Which layover airport has the shortest travel time from Chicago to Gulfport?

Flights connecting via Charlotte (CLT) have the shortest average one-way travel time: 5h 09m.

Which layover airport offers the lowest fares from Chicago to Gulfport?

Flights via Charlotte (CLT) offer the lowest average round-trip price of $283.

What is the most punctual flight time for Chicago to Gulfport flights?

Generally, flights departing at night tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

What day of the week experiences the fewest flight delays on this route?

Monday is statistically the day of the week which experiences the fewest number of delays on this flight route. Thursday has historically seen more delays on average compared to the rest of the week.

How often are flights from Chicago to Gulfport delayed?

Historically, on average around 39% of flights between Chicago and Gulfport have experienced a delay on any given week. The average delay length over the past 12 months has been 92 minutes.

Which airport is the most popular layover for flights between Chicago and Gulfport?

Atlanta (ATL) was the most common stop: 50% of momondo users choosing 1-stop flights on this route connected there.

Which layover airport has the shortest connection time from Chicago to Gulfport?

Charlotte (CLT) has the shortest average layover time for this route: 1h 04m.

What is the cheapest airline that flies from Chicago to Gulfport Biloxi Regional?

United Airlines is the most popular carrier operating from Chicago to Gulfport Biloxi Regional

What airlines fly to Gulfport?

American Airlines, Spirit Airlines and United Airlines are the top three most popular airlines that fly to Gulfport from Chicago according to our data. American Airlines is the first choice among our users, with 31% of people opting to fly with this airline when traveling to Gulfport. Keep in mind that there are 6 different airlines that fly to Gulfport on a routine basis, so you have a few additional options to choose from.

Which airline has the best punctuality record on Chicago to Gulfport flights?

According to our data, Sun Country Air have had the least number of delays on this route over the last 12 months; with about 50% of their flights experiencing any sort of delay.

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?

As of December 2025, there are 2 operators available to choose from 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.

$151 Cheap Flights from Chicago to Gulfport in 2025/26

Q: What is the typical price of a round-trip flight between Chicago and Gulfport?

Prices are currently low for flights on this route. Typical prices usually range from $376 to $502. The lowest price recently found on this route was $269.

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One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

