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Cheap flights from Chicago to Gulfport from $141

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 8/26. 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
5:00 am - 10:40 amORD  Chicago O'Hare Intl-GPT Gulfport Biloxi Regional
5h 40m1 stop Dallas/Fort Worth
American Airlines Logo
1:42 pm - 7:38 pmGPT  Gulfport Biloxi Regional-ORD Chicago O'Hare Intl
5h 56m1 stop Charlotte Douglas
$297American Airlines
Sat, Sep 26 - Sat, Oct 3
American Airlines Logo
4:53 pm - 10:30 pmORD  Chicago O'Hare Intl-GPT Gulfport Biloxi Regional
5h 37m1 stop Charlotte Douglas
American Airlines Logo
11:18 am - 6:25 pmGPT  Gulfport Biloxi Regional-ORD Chicago O'Hare Intl
7h 07m1 stop Dallas/Fort Worth
$297American Airlines
Tue, Sep 8 - Tue, Sep 15
Delta Logo
4:30 pm - 8:49 pmMDW  Chicago Midway-GPT Gulfport Biloxi Regional
4h 19m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:29 am - 10:36 amGPT  Gulfport Biloxi Regional-MDW Chicago Midway
4h 07m1 stop Atlanta Hartsfield-Jackson
$297Delta
Sat, Sep 26 - Sat, Oct 3
American Airlines Logo
5:00 am - 10:40 amORD  Chicago O'Hare Intl-GPT Gulfport Biloxi Regional
5h 40m1 stop Dallas/Fort Worth
American Airlines Logo
1:42 pm - 7:38 pmGPT  Gulfport Biloxi Regional-ORD Chicago O'Hare Intl
5h 56m1 stop Charlotte Douglas
$298American Airlines
Sat, Sep 26 - Sat, Oct 3
American Airlines Logo
6:29 am - 1:12 pmORD  Chicago O'Hare Intl-GPT Gulfport Biloxi Regional
6h 43m1 stop Charlotte Douglas
American Airlines Logo
5:42 pm - 11:59 pmGPT  Gulfport Biloxi Regional-ORD Chicago O'Hare Intl
6h 17m1 stop Charlotte Douglas
$299American Airlines
Mon, Sep 21 - Thu, Sep 24
Delta Logo
8:04 am - 1:08 pmORD  Chicago O'Hare Intl-GPT Gulfport Biloxi Regional
5h 04m1 stop Atlanta Hartsfield-Jackson
Delta Logo
10:04 am - 5:03 pmGPT  Gulfport Biloxi Regional-ORD Chicago O'Hare Intl
6h 59m1 stop Atlanta Hartsfield-Jackson
$301Delta
Tue, Dec 1 - Sat, Dec 5
Delta Logo
6:40 am - 1:11 pmORD  Chicago O'Hare Intl-GPT Gulfport Biloxi Regional
6h 31m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:59 pm - 10:18 pmGPT  Gulfport Biloxi Regional-ORD Chicago O'Hare Intl
8h 19m2 stops Atlanta Hartsfield-Jackson New York LaGuardia
$302Delta
Tue, Sep 8 - Tue, Sep 15
United Airlines Logo
12:40 pm - 7:34 pmORD  Chicago O'Hare Intl-GPT Gulfport Biloxi Regional
6h 54m1 stop Houston George Bush Intcntl
United Airlines Logo
1:54 pm - 9:36 pmGPT  Gulfport Biloxi Regional-ORD Chicago O'Hare Intl
7h 42m1 stop Houston George Bush Intcntl
$377United Airlines
Sat, Oct 31 - Wed, Nov 4
United Airlines Logo
5:30 am - 1:24 pmORD  Chicago O'Hare Intl-GPT Gulfport Biloxi Regional
7h 54m1 stop Houston George Bush Intcntl
United Airlines Logo
2:00 pm - 8:05 pmGPT  Gulfport Biloxi Regional-ORD Chicago O'Hare Intl
6h 05m1 stop Houston George Bush Intcntl
$388United Airlines
Sun, Sep 6 - Sat, Sep 12
United Airlines Logo
7:30 am - 1:24 pmORD  Chicago O'Hare Intl-GPT Gulfport Biloxi Regional
5h 54m1 stop Houston George Bush Intcntl
United Airlines Logo
2:00 pm - 9:31 pmGPT  Gulfport Biloxi Regional-ORD Chicago O'Hare Intl
7h 31m1 stop Houston George Bush Intcntl
$388United Airlines
Wed, Sep 2 - Sun, Sep 6

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United Airlines flights from Chicago to Gulfport

Our best United Airlines deals on Chicago to Gulfport flight tickets
United Airlines
Oct 31
ORD12:40 pmChicago O'Hare Intl
6h 54m
1 stop
GPT7:34 pmGulfport Biloxi Regional
Nov 4
GPT1:54 pmGulfport Biloxi Regional
7h 42m
1 stop
ORD9:36 pmChicago O'Hare Intl
$377
United Airlines
Sep 2
ORD7:30 amChicago O'Hare Intl
5h 54m
1 stop
GPT1:24 pmGulfport Biloxi Regional
Sep 6
GPT2:00 pmGulfport Biloxi Regional
7h 31m
1 stop
ORD9:31 pmChicago O'Hare Intl
$388
United Airlines
Sep 6
ORD5:30 amChicago O'Hare Intl
7h 54m
1 stop
GPT1:24 pmGulfport Biloxi Regional
Sep 12
GPT2:00 pmGulfport Biloxi Regional
6h 05m
1 stop
ORD8:05 pmChicago O'Hare Intl
$390

