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Cheap flights from Chicago to Gulfport from $181

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 8/8. 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

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago to Gulfport

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
11:00 am - 7:08 pm
ORD
-
GPT
8h 08m
1 stop
American Airlines Logo
5:45 pm - 11:52 pm
GPT
-
ORD
6h 07m
1 stop
$291American Airlines
Sat, Aug 1 - Sat, Aug 8
Delta Logo
8:03 am - 1:05 pm
ORD
-
GPT
5h 02m
1 stop
Delta Logo
5:57 pm - 11:53 pm
GPT
-
ORD
5h 56m
1 stop
$300Delta
Tue, Jul 28 - Sun, Aug 2
Delta Logo
3:40 pm - 10:08 pm
ORD
-
GPT
6h 28m
1 stop
Delta Logo
6:26 am - 2:44 pm
GPT
-
ORD
8h 18m
2 stops
$305Delta
Thu, Oct 1 - Tue, Oct 6
American Airlines Logo
5:45 pm - 11:56 pm
ORD
-
GPT
6h 11m
1 stop
American Airlines Logo
5:45 pm - 11:52 pm
GPT
-
ORD
6h 07m
1 stop
$309American Airlines
Thu, Jul 30 - Thu, Aug 6
Delta Logo
12:46 pm - 5:15 pm
MDW
-
GPT
4h 29m
1 stop
Delta Logo
6:00 pm - 10:36 pm
GPT
-
MDW
4h 36m
1 stop
$309Delta
Fri, Aug 14 - Fri, Aug 21
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
$324American Airlines
Mon, Jul 13 - Mon, Jul 20
Delta Logo
3:35 pm - 8:39 pm
ORD
-
GPT
5h 04m
1 stop
Delta Logo
5:57 pm - 11:53 pm
GPT
-
ORD
5h 56m
1 stop
$339Delta
Sat, Jul 11 - Mon, Jul 13
Delta Logo
6:00 am - 1:05 pm
MDW
-
GPT
7h 05m
1 stop
Delta Logo
5:57 pm - 10:16 pm
GPT
-
MDW
4h 19m
1 stop
$343Delta
Wed, Jul 29 - Sun, Aug 2
Delta Logo
6:35 am - 1:05 pm
ORD
-
GPT
6h 30m
1 stop
Delta Logo
5:57 pm - 11:53 pm
GPT
-
ORD
5h 56m
1 stop
$343Delta
Wed, Jul 29 - Sun, Aug 2
Multiple Airlines Logo
8:00 am - 8:51 am
ORD
-
GPT
24h 51m
1 stop
Multiple Airlines Logo
7:45 pm - 8:21 am
GPT
-
ORD
12h 36m
1 stop
$348Multiple Airlines
Thu, Nov 12 - Sun, Nov 15

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American Airlines flights from Chicago to Gulfport

Our best American Airlines deals on Chicago to Gulfport flight tickets
American Airlines
Aug 1
ORD11:00 amChicago O'Hare Intl
8h 08m
1 stop
GPT7:08 pmGulfport Biloxi Regional
Aug 8
GPT5:45 pmGulfport Biloxi Regional
6h 07m
1 stop
ORD11:52 pmChicago O'Hare Intl
$291
American Airlines
Jul 13
ORD5:00 amChicago O'Hare Intl
5h 55m
1 stop
GPT10:55 amGulfport Biloxi Regional
Jul 20
GPT6:35 pmGulfport Biloxi Regional
5h 26m
1 stop
ORD12:01 amChicago O'Hare Intl
$324
American Airlines
Sep 4
ORD7:30 amChicago O'Hare Intl
5h 47m
1 stop
GPT1:17 pmGulfport Biloxi Regional
Sep 7
GPT6:34 pmGulfport Biloxi Regional
5h 44m
1 stop
ORD12:18 amChicago O'Hare Intl
$344

Delta flights from Chicago to Gulfport

Our best Delta deals on Chicago to Gulfport flight tickets
Delta
Jul 28
ORD8:03 amChicago O'Hare Intl
5h 02m
1 stop
GPT1:05 pmGulfport Biloxi Regional
Aug 2
GPT5:57 pmGulfport Biloxi Regional
5h 56m
1 stop
ORD11:53 pmChicago O'Hare Intl
$300
Delta
Oct 1
ORD3:40 pmChicago O'Hare Intl
6h 28m
1 stop
GPT10:08 pmGulfport Biloxi Regional
Oct 6
GPT6:26 amGulfport Biloxi Regional
8h 18m
2 stops
ORD2:44 pmChicago O'Hare Intl
$305
Delta
Aug 14
MDW12:46 pmChicago Midway
4h 29m
1 stop
GPT5:15 pmGulfport Biloxi Regional
Aug 21
GPT6:00 pmGulfport Biloxi Regional
4h 36m
1 stop
MDW10:36 pmChicago Midway
$309

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 July 1, 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

Sat 8/1

11:00 am-7:08 pm

1 stop8h 08m

Gulfport Biloxi Regional

Sat 8/8

5:45 pm-11:52 pm

1 stop6h 07m

$291

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Tue 7/28

8:03 am-1:05 pm

1 stop5h 02m

Gulfport Biloxi Regional

Sun 8/2

5:57 pm-11:53 pm

1 stop5h 56m

$300

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Thu 10/1

3:40 pm-10:08 pm

1 stop6h 28m

Gulfport Biloxi Regional

Tue 10/6

6:26 am-2:44 pm

2 stops8h 18m

$305

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Thu 7/30

5:45 pm-11:56 pm

1 stop6h 11m

Gulfport Biloxi Regional

Thu 8/6

5:45 pm-11:52 pm

1 stop6h 07m

$309
Quickest round-trip

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Fri 8/14

12:46 pm-5:15 pm

1 stop4h 29m

Gulfport Biloxi Regional

Fri 8/21

6:00 pm-10:36 pm

1 stop4h 36m

$309

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Mon 7/13

5:00 am-10:55 am

1 stop5h 55m

Gulfport Biloxi Regional

Mon 7/20

6:35 pm-12:01 am

1 stop5h 26m

$324

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Sat 7/11

3:35 pm-8:39 pm

1 stop5h 04m

Gulfport Biloxi Regional

Mon 7/13

5:57 pm-11:53 pm

1 stop5h 56m

$339

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Wed 7/29

6:00 am-1:05 pm

1 stop7h 05m

Gulfport Biloxi Regional

Sun 8/2

5:57 pm-10:16 pm

1 stop4h 19m

$343

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Wed 7/29

6:35 am-1:05 pm

1 stop6h 30m

Gulfport Biloxi Regional

Sun 8/2

5:57 pm-11:53 pm

1 stop5h 56m

$343

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Thu 11/12

8:00 am-8:51 am

1 stop24h 51m

Gulfport Biloxi Regional

Sun 11/15

7:45 pm-8:21 am

1 stop12h 36m

$348

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 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 12m

Direct flights

None
The fastest flight from Chicago to Gulfport takes 4h 12m
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 12m 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
11,766 reviews
Search American Airlines flights
DeltaPriceFrom $268Free CancellationRating
7.8
8,452 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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