h 16m
1 stop
Delta Logo
5:55 pm - 10:28 pm
GPT
-
MDW
4h 33m
1 stop
$329Delta
Thu, Apr 2 - Mon, Apr 6
Multiple Airlines Logo
5:01 am - 6:40 pm
MDW
-
GPT
13h 39m
1 stop
Multiple Airlines Logo
6:54 pm - 8:07 pm
GPT
-
MDW
25h 13m
2 stops
$353Multiple Airlines
Sun, Apr 12 - Sun, Apr 19
Multiple Airlines Logo
5:05 am - 6:40 pm
MDW
-
GPT
13h 35m
1 stop
Multiple Airlines Logo
7:20 pm - 8:04 am
GPT
-
MDW
12h 44m
1 stop
$375Multiple Airlines
Mon, May 11 - Sat, May 16
Delta Logo
6:23 am - 1:09 pm
MDW
-
GPT
6h 46m
1 stop
Delta Logo
3:00 pm - 9:09 pm
GPT
-
MDW
6h 09m
1 stop
$384Delta
Mon, May 11 - Sat, May 16
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
$399Delta
Wed, Apr 15 - Wed, Apr 22
Delta Logo
10:41 am - 5:08 pm
MDW
-
GPT
6h 27m
1 stop
Delta Logo
5:55 pm - 10:28 pm
GPT
-
MDW
4h 33m
1 stop
$428Delta
Fri, May 8 - Tue, May 12
Delta Logo
6:23 am - 1:09 pm
MDW
-
GPT
6h 46m
1 stop
Delta Logo
10:08 am - 4:12 pm
GPT
-
MDW
6h 04m
1 stop
$429Delta
Tue, May 19 - Sat, May 30
Delta Logo
6:23 am - 1:09 pm
MDW
-
GPT
6h 46m
1 stop
Delta Logo
3:00 pm - 9:09 pm
GPT
-
MDW
6h 09m
1 stop
$433Delta
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 42% of cases, with the average delay over the past year being 107 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, Monday 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 48% 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 $295 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 8292 reviews
7.9Comfort
7.2Food
8.1Boarding
8.5Crew
7.8Entertainment
Airline reviews

I had a flight cancel and had it rerouted. When the rerouted they put me at a window seat instead of an isle. It was hard sitting by the window because the couple with masks on were making out. I get motion sickness which is why I need to have the isle seat.

4.0 OkayAnonymous, Mar 2026
CAE - ATL
Read more Delta reviews

I had a flight cancel and had it rerouted. When the rerouted they put me at a window seat instead of an isle. It was hard sitting by the window because the couple with masks on were making out. I get motion sickness which is why I need to have the isle seat.

NEVER MADE THE FLIGHT BECAUSE DELTA SAID THEY CAN NOT

THEY FAILED ME AND I NEVER GOT ON THE FLIGHT BECAUSE IT WAS SO DELAYED! I ENDED UP HAVING TO PAY OUT OF POCKET FOR A HOTEL AND STAY IN NASHVILLE TO CATCH A FLIGHT FOR THE FOLLOWING DAY. DELTA IS POOR CUSTOMER SERVICE>

8 hours late and the plane smelled like urine, that smell in the morning when your child wet the bed in the night.

My flight was canceled on Sunday. Rebooking took three hours. Had to pay for accommodations another night. New flight was delayed for 5 hours, all that was sent was a 12 dollar food voucher, which doesn’t tell you how to use it. Then when we landed we had to sit on the plane for an hour before we could get off.

Miserable. This entire round trip was miserable. I booked evening flights to and from Detroit on consecutive days that should have had me at my destination by 10:30. Instead I arrived after 3am on my flight to Detroit and after midnight on my return. Multiple unforced errors like awaiting bags to get put on the plane for almost an hour in Detroit and a 20 minute delay to pull up to the gate in Atlanta has me rethinking my assumption that delta is the best and most reliable airline

Perhaps when you’re sitting in 1st class and the crew closes the bathroom for the pilots, there could be a notification other than holding your hands up as a blockade when you get there and you’re told the restrooms are closed please turn around … especially at night when visibility is poor and you’re met by a flight attendants with their arms up

First class is comfortable. Enjoyed a movie and was able to relax compared to coach.

Loved flying First Class. Very comfortable. The seat was amazing. Enjoyed a movie and was able to relax so much better than in coach.

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

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)