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Cheap flights from Chicago to Gulfport from $208

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Gulfport departing on 7/19. 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 Chicago to Gulfport

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
5:00 am - 10:55 am
ORD
-
GPT
5h 55m
1 stop
American Airlines Logo
6:35 pm - 12:01 am
GPT
-
ORD
5h 26m
1 stop
$291American Airlines
Wed, Jul 8 - Sat, Jul 11
Delta Logo
1:46 pm - 8:41 pm
ORD
-
GPT
6h 55m
1 stop
Delta Logo
1:50 pm - 8:33 pm
GPT
-
ORD
6h 43m
1 stop
$300Delta
Fri, Jul 3 - Mon, Jul 13
Delta Logo
5:12 pm - 9:51 pm
MDW
-
GPT
4h 39m
1 stop
Delta Logo
1:55 pm - 9:09 pm
GPT
-
MDW
7h 14m
1 stop
$305Delta
Wed, May 27 - Wed, Jun 3
Delta Logo
2:59 pm - 9:51 pm
ORD
-
GPT
6h 52m
1 stop
Delta Logo
1:55 pm - 6:41 pm
GPT
-
ORD
4h 46m
1 stop
$305Delta
Wed, May 27 - Wed, Jun 3
Delta Logo
6:35 am - 1:05 pm
ORD
-
GPT
6h 30m
1 stop
Delta Logo
6:30 am - 12:34 pm
GPT
-
ORD
6h 04m
1 stop
$309Delta
Mon, Jul 13 - Mon, Jul 20
Delta Logo
10:35 am - 10:06 pm
ORD
-
GPT
11h 31m
2 stops
Delta Logo
10:30 am - 6:41 pm
GPT
-
ORD
8h 11m
2 stops
$310Delta
Wed, Sep 30 - Sun, Oct 4
American Airlines Logo
6:47 pm - 12:01 am
ORD
-
GPT
5h 14m
1 stop
American Airlines Logo
6:38 pm - 11:59 pm
GPT
-
ORD
5h 21m
1 stop
$315American Airlines
Fri, May 29 - Wed, Jun 3
Delta Logo
11:26 am - 5:14 pm
ORD
-
GPT
5h 48m
1 stop
Delta Logo
1:53 pm - 8:32 pm
GPT
-
ORD
6h 39m
1 stop
$319Delta
Wed, Jun 3 - Mon, Jun 8
Delta Logo
7:05 am - 5:14 pm
ORD
-
GPT
10h 09m
2 stops
Delta Logo
1:53 pm - 8:32 pm
GPT
-
ORD
6h 39m
1 stop
$324Delta
Wed, Jun 3 - Mon, Jun 8
Delta Logo
5:55 pm - 10:06 pm
ORD
-
GPT
4h 11m
1 stop
Delta Logo
2:15 pm - 6:32 pm
GPT
-
ORD
4h 17m
1 stop
$325Delta
Fri, Oct 2 - Tue, Oct 6

Delta flights from Chicago to Gulfport

Our best Delta deals on Chicago to Gulfport flight tickets
Delta
Jul 3
ORD1:46 pmChicago O'Hare Intl
6h 55m
1 stop
GPT8:41 pmGulfport Biloxi Regional
Jul 13
GPT1:50 pmGulfport Biloxi Regional
6h 43m
1 stop
ORD8:33 pmChicago O'Hare Intl
$300
Delta
May 27
MDW5:12 pmChicago Midway
4h 39m
1 stop
GPT9:51 pmGulfport Biloxi Regional
Jun 3
GPT1:55 pmGulfport Biloxi Regional
7h 14m
1 stop
MDW9:09 pmChicago Midway
$305
Delta
Jul 13
ORD6:35 amChicago O'Hare Intl
6h 30m
1 stop
GPT1:05 pmGulfport Biloxi Regional
Jul 20
GPT6:30 amGulfport Biloxi Regional
6h 04m
1 stop
ORD12:34 pmChicago O'Hare Intl
$309

American Airlines flights from Chicago to Gulfport

Our best American Airlines deals on Chicago to Gulfport flight tickets
American Airlines
Jul 8
ORD5:00 amChicago O'Hare Intl
5h 55m
1 stop
GPT10:55 amGulfport Biloxi Regional
Jul 11
GPT6:35 pmGulfport Biloxi Regional
5h 26m
1 stop
ORD12:01 amChicago O'Hare Intl
$291
American Airlines
May 29
ORD4:45 pmChicago O'Hare Intl
7h 16m
1 stop
GPT12:01 amGulfport Biloxi Regional
Jun 5
GPT6:38 pmGulfport Biloxi Regional
5h 20m
1 stop
ORD11:58 pmChicago O'Hare Intl
$300
American Airlines
May 29
ORD6:47 pmChicago O'Hare Intl
5h 14m
1 stop
GPT12:01 amGulfport Biloxi Regional
Jun 3
GPT6:38 pmGulfport Biloxi Regional
5h 21m
1 stop
ORD11:59 pmChicago O'Hare Intl
$315

