GPT - CHI

$150 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 6/7. 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 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
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
$262
Multiple Airlines
Thu 7/2Sat 7/11
GPT - ORD • 1 stop
Cheapest one-way
$150
Multiple Airlines
Sun 6/7
GPT - ORD • 2 stops
Top airlines
Cheapest • from $291 (round-trip)
Best reviews • 7.1 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Gulfport and Chicago. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $268 (round-trip)
Shortest trip • 5h 11m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 100% price drop
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 Chicago!
Flight Deals
Booking Insights
Flight 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

Thu, Jul 2 - Sat, Jul 11
Multiple Airlines Logo
7:50 pm - 9:21 am
GPT
-
ORD
13h 31m
1 stop
Multiple Airlines Logo
8:05 am - 7:41 am
ORD
-
GPT
47h 36m
2 stops
$262Multiple Airlines
Wed, Jun 17 - Tue, Jun 23
Delta Logo
5:56 pm - 10:17 pm
GPT
-
MDW
4h 21m
1 stop
Delta Logo
6:00 am - 1:07 pm
MDW
-
GPT
7h 07m
1 stop
$291Delta
Tue, Jun 2 - Tue, Jun 9
American Airlines Logo
6:38 pm - 11:59 pm
GPT
-
ORD
5h 21m
1 stop
American Airlines Logo
5:00 am - 10:52 am
ORD
-
GPT
5h 52m
1 stop
$291American Airlines
Sat, Jun 6 - Mon, Jun 8
American Airlines Logo
6:38 pm - 11:58 pm
GPT
-
ORD
5h 20m
1 stop
American Airlines Logo
6:47 pm - 12:01 am
ORD
-
GPT
5h 14m
1 stop
$300American Airlines
Thu, Aug 27 - Sun, Aug 30
Delta Logo
6:00 pm - 11:57 pm
GPT
-
ORD
5h 57m
1 stop
Delta Logo
5:30 am - 9:35 am
ORD
-
GPT
4h 05m
1 stop
$309Delta
Fri, May 29 - Mon, Jun 1
American Airlines Logo
6:38 pm - 11:59 pm
GPT
-
ORD
5h 21m
1 stop
American Airlines Logo
6:47 pm - 12:01 am
ORD
-
GPT
5h 14m
1 stop
$310American Airlines
Fri, Aug 7 - Sun, Aug 9
Delta Logo
6:00 pm - 11:53 pm
GPT
-
ORD
5h 53m
1 stop
Delta Logo
5:15 am - 9:19 am
ORD
-
GPT
4h 04m
1 stop
$317Delta
Thu, Aug 27 - Sun, Aug 30
Delta Logo
2:15 pm - 9:20 pm
GPT
-
ORD
7h 05m
1 stop
Delta Logo
9:30 am - 1:33 pm
ORD
-
GPT
4h 03m
1 stop
$329Delta
Fri, Jul 3 - Sat, Jul 11
Delta Logo
3:00 pm - 8:32 pm
GPT
-
ORD
5h 32m
1 stop
Delta Logo
3:35 pm - 8:39 pm
ORD
-
GPT
5h 04m
1 stop
$334Delta
Fri, Jul 3 - Sat, Jul 11
American Airlines Logo
7:04 am - 2:20 pm
GPT
-
ORD
7h 16m
1 stop
American Airlines Logo
5:00 am - 10:52 am
ORD
-
GPT
5h 52m
1 stop
$335American Airlines
Booking Insights

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.

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

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

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Gulfport to Chicago, 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 Gulfport to Chicago is February, where tickets cost $0 (return) on average. On the other hand, the most expensive months are July and January, where the average cost of round-trip tickets is $358 and $354 respectively.

Good to know

Low seasonNovember
Cheapest flight$150
Best time to beat the crowds with an average 38% drop in price.
Most popular time to fly with an average 20% increase in price.
Flight from Gulfport to Chicago O'Hare 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 $150 for a one-way ticket and $262 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, and oneworld are the airline alliances operating flights between Gulfport and Chicago, with SkyTeam being the most commonly used for this route.

  • 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.

Reviews of the top airline 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.
7.1
American AirlinesOverall score based on 11681 reviews
6.4Food
7.5Boarding
7.9Crew
7.2Comfort
6.9Entertainment
Airline reviews

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

10.0 ExcellentDeepa, Apr 2026
DFW - ORD
Read more American Airlines reviews

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

The staff are very, very professional. It's what flying should feel like.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

Delays with no explanation. It could have been handled better.

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

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

Information on your arrival and departure airports