Cheap Flights from Gulfport to Chicago

Compare Gulfport to Chicago flight deals

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

Book the best Chicago fare with no extra fees

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 $603. Find the lowest prices on one-way and return tickets right here.

Chicago.$560 per passenger.Departing Fri, 21 Aug, returning Sun, 23 Aug.Return flight with Delta.Outbound indirect flight with Delta, departs from Gulfport on Fri, 21 Aug, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Sun, 23 Aug, arriving in Gulfport.Price includes taxes and charges.From $560, select.

Chicago.$573 per passenger.Departing Thu, 30 Apr, returning Mon, 4 May.Return flight with Delta.Outbound indirect flight with Delta, departs from Gulfport on Thu, 30 Apr, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Mon, 4 May, arriving in Gulfport.Price includes taxes and charges.From $573, select.

Chicago.$576 per passenger.Departing Sat, 25 Apr, returning Wed, 29 Apr.Return flight with Delta.Outbound indirect flight with Delta, departs from Gulfport on Sat, 25 Apr, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Wed, 29 Apr, arriving in Gulfport.Price includes taxes and charges.From $576, select.

Chicago.$595 per passenger.Departing Thu, 1 Oct, returning Sun, 4 Oct.Return flight with Delta.Outbound indirect flight with Delta, departs from Gulfport on Thu, 1 Oct, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Sun, 4 Oct, arriving in Gulfport.Price includes taxes and charges.From $595, select.

Chicago.$595 per passenger.Departing Fri, 15 Jan, returning Mon, 18 Jan.Return flight with Delta.Outbound indirect flight with Delta, departs from Gulfport on Fri, 15 Jan, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Mon, 18 Jan, arriving in Gulfport.Price includes taxes and charges.From $595, select.

Chicago.$602 per passenger.Departing Fri, 3 Jul, returning Sun, 12 Jul.Return flight with Delta.Outbound indirect flight with Delta, departs from Gulfport on Fri, 3 Jul, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Sun, 12 Jul, arriving in Gulfport.Price includes taxes and charges.From $602, select.

Chicago.$603 per passenger.Departing Sat, 2 May, returning Sun, 3 May.Return flight with Delta.Outbound indirect flight with Delta, departs from Gulfport on Sat, 2 May, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Sun, 3 May, arriving in Gulfport.Price includes taxes and charges.From $603, select.

Chicago.$613 per passenger.Departing Tue, 8 Sep, returning Sat, 12 Sep.Return flight with Delta.Outbound indirect flight with Delta, departs from Gulfport on Tue, 8 Sep, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Sat, 12 Sep, arriving in Gulfport.Price includes taxes and charges.From $613, select.

Chicago.$850 per passenger.Departing Thu, 4 Jun, returning Sat, 6 Jun.Return flight with Delta.Outbound indirect flight with Delta, departs from Gulfport on Thu, 4 Jun, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Sat, 6 Jun, arriving in Gulfport.Price includes taxes and charges.From $850, select.

Chicago.$878 per passenger.Departing Tue, 26 May, returning Tue, 9 Jun.Return flight with Delta.Outbound indirect flight with Delta, departs from Gulfport on Tue, 26 May, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Tue, 9 Jun, arriving in Gulfport.Price includes taxes and charges.From $878, 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 August.

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Jan

Feb

Mar

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	$560
Cheapest month to fly	August

Finding cheap flights from Gulfport to Chicago: Frequently asked questions

How many airports are there in Chicago?

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, 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 $560. 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.

Which airlines fly direct from Gulfport to Chicago?

Currently, there are no airlines that fly direct from Gulfport to Chicago. But we found flights with one or more stops from $560.

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

As of April 2026, there are no flights 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 August.

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 25.4 km away from the centre of Chicago. We've found flights into this airport from $560.

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 Friday, 21 August 2026.

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

No airlines currently offer direct flights between Gulfport Airport and Chicago. Most routes have one or more stops.

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 April, the average temperature is usually around 8°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.

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

Chicago and Gulfport (where Gulfport-Biloxi International Airport is located) share the UTC-5 timezone. This means you won't need to account for any time differences.
For stress-free travel, turn up at the airport two hours ahead of international flights and an hour before domestic departures. This ensures you have enough time to catch your GPT to Chicago flight.
Longer lines at check-in and security are likely if you're heading away during high season, so give yourself some extra wiggle room. A good general rule for peak times? Get there up to four hours early for international flights and at least two hours for domestic departures.
To get to GPT from central Gulfport, it'll take around 15 minutes by car. It's roughly 5 kilometres from the airport to the city centre.
Catching an early flight from Gulfport-Biloxi International Airport to Chicago? Avoid the last-minute rush to the airport (and enjoy a little extra shut-eye) by choosing one of these hotels near GPT:
81.94% of flights departing from Gulfport-Biloxi International Airport reach their destination on schedule. With its strong on-time performance, you're unlikely to experience delays when taking off from GPT.
GPT is located at 14035 Airport Road.

