CHI - GPT

$234 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 3/25. 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
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
$234
Multiple Airlines
dim. 4/12dim. 4/19
ORD - GPT • 1 stop
Cheapest one-way
$168
Multiple Airlines
mer. 3/25
ORD - GPT • 2 stops
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 Chicago and Gulfport. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $278 (round-trip)
Shortest trip • 4h 56m (one-way)
Insights
Insights
Insights
Insights
Avoid delays
Most punctual • 45% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
When to travel
Cheapest • 33% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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

dim., avr. 12 - dim., avr. 19
Multiple Airlines Logo
5:25 am - 9:00 am
ORD
-
GPT
27h 35m
1 stop
Multiple Airlines Logo
7:20 pm - 9:40 am
GPT
-
ORD
38h 20m
2 stops
$234Multiple Airlines
mer., avr. 29 - dim., mai 3
Multiple Airlines Logo
2:15 pm - 6:40 pm
MDW
-
GPT
28h 25m
2 stops
Multiple Airlines Logo
7:20 pm - 7:46 am
GPT
-
MDW
12h 26m
1 stop
$295Multiple Airlines
lun., mai 11 - sam., mai 16
American Airlines Logo
5:00 am - 10:33 am
ORD
-
GPT
5h 33m
1 stop
American Airlines Logo
6:09 pm - 11:54 pm
GPT
-
ORD
5h 45m
1 stop
$309American Airlines
mer., avr. 29 - dim., mai 3
Multiple Airlines Logo
6:08 pm - 6:40 pm
ORD
-
GPT
24h 32m
2 stops
Multiple Airlines Logo
7:20 pm - 8:33 am
GPT
-
ORD
13h 13m
1 stop
$324Multiple Airlines
dim., avr. 12 - dim., avr. 19
Multiple Airlines Logo
5:05 am - 6:40 pm
MDW
-
GPT
13h 35m
1 stop
Multiple Airlines Logo
7:20 pm - 7:31 pm
GPT
-
MDW
48h 11m
2 stops
$326Multiple Airlines
ven., mai 8 - dim., mai 10
American Airlines Logo
6:41 pm - 11:58 pm
ORD
-
GPT
5h 17m
1 stop
American Airlines Logo
6:09 pm - 11:54 pm
GPT
-
ORD
5h 45m
1 stop
$329American Airlines
jeu., avr. 9 - jeu., avr. 16
American Airlines Logo
5:00 am - 10:33 am
ORD
-
GPT
5h 33m
1 stop
American Airlines Logo
6:09 pm - 11:54 pm
GPT
-
ORD
5h 45m
1 stop
$344American Airlines
mer., juil. 8 - mar., juil. 14
United Airlines Logo
6:30 am - 1:25 pm
ORD
-
GPT
6h 55m
1 stop
United Airlines Logo
2:00 pm - 9:40 pm
GPT
-
ORD
7h 40m
1 stop
$360United Airlines
lun., mai 11 - sam., mai 16
Delta Logo
5:10 pm - 9:51 pm
MDW
-
GPT
4h 41m
1 stop
Delta Logo
3:00 pm - 9:09 pm
GPT
-
MDW
6h 09m
1 stop
$399Delta
ven., mai 8 - mar., mai 12
Delta Logo
6:23 am - 1:09 pm
MDW
-
GPT
6h 46m
1 stop
Delta Logo
10:08 am - 4:12 pm
GPT
-
MDW
6h 04m
1 stop
$429Delta
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 April.

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 $483 respectively.

Good to know

Low seasonJanuary
Cheapest flight$168
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly with an average 4% 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 3 days, the lowest price for a flight from Chicago to Gulfport was $168 for a one-way ticket and $234 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 $373 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 $404 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 8288 reviews
7.9Comfort
7.8Entertainment
7.2Food
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.

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

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. :/

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

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

Information on your arrival and departure airports