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Cheap flights from Gulfport to Chicago from $189

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 5/27. 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

Find the cheapest flights from Gulfport to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
5:56 pm - 10:17 pm
GPT
-
MDW
4h 21m
1 stop
Delta Logo
6:00 am - 1:07 pm
MDW
-
GPT
7h 07m
1 stop
$291Delta
Wed, Jun 17 - Tue, Jun 23
Delta Logo
3:00 pm - 9:09 pm
GPT
-
MDW
6h 09m
1 stop
Delta Logo
5:10 pm - 9:51 pm
MDW
-
GPT
4h 41m
1 stop
$310Delta
Sat, May 23 - Sat, May 30
Delta Logo
1:55 pm - 9:09 pm
GPT
-
MDW
7h 14m
1 stop
Delta Logo
10:59 am - 5:14 pm
MDW
-
GPT
6h 15m
1 stop
$365Delta
Fri, May 29 - Sun, May 31
Delta Logo
6:30 am - 12:00 pm
GPT
-
MDW
5h 30m
1 stop
Delta Logo
6:00 am - 1:07 pm
MDW
-
GPT
7h 07m
1 stop
$379Delta
Tue, Jun 23 - Sun, Jun 28
Delta Logo
3:00 pm - 9:09 pm
GPT
-
MDW
6h 09m
1 stop
Delta Logo
10:59 am - 5:14 pm
MDW
-
GPT
6h 15m
1 stop
$384Delta
Sat, May 23 - Sun, May 31
Delta Logo
6:00 pm - 10:15 pm
GPT
-
MDW
4h 15m
1 stop
Delta Logo
4:22 pm - 8:39 pm
MDW
-
GPT
4h 17m
1 stop
$404Delta
Wed, Jul 15 - Sat, Jul 18
Delta Logo
3:00 pm - 10:17 pm
GPT
-
MDW
7h 17m
1 stop
Delta Logo
5:10 pm - 10:14 pm
MDW
-
GPT
5h 04m
1 stop
$409Delta
Fri, Jul 3 - Fri, Jul 10
Delta Logo
6:00 pm - 10:15 pm
GPT
-
MDW
4h 15m
1 stop
Delta Logo
4:22 pm - 8:39 pm
MDW
-
GPT
4h 17m
1 stop
$423Delta
Thu, Jul 16 - Sat, Jul 18
Delta Logo
1:55 pm - 9:09 pm
GPT
-
MDW
7h 14m
1 stop
Delta Logo
5:29 pm - 9:51 pm
MDW
-
GPT
4h 22m
1 stop
$459Delta
Tue, May 12 - Sat, May 16
Delta Logo
3:00 pm - 10:17 pm
GPT
-
MDW
7h 17m
1 stop
Delta Logo
4:22 pm - 8:39 pm
MDW
-
GPT
4h 17m
1 stop
$478Delta
Fri, Jul 3 - Sat, Jul 11

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Delta flights from Gulfport to Chicago Midway Airport

Our best Delta deals on Gulfport to Chicago Midway Airport flight tickets
Delta
Jun 17
GPT5:56 pmGulfport Biloxi Regional
4h 21m
1 stop
MDW10:17 pmChicago Midway
Jun 23
MDW6:00 amChicago Midway
7h 07m
1 stop
GPT1:07 pmGulfport Biloxi Regional
$291
Delta
May 23
GPT3:00 pmGulfport Biloxi Regional
6h 09m
1 stop
MDW9:09 pmChicago Midway
May 30
MDW5:10 pmChicago Midway
4h 41m
1 stop
GPT9:51 pmGulfport Biloxi Regional
$310
Delta
May 29
GPT1:55 pmGulfport Biloxi Regional
7h 14m
1 stop
MDW9:09 pmChicago Midway
May 31
MDW10:59 amChicago Midway
6h 15m
1 stop
GPT5:14 pmGulfport Biloxi Regional
$365

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 April 28, 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

Wed 6/17

5:56 pm-10:17 pm

1 stop4h 21m

Chicago Midway

Tue 6/23

6:00 am-1:07 pm

1 stop7h 07m

$291

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Sat 5/23

3:00 pm-9:09 pm

1 stop6h 09m

Chicago Midway

Sat 5/30

5:10 pm-9:51 pm

1 stop4h 41m

$310

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Fri 5/29

1:55 pm-9:09 pm

1 stop7h 14m

Chicago Midway

Sun 5/31

10:59 am-5:14 pm

1 stop6h 15m

$365

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Tue 6/23

6:30 am-12:00 pm

1 stop5h 30m

Chicago Midway

Sun 6/28

6:00 am-1:07 pm

1 stop7h 07m

$379

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Sat 5/23

3:00 pm-9:09 pm

1 stop6h 09m

Chicago Midway

Sun 5/31

10:59 am-5:14 pm

1 stop6h 15m

$384
Quickest round-trip

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Wed 7/15

6:00 pm-10:15 pm

1 stop4h 15m

Chicago Midway

Sat 7/18

4:22 pm-8:39 pm

1 stop4h 17m

$404

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Fri 7/3

3:00 pm-10:17 pm

1 stop7h 17m

Chicago Midway

Fri 7/10

5:10 pm-10:14 pm

1 stop5h 04m

$409

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Thu 7/16

6:00 pm-10:15 pm

1 stop4h 15m

Chicago Midway

Sat 7/18

4:22 pm-8:39 pm

1 stop4h 17m

$423

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Tue 5/12

1:55 pm-9:09 pm

1 stop7h 14m

Chicago Midway

Sat 5/16

5:29 pm-9:51 pm

1 stop4h 22m

$459

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Fri 7/3

3:00 pm-10:17 pm

1 stop7h 17m

Chicago Midway

Sat 7/11

4:22 pm-8:39 pm

1 stop4h 17m

$478

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 18 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 21m

Direct flights

None
The fastest flight from Gulfport to Chicago Midway Airport takes 4h 21m
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

Frequently asked questions about flying from Gulfport to Chicago Midway Airport

  • 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 21m.

  • 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?

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