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Cheap flights from Gulfport to Chicago from $190

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 4/6. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 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
5:57 pm - 10:31 pm
GPT
-
MDW
4h 34m
1 stop
Delta Logo
10:45 am - 5:11 pm
MDW
-
GPT
6h 26m
1 stop
$399Delta
Tue, Mar 31 - Tue, Apr 7
Delta Logo
1:55 pm - 9:09 pm
GPT
-
MDW
7h 14m
1 stop
Delta Logo
6:23 am - 1:24 pm
MDW
-
GPT
7h 01m
1 stop
$429Delta
Thu, May 21 - Sat, May 23
Delta Logo
6:00 am - 11:54 am
GPT
-
MDW
5h 54m
1 stop
Delta Logo
10:35 am - 5:17 pm
MDW
-
GPT
6h 42m
1 stop
$489Delta
Thu, Aug 27 - Sun, Aug 30
Delta Logo
6:00 am - 12:02 pm
GPT
-
MDW
6h 02m
1 stop
Delta Logo
10:45 am - 5:11 pm
MDW
-
GPT
6h 26m
1 stop
$529Delta
Thu, Apr 2 - Tue, Apr 7
Delta Logo
6:00 am - 11:54 am
GPT
-
MDW
5h 54m
1 stop
Delta Logo
1:05 pm - 5:17 pm
MDW
-
GPT
4h 12m
1 stop
$559Delta
Thu, Aug 27 - Sun, Aug 30
Delta Logo
6:00 am - 11:54 am
GPT
-
MDW
5h 54m
1 stop
Delta Logo
10:35 am - 5:17 pm
MDW
-
GPT
6h 42m
1 stop
$589Delta
Thu, Aug 27 - Sun, Aug 30
Delta Logo
6:00 am - 11:54 am
GPT
-
MDW
5h 54m
1 stop
Delta Logo
5:25 pm - 10:06 pm
MDW
-
GPT
4h 41m
1 stop
$597Delta
Thu, Aug 27 - Sun, Aug 30
Delta Logo
1:55 pm - 9:09 pm
GPT
-
MDW
7h 14m
1 stop
Delta Logo
5:25 pm - 10:07 pm
MDW
-
GPT
4h 42m
1 stop
$599Delta
Wed, Jun 3 - Mon, Jun 8
Delta Logo
5:57 pm - 10:31 pm
GPT
-
MDW
4h 34m
1 stop
Delta Logo
12:52 pm - 5:08 pm
MDW
-
GPT
4h 16m
1 stop
$624Delta
Sun, Apr 12 - Tue, Apr 14
Delta Logo
10:07 am - 9:09 pm
GPT
-
MDW
11h 02m
1 stop
Delta Logo
6:23 am - 1:09 pm
MDW
-
GPT
6h 46m
1 stop
$680Delta
Fri, May 22 - Tue, May 26

Delta flights from Gulfport to Chicago Midway Airport

Our best Delta deals on Gulfport to Chicago Midway Airport flight tickets
Delta
Mar 31
GPT5:57 pmGulfport Biloxi Regional
4h 34m
1 stop
MDW10:31 pmChicago Midway
Apr 7
MDW10:45 amChicago Midway
6h 26m
1 stop
GPT5:11 pmGulfport Biloxi Regional
$399
Delta
May 21
GPT1:55 pmGulfport Biloxi Regional
7h 14m
1 stop
MDW9:09 pmChicago Midway
May 23
MDW6:23 amChicago Midway
7h 01m
1 stop
GPT1:24 pmGulfport Biloxi Regional
$429
Delta
Aug 27
GPT6:00 amGulfport Biloxi Regional
5h 54m
1 stop
MDW11:54 amChicago Midway
Aug 30
MDW10:35 amChicago Midway
6h 42m
1 stop
GPT5:17 pmGulfport Biloxi Regional
$489

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 March 17, 2026.
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

Cheapest round-trip

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Tue 3/31

5:57 pm-10:31 pm

1 stop4h 34m

Chicago Midway

Tue 4/7

10:45 am-5:11 pm

1 stop6h 26m

$399

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Thu 5/21

1:55 pm-9:09 pm

1 stop7h 14m

Chicago Midway

Sat 5/23

6:23 am-1:24 pm

1 stop7h 01m

$429

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Thu 8/27

6:00 am-11:54 am

1 stop5h 54m

Chicago Midway

Sun 8/30

10:35 am-5:17 pm

1 stop6h 42m

$489

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Thu 4/2

6:00 am-12:02 pm

1 stop6h 02m

Chicago Midway

Tue 4/7

10:45 am-5:11 pm

1 stop6h 26m

$529

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Thu 8/27

6:00 am-11:54 am

1 stop5h 54m

Chicago Midway

Sun 8/30

1:05 pm-5:17 pm

1 stop4h 12m

$559

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Thu 8/27

6:00 am-11:54 am

1 stop5h 54m

Chicago Midway

Sun 8/30

10:35 am-5:17 pm

1 stop6h 42m

$589

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Thu 8/27

6:00 am-11:54 am

1 stop5h 54m

Chicago Midway

Sun 8/30

5:25 pm-10:06 pm

1 stop4h 41m

$597

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Wed 6/3

1:55 pm-9:09 pm

1 stop7h 14m

Chicago Midway

Mon 6/8

5:25 pm-10:07 pm

1 stop4h 42m

$599
Quickest round-trip

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Sun 4/12

5:57 pm-10:31 pm

1 stop4h 34m

Chicago Midway

Tue 4/14

12:52 pm-5:08 pm

1 stop4h 16m

$624

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Fri 5/22

10:07 am-9:09 pm

1 stop11h 02m

Chicago Midway

Tue 5/26

6:23 am-1:09 pm

1 stop6h 46m

$680

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 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

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

Fastest flight time

4h 33m

Direct flights

None
The fastest flight from Gulfport to Chicago Midway Airport takes 4h 33m
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 4h 33m.

  • 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 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.

Traveling to a place near Chicago?

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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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