GPT - CHI

$205 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 8/29. 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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Flights 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

Wed, Jul 9 - Tue, Jul 15
American Airlines Logo
6:36 pm - 11:57 pmGPT-ORD
5h 21m1 stop
American Airlines Logo
5:00 am - 10:19 amORD-GPT
5h 19m1 stop
$249American Airlines
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Tue, Jun 24 - Sat, Aug 2
American Airlines Logo
6:40 pm - 11:57 pmGPT-ORD
5h 17m1 stop
American Airlines Logo
6:25 pm - 12:05 amORD-GPT
5h 40m1 stop
$254American Airlines
Find Deal
Wed, Jun 25 - Sun, Jun 29
American Airlines Logo
7:43 pm - 12:59 amGPT-ORD
5h 16m1 stop
American Airlines Logo
5:29 am - 12:14 pmORD-GPT
6h 45m1 stop
$329American Airlines
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Fri, Jul 25 - Sun, Jul 27
Delta Logo
6:00 pm - 12:09 amGPT-ORD
6h 09m1 stop
Delta Logo
7:00 am - 1:07 pmORD-GPT
6h 07m1 stop
$344Delta
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Wed, Jul 9 - Tue, Jul 15
Delta Logo
6:07 am - 11:58 amGPT-MDW
5h 51m1 stop
Delta Logo
6:00 am - 1:07 pmMDW-GPT
7h 07m1 stop
$363Delta
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Wed, Jul 9 - Tue, Jul 15
Delta Logo
6:07 am - 11:58 amGPT-MDW
5h 51m1 stop
Delta Logo
6:00 am - 1:07 pmMDW-GPT
7h 07m1 stop
$383Delta
Find Deal
Sun, Aug 17 - Sat, Aug 23
United Airlines Logo
5:25 pm - 9:29 amGPT-ORD
16h 04m2 stops
United Airlines Logo
7:00 am - 1:27 pmORD-GPT
6h 27m1 stop
$407United Airlines
Find Deal
Fri, Aug 29 - Sun, Aug 31
United Airlines Logo
7:05 am - 10:41 pmGPT-ORD
15h 36m1 stop
United Airlines Logo
6:00 am - 1:27 pmORD-GPT
7h 27m1 stop
$417United Airlines
Find Deal
Fri, Jun 27 - Sun, Jun 29
 Logo
5:37 pm - 9:19 pmGPT-ORD
27h 42m1 stop
 Logo
9:55 am - 7:45 amORD-GPT
21h 50m2 stops
Fri, Jun 27 - Sun, Jun 29
 Logo
5:37 pm - 5:44 pmGPT-ORD
24h 07m3 stops
 Logo
7:27 am - 7:45 amORD-GPT
24h 18m1 stop
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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
High seasonMarch
Cheapest flight$205
Best time to beat the crowds with an average 38% drop in price.
Most popular time to fly and prices are also 17% 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 $205 for a one-way ticket and $249 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 $338 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 $346 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.

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 7950 reviews
7.9Entertainment
8.5Crew
7.9Comfort
8.2Boarding
7.3Food
Airline reviews

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

10.0 ExcellentHartaj, Jun 2025EWR - RDU
Read more Delta reviews

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

My flight was 6 pm 6/6. Every hour they delayed it again - air condition issues then no pilot then the crew had worked too many hours and cancelled the flight at 11 pm. Sent customers to NJ a 45 minutes uber ride to a hotel. Had to be back by 5 am for a 7 am flight and again no pilot etc with another three hours of delays.

The entertainment and wifi mostly didn't work on this flight.

Terrible entertainment system - kept freezing and audio kept cutting out. Snacks were mediocre at best for a 5 hour flight.

The check in and bag drop off for Sky Priority members is slow. The Clear security was also slow - a TSA issue.

I am still upset that my bag was lost on a recent trip to Rome ; we were inconvenienced and out €150 Euros ; delta has refused to reimburse us

I am very bothered by the events today. I can't believe the flight attendants allowed someone to take my seat and made me move. It was embarrassing. I was in the right. The lady just didn't want move. I can't believe delta would allow this to stand and disrespect my rights as a passenger. The lady complained about her leg and that she couldn't move. Firstly somehow she was able to make it to row 24. Not sure how much her leg could have hurt. Secondly, I'm in plenty of pain myself. I just finished chemotherapy a several weeks ago. My body is constantly sore. Yet deltas flight attendants didn't appropriately protect my rights. In the end they found me a seat on the plane but I want to understand how delta can operate this way. They in essence allowed a bully to get their way.

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

The flight was 2 hour delayed, otherwise everything was excellent. The delay was due to the hourly limit requirement so given that as a reason, I'm happy with the flight!

Not sure the logic of the boarding in Groups. I was loaded first on the aisle. Then the guy in the middle. Then the guy by the window. Constantly holding up the other people boarding behind them with us blocking the aisle and this happened in most of the other rows

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

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

Information on your arrival and departure airports

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