Cheap flights from Chicago Midway Airport to Gulfport from $194
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 Midway Airport to Gulfport departing on 10/24. 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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Fly from
Fly to
Route
Depart
Return
ChicagoGulfport
MDW Chicago Midway - GPT Gulfport Biloxi Regional
MDWGPT
Chicago Midway
Thu 11/19
6:08 am-7:05 pm
2 stops12h 57m
Gulfport Biloxi Regional
Sun 11/22
7:45 pm-7:47 pm
1 stop24h 02m
ChicagoGulfport
MDW Chicago Midway - GPT Gulfport Biloxi Regional
MDWGPT
Chicago Midway
Wed 2/24
5:25 pm-10:07 pm
1 stop4h 42m
Gulfport Biloxi Regional
Sat 2/27
6:00 pm-10:10 pm
1 stop4h 10m
ChicagoGulfport
MDW Chicago Midway - GPT Gulfport Biloxi Regional
MDWGPT
Chicago Midway
Thu 12/17
6:00 am-1:06 pm
1 stop7h 06m
Gulfport Biloxi Regional
Sat 1/9
4:00 pm-10:10 pm
1 stop6h 10m
ChicagoGulfport
MDW Chicago Midway - GPT Gulfport Biloxi Regional
MDWGPT
Chicago Midway
Wed 12/9
6:00 am-1:11 pm
1 stop7h 11m
Gulfport Biloxi Regional
Sat 12/12
4:00 pm-10:54 pm
1 stop6h 54m
ChicagoGulfport
MDW Chicago Midway - GPT Gulfport Biloxi Regional
MDWGPT
Chicago Midway
Wed 2/24
1:00 pm-10:07 pm
2 stops9h 07m
Gulfport Biloxi Regional
Sat 2/27
6:00 pm-10:10 pm
1 stop4h 10m
ChicagoGulfport
MDW Chicago Midway - GPT Gulfport Biloxi Regional
MDWGPT
Chicago Midway
Sat 2/27
5:25 pm-10:07 pm
1 stop4h 42m
Gulfport Biloxi Regional
Tue 3/2
6:00 am-12:33 pm
2 stops6h 33m
ChicagoGulfport
MDW Chicago Midway - GPT Gulfport Biloxi Regional
MDWGPT
Chicago Midway
Thu 12/17
6:00 am-1:06 pm
1 stop7h 06m
Gulfport Biloxi Regional
Sat 1/9
6:00 am-4:50 pm
2 stops10h 50m
ChicagoGulfport
MDW Chicago Midway - GPT Gulfport Biloxi Regional
MDWGPT
Chicago Midway
Wed 12/9
1:41 pm-9:57 pm
2 stops8h 16m
Gulfport Biloxi Regional
Sat 12/12
4:00 pm-10:54 pm
1 stop6h 54m
ChicagoGulfport
MDW Chicago Midway - GPT Gulfport Biloxi Regional
MDWGPT
Chicago Midway
Sat 2/27
1:00 pm-10:07 pm
2 stops9h 07m
Gulfport Biloxi Regional
Tue 3/2
6:00 am-12:33 pm
2 stops6h 33m
ChicagoGulfport
MDW Chicago Midway - GPT Gulfport Biloxi Regional
MDWGPT
Chicago Midway
Sun 11/15
6:08 am-8:51 am
2 stops26h 43m
Gulfport Biloxi Regional
Sun 11/22
7:45 pm-7:47 pm
1 stop24h 02m
See travel insights to Gulfport from
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
What is the cheapest airline that flies from Chicago Midway to Gulfport Biloxi Regional?
Delta is the most popular carrier operating from Chicago Midway to Gulfport Biloxi Regional
What airlines fly to Gulfport?
Southwest, Delta and Frontier are the top three most popular airlines that fly to Gulfport from Chicago Midway Airport according to our data. Southwest is the first choice among our users, with 85% of people opting to fly with this airline when traveling to Gulfport. Keep in mind that there are 3 different airlines that fly to Gulfport on a routine basis, so you have a few additional options to choose from.
How often are flights from Chicago to Gulfport delayed?
Historically, on average around 57% 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 158 minutes.
What is the most punctual flight time for Chicago to Gulfport flights?
Generally, flights departing in the early afternoon 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?
Wednesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Tuesday 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 57% 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
Frequently asked questions about flying from Chicago Midway Airport to Gulfport
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 42m 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 October 2026, 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 | ||
|---|---|---|---|---|---|
| PriceFrom $269 | Free Cancellation | Rating 7.8 8,654 reviews |
Traveling to a place near Gulfport?
Book flights to Gulfport if you plan to visit one of these locationsWhy 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.