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Cheap flights from Gulfport to Chicago from $249

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Gulfport to Chicago departing on 9/26. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Gulfport to Chicago (GPT-ORD)

Cheap round-trip flights

American Airlines Logo
6:29 pm - 11:59 pmGPT-ORD
5h 30m1 stop
American Airlines Logo
6:00 am - 11:42 amORD-GPT
5h 42m1 stop
$249American Airlines
Find Deal
Fri, Sep 26 - Tue, Sep 30
American Airlines Logo
2:01 pm - 7:05 pmGPT-ORD
5h 04m1 stop
American Airlines Logo
9:20 am - 5:00 pmORD-GPT
7h 40m1 stop
$259American Airlines
Find Deal
Thu, Sep 4 - Mon, Sep 8
Delta Logo
5:15 pm - 11:58 pmGPT-ORD
6h 43m1 stop
Delta Logo
5:25 pm - 11:22 pmORD-GPT
5h 57m1 stop
$279Delta
Find Deal
Thu, Dec 25 - Fri, Jan 2
American Airlines Logo
5:10 am - 10:59 amGPT-ORD
5h 49m1 stop
American Airlines Logo
5:08 pm - 10:42 pmORD-GPT
5h 34m1 stop
$284American Airlines
Find Deal
Tue, Sep 2 - Sat, Sep 6
United Airlines Logo
5:00 pm - 12:15 amGPT-ORD
7h 15m1 stop
United Airlines Logo
7:00 am - 1:27 pmORD-GPT
6h 27m1 stop
$301United Airlines
Find Deal
Fri, Sep 19 - Mon, Sep 22
Delta Logo
6:00 am - 8:36 pmGPT-ORD
14h 36m2 stops
Delta Logo
11:19 am - 5:17 pmORD-GPT
5h 58m1 stop
$309Delta
Find Deal
Sat, Dec 13 - Tue, Dec 16
American Airlines Logo
6:29 pm - 11:59 pmGPT-ORD
5h 30m1 stop
American Airlines Logo
5:08 pm - 10:42 pmORD-GPT
5h 34m1 stop
$318American Airlines
Find Deal
Fri, Sep 19 - Mon, Sep 22
Delta Logo
6:00 am - 8:36 pmGPT-ORD
14h 36m2 stops
Delta Logo
9:30 am - 1:34 pmORD-GPT
4h 04m1 stop
$329Delta
Find Deal
Sat, Dec 13 - Tue, Dec 16
United Airlines Logo
5:00 pm - 12:15 amGPT-ORD
7h 15m1 stop
United Airlines Logo
2:12 pm - 4:05 pmORD-GPT
25h 53m2 stops
$362United Airlines
Find Deal
Fri, Sep 19 - Mon, Sep 22
United Airlines Logo
2:02 pm - 2:30 pmGPT-ORD
24h 28m2 stops
United Airlines Logo
5:56 pm - 1:27 pmORD-GPT
19h 31m2 stops
$406United Airlines
Find Deal
Fri, Sep 19 - Mon, Sep 22

Delta flights from Gulfport to Chicago O'Hare Intl Airport

Our best Delta deals on Gulfport to Chicago O'Hare Intl Airport flight tickets
Delta
Dec 25
GPT5:15 pmGulfport Biloxi Regional
6h 43m
1 stop
ORD11:58 pmChicago O'Hare Intl
Jan 2
ORD5:25 pmChicago O'Hare Intl
5h 57m
1 stop
GPT11:22 pmGulfport Biloxi Regional
$279
Find similar
Delta
Dec 13
GPT6:00 amGulfport Biloxi Regional
14h 36m
2 stops
ORD8:36 pmChicago O'Hare Intl
Dec 16
ORD11:19 amChicago O'Hare Intl
5h 58m
1 stop
GPT5:17 pmGulfport Biloxi Regional
$309
Find similar
Delta
Aug 22
GPT6:00 pmGulfport Biloxi Regional
5h 56m
1 stop
ORD11:56 pmChicago O'Hare Intl
Aug 27
ORD9:47 amChicago O'Hare Intl
6h 26m
1 stop
GPT4:13 pmGulfport Biloxi Regional
$324
Find similar

