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Cheap flights from Chicago to Gulfport from $140

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 3/1. 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

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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.
Multiple Airlines Logo
10:25 am - 6:40 pm
ORD
-
GPT
8h 15m
1 stop
Multiple Airlines Logo
5:31 pm - 11:43 am
GPT
-
ORD
18h 12m
1 stop
$230Multiple Airlines
Sun, May 3 - Fri, May 8
Multiple Airlines Logo
8:05 am - 6:40 pm
ORD
-
GPT
10h 35m
1 stop
Multiple Airlines Logo
7:20 pm - 11:38 pm
GPT
-
ORD
28h 18m
1 stop
$231Multiple Airlines
Sun, Mar 8 - Sun, Mar 15
Multiple Airlines Logo
8:05 am - 6:40 pm
ORD
-
GPT
10h 35m
1 stop
Multiple Airlines Logo
7:20 pm - 10:52 am
GPT
-
ORD
15h 32m
2 stops
$257Multiple Airlines
Sun, Mar 8 - Sun, Mar 15
Multiple Airlines Logo
10:25 am - 6:40 pm
ORD
-
GPT
8h 15m
1 stop
Multiple Airlines Logo
5:31 pm - 11:27 am
GPT
-
ORD
17h 56m
2 stops
$265Multiple Airlines
Sun, May 3 - Fri, May 8
Delta Logo
12:47 pm - 5:11 pm
MDW
-
GPT
4h 24m
1 stop
Delta Logo
5:57 pm - 10:31 pm
GPT
-
MDW
4h 34m
1 stop
$269Delta
Tue, Mar 10 - Tue, Mar 17
Delta Logo
5:25 am - 9:40 am
ORD
-
GPT
4h 15m
1 stop
Delta Logo
5:57 pm - 11:54 pm
GPT
-
ORD
5h 57m
1 stop
$269Delta
Sat, Mar 7 - Wed, Mar 11
American Airlines Logo
4:04 pm - 11:49 pm
ORD
-
GPT
7h 45m
2 stops
American Airlines Logo
4:29 pm - 11:58 pm
GPT
-
ORD
7h 29m
1 stop
$274American Airlines
Tue, Mar 10 - Sat, Mar 14
American Airlines Logo
5:00 am - 10:13 am
ORD
-
GPT
5h 13m
1 stop
American Airlines Logo
4:29 pm - 11:58 pm
GPT
-
ORD
7h 29m
1 stop
$279American Airlines
Tue, Feb 24 - Sat, Feb 28
Delta Logo
10:45 am - 5:11 pm
MDW
-
GPT
6h 26m
1 stop
Delta Logo
6:00 am - 12:02 pm
GPT
-
MDW
6h 02m
1 stop
$374Delta
Thu, Mar 26 - Tue, Mar 31
Delta Logo
4:13 pm - 9:54 pm
MDW
-
GPT
5h 41m
1 stop
Delta Logo
9:48 am - 3:25 pm
GPT
-
MDW
5h 37m
1 stop
$414Delta
Sat, Mar 7 - Sat, Mar 14

American Airlines flights from Chicago to Gulfport

Our best American Airlines deals on Chicago to Gulfport flight tickets
American Airlines
Mar 10
ORD4:04 pmChicago O'Hare Intl
7h 45m
2 stops
GPT11:49 pmGulfport Biloxi Regional
Mar 14
GPT4:29 pmGulfport Biloxi Regional
7h 29m
1 stop
ORD11:58 pmChicago O'Hare Intl
$274
American Airlines
Feb 24
ORD5:00 amChicago O'Hare Intl
5h 13m
1 stop
GPT10:13 amGulfport Biloxi Regional
Feb 28
GPT4:29 pmGulfport Biloxi Regional
7h 29m
1 stop
ORD11:58 pmChicago O'Hare Intl
$279
American Airlines
Feb 22
ORD5:00 amChicago O'Hare Intl
5h 13m
1 stop
GPT10:13 amGulfport Biloxi Regional
Mar 7
GPT4:29 pmGulfport Biloxi Regional
7h 29m
1 stop
ORD11:58 pmChicago O'Hare Intl
$304

Delta flights from Chicago to Gulfport

Our best Delta deals on Chicago to Gulfport flight tickets
Delta
Mar 7
ORD5:25 amChicago O'Hare Intl
4h 15m
1 stop
GPT9:40 amGulfport Biloxi Regional
Mar 11
GPT5:57 pmGulfport Biloxi Regional
5h 57m
1 stop
ORD11:54 pmChicago O'Hare Intl
$269
Delta
Jun 10
ORD9:30 amChicago O'Hare Intl
4h 04m
1 stop
GPT1:34 pmGulfport Biloxi Regional
Jun 14
GPT2:15 pmGulfport Biloxi Regional
6h 03m
1 stop
ORD8:18 pmChicago O'Hare Intl
$331
Delta
Mar 26
MDW10:45 amChicago Midway
6h 26m
1 stop
GPT5:11 pmGulfport Biloxi Regional
Mar 31
GPT6:00 amGulfport Biloxi Regional
6h 02m
1 stop
MDW12:02 pmChicago Midway
$374

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 February 11, 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

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Sun 5/3

10:25 am-6:40 pm

1 stop8h 15m

Gulfport Biloxi Regional

Fri 5/8

5:31 pm-11:43 am

1 stop18h 12m

$230

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Sun 3/8

8:05 am-6:40 pm

1 stop10h 35m

Gulfport Biloxi Regional

Sun 3/15

7:20 pm-11:38 pm

1 stop28h 18m

$231

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Sun 3/8

8:05 am-6:40 pm

1 stop10h 35m

Gulfport Biloxi Regional

Sun 3/15

7:20 pm-10:52 am

2 stops15h 32m

$257

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Sun 5/3

10:25 am-6:40 pm

1 stop8h 15m

Gulfport Biloxi Regional

Fri 5/8

5:31 pm-11:27 am

2 stops17h 56m

$265

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Tue 3/10

12:47 pm-5:11 pm

1 stop4h 24m

Gulfport Biloxi Regional

Tue 3/17

5:57 pm-10:31 pm

1 stop4h 34m

$269

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Sat 3/7

5:25 am-9:40 am

1 stop4h 15m

Gulfport Biloxi Regional

Wed 3/11

5:57 pm-11:54 pm

1 stop5h 57m

$269

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Tue 3/10

4:04 pm-11:49 pm

2 stops7h 45m

Gulfport Biloxi Regional

Sat 3/14

4:29 pm-11:58 pm

1 stop7h 29m

$274

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Tue 2/24

5:00 am-10:13 am

1 stop5h 13m

Gulfport Biloxi Regional

Sat 2/28

4:29 pm-11:58 pm

1 stop7h 29m

$279

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Thu 3/26

10:45 am-5:11 pm

1 stop6h 26m

Gulfport Biloxi Regional

Tue 3/31

6:00 am-12:02 pm

1 stop6h 02m

$374

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Sat 3/7

4:13 pm-9:54 pm

1 stop5h 41m

Gulfport Biloxi Regional

Sat 3/14

9:48 am-3:25 pm

1 stop5h 37m

$414

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 August. 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 August, then departing from Chicago during the month February is also very affordable. Most momondo users find prices during this month for around $289.

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 24m

Direct flights

None
The fastest flight from Chicago to Gulfport takes 4h 24m
There are no direct flights from Chicago to Gulfport. There are no popular flight routes from Chicago to Gulfport.
Search flight deals

  • 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 24m 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
7.2
11,266 reviews
Search American Airlines flights
DeltaPriceFrom $248Free CancellationRating
7.9
8,180 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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