GPT - CHI

$132 Find Cheap Flights from Gulfport to Chicago - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Gulfport to Chicago departing on 8/30. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

Save 20% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Everything you should know

Cheapest round-trip
$301
Delta
Sat 9/12Sat 9/19
GPT - MDW • 1 stop
Cheapest one-way
$132
Multiple Airlines
Sun 8/30
GPT - ORD • 1 stop
Top airlines
Cheapest • from $301 (round-trip)
Best reviews • 7.8 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Gulfport and Chicago. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $302 (round-trip)
Shortest trip • 5h 11m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 100% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Gulfport to Chicago (GPT-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Gulfport to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Gulfport to Chicago

Sat, Sep 12 - Sat, Sep 19
Delta Logo
4:00 pm - 10:44 pm
GPT
-
MDW
6h 44m
1 stop
Delta Logo
4:30 pm - 8:49 pm
MDW
-
GPT
4h 19m
1 stop
$301Delta
Sat, Sep 12 - Sat, Sep 19
American Airlines Logo
5:42 pm - 12:01 am
GPT
-
ORD
6h 19m
1 stop
American Airlines Logo
6:45 am - 1:12 pm
ORD
-
GPT
6h 27m
1 stop
$301American Airlines
Tue, Sep 8 - Sat, Sep 12
American Airlines Logo
6:34 pm - 12:18 am
GPT
-
ORD
5h 44m
1 stop
American Airlines Logo
5:00 am - 10:40 am
ORD
-
GPT
5h 40m
1 stop
$301American Airlines
Sat, Sep 12 - Sat, Sep 19
Delta Logo
4:00 pm - 10:44 pm
GPT
-
MDW
6h 44m
1 stop
Delta Logo
9:29 am - 8:49 pm
MDW
-
GPT
11h 20m
2 stops
$306Delta
Wed, Oct 7 - Wed, Oct 14
Delta Logo
6:05 pm - 11:52 pm
GPT
-
ORD
5h 47m
1 stop
Delta Logo
1:55 pm - 10:16 pm
ORD
-
GPT
8h 21m
2 stops
$306Delta
Sat, Sep 12 - Sat, Sep 19
Delta Logo
4:00 pm - 8:56 pm
GPT
-
ORD
4h 56m
1 stop
Delta Logo
11:17 am - 8:49 pm
ORD
-
GPT
9h 32m
2 stops
$306Delta
Sat, Aug 29 - Sun, Aug 30
American Airlines Logo
1:50 pm - 7:46 pm
GPT
-
ORD
5h 56m
1 stop
American Airlines Logo
5:00 am - 10:41 am
ORD
-
GPT
5h 41m
1 stop
$310American Airlines
Thu, Aug 27 - Sun, Aug 30
Multiple Airlines Logo
7:25 pm - 1:20 pm
GPT
-
ORD
17h 55m
1 stop
Multiple Airlines Logo
7:05 am - 7:41 am
ORD
-
GPT
24h 36m
2 stops
$364Multiple Airlines
Thu, Aug 27 - Thu, Sep 3
United Airlines Logo
7:08 am - 2:50 pm
GPT
-
ORD
7h 42m
1 stop
United Airlines Logo
12:47 pm - 7:38 pm
ORD
-
GPT
6h 51m
1 stop
$375United Airlines
Sat, Aug 29 - Sat, Sep 5
United Airlines Logo
4:59 pm - 11:26 pm
GPT
-
ORD
6h 27m
1 stop
United Airlines Logo
10:40 am - 4:12 pm
ORD
-
GPT
5h 32m
1 stop
$390United Airlines
Booking Insights

KAYAK's insights & trends for Gulfport to Chicago flights

Get data-powered insights and trends into flights from Gulfport to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Gulfport to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Gulfport to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Gulfport to Chicago is January, where tickets cost $0 (return) on average. On the other hand, the most expensive months are April and August, where the average cost of round-trip tickets is $966 and $604 respectively.

Good to know

Low season

November

Cheapest flight

$132
Best time to beat the crowds with an average 43% drop in price.
Most popular time to fly and prices are also 9% lower on average.
Flight from Gulfport to Chicago O'Hare Airport

When to book flights from Gulfport to Chicago

Are your dates flexible? Find out the best times to travel from Gulfport to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Gulfport to Chicago

  • What is the cheapest flight from Gulfport to Chicago?

    In the last 5 days, the lowest price for a flight from Gulfport to Chicago was $132 for a one-way ticket and $301 for a round-trip.

  • Do I need a passport to fly between Gulfport and Chicago?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which airports will I be using when flying from Gulfport to Chicago?

    When flying out of Gulfport you will be using Gulfport Biloxi Regional. You will be landing at one of these airports: Chicago Midway or Chicago O'Hare Intl.

  • Which aircraft models fly most regularly from Gulfport to Chicago?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Gulfport to Chicago?

    SkyTeam, and oneworld are the airline alliances operating flights between Gulfport and Chicago, with SkyTeam being the most commonly used for this route.

  • Which is the best airline for flights from Gulfport to Chicago, Delta or American Airlines?

    The two airlines most popular with KAYAK users for flights from Gulfport to Chicago are Delta and American Airlines. With an average price for the route of $299 and an overall rating of 7.8, Delta is the most popular choice. American Airlines is also a great choice for the route, with an average price of $398 and an overall rating of 7.1.

