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GPT - CHI

$195 Find cheap flights from Gulfport to Chicago

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Gulfport to Chicago departing on 9/24. 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
0 bags
Thu 6/27
Thu 7/4

Search hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Gulfport to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Gulfport to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 42,816,550 times on KAYAK, and here is why:

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Cheap flight deals 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 and deals for you by selecting your travel dates.
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4:39 pm - 11:57 pmGPT-ORD
7h 18m1 stop
8:40 am - 4:09 pmORD-GPT
7h 29m1 stop
$195American Airlines
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Tue, Sep 24 - Tue, Oct 1
6:44 pm - 11:58 pmGPT-ORD
5h 14m1 stop
5:00 am - 10:08 amORD-GPT
5h 08m1 stop
$247American Airlines
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Tue, Jun 18 - Sat, Jun 22
4:39 pm - 11:57 pmGPT-ORD
7h 18m1 stop
12:19 pm - 9:32 pmORD-GPT
9h 13m2 stops
$270American Airlines
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Tue, Sep 24 - Tue, Oct 1
12:47 pm - 5:32 pmGPT-ORD
4h 45m1 stop
8:30 am - 3:46 pmORD-GPT
7h 16m1 stop
$310American Airlines
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Tue, Jun 18 - Wed, Jun 26
7:06 pm - 11:59 pmGPT-ORD
4h 53m1 stop
1:25 pm - 11:22 pmORD-GPT
9h 57m2 stops
$333Delta
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Tue, Jun 18 - Sat, Jun 22
7:06 pm - 11:59 pmGPT-ORD
4h 53m1 stop
8:30 am - 6:16 pmORD-GPT
9h 46m2 stops
$357Delta
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Tue, Jun 18 - Wed, Jun 26
5:10 pm - 12:13 amGPT-ORD
7h 03m1 stop
9:31 pm - 4:03 pmORD-GPT
18h 32m1 stop
$437United Airlines
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Fri, Jun 14 - Sun, Jun 16
5:10 pm - 12:13 amGPT-ORD
7h 03m1 stop
9:15 pm - 4:03 pmORD-GPT
18h 48m2 stops
$467United Airlines
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Fri, Jun 14 - Sun, Jun 16
9:32 am - 7:26 pmGPT-ORD
33h 54m3 stops
6:40 pm - 5:04 pmORD-GPT
22h 24m2 stops
Wed, Jul 3 - Sun, Jul 7
9:32 am - 7:26 pmGPT-ORD
33h 54m3 stops
5:34 pm - 5:04 pmORD-GPT
23h 30m3 stops
Wed, Jul 3 - Sun, Jul 7

Flights from Gulfport to Chicago - Travel Insights & Trends

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’s the cheapest day of the week to fly from Gulfport to Chicago?

The average price of all flights from Gulfport to Chicago clicked on KAYAK for each day over the last 12 months.
When flying from Gulfport to Chicago, you should consider leaving on a Tuesday and avoid Wednesdays if you are looking for the best rates. For your return to Gulfport, you’ll find the best rates on Saturdays and the most expensive ones on Thursdays.

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 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 $240 on average. On the other hand, the most expensive months are September and June, where the average cost of tickets is $541 and $523 respectively.

Which airlines provide the cheapest flights from Gulfport to Chicago?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 72 hours, the best return deals on flights connecting Gulfport to Chicago were found on American Airlines ($195) and Delta ($333). American Airlines proposed the cheapest one-way flight at $363.

Good to know

Low season

January

High season

September

Cheapest flight

$195
Best time to beat the crowds with an average 38% drop in price.
Most popular time to fly with an average 40% increase in price.
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 3 days, the lowest price for a flight from Gulfport to Chicago was $363 for a one-way ticket and $195 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?

    oneworld, SkyTeam, and Star Alliance 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 $367 and an overall rating of 8.0, Delta is the most popular choice. American Airlines is also a great choice for the route, with an average price of $366 and an overall rating of 7.3.

  • 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.

See more FAQs

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.
8.0
DeltaOverall score based on 10502 reviews
8.2Boarding
7.4Food
8.0Entertainment
7.9Comfort
8.6Crew
Airline reviews

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

10.0 ExcellentMichael, May 2024SJC - ATL
Read more about Delta reviews

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

They were an hour late and they didn’t have my wheelchair for me

The Flight crew didn’t serve us until about 1.5 hours into the flight because of turbulence but after it ended it was fine to move around. They served us water only and snacks and then NEVER, NOT ONE TIME came through to collect trash until right before landing about 1.5 hours later. There was absolutely no need for that. They crew was just standing around talking and visiting with each other and really never tried to see if we might want something besides water or even try to come pick up trash. This is VERY unusual for a Delta flight but it was not what I would have expected for a 4 hour flight.

The CX617 from HK to BKK was delayed more than 1.5 hours.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

Our second leg to Jackson WY was unable to land due to weather. We were flown back to Dallas after stopping in SLC. We were given hotel rooms and vouchers. We were told that we would be back on the same plane in the morning. Instead we were given a different flight with different seats. Not a good experience. No one knew what was going on.

Book cheap flights from Gulfport to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Gulfport to Chicago found on KAYAK in the last 72 hours.
6/6Thu
1 stopAmerican Airlines
7h 40mGPT-ORD
$363
6/6Thu
2 stopsAmerican Airlines
10h 12mGPT-ORD
$368
6/6Thu
1 stopDelta
5h 38mGPT-MDW
$419
6/6Thu
2 stopsDelta
11h 53mGPT-MDW
$734

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Gulfport - Chicago Flights

Departure:

Gulfport (GPT)United States

Return flight deals:

Chicago - Gulfport

Cabin classes: