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GPT - CHI

Find cheap flights from Gulfport to Chicago from $104

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 5/10. 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
Sat 5/18
Sat 5/25

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 44,553,814 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

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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
7:06 pm - 11:56 pmGPT-ORD
4h 50m1 stop
1:25 pm - 11:22 pmORD-GPT
9h 57m2 stops
$233Delta
Find Deal
Fri, Jun 21 - Mon, Jun 24
4:30 pm - 11:59 pmGPT-ORD
7h 29m1 stop
5:35 pm - 10:45 pmORD-GPT
5h 10m1 stop
$241American Airlines
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Wed, May 15 - Wed, May 22
5:12 pm - 11:52 pmGPT-ORD
6h 40m1 stop
5:59 pm - 11:11 pmORD-GPT
5h 12m1 stop
$273Delta
Find Deal
Tue, Apr 30 - Sat, May 4
5:12 pm - 11:52 pmGPT-ORD
6h 40m1 stop
12:15 pm - 11:11 pmORD-GPT
10h 56m2 stops
$278Delta
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Tue, Apr 30 - Sat, May 4
5:16 pm - 7:40 amGPT-ORD
14h 24m2 stops
1:32 pm - 11:12 pmORD-GPT
9h 40m2 stops
$295Delta
Find Deal
Tue, May 14 - Sat, May 18
5:16 pm - 9:26 pmGPT-ORD
4h 10m1 stop
1:32 pm - 11:12 pmORD-GPT
9h 40m2 stops
$298Delta
Find Deal
Tue, May 14 - Sat, May 18
7:09 am - 2:20 pmGPT-ORD
7h 11m1 stop
6:27 pm - 11:30 pmORD-GPT
5h 03m1 stop
$300American Airlines
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Tue, May 21 - Sat, May 25
5:27 am - 11:10 amGPT-ORD
5h 43m1 stop
1:40 pm - 9:27 pmORD-GPT
7h 47m1 stop
$301American Airlines
Find Deal
Thu, May 9 - Sun, May 12
5:00 pm - 12:12 amGPT-ORD
7h 12m1 stop
7:30 am - 7:39 pmORD-GPT
12h 09m1 stop
$514United Airlines
Find Deal
Thu, May 9 - Sun, May 12
5:00 pm - 12:12 amGPT-ORD
7h 12m1 stop
12:45 pm - 7:39 pmORD-GPT
6h 54m2 stops
$881United Airlines
Find Deal
Thu, May 9 - Sun, May 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 Tuesdays and the most expensive ones on Thursdays.

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 Delta ($233) and American Airlines ($241). Delta proposed the cheapest one-way flight at $171.

Good to know

Low season

August

High season

September

Cheapest flight

$104
Best time to beat the crowds with an average 41% drop in price.
Most popular time to fly with an average 16% 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 $104 for a one-way ticket and $233 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, oneworld, 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 $357 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 $393 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 11104 reviews
8.2boarding
7.5food
7.9comfort
8.6crew
8.0entertainment
Airline reviews

Everything was great except for the seat. The backrest would not stay in the upright position.

8.0 ExcellentEddie, Apr 2024SEA - PHX
Read more about Delta reviews

Everything was great except for the seat. The backrest would not stay in the upright position.

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

Flight delayed about 2 hrs so it made it a VERY late night

It was a crowded flight. They did the best they could.

Service was good for such a short flight. Small plane but smooth flight.

Worst flight in my life. Only was scheduled for a 45 min flight to get our connection flight. It was late by 40 minutes and we missed our connection. Delta was totally useless trying to help and unable to get my family on the next flight because they overbooked it Thus had to get a hotel at my expense and lost a day at Disney as a result. Cost me about a $1000 if you add 2 hotels meals shuttles etc to get thru the day Awful customer service by Delta in Detroit totally useless people

The experience was good and the flight departed on time and landed early

The flight was delayed but we got to our final destination.

Boarding was great. The flight landed early. It took the crew over an hour and a half to bring out drinks. I paid to upgrade my seat to Comfort+ only to be near a crying/screaming baby who was seldom quiet. Noise-cancelling earbuds didn’t even help. Waste of money to upgrade.

Seats in first class on the E175 recline too far back. I was in 2A, and the man in 1A fully reclined almost the entire flight. It took 6-7 inches of space away from me and made it very difficult to work on my laptop.

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.

Turn on the heat. Flight was way too cold from Arizona to Chicago.

Perfect flight. On time departure and early arrival. Smooth flight.

Overall pleasant was delayed and caused transportation issue when landing

The arriving flight was a few minutes late, but the gate crew helped to deplane and board our outgoing flight quickly and efficiently. We were able to depart quickly and arrive at ORD almost at the posted time. Great job.

Nothing, flight was supposed to leave at 758 am. My flight didn’t leave until 430 pm. Spent the whole day at the airport.

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.
5/10Fri
2 stops
19h 40mGPT-ORD
$104
5/10Fri
1 stop
12h 50mGPT-ORD
$167
6/6Thu
1 stopDelta
6h 38mGPT-ORD
$171
5/10Fri
3 stops
19h 35mGPT-ORD
$188
6/6Thu
1 stopDelta
4h 45mGPT-MDW
$203
5/10Fri
1 stopDelta
4h 45mGPT-MDW
$256
5/26Sun
1 stopDelta
5h 05mGPT-ORD
$256
5/5Sun
2 stopsAmerican Airlines
9h 18mGPT-ORD
$313
5/26Sun
2 stopsUnited Airlines
14h 55mGPT-ORD
$322
5/5Sun
1 stopUnited Airlines
14h 45mGPT-ORD
$439

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Gulfport - Chicago Flights

Departure:

Gulfport (GPT)United States

Return flight deals:

Chicago - Gulfport

Cabin classes: