CHI - GPT

$137 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 5/28. 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
$291
Delta
Tue 6/2Tue 6/9
MDW - GPT • 1 stop
Cheapest one-way
$137
Multiple Airlines
Thu 5/28
MDW - GPT • 2 stops
Top airlines
Cheapest • from $291 (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 52m (one-way)
Insights
Insights
Insights
Insights
Avoid delays
Most punctual • 44% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
When to travel
Cheapest • 8% 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

Tue, Jun 2 - Tue, Jun 9
Delta Logo
5:15 pm - 9:51 pm
MDW
-
GPT
4h 36m
1 stop
Delta Logo
5:56 pm - 10:17 pm
GPT
-
MDW
4h 21m
1 stop
$291Delta
Tue, Jun 2 - Tue, Jun 9
Delta Logo
2:59 pm - 9:51 pm
ORD
-
GPT
6h 52m
1 stop
Delta Logo
5:56 pm - 11:59 pm
GPT
-
ORD
6h 03m
1 stop
$291Delta
Thu, May 28 - Thu, Jun 4
Delta Logo
2:59 pm - 9:51 pm
ORD
-
GPT
6h 52m
1 stop
Delta Logo
6:02 pm - 11:59 pm
GPT
-
ORD
5h 57m
1 stop
$300Delta
Tue, May 26 - Tue, Jun 2
American Airlines Logo
5:34 pm - 12:01 am
ORD
-
GPT
6h 27m
1 stop
American Airlines Logo
6:38 pm - 11:59 pm
GPT
-
ORD
5h 21m
1 stop
$310American Airlines
Tue, Jun 2 - Tue, Jun 9
Delta Logo
5:15 pm - 9:51 pm
MDW
-
GPT
4h 36m
1 stop
Delta Logo
5:56 pm - 10:17 pm
GPT
-
MDW
4h 21m
1 stop
$317Delta
Fri, May 22 - Sat, May 30
American Airlines Logo
5:34 pm - 12:01 am
ORD
-
GPT
6h 27m
1 stop
American Airlines Logo
6:38 pm - 11:59 pm
GPT
-
ORD
5h 21m
1 stop
$335American Airlines
Tue, Jul 7 - Fri, Jul 31
Delta Logo
6:00 am - 1:05 pm
MDW
-
GPT
7h 05m
1 stop
Delta Logo
6:00 pm - 10:15 pm
GPT
-
MDW
4h 15m
1 stop
$335Delta
Tue, May 12 - Sat, May 16
American Airlines Logo
5:00 am - 10:33 am
ORD
-
GPT
5h 33m
1 stop
American Airlines Logo
5:03 pm - 11:48 pm
GPT
-
ORD
6h 45m
1 stop
$339American Airlines
Tue, May 12 - Sat, May 16
American Airlines Logo
9:55 am - 5:19 pm
ORD
-
GPT
7h 24m
2 stops
American Airlines Logo
5:03 pm - 11:48 pm
GPT
-
ORD
6h 45m
1 stop
$344American Airlines
Thu, May 21 - Fri, May 29
Multiple Airlines Logo
6:55 am - 7:10 pm
ORD
-
GPT
12h 15m
2 stops
Multiple Airlines Logo
5:31 pm - 12:23 pm
GPT
-
ORD
18h 52m
1 stop
$359Multiple 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 June.

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 March and October, where the average cost of round-trip tickets is $373 and $328 respectively.

Good to know

Low seasonJanuary
Cheapest flight$137
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly with an average 1% increase in price.
Flight from Chicago Midway 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 $137 for a one-way ticket and $291 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 $289 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 8464 reviews
8.1Boarding
7.9Comfort
8.5Crew
7.2Food
7.8Entertainment
Airline reviews

Seats in Delta Main are unbelievably close to the seat in front of. Hard to get a backpack under the seat.

8.0 ExcellentMatthew, May 2026
OKC - ATL
Read more Delta reviews

Seats in Delta Main are unbelievably close to the seat in front of. Hard to get a backpack under the seat.

The agent at check in and at the gate were less than thrilled to be at work. I'm not a fan of Kayak's placement on the plane. I got put in the middle seat and none of my preferences were used.

In ATL they have two sets of departure screens. Follow what is on your airline's departure board - the ATL Airport Authority departure board had completely incorrect details about the gate assignment for my flight, which would have made me miss boarding.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

The flight was very good and the staff was very friendly and helpful!

The only thing I would say is we tried to get on a standby earlier flight, but with our fair we couldn’t. That seems senseless to leave with open seats..

Very easy to use and convenient, you can perform any action within the same portal

In a world of delays, Delta was on time both ways! Boarding was fast and efficient. Staff was friendly. AND wifi worked.

WiFi didn’t work. Flight delayed 3 hours Crew members were illiterate Seat lean back did not work.

Flight was delayed, we could have been notified earlier and in a consistent manner. App was not refreshing for another passenger to get the latest flight status. We could have stayed and waited at the hotel instead of waiting at the airport had we known the flight was going to delayed for more than 5 hours. The toilet is too tight, and needs to be cleaned more frequently (every hour). The entertainment screen froze, the touch screen not responding to touch. We were upgraded to comfort, it is more comfortable than regular economy seats.

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.

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

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

Information on your arrival and departure airports