Cheap Flights from Gulfport to Chicago

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Travellers and cabin class, 1 Adult, Economy

Compare Gulfport to Chicago flight deals

Find the cheapest month or even day of the year to fly to Chicago

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Flight deals from Gulfport to Chicago

Looking for a cheap last-minute deal or the best return flight from Gulfport Airport to Chicago? If you want to travel next month, return fares start from Rp 5.300.607. Find the lowest prices on one-way and return tickets right here.

Chicago.Rp 2.858.110 per passenger.Departing Fri, 2 Oct.One-way flight with Delta.Outbound indirect flight with Delta, departs from Gulfport on Fri, 2 Oct, arriving in Chicago Midway.Price includes taxes and charges.From Rp 2.858.110, select.

Chicago.Rp 2.948.496 per passenger.Departing Mon, 10 Aug.One-way flight with United.Outbound indirect flight with United, departs from Gulfport on Mon, 10 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From Rp 2.948.496, select.

Chicago.Rp 3.249.784 per passenger.Departing Wed, 16 Dec.One-way flight with Delta.Outbound indirect flight with Delta, departs from Gulfport on Wed, 16 Dec, arriving in Chicago O'Hare International.Price includes taxes and charges.From Rp 3.249.784, select.

Chicago.Rp 4.718.667 per passenger.Departing Tue, 21 Jul.One-way flight with Delta.Outbound indirect flight with Delta, departs from Gulfport on Tue, 21 Jul, arriving in Chicago O'Hare International.Price includes taxes and charges.From Rp 4.718.667, select.

Find the cheapest month to fly from Gulfport to Chicago

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

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Direct flights from Gulfport to Chicago

Alternative Gulfport to Chicago routes

Looking for the cheapest, fastest or easiest route from Gulfport to Chicago? You could fly into the following airports instead.

Gulfport to Chicago: Flight information

The things to know before you go.

Cheapest flight found	Rp 2.858.110
Cheapest month to fly	October
Average flight time	2 hrs, 15 mins
Most popular airline	Sun Country Airlines
Average flights per week	1

Finding cheap flights from Gulfport to Chicago: Frequently asked questions

How many airports are there in Chicago?

There are 3 airports in Chicago: Chicago Midway, Chicago O'Hare International and Chicago Rockford.

How much are return flights from Gulfport to Chicago?

The best price we found for a return flight from Gulfport to Chicago is Rp 5.237.307. 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.

How long does it take to fly from Gulfport to Chicago?

2 hours and 15 minutes is the average flight time from Gulfport to Chicago.

Which airlines fly direct from Gulfport to Chicago?

Sun Country Airlines flies direct from Gulfport to Chicago.

How many flights are there a week from Gulfport to Chicago?

As of July 2026, there is one flight per week flying from Gulfport to Chicago.

When is the cheapest time to fly from Gulfport to Chicago?

The cheapest month to fly from Gulfport to Chicago is usually September.

Which is the cheapest airport to fly into in Chicago?

If you're flying from Gulfport Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.5 km away from the centre of Chicago. We've found flights into this airport from Rp 5.237.307.

Which upcoming date is cheapest to fly from Gulfport Airport to Chicago on?

After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Gulfport Airport to Chicago on Tuesday, 22 September 2026.

Can I get a direct flight from Gulfport Airport to Chicago?

Yes – the average flight time is 2 hours and 15 minutes.

How can I get the best flight deal from Gulfport Airport to Chicago?

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 Chicago 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.

When is the best time to book flights to Chicago?

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

What’s the weather like in Chicago?

In July, the average temperature is usually around 22°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.

Which is the cheapest airline to fly from Gulfport Airport to Chicago with?

Currently, Delta offers the cheapest flight tickets to Chicago.

How to find cheap flights to Chicago from Gulfport

Looking for cheap tickets from Gulfport to Chicago? Here are a few tips on how to secure the best flight price and make your journey as smooth as possible.

Simply hit 'search'. From British Airways to international carriers like Emirates, we compare all major airlines along with the most popular online travel agents to find the cheapest plane tickets from Gulfport to Chicago. And with us there are no hidden fees - what you see is what you pay.
Compare flight deals to Chicago from Gulfport from over 1,000 providers. Then choose the cheapest or fastest plane tickets.
Flex your dates to find the best Gulfport-Chicago ticket prices. If you are flexible when it comes to your travel dates, use Skyscanner's 'Whole month' tool to find the cheapest month, and even day to fly to Chicago from Gulfport.
Set up a Price Alert. You can easily track the fare of your cheap Gulfport-Chicago flights by creating an alert. Whenever prices go down or up, you'll get an email or push notification to help make sure you get the best possible flight deal.
Fly without stops. Only interested in direct flights between Gulfport and Chicago? Make sure to tick 'Direct flights only' when performing a search. If there are direct flights available on the route, these will appear in the results.
Find the cheapest Business class flights from Gulfport and Chicago. We scour the internet for the best Business, Premium Economy and First Class flight fares to Chicago, too. Check the difference in price as you search – you might just chance upon a last-minute low fare. Note that not all cabin classes are available for every destination or airline.
Include nearby airports in your search. Widen your search for Gulfport to Chicago flight deals by selecting the "add nearby airports" option. This will allow you to see flight prices for all the nearest airports at your departure point and your destination and could help you save next time you travel.

Combine your flight to Chicago from Gulfport with hotels and car hire

Once you've secured your cheap flight ticket from Gulfport to Chicago, discover the best prices and exclusive rates for hotels in Chicago or nearby. You can also compare hundreds of car hire companies in one go so that you get the best car hire price for your trip.