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Gulfport 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 May 16, 2026.
Use the filters below to find and compare flights from Chicago to Gulfport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Wed 7/8

5:00 am-10:55 am

1 stop5h 55m

Gulfport Biloxi Regional

Sat 7/11

6:35 pm-12:01 am

1 stop5h 26m

$291

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Fri 7/3

1:46 pm-8:41 pm

1 stop6h 55m

Gulfport Biloxi Regional

Mon 7/13

1:50 pm-8:33 pm

1 stop6h 43m

$300

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Wed 5/27

5:12 pm-9:51 pm

1 stop4h 39m

Gulfport Biloxi Regional

Wed 6/3

1:55 pm-9:09 pm

1 stop7h 14m

$305

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Wed 5/27

2:59 pm-9:51 pm

1 stop6h 52m

Gulfport Biloxi Regional

Wed 6/3

1:55 pm-6:41 pm

1 stop4h 46m

$305

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Mon 7/13

6:35 am-1:05 pm

1 stop6h 30m

Gulfport Biloxi Regional

Mon 7/20

6:30 am-12:34 pm

1 stop6h 04m

$309

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Wed 9/30

10:35 am-10:06 pm

2 stops11h 31m

Gulfport Biloxi Regional

Sun 10/4

10:30 am-6:41 pm

2 stops8h 11m

$310

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Fri 5/29

6:47 pm-12:01 am

1 stop5h 14m

Gulfport Biloxi Regional

Wed 6/3

6:38 pm-11:59 pm

1 stop5h 21m

$315

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Wed 6/3

11:26 am-5:14 pm

1 stop5h 48m

Gulfport Biloxi Regional

Mon 6/8

1:53 pm-8:32 pm

1 stop6h 39m

$319

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Wed 6/3

7:05 am-5:14 pm

2 stops10h 09m

Gulfport Biloxi Regional

Mon 6/8

1:53 pm-8:32 pm

1 stop6h 39m

$324
Quickest round-trip

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Fri 10/2

5:55 pm-10:06 pm

1 stop4h 11m

Gulfport Biloxi Regional

Tue 10/6

2:15 pm-6:32 pm

1 stop4h 17m

$325

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 Gulfport from

How to get the cheapest flight ticket from Chicago to Gulfport

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 typical price of a round-trip flight between Chicago and Gulfport?

What is the cheapest month to fly to Gulfport?

The cheapest month to fly to Gulfport from Chicago is in November. Flight prices, which tend to average around $248, are often lower during this time because this is during the off-season. If you are unable to visit Gulfport during the month of November, then departing from Chicago during the month September is also very affordable. Most momondo users find prices during this month for around $248.

When to book flights from Chicago to Gulfport

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

Cheap Chicago to Gulfport (CHI to GPT) flight deals and tips

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

Fastest flight time

4h 11m

Direct flights

None
The fastest flight from Chicago to Gulfport takes 4h 11m
There are no direct flights from Chicago to Gulfport. There are no popular flight routes from Chicago to Gulfport.
Search flight deals

Frequently asked questions about flying from Chicago to Gulfport

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

    Chicago and Gulfport Biloxi Regional are 798.7 mi apart from one another. Typically, this will take 4h 11m by plane in normal conditions.

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

    Prices for flights from Chicago to Gulfport Biloxi Regional Airport are updated daily.

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

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Gulfport Biloxi Regional Airport.

  • What documentation or ID do you need to fly to Gulfport Biloxi Regional Airport?

    The required travel and health documents for your Gulfport Biloxi Regional Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Gulfport Biloxi Regional Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

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

Best airlines flying from Chicago to Gulfport

Compare and see reviews for airlines that fly from Chicago to Gulfport with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $248Free CancellationRating
7.1
11,662 reviews
Search American Airlines flights
DeltaPriceFrom $253Free CancellationRating
7.9
8,455 reviews
Search Delta flights

Traveling to a place near Gulfport?

Book flights to Gulfport if you plan to visit one of these locations
Biloxi
Ocean Springs
D'Iberville

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Gulfport for you.

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

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

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

Once all potential Chicago to Gulfport flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

Of course. momondo tracks the price of Chicago to Gulfport flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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