CHI - GPT

$124 Find Cheap Flights from Chicago to Gulfport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Gulfport departing on 2/15. 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, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Gulfport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Gulfport, 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 Chicago to Gulfport, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$269
Delta
Sat 3/7Wed 3/11
ORD - GPT • 1 stop
Cheapest one-way
$124
Multiple Airlines
Sun 2/15
ORD - GPT • 1 stop
Top airlines
Delta
Cheapest • from $269 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
August
Cheapest • 37% price drop
April
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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 Gulfport!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Chicago to Gulfport (CHI-GPT)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Gulfport 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 Chicago to Gulfport

Sat, Mar 7 - Wed, Mar 11
Delta Logo
6:45 am - 2:06 pm
ORD
-
GPT
7h 21m
1 stop
Delta Logo
2:44 pm - 9:10 pm
GPT
-
ORD
6h 26m
1 stop
$269Delta
Tue, Feb 17 - Tue, Feb 24
American Airlines Logo
5:00 am - 10:13 am
ORD
-
GPT
5h 13m
1 stop
American Airlines Logo
6:31 am - 2:16 pm
GPT
-
ORD
7h 45m
1 stop
$274American Airlines
Thu, May 14 - Sun, May 17
Multiple Airlines Logo
5:30 am - 7:10 pm
ORD
-
GPT
13h 40m
1 stop
Multiple Airlines Logo
7:50 pm - 7:59 am
GPT
-
ORD
12h 09m
1 stop
$277Multiple Airlines
Sat, Mar 7 - Wed, Mar 11
American Airlines Logo
4:04 pm - 11:57 pm
ORD
-
GPT
7h 53m
2 stops
American Airlines Logo
4:29 pm - 12:06 am
GPT
-
ORD
7h 37m
1 stop
$309American Airlines
Thu, May 14 - Sun, May 17
Multiple Airlines Logo
5:30 am - 7:10 pm
ORD
-
GPT
13h 40m
1 stop
Multiple Airlines Logo
7:50 pm - 2:15 pm
GPT
-
ORD
18h 25m
2 stops
$320Multiple Airlines
Thu, Feb 19 - Sun, Feb 22
Multiple Airlines Logo
12:22 pm - 9:00 am
MDW
-
GPT
20h 38m
2 stops
Multiple Airlines Logo
7:20 pm - 8:27 pm
GPT
-
MDW
25h 07m
1 stop
$326Multiple Airlines
Thu, Mar 12 - Mon, Mar 16
American Airlines Logo
8:10 am - 3:59 pm
ORD
-
GPT
7h 49m
1 stop
American Airlines Logo
4:29 pm - 12:06 am
GPT
-
ORD
7h 37m
1 stop
$329American Airlines
Thu, Feb 19 - Sun, Feb 22
Delta Logo
11:18 am - 5:15 pm
ORD
-
GPT
5h 57m
1 stop
Delta Logo
6:00 pm - 11:56 pm
GPT
-
ORD
5h 56m
1 stop
$383Delta
Tue, Apr 14 - Fri, Apr 17
United Airlines Logo
5:48 am - 2:13 pm
ORD
-
GPT
8h 25m
1 stop
United Airlines Logo
2:05 pm - 7:55 pm
GPT
-
ORD
5h 50m
1 stop
$413United Airlines
Tue, Apr 14 - Fri, Apr 17
United Airlines Logo
8:51 am - 2:13 pm
ORD
-
GPT
5h 22m
1 stop
United Airlines Logo
5:15 pm - 7:36 am
GPT
-
ORD
14h 21m
2 stops
$414United Airlines
Booking Insights

KAYAK's insights & trends for Chicago to Gulfport flights

Get data-powered insights and trends into flights from Chicago to Gulfport to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Chicago to Gulfport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Gulfport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Gulfport is August, where tickets cost $248 (return) on average. On the other hand, the most expensive months are November and March, where the average cost of round-trip tickets is $518 and $489 respectively.

Good to know

Low seasonJuly
Cheapest flight$124
Best time to beat the crowds but there is an average 16% increase in price.
Most popular time to fly and prices are also 17% lower on average.
Flight from Chicago O'Hare Airport to Gulfport

When to book flights from Chicago to Gulfport

Are your dates flexible? Find out the best times to travel from Chicago to Gulfport 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 Chicago to Gulfport

  • What is the cheapest flight from Chicago to Gulfport?

    In the last 3 days, the lowest price for a flight from Chicago to Gulfport was $124 for a one-way ticket and $269 for a round-trip.

  • Do I need a passport to fly between Chicago and Gulfport?

    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 Chicago to Gulfport?

    There are 2 airports in Chicago (Chicago Midway and Chicago O'Hare Intl.) and only 1 airport in Gulfport (Gulfport Biloxi Regional). The cheapest flights are generally found on the Chicago O'Hare Airport to Gulfport Biloxi Regional flight route.

  • Which aircraft models fly most regularly from Chicago to Gulfport?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago to Gulfport?

    oneworld, and SkyTeam are the airline alliances operating flights between Chicago and Gulfport, with oneworld being the most commonly used for this route.

  • Which is the best airline for flights from Chicago to Gulfport, Delta or United Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Gulfport are Delta and United Airlines. With an average price for the route of $423 and an overall rating of 7.9, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $412 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Chicago to Gulfport?

    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 Chicago to Gulfport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Gulfport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Gulfport from Chicago 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 Chicago to Gulfport?

    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 Gulfport with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Gulfport?

    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 Gulfport from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 3 airlines serving from Chicago to Gulfport

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Gulfport. 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 Chicago to Gulfport? 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 8128 reviews
8.1Boarding
7.8Entertainment
7.9Comfort
8.5Crew
7.2Food
Airline reviews

Timing, quality of service, promptness and courtesy of the staff

10.0 ExcellentAjai, Jan 2026
DFW - ATL
Read more Delta reviews

Timing, quality of service, promptness and courtesy of the staff

It was last minute due to weather - considering - it was amazing! Good smiles, friendly staff and they were making sure we knew what was going on when and where.

delta last minute gave me a boarding pass for a different flight with no confirmation that they were changing it

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

was sitting in the jet bridge for 10 minutes in -20 degree weather waiting for my bag

Outdated equipment in disrepair, wifi inoperable. Broken seats, taped air vents, generally poor condition, the 717 showed its age and lack of upkeep.

My flight out of Baton Rouge to Atlanta was delayed by a half hour. This got us into Atlanta airport 30 minutes late. I ran through the airport to get to my connecting flight. As I approached the boarding gate, I saw the boarding door was still open and a passenger was being checked in. But when I got to the gate, the boarding agent told me they had already given away my seat and there were no empty seats on that flight. So I had to take a later flight. That has never happened to me before. Very frustrating.

Connection through Atlanta was difficult. Mechanical issue on plane caused a two hour delay. New gate was a mile away.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Always wish for more healthy, gluten free options. We have to bring our own.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

We were upgraded to First Class and it was a great flight

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

My carry on baggage was damaged. Entire trip, I had to carry the baggage. When complained to the boarding crew, they got mad at me and still asked me to valet check in the cabin baggage. Rude boarding crew!!!

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

We loved the steward on the plane. He made the night enjoyable

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

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

Information on your arrival and departure airports