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

Atlanta (ATL) has the shortest average layover time for this route: 0h 37m.

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

Atlanta (ATL) was the most common stop: 60% 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 Atlanta (ATL) have the shortest average one-way travel time: 4h 03m.

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.

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

United Airlines, Delta, and American Airlines are the most popular carriers operating from Chicago to Gulfport Biloxi Regional

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 November 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.

$214 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 $338 to $373. The lowest price recently found on this route was $249.

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Cheap round-trip flights

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5:29 pm - 10:03 pmMDW-GPT

4h 34m1 stop

5:21 pm - 10:22 pmGPT-MDW

5h 01m1 stop

$249Delta

Find Deal

Wed, Dec 17 - Wed, Dec 24

9:30 am - 1:37 pmORD-GPT

4h 07m1 stop

3:00 pm - 7:29 pmGPT-ORD

4h 29m1 stop

$249Delta

Find Deal

Tue, Mar 17 - Sat, Mar 21

6:45 am - 2:08 pmORD-GPT

7h 23m1 stop

6:03 pm - 12:02 amGPT-ORD

5h 59m1 stop

$264Delta

Find Deal

Tue, Nov 25 - Mon, Dec 1

6:00 am - 11:17 amORD-GPT

5h 17m1 stop

5:15 pm - 12:14 amGPT-ORD

6h 59m1 stop

$265United Airlines

Find Deal

Tue, Nov 25 - Sat, Dec 27

10:18 am - 6:40 pmORD-GPT

8h 22m1 stop

6:54 pm - 10:23 pmGPT-ORD

27h 29m2 stops

$272Multiple Airlines

Find Deal

Thu, Feb 19 - Mon, Feb 23

6:00 am - 1:20 pmORD-GPT

7h 20m1 stop

5:15 pm - 12:15 amGPT-ORD

7h 00m1 stop

$277United Airlines

Find Deal

Sat, Nov 22 - Mon, Nov 24

4:28 pm - 10:07 pmMDW-GPT

5h 39m1 stop

6:03 pm - 11:40 pmGPT-MDW

5h 37m1 stop

$279Delta

Find Deal

Sat, Nov 15 - Wed, Nov 19

6:35 pm - 11:57 pmORD-GPT

5h 22m1 stop

5:26 pm - 11:37 pmGPT-ORD

6h 11m1 stop

$294American Airlines

Find Deal

Fri, Nov 21 - Mon, Nov 24

11:45 am - 5:44 pmORD-GPT

5h 59m1 stop

4:39 pm - 12:07 amGPT-ORD

7h 28m1 stop

$319American Airlines

Find Deal

Wed, Feb 18 - Sat, Feb 21

6:48 am - 5:15 pmORD-GPT

10h 27m1 stop

6:51 pm - 6:46 pmGPT-ORD

23h 55m2 stops

$376Multiple Airlines

Find Deal

Tue, Nov 25 - Mon, Dec 1

Delta flights from Chicago to Gulfport

Our best Delta deals on Chicago to Gulfport flight tickets

Delta

Mar 17

ORD9:30 amChicago O'Hare Intl

4h 07m

1 stop

GPT1:37 pmGulfport Biloxi Regional

Mar 21

GPT3:00 pmGulfport Biloxi Regional

4h 29m

1 stop

ORD7:29 pmChicago O'Hare Intl

$249

Find similar

Delta

Nov 25

ORD6:45 amChicago O'Hare Intl

7h 23m

1 stop

GPT2:08 pmGulfport Biloxi Regional

Dec 1

GPT6:03 pmGulfport Biloxi Regional

5h 59m

1 stop

ORD12:02 amChicago O'Hare Intl

$264

Find similar

Delta

Nov 15

MDW4:28 pmChicago Midway

5h 39m

1 stop

GPT10:07 pmGulfport Biloxi Regional

Nov 19

GPT6:03 pmGulfport Biloxi Regional

5h 37m

1 stop

MDW11:40 pmChicago Midway

$279

Find similar

United Airlines flights from Chicago to Gulfport

Our best United Airlines deals on Chicago to Gulfport flight tickets

United Airlines

Nov 25

ORD6:00 amChicago O'Hare Intl

5h 17m

1 stop

GPT11:17 amGulfport Biloxi Regional

Dec 27

GPT5:15 pmGulfport Biloxi Regional

6h 59m

1 stop

ORD12:14 amChicago O'Hare Intl

$265

Find similar

United Airlines

Nov 22

ORD6:00 amChicago O'Hare Intl

7h 20m

1 stop

GPT1:20 pmGulfport Biloxi Regional

Nov 24

GPT5:15 pmGulfport Biloxi Regional

7h 00m

1 stop

ORD12:15 amChicago O'Hare Intl

$277

Find similar

United Airlines

Feb 19

ORD7:35 amChicago O'Hare Intl

8h 26m

1 stop

