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GPT - CHI

$99 Find cheap flights from Gulfport to Chicago

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 8/27. 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
Mon 7/8
Mon 7/15

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 43,124,673 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.
Choose your dates
4:39 pm - 11:57 pmGPT-ORD
7h 18m1 stop
5:00 am - 10:31 amORD-GPT
5h 31m1 stop
$198American Airlines
Find Deal
Tue, Sep 24 - Tue, Oct 1
2:34 pm - 10:39 pmGPT-ORD
8h 05m2 stops
9:20 am - 1:44 pmORD-GPT
4h 24m1 stop
$203Delta
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Tue, Sep 24 - Tue, Oct 1
2:34 pm - 10:39 pmGPT-ORD
8h 05m2 stops
6:00 am - 1:44 pmORD-GPT
7h 44m2 stops
$208Delta
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Tue, Sep 24 - Tue, Oct 1
4:30 pm - 9:44 pmGPT-MDW
5h 14m1 stop
6:50 pm - 11:18 pmMDW-GPT
4h 28m1 stop
$248Delta
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Sat, Oct 19 - Tue, Oct 22
12:04 pm - 7:37 pmGPT-ORD
7h 33m1 stop
9:55 am - 4:11 pmORD-GPT
6h 16m1 stop
$248American Airlines
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Sat, Oct 19 - Tue, Oct 22
6:44 pm - 11:58 pmGPT-ORD
5h 14m1 stop
4:46 pm - 11:57 pmORD-GPT
7h 11m1 stop
$283American Airlines
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Tue, Jun 18 - Sat, Jun 22
7:07 pm - 11:54 pmGPT-ORD
4h 47m1 stop
7:05 am - 1:14 pmORD-GPT
6h 09m1 stop
$293Delta
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Tue, Jul 9 - Tue, Jul 30
5:25 pm - 12:25 amGPT-ORD
7h 00m1 stop
6:00 am - 4:08 pmORD-GPT
10h 08m1 stop
$392United Airlines
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Sat, Jun 29 - Sat, Jul 6
5:25 pm - 8:54 amGPT-ORD
15h 29m2 stops
6:00 am - 4:08 pmORD-GPT
10h 08m1 stop
$492United Airlines
Find Deal
Sat, Jun 29 - Sat, Jul 6
2:00 pm - 12:13 amGPT-ORD
10h 13m1 stop
4:10 pm - 9:08 pmORD-GPT
4h 58m1 stop
$517United Airlines
Find Deal
Thu, Aug 8 - Mon, Aug 12

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 ($198) and Delta ($203). Delta proposed the cheapest one-way flight at $99.

Good to know

Low season

January

High season

September

Cheapest flight

$99
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 Midway 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 $99 for a one-way ticket and $198 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, Star Alliance, 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 $360 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 $365 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 10333 reviews
8.0Entertainment
8.2Boarding
7.4Food
7.9Comfort
8.6Crew
Airline reviews

Among the poorest flights I’ve had with Delta in a while. Entertainment system failed completely on a 7.5 hr flight. Crew seemed distracted and not the normal friendly crew. Flight overbooked it seemed… very crowded.

2.0 MediocreJim, Jun 2024ATL - ANC
Read more about Delta reviews

Among the poorest flights I’ve had with Delta in a while. Entertainment system failed completely on a 7.5 hr flight. Crew seemed distracted and not the normal friendly crew. Flight overbooked it seemed… very crowded.

If I can, I always fly Delta. I’ve found their service to always be reliable and pleasant.

You could have not cancelled the flight (AA, which I will be flying from now on) left for BOS despite the fictitious weather issues (that no one in my Boston family could see). You could have rebooked my direct flight to another direct flight instead of sending me though JFK, the worst US airport after O’Hara You could have rebooked me on a Main Cabin seat (like the one I paid for in my original ticket instead of putting me a the last row on JFK->BOS leg, pocketing the difference in ticket price But I do not really care whether you will ever do that in a future because in a future neither I nor anyone from my company (unless they pay out of pocket) nor an of my clients and partners (if they heed my advice) will ever be caught dead on any of Delta flights

Really bad baggage handling. Had my Rimowa bag badly damaged at the latches.

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

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.

Internet service was erratic. Crew service was poor and slow. My luggage on this non-stop flight was lost and not recovered

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.

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.
8/27Tue
1 stopDelta
4h 13mGPT-MDW
$99
7/4Thu
1 stopDelta
5h 36mGPT-ORD
$99
8/27Tue
2 stopsUnited Airlines
14h 10mGPT-ORD
$189
6/29Sat
1 stopUnited Airlines
7h 00mGPT-ORD
$194
7/4Thu
2 stopsUnited Airlines
12h 53mGPT-ORD
$199
6/25Tue
1 stopDelta
7h 30mGPT-ORD
$240
10/10Thu
1 stopUnited Airlines
6h 52mGPT-ORD
$254
6/27Thu
1 stopDelta
4h 42mGPT-MDW
$261
6/19Wed
3 stops
28h 28mGPT-ORD
$287
6/27Thu
2 stopsAmerican Airlines
10h 20mGPT-ORD
$369

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Last minute flights from Gulfport to Chicago

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Gulfport to Chicago that are departing in the next 10 days.
6/9Sun
multi-stopAmerican Airlines
5h 26mGPT-ORD
6/10Mon
multi-stopAmerican Airlines
7h 54mORD-GPT
$368
6/9Sun
multi-stopAmerican Airlines
5h 26mGPT-ORD
6/10Mon
multi-stopAmerican Airlines
8h 36mORD-GPT
$443
6/9Sun
multi-stopUnited Airlines
7h 03mGPT-ORD
6/10Mon
multi-stopUnited Airlines
7h 10mORD-GPT
$499
6/9Sun
multi-stopUnited Airlines
7h 03mGPT-ORD
6/10Mon
multi-stopUnited Airlines
8h 36mORD-GPT
$504
6/9Sun
multi-stopAmerican Airlines
8h 31mGPT-ORD
6/10Mon
multi-stopAmerican Airlines
8h 36mORD-GPT
$794
6/9Sun
multi-stopDelta
8h 23mGPT-MDW
6/10Mon
multi-stopDelta
4h 33mMDW-GPT
$1,435
6/9Sun
multi-stopDelta
8h 23mGPT-MDW
6/10Mon
multi-stopDelta
9h 58mMDW-GPT
$1,510
6/9Sun
multi-stopDelta
4h 42mGPT-MDW
6/10Mon
multi-stopDelta
5h 31mMDW-GPT
$1,995

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Gulfport - Chicago Flights

Departure:

Gulfport (GPT)United States

Return flight deals:

Chicago - Gulfport

Cabin classes: