Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Chicago to Gulfport from $123

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 10/30. 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

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Chicago to Gulfport

Cheap round-trip flights

American Airlines Logo
5:18 am - 11:39 amORD-GPT
6h 21m1 stop
American Airlines Logo
4:54 pm - 11:56 pmGPT-ORD
7h 02m1 stop
$249American Airlines
Find Deal
Thu, Nov 20 - Sun, Nov 23
United Airlines Logo
7:10 am - 1:25 pmORD-GPT
6h 15m1 stop
United Airlines Logo
2:00 pm - 9:36 pmGPT-ORD
7h 36m1 stop
$259United Airlines
Find Deal
Sat, Sep 27 - Tue, Sep 30
Delta Logo
5:20 am - 9:16 amORD-GPT
3h 56m1 stop
Delta Logo
6:05 pm - 11:58 pmGPT-ORD
5h 53m1 stop
$279Delta
Find Deal
Tue, Oct 14 - Fri, Oct 24
Delta Logo
4:25 pm - 9:39 pmMDW-GPT
5h 14m1 stop
Delta Logo
6:08 am - 11:48 amGPT-MDW
5h 40m1 stop
$284Delta
Find Deal
Sat, Sep 27 - Wed, Oct 1
Delta Logo
5:20 am - 9:16 amORD-GPT
3h 56m1 stop
Delta Logo
6:05 pm - 7:50 amGPT-ORD
13h 45m2 stops
$287Delta
Find Deal
Tue, Oct 14 - Wed, Oct 22
Delta Logo
5:20 am - 9:16 amORD-GPT
3h 56m1 stop
Delta Logo
2:31 pm - 6:49 pmGPT-ORD
4h 18m1 stop
$294Delta
Find Deal
Tue, Oct 14 - Wed, Oct 22
Delta Logo
4:25 pm - 9:39 pmMDW-GPT
5h 14m1 stop
Delta Logo
6:08 am - 11:48 amGPT-MDW
5h 40m1 stop
$299Delta
Find Deal
Sat, Sep 27 - Wed, Oct 1
Logo
2:41 pm - 8:59 amORD-GPT
18h 18m2 stops
Logo
6:51 pm - 10:08 amGPT-ORD
15h 17m1 stop
$301
Find Deal
Thu, Oct 9 - Mon, Oct 13
Logo
6:00 am - 7:15 pmORD-GPT
13h 15m2 stops
Logo
6:51 pm - 10:14 amGPT-ORD
15h 23m1 stop
$303
Find Deal
Thu, Oct 9 - Fri, Oct 10
Delta Logo
4:25 pm - 9:39 pmMDW-GPT
5h 14m1 stop
Delta Logo
6:08 am - 11:48 amGPT-MDW
5h 40m1 stop
$309Delta
Find Deal
Sat, Sep 27 - Wed, Oct 1

Delta flights from Chicago to Gulfport

Our best Delta deals on Chicago to Gulfport flight tickets
Delta
Oct 14
ORD5:20 amChicago O'Hare Intl
3h 56m
1 stop
GPT9:16 amGulfport Biloxi Regional
Oct 24
GPT6:05 pmGulfport Biloxi Regional
5h 53m
1 stop
ORD11:58 pmChicago O'Hare Intl
$279
Find similar
Delta
Sep 24
ORD7:20 amChicago O'Hare Intl
6h 00m
1 stop
GPT1:20 pmGulfport Biloxi Regional
Sep 29
GPT6:04 pmGulfport Biloxi Regional
5h 50m
1 stop
ORD11:54 pmChicago O'Hare Intl
$284
Find similar
Delta
Oct 14
ORD5:20 amChicago O'Hare Intl
3h 56m
1 stop
GPT9:16 amGulfport Biloxi Regional
Oct 22
GPT6:05 pmGulfport Biloxi Regional
13h 45m
2 stops
ORD7:50 amChicago O'Hare Intl
$287
Find similar

