GPT - CHI

$158 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 4/24. 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
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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$292
Typical prices: $336-$372
Multiple Airlines
Fri 4/24Sun 4/26
GPT - ORD • 1 stop
Cheapest one-way
$158
Multiple Airlines
Fri 4/24
GPT - ORD • 1 stop
Top airlines
Cheapest • from $309 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Gulfport and Chicago. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $268 (round-trip)
Shortest trip • 5h 11m (one-way)
Insights
Insights
Insights
Insights
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Booking Insights
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, Apr 24 - Sun, Apr 26
Multiple Airlines Logo
6:54 pm - 6:20 pm
GPT
-
ORD
23h 26m
1 stop
Multiple Airlines Logo
6:00 am - 6:40 pm
ORD
-
GPT
12h 40m
1 stop
$292Multiple Airlines
Thu, Apr 9 - Sun, Apr 12
American Airlines Logo
6:09 pm - 11:54 pm
GPT
-
ORD
5h 45m
1 stop
American Airlines Logo
5:00 am - 10:33 am
ORD
-
GPT
5h 33m
1 stop
$309American Airlines
Fri, Apr 24 - Sun, Apr 26
Multiple Airlines Logo
6:54 pm - 6:20 pm
GPT
-
ORD
23h 26m
1 stop
Multiple Airlines Logo
6:00 am - 6:40 pm
ORD
-
GPT
12h 40m
1 stop
$314Multiple Airlines
Tue, Mar 31 - Sat, Apr 4
American Airlines Logo
6:31 am - 1:34 pm
GPT
-
ORD
7h 03m
1 stop
American Airlines Logo
10:28 am - 3:59 pm
ORD
-
GPT
5h 31m
1 stop
$319American Airlines
Thu, Aug 27 - Sun, Aug 30
American Airlines Logo
6:27 pm - 12:06 am
GPT
-
ORD
5h 39m
1 stop
American Airlines Logo
7:10 am - 12:13 pm
ORD
-
GPT
5h 03m
1 stop
$329American Airlines
Fri, Apr 24 - Sun, Apr 26
Multiple Airlines Logo
6:54 pm - 9:17 pm
GPT
-
ORD
26h 23m
2 stops
Multiple Airlines Logo
6:00 am - 6:40 pm
ORD
-
GPT
12h 40m
1 stop
$336Multiple Airlines
Wed, Apr 1 - Sun, Apr 5
American Airlines Logo
6:00 am - 2:16 pm
GPT
-
ORD
8h 16m
1 stop
American Airlines Logo
5:00 pm - 11:57 pm
ORD
-
GPT
6h 57m
1 stop
$339American Airlines
Thu, Jul 30 - Sat, Aug 1
United Airlines Logo
5:19 pm - 12:45 am
GPT
-
ORD
7h 26m
1 stop
United Airlines Logo
5:30 am - 1:25 pm
ORD
-
GPT
7h 55m
1 stop
$360United Airlines
Tue, Mar 31 - Tue, Apr 7
Delta Logo
5:57 pm - 10:31 pm
GPT
-
MDW
4h 34m
1 stop
Delta Logo
10:45 am - 5:11 pm
MDW
-
GPT
6h 26m
1 stop
$399Delta
Thu, May 21 - Sat, May 23
Delta Logo
1:55 pm - 9:09 pm
GPT
-
MDW
7h 14m
1 stop
Delta Logo
6:23 am - 1:24 pm
MDW
-
GPT
7h 01m
1 stop
$429Delta
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.

Which airlines provide the cheapest flights from Gulfport to Chicago?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Gulfport to Chicago were found on American Airlines ($309) and United Airlines ($360).

Good to know

Low seasonNovember
Cheapest flight$158
Best time to beat the crowds with an average 26% drop in price.
Most popular time to fly with an average 2% 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 $158 for a one-way ticket and $292 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 $338 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 $323 and an overall rating of 7.1.

  • 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 8288 reviews
7.8Entertainment
7.2Food
7.9Comfort
8.1Boarding
8.5Crew
Airline reviews

Perhaps when you’re sitting in 1st class and the crew closes the bathroom for the pilots, there could be a notification other than holding your hands up as a blockade when you get there and you’re told the restrooms are closed please turn around … especially at night when visibility is poor and you’re met by a flight attendants with their arms up

10.0 ExcellentDebra, Mar 2026
PBI - ATL
Read more Delta reviews

Perhaps when you’re sitting in 1st class and the crew closes the bathroom for the pilots, there could be a notification other than holding your hands up as a blockade when you get there and you’re told the restrooms are closed please turn around … especially at night when visibility is poor and you’re met by a flight attendants with their arms up

First class is comfortable. Enjoyed a movie and was able to relax compared to coach.

Loved flying First Class. Very comfortable. The seat was amazing. Enjoyed a movie and was able to relax so much better than in coach.

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

The WiFi was not working. That made for a long flight.

Absolutely no communication on why there's a delay and multiple flight time reschedules. I would have canceled the flight and drove back home if I known it was going to be rescheduled 3 or 4 times.

Another late night flight and MORE men belligerently drinking and yelling. I had to move from first to economy because they were so obnoxious and disruptive. Crazy to go from a cozy chair to cardboard when you were supposed to be in first. Delta allows was too much drinking which leads to belligerent behavior.

I was in first class and literally the men behind me were so aggressively loud I moved myself to economy. This has become so common on Delta - people using audio without headphones, and men on 12am / late night flights drinking and yelling to talk to each other which prevents anyone around them from resting. Pretty crazy to have to move from first to economy (poorer service, less comfort...). Wild wild. Looking into other airlines.

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

Stop changing gates. Stop cancelling flights Stop moving my seat.

There was no inflight service. Once we landed we were delayed to find a gate for an hour and a half which was 1/2 the total time in the air.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

It was good experience this time. The flight was on time.

There was a delay with the plan which cause the flight to leave later and once arrived in Chicago there was another delay and some passengers missed their connecting flights

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

Overall, my last three trips on American Airlines have all been either delayed or "rescheduled" due to mechanical issues. At least on delay caused me to miss two possible connecting flights each later than the first. My last option for my last connection required the assistance of the onsite service desk (O'Hare Airport). The wait time for the service desk was such that it jeopardized getting booked on the last connecting flight available for the night. Suffice it to say, my latest experiences with American Airlines have caused me extensive loss of productive business and personal time and can therefore be classified as significantly less than satisfactory.

Waiting for gate in RDU for more than 20mins is crazy.

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

Waited for oxygen tanks for 30 minutes after boarding was complete.

We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.

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

Information on your arrival and departure airports