MDW - GPT

$181 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 8/4. 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
Delta
Tue 7/14Sat 7/18
MDW - GPT • 1 stop
Cheapest one-way
$181
Delta
Tue 8/4
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.
Insights
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Insights
Avoid delays
Sun Country Air
Most punctual • 44% 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, Jul 14 - Sat, Jul 18
Delta Logo
6:00 am - 1:05 pm
MDW
-
GPT
7h 05m
1 stop
Delta Logo
4:00 pm - 10:15 pm
GPT
-
MDW
6h 15m
1 stop
$295Delta
Fri, Aug 7 - Mon, Aug 10
Delta Logo
5:10 pm - 10:21 pm
MDW
-
GPT
5h 11m
1 stop
Delta Logo
6:00 pm - 10:36 pm
GPT
-
MDW
4h 36m
1 stop
$334Delta
Sat, Dec 12 - Fri, Dec 18
Delta Logo
12:30 pm - 10:07 pm
MDW
-
GPT
9h 37m
2 stops
Delta Logo
6:00 pm - 10:10 pm
GPT
-
MDW
4h 10m
1 stop
$339Delta
Sun, Sep 13 - Sun, Sep 20
Delta Logo
5:25 pm - 10:06 pm
MDW
-
GPT
4h 41m
1 stop
Delta Logo
5:59 pm - 10:25 pm
GPT
-
MDW
4h 26m
1 stop
$378Delta
Sat, Dec 12 - Fri, Dec 18
Delta Logo
5:25 pm - 10:07 pm
MDW
-
GPT
4h 42m
1 stop
Delta Logo
6:00 pm - 10:10 pm
GPT
-
MDW
4h 10m
1 stop
$433Delta
Sat, Jun 27 - Wed, Jul 1
Delta Logo
4:25 pm - 8:41 pm
MDW
-
GPT
4h 16m
1 stop
Delta Logo
3:00 pm - 10:17 pm
GPT
-
MDW
7h 17m
1 stop
$439Delta
Sat, Jun 27 - Wed, Jul 1
Delta Logo
9:54 am - 8:41 pm
MDW
-
GPT
10h 47m
2 stops
Delta Logo
3:00 pm - 10:17 pm
GPT
-
MDW
7h 17m
1 stop
$444Delta
Fri, Aug 7 - Mon, Aug 10
Delta Logo
1:27 pm - 10:21 pm
MDW
-
GPT
8h 54m
2 stops
Delta Logo
6:00 pm - 10:36 pm
GPT
-
MDW
4h 36m
1 stop
$463Delta
Mon, Nov 30 - Thu, Dec 3
Delta Logo
5:25 pm - 10:07 pm
MDW
-
GPT
4h 42m
1 stop
Delta Logo
6:00 pm - 10:10 pm
GPT
-
MDW
4h 10m
1 stop
$474Delta
Mon, Nov 30 - Thu, Dec 3
Delta Logo
9:30 am - 5:17 pm
MDW
-
GPT
7h 47m
2 stops
Delta Logo
6:00 pm - 10:10 pm
GPT
-
MDW
4h 10m
1 stop
$479Delta
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 50% of cases, with the average delay over the past year being 119 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 56% of their flights encountering any delays.

Find deals

Good to know

Cheapest flight$181
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 5 days, the lowest price for a flight from Chicago Midway Airport to Gulfport was $181 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.
7.8
DeltaOverall score based on 8406 reviews
8.1Boarding
7.8Comfort
7.8Entertainment
8.5Crew
7.2Food
Airline reviews

Horrible. Faucet in sink not working, wifi not working. Didn’t bring food or snacks

2.0 MediocreMargaret, Jun 2026
MSY - LGA
Read more Delta reviews

Horrible. Faucet in sink not working, wifi not working. Didn’t bring food or snacks

Flight was delayed before take off and at landing. Baggage took 20 minutes. Flight crew would not serve full soft drink and had to ask multiple times before receiving water.

From checking to boarding, it was a seamless experience. The service agents were so helpful. The flight crew was so pleasant.

Gate agent showed up 20 minutes before boarding and was not at all friendly. Had to take this flight due to the one on the day before being cancelled and any later options were already full with long standby lists. Despite having paid for Delta Comfort seats, Delta did not allow me (or anyone) to choose their seat. The agent assigned them for everyone just prior to boarding. Self seat selection was allowed on the original flight. Flight staff was great - very friendly.

Flight attendants were great. Cheerful, upbeat and friendly. Jet, in particular, was fantastic.

I have Precheck. Flew HPN to DEN and return this past weekend. Delta didn't attach my Precheck number to this trip. So it was waiting in general line especially in Denver. Unavailable.

Original flight was delayed, then cancelled and the gate staff did not expedite rebooking. Also, no instructions were given that a ticket number was needed before being called to facilitate rebooking. This could have been much more organized.

Be on time? When not on time a circling for over an hour offer more than 1 bag of chips to the passengers? It was a 7 hour flight by the time we got done.

Five hour delays every hour, I wish it were all at once

Flight delayed four separate times. I’m now one hour hours late to landing.

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)