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Cheap flights from Chicago Midway Airport to Gulfport from $108

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
7:30 am - 6:40 pm
MDW
-
GPT
11h 10m
1 stop
Multiple Airlines Logo
7:20 pm - 1:08 pm
GPT
-
MDW
17h 48m
2 stops
$245Multiple Airlines
Sun, Feb 15 - Sun, Feb 22
Delta Logo
5:40 pm - 10:15 pm
MDW
-
GPT
4h 35m
1 stop
Delta Logo
5:57 pm - 10:31 pm
GPT
-
MDW
4h 34m
1 stop
$269Delta
Thu, Mar 12 - Mon, Mar 16
Multiple Airlines Logo
7:30 am - 6:40 pm
MDW
-
GPT
11h 10m
1 stop
Multiple Airlines Logo
7:20 pm - 8:27 pm
GPT
-
MDW
25h 07m
1 stop
$277Multiple Airlines
Sun, Feb 15 - Sun, Feb 22
Delta Logo
4:30 pm - 10:15 pm
MDW
-
GPT
5h 45m
1 stop
Delta Logo
5:57 pm - 10:31 pm
GPT
-
MDW
4h 34m
1 stop
$294Delta
Sat, Apr 4 - Wed, Apr 8
Multiple Airlines Logo
9:20 am - 6:40 pm
MDW
-
GPT
9h 20m
1 stop
Multiple Airlines Logo
6:54 pm - 8:07 pm
GPT
-
MDW
25h 13m
2 stops
$305Multiple Airlines
Thu, Apr 2 - Mon, Apr 6
Multiple Airlines Logo
9:20 am - 6:40 pm
MDW
-
GPT
9h 20m
1 stop
Multiple Airlines Logo
7:20 pm - 3:59 pm
GPT
-
MDW
20h 39m
2 stops
$314Multiple Airlines
Thu, Apr 9 - Sun, Apr 12
Delta Logo
4:30 pm - 10:15 pm
MDW
-
GPT
5h 45m
1 stop
Delta Logo
6:02 pm - 10:29 pm
GPT
-
MDW
4h 27m
1 stop
$319Delta
Sat, Apr 4 - Mon, Apr 13
Delta Logo
9:35 am - 10:15 pm
MDW
-
GPT
12h 40m
2 stops
Delta Logo
6:02 pm - 10:29 pm
GPT
-
MDW
4h 27m
1 stop
$340Delta
Tue, Apr 7 - Mon, Apr 13
Delta Logo
9:30 am - 10:15 pm
MDW
-
GPT
12h 45m
2 stops
Delta Logo
5:57 pm - 10:31 pm
GPT
-
MDW
4h 34m
1 stop
$345Delta
Sat, Apr 4 - Wed, Apr 8
Multiple Airlines Logo
11:00 am - 6:40 pm
MDW
-
GPT
7h 40m
1 stop
Multiple Airlines Logo
6:54 pm - 10:19 pm
GPT
-
MDW
27h 25m
2 stops
$349Multiple Airlines
Thu, Mar 12 - Mon, Mar 16

Delta flights from Chicago Midway Airport to Gulfport

Our best Delta deals on Chicago Midway Airport to Gulfport flight tickets
Delta
Mar 12
MDW5:40 pmChicago Midway
4h 35m
1 stop
GPT10:15 pmGulfport Biloxi Regional
Mar 16
GPT5:57 pmGulfport Biloxi Regional
4h 34m
1 stop
MDW10:31 pmChicago Midway
$269
Delta
Apr 4
MDW4:30 pmChicago Midway
5h 45m
1 stop
GPT10:15 pmGulfport Biloxi Regional
Apr 8
GPT5:57 pmGulfport Biloxi Regional
4h 34m
1 stop
MDW10:31 pmChicago Midway
$294
Delta
Apr 4
MDW4:30 pmChicago Midway
5h 45m
1 stop
GPT10:15 pmGulfport Biloxi Regional
Apr 13
GPT6:02 pmGulfport Biloxi Regional
4h 27m
1 stop
MDW10:29 pmChicago Midway
$319

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 21, 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

Sun 2/15

7:30 am-6:40 pm

1 stop11h 10m

Gulfport Biloxi Regional

Sun 2/22

7:20 pm-1:08 pm

2 stops17h 48m

$245

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Thu 3/12

5:40 pm-10:15 pm

1 stop4h 35m

Gulfport Biloxi Regional

Mon 3/16

5:57 pm-10:31 pm

1 stop4h 34m

$269

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Sun 2/15

7:30 am-6:40 pm

1 stop11h 10m

Gulfport Biloxi Regional

Sun 2/22

7:20 pm-8:27 pm

1 stop25h 07m

$277

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Sat 4/4

4:30 pm-10:15 pm

1 stop5h 45m

Gulfport Biloxi Regional

Wed 4/8

5:57 pm-10:31 pm

1 stop4h 34m

$294

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Thu 4/2

9:20 am-6:40 pm

1 stop9h 20m

Gulfport Biloxi Regional

Mon 4/6

6:54 pm-8:07 pm

2 stops25h 13m

$305

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Thu 4/9

9:20 am-6:40 pm

1 stop9h 20m

Gulfport Biloxi Regional

Sun 4/12

7:20 pm-3:59 pm

2 stops20h 39m

$314

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Sat 4/4

4:30 pm-10:15 pm

1 stop5h 45m

Gulfport Biloxi Regional

Mon 4/13

6:02 pm-10:29 pm

1 stop4h 27m

$319

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Tue 4/7

9:35 am-10:15 pm

2 stops12h 40m

Gulfport Biloxi Regional

Mon 4/13

6:02 pm-10:29 pm

1 stop4h 27m

$340

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Sat 4/4

9:30 am-10:15 pm

2 stops12h 45m

Gulfport Biloxi Regional

Wed 4/8

5:57 pm-10:31 pm

1 stop4h 34m

$345

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Thu 3/12

11:00 am-6:40 pm

1 stop7h 40m

Gulfport Biloxi Regional

Mon 3/16

6:54 pm-10:19 pm

2 stops27h 25m

$349

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 27m

Direct flights

None
The fastest flight from Chicago Midway Airport to Gulfport takes 4h 27m
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 27m 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
8,089 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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