253 € Cheap Flights from Chicago to Gulfport

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Flight deals from Chicago to Gulfport

Looking for a cheap last-minute deal or the best return flight from Chicago to Gulfport Airport? If you want to travel next month, return fares start from 255 €. Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Chicago to Gulfport

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago to Gulfport flights are currently cheapest in September.

Direct flights from Chicago to Gulfport

Chicago to Gulfport: Alternative routes

Compare routes from Chicago to Gulfport below. You may find an airport to fly into that's cheaper, faster, or easier than Gulfport.

Chicago to Gulfport: Flight information

The things to know before you go.
Cheapest flight found253 €
Cheapest month to flySeptember
Average flight time2 hrs, 5 mins
Most popular airlineSun Country Airlines
Average flights per week1

Finding cheap flights from Chicago to Gulfport: Frequently asked questions

The best price we found for a return flight from Chicago to Gulfport is 253 €. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
2 hours and 5 minutes is the average flight time from Chicago to Gulfport.
Sun Country Airlines flies direct from Chicago to Gulfport.
As of July 2026, there is one flight per week flying from Chicago to Gulfport.
The cheapest month to fly from Chicago to Gulfport is usually September.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Gulfport Airport on Saturday, 26 September 2026.
Yes – the average flight time is 2 hours and 5 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Gulfport but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Gulfport is around 40 days in advance, so don’t leave your flight to the last minute.

The cheapest airline that flies to Gulfport is Delta .

Flying from Chicago to Gulfport-Biloxi International Airport (GPT): What you need to know

  • Gulfport (where Gulfport-Biloxi International Airport is located) and Chicago share the UTC-6 timezone. Easily coordinate travel plans without worrying about time differences.

  • Leave enough time to get on your flight from Chicago to GPT. A good rule of thumb is to arrive at least two hours before international departures and an hour ahead for domestic flights.

  • If you're going away during a popular month like July, get to the airport even earlier. It's smart to arrive up to four hours before an international flight and two hours ahead of a domestic departure. Check-in and security lines will be longer during peak periods like Christmas and New Year.

Airports in Chicago

Chicago O'Hare International Airport (ORD)

  • Located around 27 kilometres from the centre of Chicago, ORD can be reached in about 30 minutes by car, depending on traffic. The journey on public transport will take roughly 45 minutes.

  • Searching for a convenient hotel near Chicago O'Hare International Airport? If you're catching an early flight from Chicago to Gulfport-Biloxi International Airport, these stays will have you sleeping conveniently close to check-in:

  • When it comes to the on-time performance of Chicago O'Hare International Airport, data shows 70% of flights stick to their scheduled arrival time.

  • The address for ORD is 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • MDW is around 16 kilometres from central Chicago. It'll take 25 minutes or so to get to the airport by car from the city centre. Public transport takes approximately 30 minutes.

  • Taking off bright and early? Think about checking in to one of these hotels near Chicago Midway International Airport the day before your Chicago to GPT flight:

  • Chicago Midway International Airport has an on-time performance of 76%. This figure reflects how frequently flights that leave from this airport reach their destination on time.

  • You'll find MDW at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • From the centre of Chicago, RFD is around 145 kilometres away. It takes roughly 1 hour 40 minutes to reach the airport by car and 2 hours or so if you use public transport.

  • Sleep a little longer, move a little slower, and still make your Chicago to Gulfport-Biloxi International Airport flight with plenty of time to spare. These hotels near Chicago Rockford International Airport make departure day a breeze if you're flying out early:

  • The on-time performance record of RFD is 71%. To put it simply, that's how frequently flights that depart this airport arrive at their destination as planned.

  • The address of Chicago Rockford International Airport is 2 Airport Cir.

About Gulfport-Biloxi International Airport (GPT)

Getting from Gulfport-Biloxi International Airport (GPT) to central Gulfport

  • Central Gulfport is around 11 kilometres from Gulfport-Biloxi International Airport and takes about 15 minutes to reach by car. Look into how to get from the airport to the city, whether that's with a taxi, car hire or ride-share.

  • It typically takes 35 minutes if you're travelling by public transport.

How to find the cheapest flights from Chicago to Gulfport-Biloxi International Airport (GPT)

  • 169 € is the lowest price for a one-way ticket from Chicago to Gulfport-Biloxi International Airport. Return flights start from 253 €. These prices may change based on demand and availability.

  • Don't wait until the last moment. You're more likely to find cheap flights from Chicago to GPT if you book in advance. Airlines often offer some great early bird rates.

  • Cheap Chicago to Gulfport-Biloxi International Airport tickets are easier to find when your travel dates are flexible. Try using the 'Whole month' tool to compare fares across each month and then pick the cheapest day.

  • Snapping up a cheap plane ticket from Chicago to GPT is a breeze with Price Alerts. All you need to do is create one of these automatic alerts and we'll get in touch when there's a price drop.

  • Tailor your flights using filters. Pick your departure and arrival times, airlines and total journey duration. You can also sort the results by 'Fastest,' 'Cheapest' or 'Best' flights from Chicago to Gulfport-Biloxi International Airport.

The best time to fly from Chicago to Gulfport-Biloxi International Airport (GPT)

  • Think about the kind of experience you want when planning the timing of your trip. January is the quietest month to visit Gulfport. June is when most people book flights from Chicago to Gulfport-Biloxi International Airport (GPT), which may be perfect if you're chasing more excitement.

  • Before locking in your Chicago to GPT plane ticket, consider what kind of weather you prefer. August is the warmest month in Gulfport, with temperatures ranging from 24ºC (75ºF) to 35ºC (95ºF).

  • If you like cooler conditions, search for a cheap ticket from Chicago to Gulfport-Biloxi International Airport in January when temperatures are between 3ºC (37ºF) and 18ºC (64ºF).

More about Gulfport

  • When it comes to looking for somewhere to lay your head, you'll find the top stays in Gulfport right here. Explore these options as soon as you've locked in your flight from Chicago to Gulfport-Biloxi International Airport:

  • Every great holiday has to include a little sightseeing. Ocean Adventures Marine Park, Mississippi Aquarium and The Institute for Marine Mammal Studies are essential stops on your Gulfport itinerary.

Explore more of the United States

  • You've seen Gulfport, now it's time to explore more of the United States. Journey about 113 kilometres southwest to New Orleans to check off its must-visit sights. From Bourbon St to French Quarter and Cafe Du Monde, you've got a jam-packed schedule ahead.

  • If you're interested in discovering another major destination in the United States, head for Baton Rouge, roughly 209 kilometres west of Gulfport. St. Joseph Cathedral, USS Kidd and 13th Gate Haunted House are key reasons to visit.

Prices shown on this page are estimated lowest prices only. Found in the last 12 days.