CHI - GPT

$175 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 10/6. 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

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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Flights 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

Fri, Sep 12 - Fri, Sep 19
American Airlines Logo
4:12 pm - 11:32 pmORD-GPT
7h 20m1 stop
American Airlines Logo
2:01 pm - 8:27 pmGPT-ORD
6h 26m1 stop
$248American Airlines
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Thu, Aug 21 - Wed, Sep 3
American Airlines Logo
6:25 pm - 11:59 pmORD-GPT
5h 34m1 stop
American Airlines Logo
2:01 pm - 7:05 pmGPT-ORD
5h 04m1 stop
$249American Airlines
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Fri, Aug 15 - Mon, Aug 18
Delta Logo
7:05 am - 1:21 pmORD-GPT
6h 16m1 stop
Delta Logo
6:00 pm - 11:56 pmGPT-ORD
5h 56m1 stop
$259Delta
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Fri, Aug 15 - Mon, Aug 18
American Airlines Logo
3:32 pm - 10:24 pmORD-GPT
6h 52m2 stops
American Airlines Logo
6:12 pm - 11:43 pmGPT-ORD
5h 31m1 stop
$264American Airlines
Find Deal
Wed, Aug 27 - Wed, Sep 3
Delta Logo
4:25 pm - 9:38 pmMDW-GPT
5h 13m1 stop
Delta Logo
5:00 pm - 9:26 pmGPT-MDW
4h 26m1 stop
$279Delta
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Mon, Aug 18 - Tue, Aug 26
Delta Logo
3:30 pm - 9:38 pmORD-GPT
6h 08m1 stop
Delta Logo
6:00 am - 12:16 pmGPT-ORD
6h 16m1 stop
$279Delta
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Thu, Aug 14 - Mon, Aug 18
 Logo
5:21 pm - 7:45 amORD-GPT
14h 24m1 stop
 Logo
5:37 pm - 10:31 amGPT-ORD
16h 54m2 stops
Thu, Sep 4 - Tue, Sep 9
United Airlines Logo
7:15 am - 7:59 pmORD-GPT
12h 44m2 stops
United Airlines Logo
5:00 pm - 12:15 amGPT-ORD
7h 15m1 stop
$428United Airlines
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Sat, Aug 16 - Mon, Aug 18
United Airlines Logo
7:25 am - 9:44 pmORD-GPT
14h 19m2 stops
United Airlines Logo
5:25 pm - 11:12 pmGPT-ORD
5h 47m1 stop
$436United Airlines
Find Deal
Thu, Aug 14 - Mon, Aug 18
 Logo
5:21 pm - 7:45 amORD-GPT
14h 24m1 stop
 Logo
5:37 pm - 4:10 pmGPT-ORD
22h 33m3 stops
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’s the cheapest day of the week to fly from Chicago to Gulfport?

The average price of all round-trip flights from Chicago to Gulfport clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Gulfport on a Wednesday and more expensive on a Sunday. On your return trip to Chicago, you should consider flying back on a Saturday, and avoid Sundays for better deals.

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 $266 (return) on average. On the other hand, the most expensive months are February and July, where the average cost of round-trip tickets is $573 and $562 respectively.

Good to know

Low seasonMay
Cheapest flight$175
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly and prices are also 6% 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 $175 for a one-way ticket and $248 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?

    SkyTeam, Star Alliance, and oneworld are the airline alliances operating flights between Chicago and Gulfport, with SkyTeam 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 $418 and an overall rating of 8.0, Delta is the most popular choice. American Airlines is also a great choice for the route, with an average price of $357 and an overall rating of 7.2.

  • 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.
8.0
DeltaOverall score based on 7980 reviews
7.9Entertainment
7.9Comfort
8.2Boarding
7.3Food
8.5Crew
Airline reviews

My experience on any Delta flight is always overshadowed by the time Delta removed me from a flight for no apparent reason.

2.0 MediocreGim, Jul 2025BGM - DTW
Read more Delta reviews

My experience on any Delta flight is always overshadowed by the time Delta removed me from a flight for no apparent reason.

Delayed and took off even later than the scheduled delay time

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Great experience on Delta. Staff from baggage check to flight attendants were very courteous and professional. My only issue was a personal preference for pretzels instead of the chips and cookies that were offered.

There was no problems, just a little uncomfortable with seats that do not lay back a little

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

Flight was delayed, 30+ bags had to be gate checked. Crew were very friendly!

Everything was good until we were boarding our connection flight in Atlanta, we were told to gate check our carry-on, but when we got inside the plane, there was plenty of room in the overhead.

Did not know my son and I had different seating arrangements. He was fine, but it was disappointing.

Flight was canceled, and no effort was made to help with rebooking, no hotel vouchers, no car transportation and minimal food voucher and most places for food were closed by the time the voucher was given. Waited for 3 hours for bags. Simply the worst travel experience I have ever had

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

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

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