American Airlines flights from Chicago to Gulfport

Our best American Airlines deals on Chicago to Gulfport flight tickets
American Airlines
Sep 8
ORD4:53 pmChicago O'Hare Intl
5h 37m
1 stop
GPT10:30 pmGulfport Biloxi Regional
Sep 15
GPT11:18 amGulfport Biloxi Regional
7h 07m
1 stop
ORD6:25 pmChicago O'Hare Intl
$297
American Airlines
Sep 26
ORD5:00 amChicago O'Hare Intl
5h 40m
1 stop
GPT10:40 amGulfport Biloxi Regional
Oct 3
GPT1:42 pmGulfport Biloxi Regional
5h 56m
1 stop
ORD7:38 pmChicago O'Hare Intl
$298
American Airlines
Sep 21
ORD6:29 amChicago O'Hare Intl
6h 43m
1 stop
GPT1:12 pmGulfport Biloxi Regional
Sep 24
GPT5:42 pmGulfport Biloxi Regional
6h 17m
1 stop
ORD11:59 pmChicago O'Hare Intl
$299

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 August 14, 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 Chicago O'Hare Intl - GPT Gulfport Biloxi Regional

ORDGPT

Chicago O'Hare Intl

Sat 9/26

5:00 am-10:40 am

1 stop5h 40m

Gulfport Biloxi Regional

Sat 10/3

1:42 pm-7:38 pm

1 stop5h 56m

$297

ChicagoGulfport

ORD Chicago O'Hare Intl - GPT Gulfport Biloxi Regional

ORDGPT

Chicago O'Hare Intl

Tue 9/8

4:53 pm-10:30 pm

1 stop5h 37m

Gulfport Biloxi Regional

Tue 9/15

11:18 am-6:25 pm

1 stop7h 07m

$297
Quickest round-trip

ChicagoGulfport

MDW Chicago Midway - GPT Gulfport Biloxi Regional

MDWGPT

Chicago Midway

Sat 9/26

4:30 pm-8:49 pm

1 stop4h 19m

Gulfport Biloxi Regional

Sat 10/3

6:29 am-10:36 am

1 stop4h 07m

$297

ChicagoGulfport

ORD Chicago O'Hare Intl - GPT Gulfport Biloxi Regional

ORDGPT

Chicago O'Hare Intl

Sat 9/26

5:00 am-10:40 am

1 stop5h 40m

Gulfport Biloxi Regional

Sat 10/3

1:42 pm-7:38 pm

1 stop5h 56m

$298

ChicagoGulfport

ORD Chicago O'Hare Intl - GPT Gulfport Biloxi Regional

ORDGPT

Chicago O'Hare Intl

Mon 9/21

6:29 am-1:12 pm

1 stop6h 43m

Gulfport Biloxi Regional

Thu 9/24

5:42 pm-11:59 pm

1 stop6h 17m

$299

ChicagoGulfport

ORD Chicago O'Hare Intl - GPT Gulfport Biloxi Regional

ORDGPT

Chicago O'Hare Intl

Tue 12/1

8:04 am-1:08 pm

1 stop5h 04m

Gulfport Biloxi Regional

Sat 12/5

10:04 am-5:03 pm

1 stop6h 59m

$301

ChicagoGulfport

ORD Chicago O'Hare Intl - GPT Gulfport Biloxi Regional

ORDGPT

Chicago O'Hare Intl

Tue 9/8

6:40 am-1:11 pm

1 stop6h 31m

Gulfport Biloxi Regional

Tue 9/15

1:59 pm-10:18 pm

2 stops8h 19m

$302

ChicagoGulfport

ORD Chicago O'Hare Intl - GPT Gulfport Biloxi Regional

ORDGPT

Chicago O'Hare Intl

Sat 10/31

12:40 pm-7:34 pm

1 stop6h 54m

Gulfport Biloxi Regional

Wed 11/4

1:54 pm-9:36 pm

1 stop7h 42m

$377

ChicagoGulfport

ORD Chicago O'Hare Intl - GPT Gulfport Biloxi Regional

ORDGPT

Chicago O'Hare Intl

Sun 9/6

5:30 am-1:24 pm

1 stop7h 54m

Gulfport Biloxi Regional

Sat 9/12

2:00 pm-8:05 pm

1 stop6h 05m

$388

ChicagoGulfport

ORD Chicago O'Hare Intl - GPT Gulfport Biloxi Regional

ORDGPT

Chicago O'Hare Intl

Wed 9/2

7:30 am-1:24 pm

1 stop5h 54m

Gulfport Biloxi Regional

Sun 9/6

2:00 pm-9:31 pm

1 stop7h 31m

$388

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 February. Flight prices, which tend to average around $289, are often lower during this time because this is during the off-season. If you are unable to visit Gulfport during the month of February, then departing from Chicago during the month August is also very affordable. Most momondo users find prices during this month for around $296.

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 19m

Direct flights

None
The fastest flight from Chicago to Gulfport takes 4h 19m
There are no direct flights from Chicago to Gulfport. There are no popular flight routes from Chicago to Gulfport.
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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 19m 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
11,929 reviews
Search American Airlines flights
DeltaPriceFrom $268Free CancellationRating
7.8
8,502 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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