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Cheap flights from Gulfport to Chicago from $153

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Gulfport to Chicago departing on 12/4. 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 Gulfport to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
5:21 pm - 10:22 pmGPT-MDW
5h 01m1 stop
Delta Logo
6:00 am - 10:40 amMDW-GPT
4h 40m1 stop
$249Delta
Find Deal
Wed, Dec 24 - Sat, Dec 27
Delta Logo
6:03 pm - 11:40 pmGPT-MDW
5h 37m1 stop
Delta Logo
12:47 pm - 5:13 pmMDW-GPT
4h 26m1 stop
$279Delta
Find Deal
Wed, Nov 12 - Sun, Nov 16
Delta Logo
10:35 am - 3:44 pmGPT-MDW
5h 09m1 stop
Delta Logo
12:50 pm - 5:16 pmMDW-GPT
4h 26m1 stop
$294Delta
Find Deal
Sat, Dec 13 - Tue, Dec 16
Delta Logo
6:00 am - 6:18 pmGPT-MDW
12h 18m2 stops
Delta Logo
10:49 am - 5:16 pmMDW-GPT
6h 27m1 stop
$329Delta
Find Deal
Sat, Dec 13 - Tue, Dec 16
Multiple Airlines Logo
7:55 pm - 1:21 pmGPT-MDW
17h 26m2 stops
Multiple Airlines Logo
3:10 pm - 7:10 pmMDW-GPT
28h 00m1 stop
$335Multiple Airlines
Find Deal
Sun, Dec 21 - Wed, Dec 24
Delta Logo
6:00 am - 6:18 pmGPT-MDW
12h 18m2 stops
Delta Logo
1:14 pm - 2:08 pmMDW-GPT
24h 54m2 stops
$368Delta
Find Deal
Sat, Dec 13 - Tue, Dec 16
Delta Logo
5:21 pm - 10:22 pmGPT-MDW
5h 01m1 stop
Delta Logo
3:29 pm - 9:40 pmMDW-GPT
6h 11m1 stop
$593Delta
Find Deal
Sun, Dec 21 - Wed, Dec 24
Delta Logo
4:00 pm - 10:09 pmGPT-MDW
6h 09m1 stop
Delta Logo
9:34 am - 5:17 pmMDW-GPT
7h 43m2 stops
$697Delta
Find Deal
Thu, Jan 15 - Mon, Jan 19
Delta Logo
10:35 am - 6:08 pmGPT-MDW
7h 33m2 stops
Delta Logo
12:47 pm - 5:13 pmMDW-GPT
4h 26m1 stop
$901Delta
Find Deal
Wed, Nov 12 - Sun, Nov 16
Delta Logo
10:35 am - 6:08 pmGPT-MDW
7h 33m2 stops
Delta Logo
9:34 am - 5:13 pmMDW-GPT
7h 39m2 stops
$2,736Delta
Find Deal
Wed, Nov 12 - Sun, Nov 16

Delta flights from Gulfport to Chicago Midway Airport

Our best Delta deals on Gulfport to Chicago Midway Airport flight tickets
Delta
Dec 24
GPT5:21 pmGulfport Biloxi Regional
5h 01m
1 stop
MDW10:22 pmChicago Midway
Dec 27
MDW6:00 amChicago Midway
4h 40m
1 stop
GPT10:40 amGulfport Biloxi Regional
$249
Find similar
Delta
Nov 12
GPT6:03 pmGulfport Biloxi Regional
5h 37m
1 stop
MDW11:40 pmChicago Midway
Nov 16
MDW12:47 pmChicago Midway
4h 26m
1 stop
GPT5:13 pmGulfport Biloxi Regional
$279
Find similar
Delta
Dec 13
GPT10:35 amGulfport Biloxi Regional
5h 09m
1 stop
MDW3:44 pmChicago Midway
Dec 16
MDW12:50 pmChicago Midway
4h 26m
1 stop
GPT5:16 pmGulfport Biloxi Regional
$294
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Gulfport to Chicago Midway Airport 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 October 30, 2025.
Use the filters below to find and compare flights from Gulfport to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Wed 12/24