5:31 pm - 9:53 pm

MDW

GPT

4h 22m1 stop

4:00 pm - 10:07 pm

GPT

MDW

6h 07m1 stop

$269Delta

Wed, Jan 7 - Sat, Jan 10

10:35 am - 3:58 pm

ORD

GPT

5h 23m1 stop

5:13 pm - 12:28 am

GPT

ORD

7h 15m1 stop

$269United Airlines

Wed, Jan 7 - Sat, Jan 10

4:02 pm - 11:08 pm

ORD

GPT

7h 06m2 stops

5:29 pm - 11:27 pm

GPT

ORD

5h 58m1 stop

$274American Airlines

Sat, Jan 10 - Thu, Jan 15

5:15 am - 9:00 am

ORD

GPT

27h 45m2 stops

6:54 pm - 4:58 pm

GPT

ORD

22h 04m1 stop

$294Multiple Airlines

Thu, Jan 15 - Mon, Jan 19

8:54 am - 3:58 pm

ORD

GPT

7h 04m1 stop

1:57 pm - 9:26 pm

GPT

ORD

7h 29m1 stop

$298United Airlines

Thu, Jan 15 - Mon, Jan 19

10:19 am - 6:03 pm

ORD

GPT

7h 44m1 stop

1:45 pm - 10:16 pm

GPT

ORD

8h 31m2 stops

$309American Airlines

Wed, Jan 7 - Sat, Jan 10

8:54 am - 3:58 pm

ORD

GPT

7h 04m1 stop

5:13 pm - 12:28 am

GPT

ORD

7h 15m1 stop

$339United Airlines

Wed, Jan 14 - Sat, Jan 17

6:00 am - 6:14 pm

ORD

GPT

12h 14m2 stops

6:54 pm - 5:03 pm

GPT

ORD

22h 09m1 stop

$365Multiple Airlines

Mon, Feb 16 - Fri, Feb 20

10:49 am - 7:04 pm

ORD

GPT

8h 15m1 stop

5:16 pm - 10:26 pm

GPT

ORD

5h 10m1 stop

$372American Airlines

Wed, Mar 25 - Tue, Mar 31

8:54 am - 3:58 pm

ORD

GPT

7h 04m1 stop

1:57 pm - 9:26 pm

GPT

ORD

7h 29m1 stop

$374United Airlines

Mon, Jan 12 - Mon, Jan 19

Delta flights from Chicago to Gulfport

Our best Delta deals on Chicago to Gulfport flight tickets

Delta

Jan 7

MDW5:31 pmChicago Midway

4h 22m

1 stop

GPT9:53 pmGulfport Biloxi Regional

Jan 10

GPT4:00 pmGulfport Biloxi Regional

6h 07m

1 stop

MDW10:07 pmChicago Midway

$269

Find similar

Delta

Dec 24

ORD5:31 pmChicago O'Hare Intl

4h 09m

1 stop

GPT9:40 pmGulfport Biloxi Regional

Dec 29

GPT5:21 pmGulfport Biloxi Regional

6h 41m

1 stop

ORD12:02 amChicago O'Hare Intl

$379

Find similar

Delta

Jan 3

MDW6:00 amChicago Midway

7h 26m

1 stop

GPT1:26 pmGulfport Biloxi Regional

Jan 7

GPT6:05 amGulfport Biloxi Regional

4h 22m

1 stop

MDW10:27 amChicago Midway

$383

Find similar

United Airlines flights from Chicago to Gulfport

Our best United Airlines deals on Chicago to Gulfport flight tickets

United Airlines

Feb 24

ORD7:35 amChicago O'Hare Intl

5h 45m

1 stop

GPT1:20 pmGulfport Biloxi Regional

Mar 3

GPT4:55 pmGulfport Biloxi Regional

6h 09m

1 stop

ORD11:04 pmChicago O'Hare Intl

$269

Find similar

United Airlines

Jan 15

ORD8:54 amChicago O'Hare Intl

7h 04m

1 stop

GPT3:58 pmGulfport Biloxi Regional

Jan 19

GPT1:57 pmGulfport Biloxi Regional

7h 29m

1 stop

ORD9:26 pmChicago O'Hare Intl

$298

Find similar

United Airlines

Jan 14

ORD8:54 amChicago O'Hare Intl

7h 04m

1 stop

GPT3:58 pmGulfport Biloxi Regional

Jan 17

GPT5:13 pmGulfport Biloxi Regional

7h 15m

1 stop

ORD12:28 amChicago O'Hare Intl

$339

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Wed 1/7

5:31 pm-9:53 pm

1 stop4h 22m

Gulfport Biloxi Regional

Sat 1/10

4:00 pm-10:07 pm

1 stop6h 07m

$269

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Wed 1/7

10:35 am-3:58 pm

1 stop5h 23m

Gulfport Biloxi Regional

Sat 1/10

5:13 pm-12:28 am

1 stop7h 15m

$269

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Sat 1/10

4:02 pm-11:08 pm

2 stops7h 06m

Gulfport Biloxi Regional

Thu 1/15

5:29 pm-11:27 pm

1 stop5h 58m

$274

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Thu 1/15

5:15 am-9:00 am

2 stops27h 45m

Gulfport Biloxi Regional

Mon 1/19

6:54 pm-4:58 pm

1 stop22h 04m

$294

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Thu 1/15

8:54 am-3:58 pm

1 stop7h 04m

Gulfport Biloxi Regional

Mon 1/19

1:57 pm-9:26 pm

1 stop7h 29m

$298

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Wed 1/7

10:19 am-6:03 pm

1 stop7h 44m

Gulfport Biloxi Regional

Sat 1/10

1:45 pm-10:16 pm

2 stops8h 31m

$309

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Wed 1/14

8:54 am-3:58 pm

1 stop7h 04m

Gulfport Biloxi Regional

Sat 1/17

5:13 pm-12:28 am

1 stop7h 15m

$339

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Mon 2/16

6:00 am-6:14 pm

2 stops12h 14m

Gulfport Biloxi Regional

Fri 2/20

6:54 pm-5:03 pm

1 stop22h 09m

$365

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Wed 3/25

10:49 am-7:04 pm

1 stop8h 15m

Gulfport Biloxi Regional

Tue 3/31

5:16 pm-10:26 pm

1 stop5h 10m

$372

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Mon 1/12

8:54 am-3:58 pm

1 stop7h 04m

Gulfport Biloxi Regional

Mon 1/19

1:57 pm-9:26 pm

