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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 4/8. 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
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
6:00 am - 6:40 pm
MDW
-
GPT
12h 40m
2 stops
Multiple Airlines Logo
7:20 pm - 8:04 am
GPT
-
MDW
12h 44m
1 stop
$274Multiple Airlines
Thu, Apr 16 - Sun, Apr 19
Multiple Airlines Logo
3:08 pm - 9:00 am
ORD
-
GPT
17h 52m
1 stop
Multiple Airlines Logo
7:20 pm - 11:33 am
GPT
-
ORD
40h 13m
2 stops
$279Multiple Airlines
Thu, Apr 16 - Thu, Apr 23
Multiple Airlines Logo
8:52 pm - 9:00 am
ORD
-
GPT
12h 08m
1 stop
Multiple Airlines Logo
7:20 pm - 10:23 am
GPT
-
ORD
39h 03m
2 stops
$281Multiple Airlines
Thu, Apr 16 - Sun, Apr 19
Multiple Airlines Logo
3:08 pm - 9:00 am
ORD
-
GPT
17h 52m
1 stop
Multiple Airlines Logo
7:20 pm - 9:05 am
GPT
-
ORD
13h 45m
1 stop
$290Multiple Airlines
Thu, Apr 16 - Thu, Apr 23
Delta Logo
5:15 am - 9:24 am
ORD
-
GPT
4h 09m
1 stop
Delta Logo
10:09 am - 4:42 pm
GPT
-
ORD
6h 33m
1 stop
$291Delta
Sat, Apr 25 - Sat, May 2
American Airlines Logo
6:41 pm - 11:58 pm
ORD
-
GPT
5h 17m
1 stop
American Airlines Logo
5:03 pm - 11:48 pm
GPT
-
ORD
6h 45m
1 stop
$310American Airlines
Mon, May 11 - Sat, May 16
American Airlines Logo
5:00 am - 10:33 am
ORD
-
GPT
5h 33m
1 stop
American Airlines Logo
6:09 pm - 11:54 pm
GPT
-
ORD
5h 45m
1 stop
$329American Airlines
Mon, May 11 - Sat, May 16
Delta Logo
5:15 am - 9:24 am
ORD
-
GPT
4h 09m
1 stop
Delta Logo
3:00 pm - 8:16 pm
GPT
-
ORD
5h 16m
1 stop
$334Delta
Mon, Apr 13 - Sat, Apr 18
American Airlines Logo
6:41 pm - 11:58 pm
ORD
-
GPT
5h 17m
1 stop
American Airlines Logo
6:09 pm - 11:54 pm
GPT
-
ORD
5h 45m
1 stop
$339American Airlines
Fri, Apr 10 - Mon, Apr 13
Delta Logo
6:23 am - 1:09 pm
MDW
-
GPT
6h 46m
1 stop
Delta Logo
3:00 pm - 9:09 pm
GPT
-
MDW
6h 09m
1 stop
$365Delta
Mon, May 11 - Sat, May 16

United Airlines flights from Chicago to Gulfport

Our best United Airlines deals on Chicago to Gulfport flight tickets
United Airlines
Apr 25
ORD12:43 pmChicago O'Hare Intl
7h 10m
1 stop
GPT7:53 pmGulfport Biloxi Regional
May 2
GPT2:00 pmGulfport Biloxi Regional
7h 51m
1 stop
ORD9:51 pmChicago O'Hare Intl
$409
United Airlines
Apr 21
ORD5:48 amChicago O'Hare Intl
8h 25m
1 stop
GPT2:13 pmGulfport Biloxi Regional
Apr 25
GPT4:26 pmGulfport Biloxi Regional
8h 19m
1 stop
ORD12:45 amChicago O'Hare Intl
$444
United Airlines
May 2
ORD2:10 pmChicago O'Hare Intl
5h 43m
1 stop
GPT7:53 pmGulfport Biloxi Regional
May 6
GPT4:55 pmGulfport Biloxi Regional
7h 50m
1 stop
ORD12:45 amChicago O'Hare Intl
$451

American Airlines flights from Chicago to Gulfport

Our best American Airlines deals on Chicago to Gulfport flight tickets
American Airlines
May 11
ORD5:00 amChicago O'Hare Intl
5h 33m
1 stop
GPT10:33 amGulfport Biloxi Regional
May 16
GPT5:03 pmGulfport Biloxi Regional
6h 45m
1 stop
ORD11:48 pmChicago O'Hare Intl
$310
American Airlines
May 11
ORD5:00 amChicago O'Hare Intl
5h 33m
1 stop
GPT10:33 amGulfport Biloxi Regional
May 16
GPT6:09 pmGulfport Biloxi Regional
5h 45m
1 stop
ORD11:54 pmChicago O'Hare Intl
$329
American Airlines
Apr 7
ORD4:17 pmChicago O'Hare Intl
7h 09m
1 stop
GPT11:26 pmGulfport Biloxi Regional
Apr 11
GPT6:09 pmGulfport Biloxi Regional
5h 45m
1 stop
ORD11:54 pmChicago O'Hare Intl
$339

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 March 28, 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

MDW - GPT

MDWGPT

Chicago Midway

Thu 4/16

6:00 am-6:40 pm

2 stops12h 40m

Gulfport Biloxi Regional

Sun 4/19

7:20 pm-8:04 am

1 stop12h 44m

$274

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Thu 4/16

3:08 pm-9:00 am

1 stop17h 52m

Gulfport Biloxi Regional

Thu 4/23

7:20 pm-11:33 am

2 stops40h 13m

$279

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Thu 4/16

8:52 pm-9:00 am

1 stop12h 08m

Gulfport Biloxi Regional

Sun 4/19

7:20 pm-10:23 am

2 stops39h 03m

$281

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Thu 4/16

3:08 pm-9:00 am

1 stop17h 52m

Gulfport Biloxi Regional

Thu 4/23

7:20 pm-9:05 am

1 stop13h 45m

$290

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Sat 4/25

5:15 am-9:24 am

1 stop4h 09m

Gulfport Biloxi Regional

Sat 5/2

10:09 am-4:42 pm

1 stop6h 33m

$291

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Mon 5/11

6:41 pm-11:58 pm

1 stop5h 17m

Gulfport Biloxi Regional

Sat 5/16

5:03 pm-11:48 pm

1 stop6h 45m

$310

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Mon 5/11

5:00 am-10:33 am

1 stop5h 33m

Gulfport Biloxi Regional

Sat 5/16

6:09 pm-11:54 pm

1 stop5h 45m

$329
Quickest round-trip

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Mon 4/13

5:15 am-9:24 am

1 stop4h 09m

Gulfport Biloxi Regional

Sat 4/18

3:00 pm-8:16 pm

1 stop5h 16m

$334

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Fri 4/10

6:41 pm-11:58 pm

1 stop5h 17m

Gulfport Biloxi Regional

Mon 4/13

6:09 pm-11:54 pm

1 stop5h 45m

$339

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Mon 5/11

6:23 am-1:09 pm

1 stop6h 46m

Gulfport Biloxi Regional

Sat 5/16

3:00 pm-9:09 pm

1 stop6h 09m

$365

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 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 July is also very affordable. Most momondo users find prices during this month for around $268.

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 04m

Direct flights

None
The fastest flight from Chicago to Gulfport takes 4h 04m
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 04m 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
11,520 reviews
Search American Airlines flights
DeltaPriceFrom $248Free CancellationRating
7.9
8,356 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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