How often are flights from Chicago to Gulfport delayed?

Historically, on average around 33% 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 93 minutes.

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.

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.

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

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

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

Prices for flights from Chicago Midway Airport to Gulfport Biloxi Regional Airport are refreshed on a daily basis.

How many operators does momondo search for flights from Chicago Midway Airport to Gulfport Biloxi Regional Airport?

As of December 2025, there is 1 operator available to choose from for flights from Chicago Midway Airport to Gulfport Biloxi Regional Airport.

How old do you have to be to fly from Chicago Midway Airport to Gulfport Biloxi Regional Airport?

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago Midway Airport to Gulfport Biloxi Regional Airport.

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

The travel and health documents required for your trip to Gulfport Biloxi Regional Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Gulfport Biloxi Regional Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$255 Cheap Flights from Chicago Midway Airport to Gulfport in 2025/26

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Find the cheapest flights from Chicago Midway Airport to Gulfport

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

10:46 am - 5:15 pm

MDW

GPT

6h 29m1 stop

4:00 pm - 10:22 pm

GPT

MDW

6h 22m1 stop

$289Delta

Mon, Feb 2 - Sat, Feb 7

10:48 am - 5:15 pm

MDW

GPT

6h 27m1 stop

6:05 am - 11:59 am

GPT

MDW

5h 54m1 stop

$457Delta

Sun, Feb 1 - Tue, Feb 3

10:53 am - 5:15 pm

MDW

GPT

6h 22m1 stop

6:00 pm - 10:42 pm

GPT

MDW

4h 42m1 stop

$497Delta

Mon, Feb 16 - Fri, Feb 20

12:47 pm - 5:17 pm

MDW

GPT

4h 30m1 stop

10:04 am - 3:25 pm

GPT

MDW

5h 21m1 stop

$499Delta

Tue, Mar 17 - Sat, Mar 21

3:10 pm - 9:25 am

MDW

GPT

18h 15m1 stop

6:51 pm - 1:21 pm

GPT

MDW

18h 30m2 stops

$713Multiple Airlines

Mon, Dec 29 - Fri, Jan 2

10:53 am - 5:15 pm

MDW

GPT

6h 22m1 stop

6:00 pm - 10:42 pm

GPT

MDW

4h 42m1 stop

$749Delta

Fri, Feb 13 - Mon, Feb 16

3:29 pm - 9:40 pm

MDW

GPT

6h 11m1 stop

10:42 am - 4:20 pm

GPT

MDW

5h 38m1 stop

$759Delta

Wed, Dec 31 - Fri, Jan 2

9:33 am - 5:15 pm

MDW

GPT

7h 42m2 stops

4:00 pm - 10:22 pm

GPT

MDW

6h 22m1 stop

$791Delta

Mon, Feb 2 - Sat, Feb 7

12:47 pm - 5:17 pm

MDW

GPT

4h 30m1 stop

6:00 am - 12:29 pm

GPT

MDW

6h 29m2 stops

$806Delta

Tue, Mar 17 - Sat, Mar 21

1:26 pm - 9:53 pm

MDW

GPT

8h 27m2 stops

6:05 am - 11:59 am

GPT

MDW

5h 54m1 stop

$875Delta

Sun, Feb 1 - Tue, Feb 3

Delta flights from Chicago Midway Airport to Gulfport

Our best Delta deals on Chicago Midway Airport to Gulfport flight tickets

Delta

Feb 2

MDW10:46 amChicago Midway

6h 29m

1 stop

GPT5:15 pmGulfport Biloxi Regional

Feb 7

GPT4:00 pmGulfport Biloxi Regional

6h 22m

1 stop

MDW10:22 pmChicago Midway

$289

Find similar

Delta

Jan 17

MDW5:31 pmChicago Midway

4h 22m

1 stop

GPT9:53 pmGulfport Biloxi Regional

Jan 20

GPT10:21 amGulfport Biloxi Regional

7h 08m

1 stop

MDW5:29 pmChicago Midway

$338

Find similar

Delta

Feb 1

MDW10:48 amChicago Midway

6h 27m

1 stop

GPT5:15 pmGulfport Biloxi Regional

Feb 3

GPT6:05 amGulfport Biloxi Regional

5h 54m

1 stop

MDW11:59 amChicago Midway

$457

Find similar

momondo Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to Gulfport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Mon 2/2