1 stop7h 29m

$374

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

Delays

Layovers

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 April is also very affordable. Most momondo users find prices during this month for around $328.

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

Fastest flight time	4h 11m
Direct flights	None

The fastest flight from Chicago to Gulfport takes 4h 11m

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 11m 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?
As of December 2025, there are 2 operators available to choose from 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?
Based on momondo bookings for flights between Chicago and Gulfport, the leading airline is American Airlines, making up 52% of the total bookings. Other popular airlines include Delta with 31% and United Airlines with 17%.

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 Airlines	PriceFrom $248	Free Cancellation	Rating 7.2 11,050 reviews		Search American Airlines flights
Delta	PriceFrom $248	Free Cancellation	Rating 7.9 8,021 reviews		Search Delta flights

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

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Cheap flights from Chicago to Gulfport from $151

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 12/31. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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How to get the cheapest flight ticket from Chicago to Gulfport

What is the typical price of a round-trip flight between Chicago and Gulfport?

What is the cheapest month to fly to Gulfport?

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?

What is the cheapest airline that flies from Chicago to Gulfport Biloxi Regional?

United Airlines is the most popular carrier operating from Chicago to Gulfport Biloxi Regional

What airlines fly to Gulfport?

How often are flights from Chicago to Gulfport delayed?

Historically, on average around 39% of flights between Chicago and Gulfport have experienced a delay on any given week. The average delay length over the past 12 months has been 92 minutes.

What is the most punctual flight time for Chicago to Gulfport flights?

Generally, flights departing at night tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

What day of the week experiences the fewest flight delays on this route?

Monday is statistically the day of the week which experiences the fewest number of delays on this flight route. Thursday has historically seen more delays on average compared to the rest of the week.

Which airline has the best punctuality record on Chicago to Gulfport flights?

According to our data, Sun Country Air have had the least number of delays on this route over the last 12 months; with about 50% of their flights experiencing any sort of delay.

Which airport is the most popular layover for flights between Chicago and Gulfport?

Atlanta (ATL) was the most common stop: 50% of momondo users choosing 1-stop flights on this route connected there.

Which layover airport offers the lowest fares from Chicago to Gulfport?

Flights via Charlotte (CLT) offer the lowest average round-trip price of $283.

Which layover airport has the shortest travel time from Chicago to Gulfport?

Flights connecting via Charlotte (CLT) have the shortest average one-way travel time: 5h 09m.

Which layover airport has the shortest connection time from Chicago to Gulfport?

Charlotte (CLT) has the shortest average layover time for this route: 1h 04m.

When to book flights from Chicago to Gulfport

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

Direct flights

How far is Chicago to Gulfport Biloxi Regional by plane?

When did momondo last update prices for flights from Chicago to Gulfport Biloxi Regional Airport?

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?

What documentation or ID do you need to fly to Gulfport Biloxi Regional Airport?

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

Traveling to a place near Gulfport?

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Gulfport?

Can I find flights from Chicago to Gulfport with flexible booking policies on momondo?

How can momondo help me find flights from Chicago to Gulfport?

I’m not ready to book a flight from Chicago to Gulfport right now. Can momondo alert me if prices change?

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.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Airports servicing Mississippi