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Cheap flights from Chicago Midway Airport to Gulfport from $107

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 2/15. 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.
Multiple Airlines Logo
4:46 pm - 5:40 pm
MDW
-
GPT
24h 54m1 stop
Multiple Airlines Logo
7:20 pm - 8:53 pm
GPT
-
MDW
25h 33m1 stop
$250Multiple Airlines
Sat, Mar 7 - Sun, Mar 15
Multiple Airlines Logo
7:30 am - 6:40 pm
MDW
-
GPT
11h 10m1 stop
Multiple Airlines Logo
6:54 pm - 10:19 pm
GPT
-
MDW
27h 25m2 stops
$259Multiple Airlines
Thu, Mar 5 - Mon, Mar 9
Delta Logo
10:49 am - 5:15 pm
MDW
-
GPT
6h 26m1 stop
Delta Logo
6:00 pm - 10:31 pm
GPT
-
MDW
4h 31m1 stop
$269Delta
Fri, Feb 20 - Thu, Feb 26
Delta Logo
10:48 am - 5:15 pm
MDW
-
GPT
6h 27m1 stop
Delta Logo
6:08 pm - 10:22 pm
GPT
-
MDW
4h 14m1 stop
$279Delta
Thu, Jan 22 - Mon, Jan 26
Multiple Airlines Logo
9:16 pm - 8:00 am
MDW
-
GPT
34h 44m2 stops
Multiple Airlines Logo
7:20 pm - 1:08 pm
GPT
-
MDW
17h 48m1 stop
$296Multiple Airlines
Sat, Mar 7 - Sun, Mar 15
Multiple Airlines Logo
6:48 pm - 6:40 pm
MDW
-
GPT
47h 52m2 stops
Multiple Airlines Logo
7:20 pm - 2:26 pm
GPT
-
MDW
19h 06m1 stop
$326Multiple Airlines
Fri, Feb 20 - Thu, Feb 26
Multiple Airlines Logo
6:48 pm - 6:40 pm
MDW
-
GPT
47h 52m2 stops
Multiple Airlines Logo
7:20 pm - 2:26 pm
GPT
-
MDW
19h 06m1 stop
$338Multiple Airlines
Fri, Feb 20 - Thu, Feb 26
Delta Logo
12:45 pm - 5:15 pm
MDW
-
GPT
4h 30m1 stop
Delta Logo
5:57 pm - 10:31 pm
GPT
-
MDW
4h 34m1 stop
$374Delta
Thu, Mar 5 - Mon, Mar 9
Multiple Airlines Logo
10:50 am - 6:40 pm
MDW
-
GPT
7h 50m1 stop
Multiple Airlines Logo
7:20 pm - 2:11 pm
GPT
-
MDW
18h 51m1 stop
$387Multiple Airlines
Thu, Mar 26 - Sun, Mar 29
Delta Logo
5:40 pm - 10:15 pm
MDW
-
GPT
4h 35m1 stop
Delta Logo
9:48 am - 3:25 pm
GPT
-
MDW
5h 37m1 stop
$404Delta
Tue, Mar 10 - Sat, Mar 14

Delta flights from Chicago Midway Airport to Gulfport

Our best Delta deals on Chicago Midway Airport to Gulfport flight tickets
Delta
Feb 20
MDW10:49 amChicago Midway
6h 26m
1 stop
GPT5:15 pmGulfport Biloxi Regional
Feb 26
GPT6:00 pmGulfport Biloxi Regional
4h 31m
1 stop
MDW10:31 pmChicago Midway
$269
Delta
Jan 22
MDW10:48 amChicago Midway
6h 27m
1 stop
GPT5:15 pmGulfport Biloxi Regional
Jan 26
GPT6:08 pmGulfport Biloxi Regional
4h 14m
1 stop
MDW10:22 pmChicago Midway
$279
Delta
Mar 5
MDW12:45 pmChicago Midway
4h 30m
1 stop
GPT5:15 pmGulfport Biloxi Regional
Mar 9
GPT5:57 pmGulfport Biloxi Regional
4h 34m
1 stop
MDW10:31 pmChicago Midway
$374

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 January 8, 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

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Sat 3/7

4:46 pm-5:40 pm

1 stop24h 54m

Gulfport Biloxi Regional

Sun 3/15

7:20 pm-8:53 pm

1 stop25h 33m

$250

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Thu 3/5

7:30 am-6:40 pm

1 stop11h 10m

Gulfport Biloxi Regional

Mon 3/9

6:54 pm-10:19 pm

2 stops27h 25m

$259

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Fri 2/20

10:49 am-5:15 pm

1 stop6h 26m

Gulfport Biloxi Regional

Thu 2/26

6:00 pm-10:31 pm

1 stop4h 31m

$269

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Thu 1/22

10:48 am-5:15 pm

1 stop6h 27m

Gulfport Biloxi Regional

Mon 1/26

6:08 pm-10:22 pm

1 stop4h 14m

$279

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Sat 3/7

9:16 pm-8:00 am

2 stops34h 44m

Gulfport Biloxi Regional

Sun 3/15

7:20 pm-1:08 pm

1 stop17h 48m

$296

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Fri 2/20

6:48 pm-6:40 pm

2 stops47h 52m

Gulfport Biloxi Regional

Thu 2/26

7:20 pm-2:26 pm

1 stop19h 06m

$326

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Fri 2/20

6:48 pm-6:40 pm

2 stops47h 52m

Gulfport Biloxi Regional

Thu 2/26

7:20 pm-2:26 pm

1 stop19h 06m

$338

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Thu 3/5

12:45 pm-5:15 pm

1 stop4h 30m

Gulfport Biloxi Regional

Mon 3/9

5:57 pm-10:31 pm

1 stop4h 34m

$374

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Thu 3/26

10:50 am-6:40 pm

1 stop7h 50m

Gulfport Biloxi Regional

Sun 3/29

7:20 pm-2:11 pm

1 stop18h 51m

$387

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Tue 3/10

5:40 pm-10:15 pm

1 stop4h 35m

Gulfport Biloxi Regional

Sat 3/14

9:48 am-3:25 pm

1 stop5h 37m

$404

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

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 $253Free CancellationRating
7.9
8,025 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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