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Cheap flights from Chicago Midway Airport to Gulfport from $209

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Gulfport departing on 5/29. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Chicago Midway Airport to Gulfport

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
5:25 pm - 10:07 pm
MDW
-
GPT
4h 42m
1 stop
Delta Logo
6:00 am - 11:56 am
GPT
-
MDW
5h 56m
1 stop
$291Delta
Tue, Nov 3 - Sat, Nov 7
Delta Logo
5:25 pm - 10:06 pm
MDW
-
GPT
4h 41m
1 stop
Delta Logo
6:00 am - 11:56 am
GPT
-
MDW
5h 56m
1 stop
$300Delta
Fri, Oct 2 - Tue, Oct 6
Delta Logo
5:25 pm - 10:06 pm
MDW
-
GPT
4h 41m
1 stop
Delta Logo
10:30 am - 6:37 pm
GPT
-
MDW
8h 07m
2 stops
$305Delta
Fri, Oct 2 - Tue, Oct 6
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
$310Delta
Wed, Jun 17 - Tue, Jun 23
Delta Logo
10:35 am - 5:17 pm
MDW
-
GPT
6h 42m
1 stop
Delta Logo
6:00 am - 12:33 pm
GPT
-
MDW
6h 33m
2 stops
$314Delta
Thu, Nov 5 - Sun, Nov 8
Delta Logo
9:30 am - 5:17 pm
MDW
-
GPT
7h 47m
2 stops
Delta Logo
6:00 am - 12:33 pm
GPT
-
MDW
6h 33m
2 stops
$319Delta
Thu, Nov 5 - Sun, Nov 8
Delta Logo
10:35 am - 5:17 pm
MDW
-
GPT
6h 42m
1 stop
Delta Logo
6:00 am - 11:56 am
GPT
-
MDW
5h 56m
1 stop
$325Delta
Wed, Nov 4 - Sun, Nov 8
Delta Logo
1:00 pm - 10:07 pm
MDW
-
GPT
9h 07m
2 stops
Delta Logo
10:30 am - 4:25 pm
GPT
-
MDW
5h 55m
1 stop
$330Delta
Fri, Nov 6 - Tue, Nov 10
Delta Logo
10:35 am - 5:17 pm
MDW
-
GPT
6h 42m
1 stop
Delta Logo
6:00 am - 11:56 am
GPT
-
MDW
5h 56m
1 stop
$334Delta
Thu, Nov 5 - Sun, Nov 8
Delta Logo
5:25 pm - 10:06 pm
MDW
-
GPT
4h 41m
1 stop
Delta Logo
10:30 am - 4:25 pm
GPT
-
MDW
5h 55m
1 stop
$335Delta
Fri, Oct 2 - Tue, Oct 6

Delta flights from Chicago Midway Airport to Gulfport

Our best Delta deals on Chicago Midway Airport to Gulfport flight tickets
Delta
Nov 3
MDW5:25 pmChicago Midway
4h 42m
1 stop
GPT10:07 pmGulfport Biloxi Regional
Nov 7
GPT6:00 amGulfport Biloxi Regional
5h 56m
1 stop
MDW11:56 amChicago Midway
$291
Delta
Oct 2
MDW5:25 pmChicago Midway
4h 41m
1 stop
GPT10:06 pmGulfport Biloxi Regional
Oct 6
GPT6:00 amGulfport Biloxi Regional
5h 56m
1 stop
MDW11:56 amChicago Midway
$300
Delta
Oct 2
MDW5:25 pmChicago Midway
4h 41m
1 stop
GPT10:06 pmGulfport Biloxi Regional
Oct 6
GPT10:30 amGulfport Biloxi Regional
8h 07m
2 stops
MDW6:37 pmChicago Midway
$305

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Gulfport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated May 22, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Gulfport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Tue 11/3

