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Cheap flights from Chicago Midway Airport to Gulfport from $149

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 1/19. 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
5:31 pm - 9:53 pm
MDW
-
GPT
4h 22m1 stop
Delta Logo
4:00 pm - 10:07 pm
GPT
-
MDW
6h 07m1 stop
$199Delta
Tue, Jan 6 - Tue, Jan 13
Delta Logo
9:32 am - 9:33 am
MDW
-
GPT
24h 01m2 stops
Delta Logo
4:00 pm - 10:07 pm
GPT
-
MDW
6h 07m1 stop
$246Delta
Wed, Jan 7 - Sat, Jan 10
Delta Logo
9:32 am - 9:53 pm
MDW
-
GPT
12h 21m2 stops
Delta Logo
4:00 pm - 12:48 pm
GPT
-
MDW
20h 48m2 stops
$318Delta
Wed, Jan 7 - Sat, Jan 10
Delta Logo
5:38 pm - 10:19 pm
MDW
-
GPT
4h 41m1 stop
Delta Logo
6:02 pm - 10:29 pm
GPT
-
MDW
4h 27m1 stop
$393Delta
Tue, Mar 17 - Sun, Mar 22
Delta Logo
1:05 pm - 5:17 pm
MDW
-
GPT
4h 12m1 stop
Delta Logo
6:00 am - 11:56 am
GPT
-
MDW
5h 56m1 stop
$457Delta
Tue, Jun 2 - Fri, Jun 5
Delta Logo
12:47 pm - 5:17 pm
MDW
-
GPT
4h 30m1 stop
Delta Logo
10:04 am - 3:25 pm
GPT
-
MDW
5h 21m1 stop
$498Delta
Tue, Mar 17 - Sat, Mar 21
Delta Logo
10:49 am - 5:16 pm
MDW
-
GPT
6h 27m1 stop
Delta Logo
5:21 pm - 10:22 pm
GPT
-
MDW
5h 01m1 stop
$518Delta
Fri, Dec 19 - Tue, Dec 23
Delta Logo
6:00 am - 1:26 pm
MDW
-
GPT
7h 26m1 stop
Delta Logo
4:00 pm - 10:07 pm
GPT
-
MDW
6h 07m1 stop
$563Delta
Fri, Jan 2 - Mon, Jan 5
Delta Logo
9:50 am - 4:35 pm
MDW
-
GPT
6h 45m1 stop
Delta Logo
6:00 am - 11:58 am
GPT
-
MDW
5h 58m1 stop
$618Delta
Tue, Dec 30 - Fri, Jan 2
Delta Logo
6:08 pm - 9:40 pm
MDW
-
GPT
27h 32m2 stops
Delta Logo
5:21 pm - 12:48 pm
GPT
-
MDW
19h 27m2 stops
$646Delta
Tue, Dec 30 - Sun, Jan 4

Delta flights from Chicago Midway Airport to Gulfport

Our best Delta deals on Chicago Midway Airport to Gulfport flight tickets
Delta
Jan 6
MDW5:31 pmChicago Midway
4h 22m
1 stop
GPT9:53 pmGulfport Biloxi Regional
Jan 13
GPT4:00 pmGulfport Biloxi Regional
6h 07m
1 stop
MDW10:07 pmChicago Midway
$199
Find similar
Delta
Jan 7
MDW9:32 amChicago Midway
24h 01m
2 stops
GPT9:33 amGulfport Biloxi Regional
Jan 10
GPT4:00 pmGulfport Biloxi Regional
6h 07m
1 stop
MDW10:07 pmChicago Midway
$246
Find similar
Delta
Jan 7
MDW9:32 amChicago Midway
12h 21m
2 stops
GPT9:53 pmGulfport Biloxi Regional
Jan 10
GPT4:00 pmGulfport Biloxi Regional
20h 48m
2 stops
MDW12:48 pmChicago Midway
$318
Find similar

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 December 4, 2025.
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

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Tue 1/6

5:31 pm-9:53 pm

1 stop4h 22m

Gulfport Biloxi Regional

Tue 1/13

4:00 pm-10:07 pm

1 stop6h 07m

$199

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Wed 1/7

9:32 am-9:33 am

2 stops24h 01m

Gulfport Biloxi Regional

Sat 1/10

4:00 pm-10:07 pm

1 stop6h 07m

$246

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Wed 1/7

9:32 am-9:53 pm

2 stops12h 21m

Gulfport Biloxi Regional

Sat 1/10

4:00 pm-12:48 pm

2 stops20h 48m

$318

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Tue 3/17

5:38 pm-10:19 pm

1 stop4h 41m

Gulfport Biloxi Regional

Sun 3/22

6:02 pm-10:29 pm

1 stop4h 27m

$393

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Tue 6/2

1:05 pm-5:17 pm

1 stop4h 12m

Gulfport Biloxi Regional

Fri 6/5

6:00 am-11:56 am

1 stop5h 56m

$457

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Tue 3/17

12:47 pm-5:17 pm

1 stop4h 30m

Gulfport Biloxi Regional

Sat 3/21

10:04 am-3:25 pm

1 stop5h 21m

$498

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Fri 12/19

10:49 am-5:16 pm

1 stop6h 27m

Gulfport Biloxi Regional

Tue 12/23

5:21 pm-10:22 pm

1 stop5h 01m

$518

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Fri 1/2

6:00 am-1:26 pm

1 stop7h 26m

Gulfport Biloxi Regional

Mon 1/5

4:00 pm-10:07 pm

1 stop6h 07m

$563

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Tue 12/30

9:50 am-4:35 pm

1 stop6h 45m

Gulfport Biloxi Regional

Fri 1/2

6:00 am-11:58 am

1 stop5h 58m

$618

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Tue 12/30

6:08 pm-9:40 pm

2 stops27h 32m

Gulfport Biloxi Regional

Sun 1/4

5:21 pm-12:48 pm

2 stops19h 27m

$646

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 day to depart on your flight to Gulfport?

The cheapest day to depart from Chicago Midway Airport to Gulfport is on a Tuesday when prices can be found for as low as $314. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Chicago Midway Airport to Gulfport for around $464.

What is the cheapest time of day to depart on your flight to Gulfport?

According to our data, the cheapest time of day to fly to Gulfport is in the morning. momondo users have found flights departing from Chicago Midway Airport to Gulfport in the morning for as low as $390. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In contrast, the most expensive time of day to depart to Gulfport is at noon when prices are around $493.

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 12m

Direct flights

None
The fastest flight from Chicago Midway Airport to Gulfport takes 4h 12m
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

  • 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 12m 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
8,011 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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