MDW - GPT

$136 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 2/15. 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
$254
Multiple Airlines
Sun 2/15Thu 2/19
MDW - GPT • 1 stop
Cheapest one-way
$136
Multiple Airlines
Sun 2/15
MDW - GPT • 1 stop
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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

Sun, Feb 15 - Thu, Feb 19
Multiple Airlines Logo
7:30 am - 6:40 pm
MDW
-
GPT
11h 10m
1 stop
Multiple Airlines Logo
7:20 pm - 2:26 pm
GPT
-
MDW
19h 06m
1 stop
$254Multiple Airlines
Tue, Mar 17 - Tue, Mar 24
Delta Logo
10:45 am - 5:11 pm
MDW
-
GPT
6h 26m
1 stop
Delta Logo
5:57 pm - 10:31 pm
GPT
-
MDW
4h 34m
1 stop
$269Delta
Sun, Mar 8 - Fri, Mar 13
Multiple Airlines Logo
8:00 am - 6:40 pm
MDW
-
GPT
10h 40m
1 stop
Multiple Airlines Logo
6:54 pm - 7:47 pm
GPT
-
MDW
48h 53m
2 stops
$286Multiple Airlines
Thu, Feb 19 - Sun, Feb 22
Multiple Airlines Logo
7:30 am - 6:40 pm
MDW
-
GPT
11h 10m
1 stop
Multiple Airlines Logo
7:20 pm - 1:08 pm
GPT
-
MDW
17h 48m
2 stops
$317Multiple Airlines
Thu, Feb 19 - Sun, Feb 22
Multiple Airlines Logo
7:30 am - 6:40 pm
MDW
-
GPT
11h 10m
1 stop
Multiple Airlines Logo
7:20 pm - 8:27 pm
GPT
-
MDW
25h 07m
1 stop
$358Multiple Airlines
Fri, Feb 20 - Mon, Feb 23
Delta Logo
12:45 pm - 5:15 pm
MDW
-
GPT
4h 30m
1 stop
Delta Logo
6:00 pm - 10:31 pm
GPT
-
MDW
4h 31m
1 stop
$359Delta
Thu, Mar 19 - Sun, Mar 22
Multiple Airlines Logo
11:00 am - 6:40 pm
MDW
-
GPT
7h 40m
1 stop
Multiple Airlines Logo
7:20 pm - 2:21 pm
GPT
-
MDW
19h 01m
1 stop
$363Multiple Airlines
Tue, Mar 17 - Mon, Mar 23
Delta Logo
10:45 am - 5:11 pm
MDW
-
GPT
6h 26m
1 stop
Delta Logo
5:57 pm - 9:56 am
GPT
-
MDW
15h 59m
1 stop
$378Delta
Fri, Feb 20 - Fri, Mar 6
Delta Logo
12:45 pm - 5:15 pm
MDW
-
GPT
4h 30m
1 stop
Delta Logo
6:00 pm - 10:31 pm
GPT
-
MDW
4h 31m
1 stop
$379Delta
Wed, Mar 18 - Tue, Mar 24
Delta Logo
9:35 am - 10:15 pm
MDW
-
GPT
12h 40m
2 stops
Delta Logo
5:57 pm - 10:31 pm
GPT
-
MDW
4h 34m
1 stop
$389Delta
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 29% of cases, with the average delay over the past year being 74 minutes.

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

Typically, flights leaving in the morning 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 Thursday 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 44% of their flights encountering any delays.

Good to know

Cheapest flight$136
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 $136 for a one-way ticket and $254 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 8130 reviews
7.2Food
8.1Boarding
8.5Crew
7.8Entertainment
7.9Comfort
Airline reviews

I didn't take this flight. I changed the flight. Why am I getting surveys and notifications on flights that I change. Seems like a defect with Kayak.

2.0 MediocreTodd, Jan 2026
IAH - ATL
Read more Delta reviews

I didn't take this flight. I changed the flight. Why am I getting surveys and notifications on flights that I change. Seems like a defect with Kayak.

Delta One is extraordinary. I fly business when somebody hires me. I just wonder why there is such a chasm between business class and the insanely inhumane and nonsensical coach. The seats are not large enough to fit even my tiny wife. We fly 10% of what we did because we don’t want to pay 5-10 k but for $400 it’s unbearable. It seems like the accountants took over and made stupid decisions. Screw in 20 extra seats and make it so unbearable that people fly 90% less. Just put the damn price up and put some proper chairs in. But business, yay.

Timing, quality of service, promptness and courtesy of the staff

It was last minute due to weather - considering - it was amazing! Good smiles, friendly staff and they were making sure we knew what was going on when and where.

delta last minute gave me a boarding pass for a different flight with no confirmation that they were changing it

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

was sitting in the jet bridge for 10 minutes in -20 degree weather waiting for my bag

Outdated equipment in disrepair, wifi inoperable. Broken seats, taped air vents, generally poor condition, the 717 showed its age and lack of upkeep.

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

Information on your arrival and departure airports