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

The lowest price we've seen for a one-way Gulfport-Biloxi International Airport to Chicago flight is $357. The cheapest price for a return flight is $560. Keep in mind fares may change due to availability at the time of booking.
Don't leave things to the last minute. You're more likely to find cheap flights from GPT to Chicago if you book early. Airlines often offer some great early bird discounts.
If you have flexibility with your trip dates, try using the 'Whole month' tool. It'll find the lowest price across each month when searching for a Gulfport-Biloxi International Airport to Chicago ticket.
Picking up a cheap flight from GPT to Chicago is a breeze with Price Alerts. Simply create one of these automatic notifications and we'll notify you when a better deal is available.
Tailor your flights with filters. Select your arrival and departure times, total journey duration and airlines. You can also sort the results by 'Best,' 'Cheapest' or 'Fastest' flights from Gulfport-Biloxi International Airport to Chicago.

Airports in Chicago

O'Hare International Airport (ORD)

O'Hare International Airport (ORD) to the centre of Chicago takes about 35 minutes to reach by car. The centre is roughly 40 kilometres away.
When travelling by public transport, expect a journey time of about 55 minutes.
Consider staying in a hotel close to ORD if you're coming in on a late flight from Gulfport-Biloxi International Airport to Chicago. Check in to one of these options and make your arrival easier:
Go where the road takes you with an O'Hare International Airport rental car. Book your wheels from Routes Car Rentals, Dollar or Budget and see more of Chicago and beyond.
Booking your ride from O'Hare International Airport around four weeks in advance of your flight from GPT to Chicago can help you lock in the best possible rate.
You'll find ORD at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

After your flight from Gulfport-Biloxi International Airport to Chicago has arrived, you can get to the city centre in around 20 minutes by car. Central Chicago is roughly 19 kilometres from Chicago Midway International Airport (MDW).
If you're travelling on public transport, it'll take about 45 minutes.
There are some great places ready to welcome you near MDW. Tuck yourself in and get cosy after your GPT to Chicago flight at one of these perfectly located options:
Forget about public transport schedules or slow-moving cab lines. Grab a Chicago Midway International Airport rental car and take your trip in whatever direction you choose. Compare availability and rates from Dollar, Hertz and Budget.
Avoid potential price surges. Securing your ride four weeks ahead of your arrival at MDW will save you money.
Chicago Midway International Airport can be found at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

Step off your flight from Gulfport-Biloxi International Airport to Chicago and head for your hotel or jump right into exploring. The centre of Chicago is around 137 kilometres from Chicago Rockford International Airport (RFD) and usually takes 1 hour 25 minutes to drive there.
Public transport can get you there in about 4 hours 15 minutes.
If you don't want to make the journey to the centre, choose a hotel near RFD. Make yourself comfortable at one of these stays after your GPT to Chicago flight:
Stay in control of the next chapter of your journey by picking up a Chicago Rockford International Airport rental car. Budget, Alamo and National will get you on the road.
If you're looking for a specific model or make, booking early increases your chances of getting what you want. Book your ride from RFD a couple of weeks ahead of your flight from Gulfport-Biloxi International Airport to Chicago.
The address for Chicago Rockford International Airport is 2 Airport Cir.

Best time to go to Chicago

Before locking in your flights from Gulfport-Biloxi International Airport to Chicago, consider which time of year works best for you. High season in Chicago offers a bustling atmosphere and plenty to do, while the off-season brings cheaper hotel deals and fewer crowds.
Lock in a Gulfport-Biloxi International Airport to Chicago flight ticket with a departure in July if you want to explore the city during its warmest month. Expect temperatures to range from 15ºC to 29ºC.
January sees average temperatures of between -12ºC and 3ºC. Search for a cheap ticket from GPT to Chicago around that time if you want to travel when it's cooler.

More about Chicago

When it comes to searching for somewhere to rest your head, you'll find the top stays in Chicago right here. Explore these options as soon as you've locked in your flight from Gulfport-Biloxi International Airport to Chicago:
All great holidays should include a little sightseeing. Art Institute of Chicago, Millennium Park and LandShark Beer Garden at Navy Pier are must-do's during your Chicago adventure.

Explore more of United States

You've seen Chicago, now it's time to discover other parts of United States. Travel around 451 kilometres south-east to Columbus to tick off its top sights. From Franklin Park Conservatory and Botanical Gardens to Ohio Statehouse and German Village, your itinerary will be busy.
Indianapolis is another well-known destination in United States and is around 257 kilometres south-east of Chicago. No journey is complete without dropping by The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.