American Airlines flights from Gulfport to Chicago O'Hare Intl Airport

Our best American Airlines deals on Gulfport to Chicago O'Hare Intl Airport flight tickets
American Airlines
Sep 26
GPT6:29 pmGulfport Biloxi Regional
5h 30m
1 stop
ORD11:59 pmChicago O'Hare Intl
Sep 30
ORD6:00 amChicago O'Hare Intl
5h 42m
1 stop
GPT11:42 amGulfport Biloxi Regional
$249
Find similar
American Airlines
Sep 4
GPT2:01 pmGulfport Biloxi Regional
5h 04m
1 stop
ORD7:05 pmChicago O'Hare Intl
Sep 8
ORD9:20 amChicago O'Hare Intl
7h 40m
1 stop
GPT5:00 pmGulfport Biloxi Regional
$259
Find similar
American Airlines
Sep 2
GPT5:10 amGulfport Biloxi Regional
5h 49m
1 stop
ORD10:59 amChicago O'Hare Intl
Sep 6
ORD5:08 pmChicago O'Hare Intl
5h 34m
1 stop
GPT10:42 pmGulfport Biloxi Regional
$284
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Gulfport to Chicago O'Hare Intl Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated August 21, 2025.
Use the filters below to find and compare flights from Gulfport to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Fri 9/26

6:29 pm-11:59 pm

1 stop5h 30m

Chicago O'Hare Intl

Tue 9/30

6:00 am-11:42 am

1 stop5h 42m

$249

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Thu 9/4

2:01 pm-7:05 pm

1 stop5h 04m

Chicago O'Hare Intl

Mon 9/8

9:20 am-5:00 pm

1 stop7h 40m

$259

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Thu 12/25

5:15 pm-11:58 pm

1 stop6h 43m

Chicago O'Hare Intl

Fri 1/2

5:25 pm-11:22 pm

1 stop5h 57m

$279

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Tue 9/2

5:10 am-10:59 am

1 stop5h 49m

Chicago O'Hare Intl

Sat 9/6

5:08 pm-10:42 pm

1 stop5h 34m

$284

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Fri 9/19

5:00 pm-12:15 am

1 stop7h 15m

Chicago O'Hare Intl

Mon 9/22

7:00 am-1:27 pm

1 stop6h 27m

$301

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Sat 12/13

6:00 am-8:36 pm

2 stops14h 36m

Chicago O'Hare Intl

Tue 12/16

11:19 am-5:17 pm

1 stop5h 58m

$309

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Fri 9/19

6:29 pm-11:59 pm

1 stop5h 30m

Chicago O'Hare Intl

Mon 9/22

5:08 pm-10:42 pm

1 stop5h 34m

$318

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Sat 12/13

6:00 am-8:36 pm

2 stops14h 36m

Chicago O'Hare Intl

Tue 12/16

9:30 am-1:34 pm

1 stop4h 04m

$329

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Fri 9/19

5:00 pm-12:15 am

1 stop7h 15m

Chicago O'Hare Intl

Mon 9/22

2:12 pm-4:05 pm

2 stops25h 53m

$362

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Fri 9/19

2:02 pm-2:30 pm

2 stops24h 28m

Chicago O'Hare Intl

Mon 9/22

5:56 pm-1:27 pm

2 stops19h 31m

$406

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 12 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Gulfport to Chicago O'Hare Intl Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Saturday when prices can be found for as low as $280. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Gulfport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $672.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Gulfport in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $325 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $394. Of course, these prices can vary depending on the time of year and what airport you fly to.

When to book flights from Gulfport to Chicago O'Hare Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Gulfport to Chicago O'Hare Intl Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Gulfport to Chicago O'Hare Intl Airport (GPT to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Gulfport to Chicago O'Hare Intl Airport

Direct flights

None
There are no direct flights from Gulfport to Chicago O'Hare Intl Airport. There are no popular flight routes from Gulfport to Chicago O'Hare Intl Airport.
Search flight deals

  • How far is Gulfport Biloxi Regional to Chicago O'Hare Intl by plane?

    There are 804.5 mi between Gulfport Biloxi Regional and Chicago O'Hare Intl. By plane, this route typically takes 4h 50m.

  • When did momondo last update prices for flights from Gulfport Biloxi Regional Airport to Chicago O'Hare Intl Airport?

    Prices for flights from Gulfport Biloxi Regional Airport to Chicago O'Hare Intl Airport were last updated today.

  • How many operators does momondo search for flights from Gulfport Biloxi Regional Airport to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from Gulfport Biloxi Regional Airport to Chicago O'Hare Intl Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Gulfport Biloxi Regional Airport to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The travel and health documents you'll need for your trip to Chicago O'Hare Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago O'Hare Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Gulfport to Chicago O'Hare Intl Airport?

Best airlines flying from Gulfport to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Gulfport to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $248Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Rockford
South Haven
Schaumburg
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Racine
Hammond
Tinley Park
Orland Park
Elgin
Aurora
Janesville
Benton Harbor

Why use momondo?

Why should I use momondo to find a flight deal from Gulfport to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Gulfport to Chicago. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Gulfport to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Gulfport with this policy.

How can momondo help me find flights from Gulfport to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Gulfport.

I’m not ready to book a flight from Gulfport to Chicago right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Gulfport to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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