  • How does KAYAK find such low prices on flights from Gulfport to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Gulfport to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Gulfport to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Gulfport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Gulfport to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Gulfport with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Gulfport to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Gulfport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from Gulfport to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Gulfport to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Gulfport to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.8
DeltaOverall score based on 8497 reviews
7.2Food
8.1Boarding
7.8Comfort
8.5Crew
7.8Entertainment
Airline reviews

It was as good as it could be. Flying is not a pleasant experience these days.

8.0 ExcellentMark, Jun 2026
LAX - ORD
Read more Delta reviews

It was as good as it could be. Flying is not a pleasant experience these days.

There was an unruly family behind us that made the short flight miserable!!! The cabin crew did nothing to contain it.

Flight delay was frustrating, also you cannot checkin online without delta app, web browser check-in throw errors

Got on the plane and sat there for an hour before departure.

Cramped seating for me. Luckily it wasn’t a long flight

5 hour delay. They blamed the weather but it was the computer issues they had been dealing with for days.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

long flights are never truly comfortable but the airline did their best. crew was great and the flight was safe.

The captain was amazing and kept us informed throughout that there would be some rough air. The flight also got delayed but we were able to actually leave on time, which was great.

The staff did not do a good job of getting everyone boarded quickly, so we missed our take off window and had to sit on the tarmac for 20+ min waiting for our turn. The plan was old. Pockets on the back of seats were torn and tearing off. One of the attendants was rude-she would ask a question but he walking away before you finished answering so she kept getting our drink orders wrong.

My seat had a worn out cushion, which made it a bit uncomfortable. Other than that, the flight was excellent.

Take this flight regularly. Every single week same thing. Departure delayed. Make up some time in the air. Land at ORD and then wait for gate in "L" concourse Terminal 3 for 30-40 min-which yields a very delayed final arrival. Plus I get to taxi around and see every runway and drive over the bridge (IFKYK) over the expressway 2-4 times in most cases. Change the sched of incoming plane/work with FAA to improve traffic flow at ORD/change the timing of these flights. Whatever it takes. But do better.

- flight was delayed several hours due to weather (understandable) - flight delayed further and we were told by attendants "we are not sure where the pilots are but they are on their way" as we have to find different pilots for the flight - announcements over the PA were somewhat unprofessional by the attendants, seems they need more training and were not reading off the script. They showed their young age and immaturity in their communications with the passengers. They were not clear and lacked professional communication language. - going from a hub to hub we were also parked at the tarmac at ohare for an additional hour and kept being told "few more minutes". Please just let the passengers know the real wait time instead of hiding the truth. We understand there is traffic and weather delays, but we just want transparency. There are several logistics of our lives that revolve around what the attendants and pilots are sharing with us but they are not being transparant.

Boarding and Delays The boarding process for my American Airlines flight from Copenhagen to Philadelphia was a bit tricky. We experienced a gate change that required a long walk to a new area of the airport. Additionally, boarding was not via a jet bridge; we had to take a shuttle bus to the plane and then carry our luggage up the stairs ourselves. Furthermore, the bag drop didn't open until about 12:20 PM, which was only three hours before our scheduled departure. This meant I couldn't drop my bag off early and had to wait outside of security in order to drop off my bag and use the kiosk. The bag drop self-service kiosks also didn't open until about 12:00 PM when an American Airlines employee unlocked them so that we could print out our boarding passes and bag tags, which further created a backlog. The flight was delayed by over an hour because we had to wait for one of the tires on the plane to be changed. Flight Attendant Professionalism On a positive note, the flight attendant was very professional when handling a passenger who was sitting in the wrong seat. Even though the passenger was persistent and reluctant to move, the flight attendant calmly ensured the assigned passenger could take their seat. Kudos to the flight attendant for keeping his calm and composure, not allowing the issue to escalate, and handling it well under pressure while a line of passengers waited in the aisle to board. In-Flight Service The in-flight service was also fast, prompt, and efficient, although service had to be suspended for the last two hours of the flight due to weather and turbulence, which was outside of the crew's control. Limited Flight Options Please note that American Airlines only operates one flight per day in and out of Copenhagen. This means there are limited options available if your flight is delayed or canceled, which is something to take into consideration when booking.

I will never but. through kayak again. and American Airlines. I will never fly again on. They're both thieves.

Nothing, I wont be flying American Airlines again and will not be recommending anyone to fly American Airlines. It was the worst experience flying I've ever had.

My luggage was not sent with us. Not sure if this is Envoy Air responsibility but that was a very BAD experience

The planes can use an actual cleaning. The armrest and seats do not appear to be cleaned on this one and most other planes.

Flight was delayed…once landed at ORD, no gates were available so made us wait for 56 minutes after we landed to let us out of the aircraft!

American Airlines gets worse every time I fly them. This is the 3rd time they lost my bags in a year. I also think their employees do not care when I communicate that I’m unsatisfied with the airlines. I’m a credit card holder, fly first class, and an advantage member but I think that I’m finally going to make the switch to Delta.

Everything you need to know for your flight from Gulfport to Chicago

Information on your arrival and departure airports