GPT - CHI

$226 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 10/15. 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

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

Thu, Nov 13 - Sun, Nov 16
Multiple Airlines Logo
7:55 pm - 10:10 pmGPT-MDW
26h 15m1 stop
Multiple Airlines Logo
6:06 pm - 8:59 amMDW-GPT
14h 53m1 stop
$228Multiple Airlines
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Fri, Oct 3 - Sun, Oct 5
Multiple Airlines Logo
6:51 pm - 10:17 amGPT-ORD
15h 26m1 stop
Multiple Airlines Logo
8:05 am - 8:59 amORD-GPT
24h 54m1 stop
$228Multiple Airlines
Find Deal
Fri, Oct 17 - Sun, Oct 19
Multiple Airlines Logo
6:51 pm - 10:14 amGPT-ORD
15h 23m1 stop
Multiple Airlines Logo
6:00 am - 7:15 pmORD-GPT
13h 15m1 stop
$236Multiple Airlines
Find Deal
Sat, Nov 15 - Tue, Nov 18
Delta Logo
3:30 pm - 9:53 pmGPT-ORD
6h 23m1 stop
Delta Logo
1:09 pm - 5:13 pmORD-GPT
4h 04m1 stop
$249Delta
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Thu, Nov 13 - Sun, Nov 16
Multiple Airlines Logo
7:55 pm - 1:16 pmGPT-ORD
17h 21m2 stops
Multiple Airlines Logo
7:05 am - 8:59 amORD-GPT
25h 54m1 stop
$254Multiple Airlines
Find Deal
Tue, Sep 30 - Sat, Oct 4
United Airlines Logo
5:25 pm - 12:14 amGPT-ORD
6h 49m1 stop
United Airlines Logo
7:10 am - 1:25 pmORD-GPT
6h 15m1 stop
$259United Airlines
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Wed, Dec 24 - Sat, Dec 27
Delta Logo
6:00 am - 12:05 pmGPT-ORD
6h 05m1 stop
Delta Logo
5:40 am - 10:31 amORD-GPT
4h 51m1 stop
$279Delta
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Sat, Dec 13 - Tue, Dec 16
American Airlines Logo
7:15 am - 2:17 pmGPT-ORD
7h 02m1 stop
American Airlines Logo
3:44 pm - 10:46 pmORD-GPT
7h 02m1 stop
$319American Airlines
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Fri, Feb 20 - Sat, Feb 21
United Airlines Logo
5:15 pm - 9:25 amGPT-ORD
16h 10m2 stops
United Airlines Logo
12:45 pm - 7:42 pmORD-GPT
6h 57m1 stop
$398United Airlines
Find Deal
Wed, Dec 24 - Sat, Dec 27
American Airlines Logo
7:05 am - 3:27 pmGPT-ORD
8h 22m2 stops
American Airlines Logo
8:03 am - 4:08 pmORD-GPT
8h 05m1 stop
$618American 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
$228
Multiple Airlines
Thu 11/13Sun 11/16
GPT - MDW • 1 stop
Cheapest one-way
$226
Delta
Wed 10/15
GPT - MDW • 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.

How much is a round-trip flight from Gulfport to Chicago?

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$226
Best time to beat the crowds with an average 44% drop in price.
Most popular time to fly and prices are also 24% lower on average.
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 $226 for a one-way ticket and $228 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 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 7954 reviews
7.9Comfort
7.3Food
8.5Crew
7.9Entertainment
8.2Boarding
Airline reviews

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

10.0 ExcellentAnonymous, Sep 2025CLT - BOS
Read more Delta reviews

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Mechanic delay in addition to a 2 hour change in takeoff time was frustrating.

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

The flight attendants in SLC were rude. I arrived 40 minutes early to gate. Ticket said I needed check in for seat assignments and tried check in and attendants said they weren’t doing it. And proceeded to never call me to give me a ticket so when time to board I received the very last seat. Please relay to employees to do their job better..,

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.

My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end

Was not able to watch most shows on the entertainment site. They would not load

On Wednesday, July 30 we were in mid flight from Manchester to Charlotte and we turned around because the right engine was malfunctioning. That was the last flight out of Manchester that night. I was rebooked for Thursday, which became a weather event Friday. There were no seats left on the flight from Manchester to Charlotte. Consequently I didn’t leave Manchester until Saturday morning and we flew to Chicago so to say the least my scheduled flight and return to Iowa was three days off and it messed with my business schedule. Consequently cash flow. I would like some sort of acknowledgment of this event.

Dreadful experience. Our flight was delayed more than 8 hours due to a maintenance issue and the assistance from rebooking was poor. I was travelling with a bad knee and needed assistance waited in one place more than 3 hours before someone came with a wheelchair. The woman next to me was a 91 year old great grandmother who had waited more than 4 hours. There were moments of support from the staff but it appeared as they were going against the direction of management. It was apathy, lack of ownership and dismissive responses with small moments of kindness and understanding typically from grey haired, female, veteran staff..

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

The flight was fine and the crew awesome. The problem is ORD and AA. Computers went down, ORD fell apart and a 40 min flight turned into a 3 hour trip. Guess the answer is to not try and fly to ORD after noon. But, as I said, crew was awesome and did everything they could to lesson the flight time.

The flight was fine but the 8 hour delay in Chicago was awful - 5 gate changes and repeated delays without an explanation. No vouchers. Nothing.

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

Information on your arrival and departure airports

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