5:25 pm-10:07 pm

1 stop4h 42m

Gulfport Biloxi Regional

Sat 11/7

6:00 am-11:56 am

1 stop5h 56m

$291

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Fri 10/2

5:25 pm-10:06 pm

1 stop4h 41m

Gulfport Biloxi Regional

Tue 10/6

6:00 am-11:56 am

1 stop5h 56m

$300

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Fri 10/2

5:25 pm-10:06 pm

1 stop4h 41m

Gulfport Biloxi Regional

Tue 10/6

10:30 am-6:37 pm

2 stops8h 07m

$305

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Wed 6/17

6:00 am-1:07 pm

1 stop7h 07m

Gulfport Biloxi Regional

Tue 6/23

5:56 pm-10:17 pm

1 stop4h 21m

$310

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Thu 11/5

10:35 am-5:17 pm

1 stop6h 42m

Gulfport Biloxi Regional

Sun 11/8

6:00 am-12:33 pm

2 stops6h 33m

$314

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Thu 11/5

9:30 am-5:17 pm

2 stops7h 47m

Gulfport Biloxi Regional

Sun 11/8

6:00 am-12:33 pm

2 stops6h 33m

$319

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Wed 11/4

10:35 am-5:17 pm

1 stop6h 42m

Gulfport Biloxi Regional

Sun 11/8

6:00 am-11:56 am

1 stop5h 56m

$325

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Fri 11/6

1:00 pm-10:07 pm

2 stops9h 07m

Gulfport Biloxi Regional

Tue 11/10

10:30 am-4:25 pm

1 stop5h 55m

$330

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Thu 11/5

10:35 am-5:17 pm

1 stop6h 42m

Gulfport Biloxi Regional

Sun 11/8

6:00 am-11:56 am

1 stop5h 56m

$334
Quickest round-trip

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Fri 10/2

5:25 pm-10:06 pm

1 stop4h 41m

Gulfport Biloxi Regional

Tue 10/6

10:30 am-4:25 pm

1 stop5h 55m

$335

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Gulfport from

How to get the cheapest flight ticket from Chicago Midway Airport to Gulfport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies from Chicago Midway to Gulfport Biloxi Regional?

Delta is the most popular carrier operating from Chicago Midway to Gulfport Biloxi Regional

What airlines fly to Gulfport?

Southwest, Delta and Frontier are the top three most popular airlines that fly to Gulfport from Chicago Midway Airport according to our data. Southwest is the first choice among our users, with 79% of people opting to fly with this airline when traveling to Gulfport. Keep in mind that there are 3 different airlines that fly to Gulfport on a routine basis, so you have a few additional options to choose from.

When to book flights from Chicago Midway Airport to Gulfport

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Gulfport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Gulfport (MDW to GPT) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Gulfport

Fastest flight time

4h 21m

Direct flights

None
The fastest flight from Chicago Midway Airport to Gulfport takes 4h 21m
There are no direct flights from Chicago Midway Airport to Gulfport. There are no popular flight routes from Chicago Midway Airport to Gulfport.
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Gulfport

  • How far is Chicago Midway to Gulfport Biloxi Regional by plane?

    There are 792.0 mi between Chicago Midway and Gulfport Biloxi Regional. Typically, this will take 4h 21m by plane in normal conditions.

  • When did momondo last update prices for flights from Chicago Midway Airport to Gulfport Biloxi Regional Airport?

    Prices for flights from Chicago Midway Airport to Gulfport Biloxi Regional Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Chicago Midway Airport to Gulfport Biloxi Regional Airport?

  • How old do you have to be to fly from Chicago Midway Airport to Gulfport Biloxi Regional Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago Midway Airport to Gulfport Biloxi Regional Airport.

  • What documentation or ID do you need to fly to Gulfport Biloxi Regional Airport?

    The travel and health documents required for your trip to Gulfport Biloxi Regional Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Gulfport Biloxi Regional Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular airline from Chicago Midway Airport to Gulfport?

Best airlines flying from Chicago Midway Airport to Gulfport

Compare and see reviews for airlines that fly from Chicago Midway Airport to Gulfport with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $269Free CancellationRating
7.9
8,449 reviews
Search Delta flights

Traveling to a place near Gulfport?

Book flights to Gulfport if you plan to visit one of these locations
Biloxi
Ocean Springs
D'Iberville

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Gulfport?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Gulfport. momondo saves you time and could save you money on your trip.

Can I find flights from Chicago to Gulfport with flexible booking policies on momondo?

momondo does allow users to show only those flights to Gulfport from Chicago which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Chicago to Gulfport?

momondo helps you find the best flight between Chicago and Gulfport by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Chicago to Gulfport right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Gulfport, momondo offers a useful price alert feature which will track prices for flights to Gulfport from Chicago and alert you when they change.

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