5:21 pm-10:22 pm

1 stop5h 01m

Chicago Midway

Sat 12/27

6:00 am-10:40 am

1 stop4h 40m

$249

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Wed 11/12

6:03 pm-11:40 pm

1 stop5h 37m

Chicago Midway

Sun 11/16

12:47 pm-5:13 pm

1 stop4h 26m

$279

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Sat 12/13

10:35 am-3:44 pm

1 stop5h 09m

Chicago Midway

Tue 12/16

12:50 pm-5:16 pm

1 stop4h 26m

$294

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Sat 12/13

6:00 am-6:18 pm

2 stops12h 18m

Chicago Midway

Tue 12/16

10:49 am-5:16 pm

1 stop6h 27m

$329

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Sun 12/21

7:55 pm-1:21 pm

2 stops17h 26m

Chicago Midway

Wed 12/24

3:10 pm-7:10 pm

1 stop28h 00m

$335

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Sat 12/13

6:00 am-6:18 pm

2 stops12h 18m

Chicago Midway

Tue 12/16

1:14 pm-2:08 pm

2 stops24h 54m

$368

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Sun 12/21

5:21 pm-10:22 pm

1 stop5h 01m

Chicago Midway

Wed 12/24

3:29 pm-9:40 pm

1 stop6h 11m

$593

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Thu 1/15

4:00 pm-10:09 pm

1 stop6h 09m

Chicago Midway

Mon 1/19

9:34 am-5:17 pm

2 stops7h 43m

$697

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Wed 11/12

10:35 am-6:08 pm

2 stops7h 33m

Chicago Midway

Sun 11/16

12:47 pm-5:13 pm

1 stop4h 26m

$901

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Wed 11/12

10:35 am-6:08 pm

2 stops7h 33m

Chicago Midway

Sun 11/16

9:34 am-5:13 pm

2 stops7h 39m

$2,736

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 17 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Gulfport to Chicago Midway Airport

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 Gulfport Biloxi Regional to Chicago Midway?

Delta is the most popular carrier operating from Gulfport Biloxi Regional to Chicago Midway

What airlines fly to Chicago Midway Airport?

Southwest, Delta and Spirit Airlines are the top three most popular airlines that fly to Chicago Midway Airport from Gulfport according to our data. Southwest is the first choice among our users, with 77% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 3 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.

When to book flights from Gulfport to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Gulfport to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Gulfport to Chicago Midway Airport (GPT to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Gulfport to Chicago Midway Airport

Direct flights

None
There are no direct flights from Gulfport to Chicago Midway Airport. There are no popular flight routes from Gulfport to Chicago Midway Airport.
Search flight deals

  • How far is Gulfport Biloxi Regional to Chicago Midway by plane?

    A flight from Gulfport Biloxi Regional to Chicago Midway will travel around 792.0 mi. In terms of flight time, this usually takes a little over 5h 01m.

  • When did momondo last update prices for flights from Gulfport Biloxi Regional Airport to Chicago Midway Airport?

    Prices for flights from Gulfport Biloxi Regional Airport to Chicago Midway Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Gulfport Biloxi Regional Airport to Chicago Midway Airport?

  • How old do you have to be to fly from Gulfport Biloxi Regional Airport to Chicago Midway Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Gulfport Biloxi Regional Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Gulfport to Chicago Midway Airport?

Best airlines flying from Gulfport to Chicago Midway Airport

Compare and see reviews for airlines that fly from Gulfport to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $116Free CancellationRating
7.9
7,998 reviews
Search Delta flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Gulfport to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Gulfport to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from Gulfport to Chicago with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Gulfport to Chicago flights to just show those with flexible booking policies.

How can momondo help me find flights from Gulfport to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Gulfport.

I’m not ready to book a flight from Gulfport to Chicago right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Gulfport to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

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