10:46 am-5:15 pm

1 stop6h 29m

Gulfport Biloxi Regional

Sat 2/7

4:00 pm-10:22 pm

1 stop6h 22m

$289

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Sun 2/1

10:48 am-5:15 pm

1 stop6h 27m

Gulfport Biloxi Regional

Tue 2/3

6:05 am-11:59 am

1 stop5h 54m

$457

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Mon 2/16

10:53 am-5:15 pm

1 stop6h 22m

Gulfport Biloxi Regional

Fri 2/20

6:00 pm-10:42 pm

1 stop4h 42m

$497

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Tue 3/17

12:47 pm-5:17 pm

1 stop4h 30m

Gulfport Biloxi Regional

Sat 3/21

10:04 am-3:25 pm

1 stop5h 21m

$499

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Mon 12/29

3:10 pm-9:25 am

1 stop18h 15m

Gulfport Biloxi Regional

Fri 1/2

6:51 pm-1:21 pm

2 stops18h 30m

$713

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Fri 2/13

10:53 am-5:15 pm

1 stop6h 22m

Gulfport Biloxi Regional

Mon 2/16

6:00 pm-10:42 pm

1 stop4h 42m

$749

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Wed 12/31

3:29 pm-9:40 pm

1 stop6h 11m

Gulfport Biloxi Regional

Fri 1/2

10:42 am-4:20 pm

1 stop5h 38m

$759

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Mon 2/2

9:33 am-5:15 pm

2 stops7h 42m

Gulfport Biloxi Regional

Sat 2/7

4:00 pm-10:22 pm

1 stop6h 22m

$791

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Tue 3/17

12:47 pm-5:17 pm

1 stop4h 30m

Gulfport Biloxi Regional

Sat 3/21

6:00 am-12:29 pm

2 stops6h 29m

$806

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Sun 2/1

1:26 pm-9:53 pm

2 stops8h 27m

Gulfport Biloxi Regional

Tue 2/3

6:05 am-11:59 am

1 stop5h 54m

$875

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

How to get the cheapest flight ticket from Chicago Midway Airport 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

Delays

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

The cheapest day to depart from Chicago Midway Airport 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 Midway Airport 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 Midway Airport 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 Midway Airport to Gulfport

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Gulfport according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Chicago Midway Airport to Gulfport (MDW to GPT) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Gulfport

Fastest flight time	4h 30m
Direct flights	None

The fastest flight from Chicago Midway Airport to Gulfport takes 4h 30m

There are no direct flights from Chicago Midway Airport to Gulfport. There are no popular flight routes from Chicago Midway Airport to Gulfport.

Search flight deals

How far is Chicago Midway to Gulfport Biloxi Regional by plane?
There are 792.0 mi between Chicago Midway and Gulfport Biloxi Regional. Typically, this will take 4h 30m by plane in normal conditions.
When did momondo last update prices for flights from Chicago Midway Airport to Gulfport Biloxi Regional Airport?
Prices for flights from Chicago Midway Airport to Gulfport Biloxi Regional Airport are refreshed on a daily basis.
How many operators does momondo search for flights from Chicago Midway Airport to Gulfport Biloxi Regional Airport?
As of December 2025, there is 1 operator available to choose from for flights from Chicago Midway Airport to Gulfport Biloxi Regional Airport.
How old do you have to be to fly from Chicago Midway Airport to Gulfport Biloxi Regional Airport?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago Midway Airport to Gulfport Biloxi Regional Airport.
What documentation or ID do you need to fly to Gulfport Biloxi Regional Airport?
The travel and health documents required for your trip to Gulfport Biloxi Regional Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Gulfport Biloxi Regional Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular airline from Chicago Midway Airport to Gulfport?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Chicago Midway Airport to Gulfport is Delta (100% of total bookings).

Best airlines flying from Chicago Midway Airport to Gulfport

Compare and see reviews for airlines that fly from Chicago Midway Airport to Gulfport with momondo

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $269	Free Cancellation	Rating 7.9 8,008 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?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Gulfport. momondo saves you time and could save you money on your trip.

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

momondo does allow users to show only those flights to Gulfport from Chicago which offer a flexible booking policy as well as other useful filters and features.

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

momondo helps you find the best flight between Chicago and Gulfport by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

If you are simply researching potential flights to Gulfport, momondo offers a useful price alert feature which will track prices for flights to Gulfport from Chicago and alert you when they change.

An easier way to manage your Gulfport trip

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Cheap flights from Chicago Midway Airport to Gulfport from $289

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Find the cheapest flights from Chicago Midway Airport to Gulfport

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Delta flights from Chicago Midway Airport to Gulfport

Our best Delta deals on Chicago Midway Airport to Gulfport flight tickets

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Use the filters below to find and compare flights from Chicago Midway Airport to Gulfport that are best for you.

See travel insights to Gulfport from

How to get the cheapest flight ticket from Chicago Midway Airport to Gulfport

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

The cheapest day to depart from Chicago Midway Airport 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 Midway Airport to Gulfport for around $464.

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

How often are flights from Chicago to Gulfport delayed?

Historically, on average around 33% 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 93 minutes.

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

Generally, flights departing in the morning 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.

When to book flights from Chicago Midway Airport to Gulfport

Cheap Chicago Midway Airport to Gulfport (MDW to GPT) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Gulfport

Fastest flight time

Direct flights

How far is Chicago Midway to Gulfport Biloxi Regional by plane?

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

How many operators does momondo search for flights from Chicago Midway Airport to Gulfport Biloxi Regional Airport?

How old do you have to be to fly from Chicago Midway Airport 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 Midway Airport to Gulfport?

Best airlines flying from Chicago Midway Airport to Gulfport

Compare and see reviews for airlines that fly from Chicago Midway Airport 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