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GPT - MDW

$201 Find Cheap Flights from Gulfport to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Gulfport to Midway departing on 4/22. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Gulfport to Chicago, 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 Gulfport to Chicago, as well as popular online travel agencies
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Cheap Flight Deals from Gulfport to Midway (GPT-MDW)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Gulfport to Midway 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.

Recent round-trip flight deals from Gulfport to Midway

KAYAK's recommended round-trip deals from the most popular airlines that fly from Gulfport to Midway.
Discover the best prices for you by selecting your travel dates on KAYAK.
Choose your dates
6:02 pm - 10:22 pmGPT-MDW
4h 20m1 stop
12:48 pm - 5:16 pmMDW-GPT
4h 28m1 stop
$249Delta
Find Deal
Thu, May 1 - Tue, May 6
10:04 am - 4:12 pmGPT-MDW
6h 08m1 stop
6:04 am - 12:12 pmMDW-GPT
6h 08m1 stop
$259Delta
Find Deal
Thu, Apr 10 - Mon, Apr 14
10:30 am - 2:56 pmGPT-MDW
4h 26m1 stop
3:40 pm - 10:06 pmMDW-GPT
6h 26m1 stop
$368Delta
Find Deal
Wed, Jul 9 - Tue, Jul 15
10:30 am - 2:56 pmGPT-MDW
4h 26m1 stop
3:40 pm - 10:06 pmMDW-GPT
6h 26m1 stop
$423Delta
Find Deal
Wed, Jul 9 - Tue, Jul 15
9:20 am - 3:20 pmGPT-MDW
6h 00m1 stop
4:15 pm - 9:36 pmMDW-GPT
5h 21m1 stop
$467Delta
Find Deal
Wed, Jun 4 - Sat, Jun 7
6:00 am - 11:55 amGPT-MDW
5h 55m1 stop
10:35 am - 5:16 pmMDW-GPT
6h 41m1 stop
$563Delta
Find Deal
Thu, Jul 24 - Mon, Jul 28
10:06 am - 3:39 pmGPT-MDW
5h 33m1 stop
6:00 am - 1:17 pmMDW-GPT
7h 17m1 stop
$685Delta
Find Deal
Thu, Jun 19 - Mon, Jun 23
10:06 am - 3:39 pmGPT-MDW
5h 33m1 stop
6:00 am - 1:17 pmMDW-GPT
7h 17m1 stop
$689Delta
Find Deal
Thu, Jun 19 - Mon, Jun 23
6:02 pm - 10:22 pmGPT-MDW
4h 20m1 stop
9:20 am - 5:16 pmMDW-GPT
7h 56m2 stops
$786Delta
Find Deal
Thu, May 1 - Tue, May 6
10:04 am - 6:02 pmGPT-MDW
7h 58m2 stops
6:04 am - 12:12 pmMDW-GPT
6h 08m1 stop
$791Delta
Find Deal
Thu, Apr 10 - Mon, Apr 14

Good to know

Cheapest flight

$201
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
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 Gulfport to Chicago Midway Airport flights

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

    In the last 3 days, the lowest price for a flight from Gulfport to Chicago Midway Airport was $201 for a one-way ticket and $249 for a round-trip.

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

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

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

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

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

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

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

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

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

    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 Gulfport to Chicago Midway Airport.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Gulfport 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 Gulfport to Chicago Midway Airport?

    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 Chicago Midway Airport with an airline and back to Gulfport with another airline. Booking your flights between Gulfport and MDW 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 Gulfport to Chicago Midway Airport?

    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 Chicago Midway Airport from Gulfport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top airline flying from Gulfport to Midway

 
See real verified KAYAK customer reviews for airlines flying from Gulfport to Chicago. 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 Gulfport to Midway? 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.
8.0
DeltaOverall score based on 7895 reviews
8.5Crew
8.2Boarding
8.0Comfort
7.3Food
7.9Entertainment
Airline reviews

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

10.0 ExcellentTiffany, Mar 2025MIA - DCA
Read more Delta reviews

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

The plane was old with small storage areas that had problems closing/latching and not enough storage for everyone, and worn, damaged seats. Service was great but feel a little unsafe on such well used planes.

Terrible and im avoiding them in the future. My initial flight was delayed causing me to rebook my flight and when speaking with the representative to rebook I explained this is the second time my flights were delayed and they did nothing to help me. I wasn't booked to comfort plus or given a voucher or anything. I was almost late for my meeting that I needed to attend on Monday because of the games delta played delaying my flights even more and putting me in the very back of the plane next to an extremely intoxicated passenger

Flights on time. .Ride was as comfortable as can be expected in steerage. Luggage arrived at destination. Attendants were fairly friendly.

Great staff. Wifi is terrible. Signing up for skylines is a painstaking process. Had to call customer service just to get my flight itinerary and confirmation sent to me. Consistent delays. A well staffed company that is run so poorly. Upper management needs to be renewed.

The WiFi didn't seem as fast as it normally is

Thank you for not flipping the plane on the run way. You guys get a 5 star rating for the flight!!!

The crew was wonderful and attentive. The seats near exit row were restrictive. Offer healthy snacks please

Delta is a premier airline so my expectations are most always met.

Seats are much much more comfortable than United, which is what I usually fly

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

Information on your arrival and departure airports

Midway (MDW)
Gulfport (GPT)

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