CHI - GPT

$163 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 7/29. 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, 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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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$281
Typical prices: $587-$335
American Airlines
Tue 7/14Sat 7/18
ORD - GPT • 1 stop
Cheapest one-way
$163
Multiple Airlines
Wed 7/29
ORD - GPT • 1 stop
Top airlines
Cheapest • from $281 (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 Chicago and Gulfport. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $394 (round-trip)
Shortest trip • 4h 46m (one-way)
Insights
Insights
Insights
Insights
Avoid delays
Most punctual • 36% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
When to travel
Cheapest • 14% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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 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

Tue, Jul 14 - Sat, Jul 18
American Airlines Logo
4:45 pm - 11:56 pm
ORD
-
GPT
7h 11m
1 stop
American Airlines Logo
6:35 pm - 12:01 am
GPT
-
ORD
5h 26m
1 stop
$281American Airlines
Tue, Jul 28 - Sat, Aug 1
American Airlines Logo
6:47 pm - 11:56 pm
ORD
-
GPT
5h 09m
1 stop
American Airlines Logo
7:04 am - 2:20 pm
GPT
-
ORD
7h 16m
1 stop
$286American Airlines
Tue, Jul 21 - Mon, Jul 27
Delta Logo
5:10 pm - 10:14 pm
MDW
-
GPT
5h 04m
1 stop
Delta Logo
5:57 pm - 10:15 pm
GPT
-
MDW
4h 18m
1 stop
$295Delta
Sat, Jul 4 - Tue, Jul 7
American Airlines Logo
12:33 pm - 6:04 pm
ORD
-
GPT
5h 31m
1 stop
American Airlines Logo
6:35 pm - 12:01 am
GPT
-
ORD
5h 26m
1 stop
$295American Airlines
Sat, Aug 1 - Fri, Aug 7
American Airlines Logo
5:36 pm - 11:56 pm
ORD
-
GPT
6h 20m
1 stop
American Airlines Logo
6:34 pm - 12:18 am
GPT
-
ORD
5h 44m
1 stop
$300American Airlines
Thu, Jul 9 - Thu, Jul 16
American Airlines Logo
6:47 pm - 11:56 pm
ORD
-
GPT
5h 09m
1 stop
American Airlines Logo
6:35 pm - 12:01 am
GPT
-
ORD
5h 26m
1 stop
$309American Airlines
Thu, Jun 25 - Wed, Jul 22
Delta Logo
6:00 am - 1:07 pm
MDW
-
GPT
7h 07m
1 stop
Delta Logo
5:57 pm - 10:15 pm
GPT
-
MDW
4h 18m
1 stop
$310Delta
Thu, Jun 25 - Tue, Jul 21
Delta Logo
6:35 am - 1:07 pm
ORD
-
GPT
6h 32m
1 stop
Delta Logo
5:57 pm - 11:53 pm
GPT
-
ORD
5h 56m
1 stop
$310Delta
Tue, Jun 30 - Wed, Jul 29
American Airlines Logo
5:00 am - 10:52 am
ORD
-
GPT
5h 52m
1 stop
American Airlines Logo
6:35 pm - 12:01 am
GPT
-
ORD
5h 26m
1 stop
$311American Airlines
Fri, Jun 26 - Sat, Jul 25
American Airlines Logo
6:47 pm - 11:59 pm
ORD
-
GPT
5h 12m
1 stop
American Airlines Logo
6:35 pm - 12:01 am
GPT
-
ORD
5h 26m
1 stop
$315American 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.

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

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Gulfport departing in July.

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 January, where tickets cost $248 (return) on average. On the other hand, the most expensive months are May and March, where the average cost of round-trip tickets is $398 and $373 respectively.

Good to know

Low seasonJanuary
Cheapest flight$163
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly with an average 2% increase in price.
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 5 days, the lowest price for a flight from Chicago to Gulfport was $163 for a one-way ticket and $281 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 Midway 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 American Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Gulfport are Delta and American Airlines. With an average price for the route of $427 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 $324 and an overall rating of 7.1.

  • 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 airlines flying 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 8396 reviews
7.2Food
8.1Boarding
8.5Crew
7.8Entertainment
7.8Comfort
Airline reviews

Should never have had to go to Detroit from Orlando back to Tennessee!

6.0 GoodCynthia, Jun 2026
DTW - TYS
Read more Delta reviews

Should never have had to go to Detroit from Orlando back to Tennessee!

Got rerouted from a straight flight from Orlando to Atlanta to Knoxville to a flight from Orlando to Detroit to Knoxville! Seriously!! Flight delay out of Detroit! Long day for what should have been a pretty easy travel day!

Two delays on two separate planes with parts they could not easily find and replace.

Checkin was good, fllight ws good. Onlly complaint is lack of foot on 6 hour flight from Seattle to Boston. Snacks were flimsy - chips and cookies. could have offered something more substantial for such a long flight. I know you can buy food in airport but for the price you pay for a ticket, they should step up for the passengers.

Only beverages were offered to first class and I thought the flight attendant could have also served the Delta Comfort as well instead of sitting down and staring at her phone and walking past all of us to the back of the plane to charge her phone more. There was a complete lack of turbulence and was safe enough for flights attendant to walk around in the front of the plane, collect trash and serve a few people water and turn off the seat belt light. Also didn’t enforce people putting their seats into the upright position and allowed two passengers to remain reclined during landing. They seemed out to lunch completely. Usually my experience on Delta is much better.

Long story short, it was one of the better flight experiences I've had in some time when compared with other airlines.

Flight was great! This flight from Atlanta was even better than when I paid for Comfort from SNA to Atlanta.

Connection flights should be spaced out farther because too close I missed my connection.

Definitely a southern flavor. Cordiality was evident even though no drinks or snacks were served.

On time! There were plenty of airport employees who were able to keep us moving in the right direction. The crew on the plane were professional.

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

It wa sort of on time; the cab was left with some trash

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

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

Information on your arrival and departure airports