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Cheap flights from Gulfport to Chicago from $149

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 8/4. 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
1 adult, Economy, 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
4:00 pm - 10:15 pm
GPT
-
MDW
6h 15m
1 stop
Delta Logo
4:39 pm - 8:53 pm
MDW
-
GPT
4h 14m
1 stop
$281Delta
Sat, Aug 1 - Sat, Aug 8
Delta Logo
4:00 pm - 10:15 pm
GPT
-
MDW
6h 15m
1 stop
Delta Logo
4:39 pm - 8:53 pm
MDW
-
GPT
4h 14m
1 stop
$291Delta
Sat, Aug 1 - Sat, Aug 8
Delta Logo
10:06 am - 3:40 pm
GPT
-
MDW
5h 34m
1 stop
Delta Logo
11:05 am - 5:12 pm
MDW
-
GPT
6h 07m
1 stop
$345Delta
Sat, Jul 4 - Wed, Jul 8
Delta Logo
5:57 pm - 10:15 pm
GPT
-
MDW
4h 18m
1 stop
Delta Logo
6:00 am - 1:05 pm
MDW
-
GPT
7h 05m
1 stop
$380Delta
Wed, Jul 8 - Wed, Jul 15
Delta Logo
6:00 pm - 10:36 pm
GPT
-
MDW
4h 36m
1 stop
Delta Logo
6:05 am - 1:03 pm
MDW
-
GPT
6h 58m
1 stop
$414Delta
Thu, Aug 27 - Sun, Aug 30
Delta Logo
6:00 pm - 10:36 pm
GPT
-
MDW
4h 36m
1 stop
Delta Logo
6:05 am - 1:03 pm
MDW
-
GPT
6h 58m
1 stop
$435Delta
Thu, Aug 27 - Sun, Aug 30
Delta Logo
5:57 pm - 10:15 pm
GPT
-
MDW
4h 18m
1 stop
Delta Logo
6:00 am - 1:05 pm
MDW
-
GPT
7h 05m
1 stop
$449Delta
Wed, Jul 15 - Mon, Jul 20
Delta Logo
6:00 pm - 10:10 pm
GPT
-
MDW
4h 10m
1 stop
Delta Logo
5:25 pm - 10:07 pm
MDW
-
GPT
4h 42m
1 stop
$490Delta
Wed, Nov 4 - Sun, Nov 8
Delta Logo
5:57 pm - 10:15 pm
GPT
-
MDW
4h 18m
1 stop
Delta Logo
1:18 pm - 10:14 pm
MDW
-
GPT
8h 56m
2 stops
$495Delta
Wed, Jul 8 - Wed, Jul 15
Delta Logo
4:00 pm - 10:15 pm
GPT
-
MDW
6h 15m
1 stop
Delta Logo
6:00 am - 1:05 pm
MDW
-
GPT
7h 05m
1 stop
$500Delta
Sat, Jul 18 - Thu, Jul 23

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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
Aug 1
GPT4:00 pmGulfport Biloxi Regional
6h 15m
1 stop
MDW10:15 pmChicago Midway
Aug 8
MDW4:39 pmChicago Midway
4h 14m
1 stop
GPT8:53 pmGulfport Biloxi Regional
$281
Delta
Jul 4
GPT10:06 amGulfport Biloxi Regional
5h 34m
1 stop
MDW3:40 pmChicago Midway
Jul 8
MDW11:05 amChicago Midway
6h 07m
1 stop
GPT5:12 pmGulfport Biloxi Regional
$345
Delta
Jul 8
GPT5:57 pmGulfport Biloxi Regional
4h 18m
1 stop
MDW10:15 pmChicago Midway
Jul 15
MDW6:00 amChicago Midway
7h 05m
1 stop
GPT1:05 pmGulfport Biloxi Regional
$380

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 June 11, 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

Sat 8/1

4:00 pm-10:15 pm

1 stop6h 15m

Chicago Midway

Sat 8/8

4:39 pm-8:53 pm

1 stop4h 14m

$281

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Sat 8/1

4:00 pm-10:15 pm

1 stop6h 15m

Chicago Midway

Sat 8/8

4:39 pm-8:53 pm

1 stop4h 14m

$291

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Sat 7/4

10:06 am-3:40 pm

1 stop5h 34m

Chicago Midway

Wed 7/8

11:05 am-5:12 pm

1 stop6h 07m

$345

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Wed 7/8

5:57 pm-10:15 pm

1 stop4h 18m

Chicago Midway

Wed 7/15

6:00 am-1:05 pm

1 stop7h 05m

$380

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Thu 8/27

6:00 pm-10:36 pm

1 stop4h 36m

Chicago Midway

Sun 8/30

6:05 am-1:03 pm

1 stop6h 58m

$414

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Thu 8/27

6:00 pm-10:36 pm

1 stop4h 36m

Chicago Midway

Sun 8/30

6:05 am-1:03 pm

1 stop6h 58m

$435

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Wed 7/15

5:57 pm-10:15 pm

1 stop4h 18m

Chicago Midway

Mon 7/20

6:00 am-1:05 pm

1 stop7h 05m

$449
Quickest round-trip

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Wed 11/4

6:00 pm-10:10 pm

1 stop4h 10m

Chicago Midway

Sun 11/8

5:25 pm-10:07 pm

1 stop4h 42m

$490

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Wed 7/8

5:57 pm-10:15 pm

1 stop4h 18m

Chicago Midway

Wed 7/15

1:18 pm-10:14 pm

2 stops8h 56m

$495

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Sat 7/18

4:00 pm-10:15 pm

1 stop6h 15m

Chicago Midway

Thu 7/23

6:00 am-1:05 pm

1 stop7h 05m

$500

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 10m

Direct flights

None
The fastest flight from Gulfport to Chicago Midway Airport takes 4h 10m
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 10m.

  • 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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