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Cheap flights from Gulfport to Chicago from $169

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 9/6. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Gulfport to Chicago

Cheap round-trip flights

Delta Logo
3:45 pm - 9:12 pmGPT-MDW
5h 27m1 stop
Delta Logo
4:25 pm - 9:38 pmMDW-GPT
5h 13m1 stop
$249Delta
Find Deal
Sat, Aug 23 - Tue, Aug 26
Delta Logo
3:45 pm - 9:12 pmGPT-MDW
5h 27m1 stop
Delta Logo
12:43 pm - 5:15 pmMDW-GPT
4h 32m1 stop
$259Delta
Find Deal
Sat, Aug 16 - Wed, Aug 20
Delta Logo
6:09 am - 11:48 amGPT-MDW
5h 39m1 stop
Delta Logo
4:25 pm - 9:38 pmMDW-GPT
5h 13m1 stop
$279Delta
Find Deal
Wed, Aug 20 - Wed, Aug 27
Delta Logo
6:09 am - 6:37 pmGPT-MDW
12h 28m2 stops
Delta Logo
4:25 pm - 9:38 pmMDW-GPT
5h 13m1 stop
$284Delta
Find Deal
Sat, Aug 23 - Tue, Aug 26
Delta Logo
6:09 am - 6:37 pmGPT-MDW
12h 28m2 stops
Delta Logo
9:30 am - 9:38 pmMDW-GPT
12h 08m2 stops
$320Delta
Find Deal
Sat, Aug 23 - Tue, Aug 26
Delta Logo
6:09 am - 6:37 pmGPT-MDW
12h 28m2 stops
Delta Logo
6:17 pm - 9:28 amMDW-GPT
15h 11m2 stops
$373Delta
Find Deal
Sat, Aug 23 - Tue, Aug 26
Delta Logo
6:05 pm - 10:14 pmGPT-MDW
4h 09m1 stop
Delta Logo
10:35 am - 2:58 pmMDW-GPT
4h 23m1 stop
$379Delta
Find Deal
Thu, Oct 16 - Sat, Oct 18
Delta Logo
6:08 am - 11:48 amGPT-MDW
5h 40m1 stop
Delta Logo
12:43 pm - 5:19 pmMDW-GPT
4h 36m1 stop
$434Delta
Find Deal
Fri, Sep 26 - Tue, Sep 30
Delta Logo
6:09 am - 11:48 amGPT-MDW
5h 39m1 stop
Delta Logo
10:31 am - 2:59 pmMDW-GPT
4h 28m1 stop
$449Delta
Find Deal
Sun, Aug 17 - Sat, Aug 23
Delta Logo
6:08 am - 11:48 amGPT-MDW
5h 40m1 stop
Delta Logo
12:43 pm - 5:19 pmMDW-GPT
4h 36m1 stop
$523Delta
Find Deal
Sun, Sep 21 - Wed, Sep 24

Delta flights from Gulfport to Chicago Midway Airport

Our best Delta deals on Gulfport to Chicago Midway Airport flight tickets
Delta
Aug 23
GPT3:45 pmGulfport Biloxi Regional
5h 27m
1 stop
MDW9:12 pmChicago Midway
Aug 26
MDW4:25 pmChicago Midway
5h 13m
1 stop
GPT9:38 pmGulfport Biloxi Regional
$249
Find similar
Delta
Aug 16
GPT3:45 pmGulfport Biloxi Regional
5h 27m
1 stop
MDW9:12 pmChicago Midway
Aug 20
MDW12:43 pmChicago Midway
4h 32m
1 stop
GPT5:15 pmGulfport Biloxi Regional
$259
Find similar
Delta
Aug 20
GPT6:09 amGulfport Biloxi Regional
5h 39m
1 stop
MDW11:48 amChicago Midway
Aug 27
MDW4:25 pmChicago Midway
5h 13m
1 stop
GPT9:38 pmGulfport Biloxi Regional
$279
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 August 1, 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

Sat 8/23

3:45 pm-9:12 pm

1 stop5h 27m

Chicago Midway

Tue 8/26

4:25 pm-9:38 pm

1 stop5h 13m

$249

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Sat 8/16

3:45 pm-9:12 pm

1 stop5h 27m

Chicago Midway

Wed 8/20

12:43 pm-5:15 pm

1 stop4h 32m

$259

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Wed 8/20

6:09 am-11:48 am

1 stop5h 39m

Chicago Midway

Wed 8/27

4:25 pm-9:38 pm

1 stop5h 13m

$279

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Sat 8/23

6:09 am-6:37 pm

2 stops12h 28m

Chicago Midway

Tue 8/26

4:25 pm-9:38 pm

1 stop5h 13m

$284

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Sat 8/23

6:09 am-6:37 pm

2 stops12h 28m

Chicago Midway

Tue 8/26

9:30 am-9:38 pm

2 stops12h 08m

$320

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Sat 8/23

6:09 am-6:37 pm

2 stops12h 28m

Chicago Midway

Tue 8/26

6:17 pm-9:28 am

2 stops15h 11m

$373

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Thu 10/16

6:05 pm-10:14 pm

1 stop4h 09m

Chicago Midway

Sat 10/18

10:35 am-2:58 pm

1 stop4h 23m

$379

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Fri 9/26

6:08 am-11:48 am

1 stop5h 40m

Chicago Midway

Tue 9/30

12:43 pm-5:19 pm

1 stop4h 36m

$434

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Sun 8/17

6:09 am-11:48 am

1 stop5h 39m

Chicago Midway

Sat 8/23

10:31 am-2:59 pm

1 stop4h 28m

$449

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Sun 9/21

6:08 am-11:48 am

1 stop5h 40m

Chicago Midway

Wed 9/24

12:43 pm-5:19 pm

1 stop4h 36m

$523

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 15 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 75% 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

Best Price Found

$169

Fastest flight time

4h 09m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Gulfport in the past 72 hours is $169. The best round-trip flight deal from Gulfport to Chicago Midway Airport found on momondo in the last 72 hours is $249.
The fastest flight from Gulfport to Chicago Midway Airport takes 4h 09m
There are no direct flights from Gulfport to Chicago Midway Airport. Popular non-direct route for this connection is Gulfport Biloxi Regional Airport - Chicago Midway Airport.
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  • 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 4h 09m.

  • 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
8.0
7,981 reviews
Search Delta flights

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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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