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Cheap flights from Chicago Midway Airport to Gulfport from $251

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 8/6. 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
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

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
6:05 am - 1:11 pm
MDW
-
GPT
7h 06m
1 stop
Delta Logo
5:59 pm - 10:44 pm
GPT
-
MDW
4h 45m
1 stop
$301Delta
Wed, Sep 9 - Wed, Sep 16
Delta Logo
1:25 pm - 8:53 pm
MDW
-
GPT
7h 28m
2 stops
Delta Logo
4:00 pm - 10:36 pm
GPT
-
MDW
6h 36m
1 stop
$306Delta
Sat, Aug 29 - Sat, Sep 5
Delta Logo
9:29 am - 8:49 pm
MDW
-
GPT
11h 20m
2 stops
Delta Logo
5:59 pm - 10:44 pm
GPT
-
MDW
4h 45m
1 stop
$306Delta
Wed, Sep 9 - Wed, Sep 16
Delta Logo
4:30 pm - 8:49 pm
MDW
-
GPT
4h 19m
1 stop
Delta Logo
5:59 pm - 10:44 pm
GPT
-
MDW
4h 45m
1 stop
$330Delta
Tue, Sep 8 - Tue, Sep 15

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Delta flights from Chicago Midway Airport to Gulfport

Our best Delta deals on Chicago Midway Airport to Gulfport flight tickets
Delta
Sep 9
MDW6:05 amChicago Midway
7h 06m
1 stop
GPT1:11 pmGulfport Biloxi Regional
Sep 16
GPT5:59 pmGulfport Biloxi Regional
4h 45m
1 stop
MDW10:44 pmChicago Midway
$301
Delta
Sep 9
MDW9:29 amChicago Midway
11h 20m
2 stops
GPT8:49 pmGulfport Biloxi Regional
Sep 16
GPT5:59 pmGulfport Biloxi Regional
4h 45m
1 stop
MDW10:44 pmChicago Midway
$306
Delta
Sep 8
MDW4:30 pmChicago Midway
4h 19m
1 stop
GPT8:49 pmGulfport Biloxi Regional
Sep 15
GPT5:59 pmGulfport Biloxi Regional
4h 45m
1 stop
MDW10:44 pmChicago Midway
$330

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 July 29, 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

Wed 9/9

6:05 am-1:11 pm

1 stop7h 06m

Gulfport Biloxi Regional

Wed 9/16

5:59 pm-10:44 pm

1 stop4h 45m

$301

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Sat 8/29

1:25 pm-8:53 pm

2 stops7h 28m

Gulfport Biloxi Regional

Sat 9/5

4:00 pm-10:36 pm

1 stop6h 36m

$306

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Wed 9/9

9:29 am-8:49 pm

2 stops11h 20m

Gulfport Biloxi Regional

Wed 9/16

5:59 pm-10:44 pm

1 stop4h 45m

$306
Quickest round-trip

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Tue 9/8

4:30 pm-8:49 pm

1 stop4h 19m

Gulfport Biloxi Regional

Tue 9/15

5:59 pm-10:44 pm

1 stop4h 45m

$330
Cheapest one-way

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Thu 8/6

6:05 am-6:45 pm

2 stops12h 40m

$251

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Tue 8/4

6:05 am-1:03 pm

1 stop6h 58m

$267

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Tue 8/4

1:25 pm-10:21 pm

2 stops8h 56m

$272

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Thu 9/3

11:50 am-7:41 am

2 stops19h 51m

$285

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Thu 8/6

6:05 am-1:03 pm

1 stop6h 58m

$306
Quickest one-way

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Fri 8/7

12:46 pm-5:15 pm

1 stop4h 29m

$306

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 14 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 83% 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 31m

Direct flights

None
The fastest flight from Chicago Midway Airport to Gulfport takes 4h 31m
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 31m 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
7.8
8,486 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.

An easier way to manage your Gulfport trip

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