United Airlines flights from Chicago to Gulfport

Our best United Airlines deals on Chicago to Gulfport flight tickets
United Airlines
Sep 27
ORD7:10 amChicago O'Hare Intl
6h 15m
1 stop
GPT1:25 pmGulfport Biloxi Regional
Sep 30
GPT2:00 pmGulfport Biloxi Regional
7h 36m
1 stop
ORD9:36 pmChicago O'Hare Intl
$259
Find similar
United Airlines
Sep 26
ORD2:20 pmChicago O'Hare Intl
5h 35m
1 stop
GPT7:55 pmGulfport Biloxi Regional
Sep 28
GPT5:25 pmGulfport Biloxi Regional
6h 49m
1 stop
ORD12:14 amChicago O'Hare Intl
$312
Find similar
United Airlines
Sep 18
ORD10:35 amChicago O'Hare Intl
5h 30m
1 stop
GPT4:05 pmGulfport Biloxi Regional
Sep 20
GPT2:02 pmGulfport Biloxi Regional
7h 38m
1 stop
ORD9:40 pmChicago O'Hare Intl
$339
Find similar

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 September 15, 2025.
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

Thu 11/20

5:18 am-11:39 am

1 stop6h 21m

Gulfport Biloxi Regional

Sun 11/23

4:54 pm-11:56 pm

1 stop7h 02m

$249

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Sat 9/27

7:10 am-1:25 pm

1 stop6h 15m

Gulfport Biloxi Regional

Tue 9/30

2:00 pm-9:36 pm

1 stop7h 36m

$259

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Tue 10/14

5:20 am-9:16 am

1 stop3h 56m

Gulfport Biloxi Regional

Fri 10/24

6:05 pm-11:58 pm

1 stop5h 53m

$279

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Sat 9/27

4:25 pm-9:39 pm

1 stop5h 14m

Gulfport Biloxi Regional

Wed 10/1

6:08 am-11:48 am

1 stop5h 40m

$284

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Tue 10/14

5:20 am-9:16 am

1 stop3h 56m

Gulfport Biloxi Regional

Wed 10/22

6:05 pm-7:50 am

2 stops13h 45m

$287

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Tue 10/14

5:20 am-9:16 am

1 stop3h 56m

Gulfport Biloxi Regional

Wed 10/22

2:31 pm-6:49 pm

1 stop4h 18m

$294

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Sat 9/27

4:25 pm-9:39 pm

1 stop5h 14m

Gulfport Biloxi Regional

Wed 10/1

6:08 am-11:48 am

1 stop5h 40m

$299

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Thu 10/9

2:41 pm-8:59 am

2 stops18h 18m

Gulfport Biloxi Regional

Mon 10/13

6:51 pm-10:08 am

1 stop15h 17m

$301

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Thu 10/9

6:00 am-7:15 pm

2 stops13h 15m

Gulfport Biloxi Regional

Fri 10/10

6:51 pm-10:14 am

1 stop15h 23m

$303

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Sat 9/27

4:25 pm-9:39 pm

1 stop5h 14m

Gulfport Biloxi Regional

Wed 10/1

6:08 am-11:48 am

1 stop5h 40m

$309

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 March is also very affordable. Most momondo users find prices during this month for around $326.

What is the cheapest day to depart on your flight to Gulfport?

The cheapest day to depart from Chicago to Gulfport is on a Tuesday when prices can be found for as low as $314. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Chicago to Gulfport for around $464.

What is the cheapest time of day to depart on your flight to Gulfport?

According to our data, the cheapest time of day to fly to Gulfport is in the morning. momondo users have found flights departing from Chicago to Gulfport in the morning for as low as $390. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In contrast, the most expensive time of day to depart to Gulfport is at noon when prices are around $493.

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

Direct flights

None
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 3h 56m 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
10,000 reviews
Search American Airlines flights
DeltaPriceFrom $253Free CancellationRating
7.9
7,954 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.

An easier way to manage your Gulfport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Wed 10/15
Wed 10/22
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States