GPT - CHI

$122 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 12/4. 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

KAYAK searches 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
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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

Fri, Dec 12 - Sun, Dec 14
Multiple Airlines Logo
6:51 pm - 11:54 amGPT-ORD
17h 03m2 stops
Multiple Airlines Logo
8:45 am - 8:59 amORD-GPT
24h 14m1 stop
$209Multiple Airlines
Find Deal
Fri, Dec 12 - Sun, Dec 14
Multiple Airlines Logo
6:51 pm - 12:39 pmGPT-ORD
17h 48m1 stop
Multiple Airlines Logo
8:45 am - 8:59 amORD-GPT
24h 14m1 stop
$220Multiple Airlines
Find Deal
Tue, Nov 25 - Wed, Nov 26
Multiple Airlines Logo
5:55 pm - 9:47 amGPT-ORD
15h 52m1 stop
Multiple Airlines Logo
6:15 pm - 7:15 pmORD-GPT
25h 00m1 stop
$230Multiple Airlines
Find Deal
Wed, Dec 24 - Sat, Dec 27
Delta Logo
5:21 pm - 10:22 pmGPT-MDW
5h 01m1 stop
Delta Logo
6:00 am - 10:40 amMDW-GPT
4h 40m1 stop
$249Delta
Find Deal
Fri, Nov 21 - Sat, Nov 22
Delta Logo
6:03 pm - 12:02 amGPT-ORD
5h 59m1 stop
Delta Logo
4:26 pm - 10:07 pmORD-GPT
5h 41m1 stop
$249Delta
Find Deal
Wed, Nov 12 - Sun, Nov 16
American Airlines Logo
5:26 pm - 11:37 pmGPT-ORD
6h 11m1 stop
American Airlines Logo
5:00 am - 12:23 pmORD-GPT
7h 23m1 stop
$259American Airlines
Find Deal
Mon, Nov 17 - Sun, Nov 23
United Airlines Logo
5:15 pm - 11:10 pmGPT-ORD
5h 55m1 stop
United Airlines Logo
6:00 am - 11:17 amORD-GPT
5h 17m1 stop
$264United Airlines
Find Deal
Tue, Nov 25 - Wed, Nov 26
Multiple Airlines Logo
5:55 pm - 9:47 amGPT-ORD
15h 52m1 stop
Multiple Airlines Logo
6:35 pm - 7:15 pmORD-GPT
24h 40m2 stops
$268Multiple Airlines
Find Deal
Wed, Nov 12 - Sun, Nov 16
United Airlines Logo
5:15 pm - 12:15 amGPT-ORD
7h 00m1 stop
United Airlines Logo
7:10 am - 1:20 pmORD-GPT
6h 10m1 stop
$279United Airlines
Find Deal
Thu, Jan 8 - Sun, Jan 11
American Airlines Logo
1:03 pm - 8:39 pmGPT-ORD
7h 36m1 stop
American Airlines Logo
3:21 pm - 10:41 pmORD-GPT
7h 20m1 stop
$319American Airlines
Find Deal

Everything you should know

Top airlines
Delta
Cheapest • from $249 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Cheapest round-trip
$209
Typical prices: $478-$598
Multiple Airlines
Fri 12/12Sun 12/14
GPT - ORD • 2 stops
Cheapest one-way
$122
Typical prices: $318-$433
Multiple Airlines
Thu 12/4
GPT - ORD • 1 stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
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’s the cheapest day of the week to fly from Gulfport to Chicago?

The average price of all round-trip flights from Gulfport to Chicago clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Chicago on a Saturday and more expensive on a Sunday. On your return trip to Gulfport, you should consider flying back on a Wednesday, and avoid Sundays for better deals.

Good to know

Low seasonApril
Cheapest flight$122
Best time to beat the crowds with an average 42% drop in price.
Most popular time to fly and prices are also 22% 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 3 days, the lowest price for a flight from Gulfport to Chicago was $122 for a one-way ticket and $209 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 $408 and an overall rating of 7.9, Delta is the most popular choice. American Airlines is also a great choice for the route, with an average price of $404 and an overall rating of 7.2.

  • 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.
7.9
DeltaOverall score based on 7992 reviews
7.9Comfort
7.9Entertainment
7.3Food
8.2Boarding
8.5Crew
Airline reviews

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

8.0 ExcellentJulie, Oct 2025LAX - SFO
Read more Delta reviews

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

The customer service before board was very rude and when I expressed my concerns about making the connecting flight she laughed and told me I bought the wrong ticket. I explained once it showed the flight was delayed it no longer let me change seats or anything. I was trying to upgrade to make sure I would get to the next gate on time.

Non stop on long haul is the way to go. Great experience

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

They changed planes and the new plane couldn’t carry enough fuel to fly across the country so we had to stop in Kansas City to refuel. Flight was delayed .

Flight was too crowded and seats are too small, especially since passengrs are getting larger. Having a middle seat is ALWAYS tough! Woman on my left was large & kept creeping in to my space. Flight personnel were great! Have more savory rather than sweet snacks please.

Flight was crowded and the woman sitting on my left was large & kept crouching in to my space. You need bigger seats or smaller passengers to fit into the seats you DO have! Snack were OK. Would appreciate if airlines had more savory rather than sweet snacks, thank you!

Delayed flight (1hour) plus a long layover after an overnight flight with no backup plane available.

We were delayed, which I think had to do with air traffic control. Otherwise, everything was great.

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

Excellent - explanations were clear staff was nice and flight was comfortable

Lost bag and 2 days no word leaving for cruise no clothes or stuff

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

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

Information on your arrival and departure airports

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