GPT4:01 pmGulfport Biloxi Regional

Feb 23

GPT4:55 pmGulfport Biloxi Regional

7h 31m

1 stop

ORD12:26 amChicago O'Hare Intl

$315

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Wed 12/17

5:29 pm-10:03 pm

1 stop4h 34m

Gulfport Biloxi Regional

Wed 12/24

5:21 pm-10:22 pm

1 stop5h 01m

$249

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Tue 3/17

9:30 am-1:37 pm

1 stop4h 07m

Gulfport Biloxi Regional

Sat 3/21

3:00 pm-7:29 pm

1 stop4h 29m

$249

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Tue 11/25

6:45 am-2:08 pm

1 stop7h 23m

Gulfport Biloxi Regional

Mon 12/1

6:03 pm-12:02 am

1 stop5h 59m

$264

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Tue 11/25

6:00 am-11:17 am

1 stop5h 17m

Gulfport Biloxi Regional

Sat 12/27

5:15 pm-12:14 am

1 stop6h 59m

$265

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Thu 2/19

10:18 am-6:40 pm

1 stop8h 22m

Gulfport Biloxi Regional

Mon 2/23

6:54 pm-10:23 pm

2 stops27h 29m

$272

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Sat 11/22

6:00 am-1:20 pm

1 stop7h 20m

Gulfport Biloxi Regional

Mon 11/24

5:15 pm-12:15 am

1 stop7h 00m

$277

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Sat 11/15

4:28 pm-10:07 pm

1 stop5h 39m

Gulfport Biloxi Regional

Wed 11/19

6:03 pm-11:40 pm

1 stop5h 37m

$279

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Fri 11/21

6:35 pm-11:57 pm

1 stop5h 22m

Gulfport Biloxi Regional

Mon 11/24

5:26 pm-11:37 pm

1 stop6h 11m

$294

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Wed 2/18

11:45 am-5:44 pm

1 stop5h 59m

Gulfport Biloxi Regional

Sat 2/21

4:39 pm-12:07 am

1 stop7h 28m

$319

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Tue 11/25

6:48 am-5:15 pm

1 stop10h 27m

Gulfport Biloxi Regional

Mon 12/1

6:51 pm-6:46 pm

2 stops23h 55m

$376

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 17 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

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 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 4h 07m 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 November 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 50% of the total bookings. Other popular airlines include Delta with 34% and United Airlines with 16%.

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 11,038 reviews		Search American Airlines flights
Delta	PriceFrom $248	Free Cancellation	Rating 7.9 8,002 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 $249

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Gulfport departing on 12/17. 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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Delta flights from Chicago to Gulfport

Our best Delta deals on Chicago to Gulfport flight tickets

United Airlines flights from Chicago to Gulfport

Our best United Airlines deals on Chicago to Gulfport flight tickets

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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?

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, Delta, and American Airlines are the most popular carriers operating from Chicago to Gulfport Biloxi Regional

What airlines fly to Gulfport?

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

Atlanta (ATL) was the most common stop: 60% 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 Atlanta (ATL) have the shortest average one-way travel time: 4h 03m.

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

Atlanta (ATL) has the shortest average layover time for this route: 0h 37m.

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

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

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