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Cheap flights from Chicago Midway Airport to Gulfport from $148

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 10/30. 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

Delta Logo
4:25 pm - 9:39 pmMDW-GPT
5h 14m1 stop
Delta Logo
6:08 am - 11:48 amGPT-MDW
5h 40m1 stop
$284Delta
Find Deal
Sat, Sep 27 - Tue, Sep 30
Delta Logo
4:25 pm - 9:39 pmMDW-GPT
5h 14m1 stop
Delta Logo
6:08 am - 11:48 amGPT-MDW
5h 40m1 stop
$299Delta
Find Deal
Sat, Sep 27 - Wed, Oct 1
Delta Logo
4:25 pm - 9:39 pmMDW-GPT
5h 14m1 stop
Delta Logo
6:08 am - 11:48 amGPT-MDW
5h 40m1 stop
$309Delta
Find Deal
Sat, Sep 27 - Wed, Oct 1
Delta Logo
5:04 pm - 9:50 pmMDW-GPT
4h 46m1 stop
Delta Logo
6:05 pm - 10:14 pmGPT-MDW
4h 09m1 stop
$318Delta
Find Deal
Wed, Oct 15 - Tue, Oct 21
Delta Logo
4:25 pm - 9:39 pmMDW-GPT
5h 14m1 stop
Delta Logo
6:08 am - 11:48 amGPT-MDW
5h 40m1 stop
$324Delta
Find Deal
Sat, Sep 27 - Wed, Oct 1
Delta Logo
4:25 pm - 9:39 pmMDW-GPT
5h 14m1 stop
Delta Logo
6:04 pm - 8:40 amGPT-MDW
14h 36m2 stops
$387Delta
Find Deal
Sat, Sep 27 - Wed, Oct 1
Delta Logo
4:25 pm - 9:39 pmMDW-GPT
5h 14m1 stop
Delta Logo
6:04 pm - 8:40 amGPT-MDW
14h 36m2 stops
$412Delta
Find Deal
Sat, Sep 27 - Wed, Oct 1
Delta Logo
5:34 pm - 10:07 pmMDW-GPT
4h 33m1 stop
Delta Logo
12:30 pm - 4:39 pmGPT-MDW
4h 09m1 stop
$429Delta
Find Deal
Sun, Nov 23 - Fri, Nov 28
Multiple Airlines Logo
5:20 pm - 7:19 pmMDW-GPT
49h 59m2 stops
Multiple Airlines Logo
7:55 pm - 4:20 pmGPT-MDW
20h 25m1 stop
$499Multiple Airlines
Find Deal
Tue, Oct 14 - Thu, Oct 23
Multiple Airlines Logo
7:57 am - 9:25 amMDW-GPT
25h 28m1 stop
Multiple Airlines Logo
7:50 pm - 7:02 amGPT-MDW
11h 12m1 stop
$652Multiple Airlines
Find Deal
Mon, Dec 22 - Sun, Jan 4

Delta flights from Chicago Midway Airport to Gulfport

Our best Delta deals on Chicago Midway Airport to Gulfport flight tickets
Delta
Sep 27
MDW4:25 pmChicago Midway
5h 14m
1 stop
GPT9:39 pmGulfport Biloxi Regional
Sep 30
GPT6:08 amGulfport Biloxi Regional
5h 40m
1 stop
MDW11:48 amChicago Midway
$284
Find similar
Delta
Sep 27
MDW4:25 pmChicago Midway
5h 14m
1 stop
GPT9:39 pmGulfport Biloxi Regional
Oct 1
GPT6:08 amGulfport Biloxi Regional
5h 40m
1 stop
MDW11:48 amChicago Midway
$299
Find similar
Delta
Sep 27
MDW4:25 pmChicago Midway
5h 14m
1 stop
GPT9:39 pmGulfport Biloxi Regional
Oct 1
GPT6:08 amGulfport Biloxi Regional
5h 40m
1 stop
MDW11:48 amChicago Midway
$309
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 September 16, 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

Sat 9/27

4:25 pm-9:39 pm

1 stop5h 14m

Gulfport Biloxi Regional

Tue 9/30

6:08 am-11:48 am

1 stop5h 40m

$284

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Sat 9/27

4:25 pm-9:39 pm

1 stop5h 14m

Gulfport Biloxi Regional

Wed 10/1

6:08 am-11:48 am

1 stop5h 40m

$299

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Sat 9/27

4:25 pm-9:39 pm

1 stop5h 14m

Gulfport Biloxi Regional

Wed 10/1

6:08 am-11:48 am

1 stop5h 40m

$309

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Wed 10/15

5:04 pm-9:50 pm

1 stop4h 46m

Gulfport Biloxi Regional

Tue 10/21

6:05 pm-10:14 pm

1 stop4h 09m

$318

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Sat 9/27

4:25 pm-9:39 pm

1 stop5h 14m

Gulfport Biloxi Regional

Wed 10/1

6:08 am-11:48 am

1 stop5h 40m

$324

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Sat 9/27

4:25 pm-9:39 pm

1 stop5h 14m

Gulfport Biloxi Regional

Wed 10/1

6:04 pm-8:40 am

2 stops14h 36m

$387

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Sat 9/27

4:25 pm-9:39 pm

1 stop5h 14m

Gulfport Biloxi Regional

Wed 10/1

6:04 pm-8:40 am

2 stops14h 36m

$412

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Sun 11/23

5:34 pm-10:07 pm

1 stop4h 33m

Gulfport Biloxi Regional

Fri 11/28

12:30 pm-4:39 pm

1 stop4h 09m

$429

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Tue 10/14

5:20 pm-7:19 pm

2 stops49h 59m

Gulfport Biloxi Regional

Thu 10/23

7:55 pm-4:20 pm

1 stop20h 25m

$499

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Mon 12/22

7:57 am-9:25 am

1 stop25h 28m

Gulfport Biloxi Regional

Sun 1/4

7:50 pm-7:02 am

1 stop11h 12m

$652

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

Direct flights

None
There are no direct flights from Chicago Midway Airport to Gulfport. There are no popular flight routes from Chicago Midway Airport to Gulfport.
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  • 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 26m 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
7,957 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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