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Cheap flights from Gulfport to Chicago from $226

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Gulfport to Chicago departing on 10/15. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Gulfport to Chicago

Cheap round-trip flights

Logo
6:51 pm - 10:17 amGPT-ORD
15h 26m1 stop
Logo
8:05 am - 8:59 amORD-GPT
24h 54m1 stop
$228
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Fri, Oct 3 - Sun, Oct 5
Logo
6:51 pm - 10:08 amGPT-ORD
15h 17m1 stop
Logo
6:58 pm - 7:15 pmORD-GPT
24h 17m1 stop
$236
Find Deal
Mon, Oct 13 - Wed, Oct 15
Delta Logo
3:30 pm - 9:53 pmGPT-ORD
6h 23m1 stop
Delta Logo
1:09 pm - 5:13 pmORD-GPT
4h 04m1 stop
$249Delta
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Sat, Nov 15 - Tue, Nov 18
Logo
6:51 pm - 10:08 amGPT-ORD
15h 17m1 stop
Logo
11:00 am - 7:15 pmORD-GPT
32h 15m2 stops
$262
Find Deal
Mon, Oct 13 - Wed, Oct 15
Logo
6:51 pm - 10:17 amGPT-ORD
15h 26m1 stop
Logo
11:36 am - 8:59 amORD-GPT
21h 23m2 stops
$264
Find Deal
Fri, Oct 3 - Sun, Oct 5
Delta Logo
6:04 pm - 11:54 pmGPT-ORD
5h 50m1 stop
Delta Logo
1:05 pm - 5:19 pmORD-GPT
4h 14m1 stop
$284Delta
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Fri, Sep 26 - Tue, Sep 30
United Airlines Logo
2:00 pm - 9:36 pmGPT-ORD
7h 36m1 stop
United Airlines Logo
10:35 am - 4:12 pmORD-GPT
5h 37m1 stop
$312United Airlines
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Fri, Sep 26 - Mon, Sep 29
American Airlines Logo
5:20 am - 10:36 amGPT-ORD
5h 16m1 stop
American Airlines Logo
6:46 am - 1:20 pmORD-GPT
6h 34m1 stop
$344American Airlines
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Fri, Nov 21 - Mon, Nov 24
United Airlines Logo
11:57 am - 5:09 pmGPT-ORD
5h 12m1 stop
United Airlines Logo
7:10 am - 1:25 pmORD-GPT
6h 15m1 stop
$444United Airlines
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Thu, Sep 25 - Sun, Sep 28
American Airlines Logo
7:05 am - 3:27 pmGPT-ORD
8h 22m2 stops
American Airlines Logo
8:03 am - 4:08 pmORD-GPT
8h 05m1 stop
$618American Airlines
Find Deal
Wed, Dec 24 - Sat, Dec 27

United Airlines flights from Gulfport to Chicago

Our best United Airlines deals on Gulfport to Chicago flight tickets
United Airlines
Sep 26
GPT2:00 pmGulfport Biloxi Regional
7h 36m
1 stop
ORD9:36 pmChicago O'Hare Intl
Sep 29
ORD10:35 amChicago O'Hare Intl
5h 37m
1 stop
GPT4:12 pmGulfport Biloxi Regional
$312
Find similar
United Airlines
Sep 25
GPT11:57 amGulfport Biloxi Regional
5h 12m
1 stop
ORD5:09 pmChicago O'Hare Intl
Sep 28
ORD7:10 amChicago O'Hare Intl
6h 15m
1 stop
GPT1:25 pmGulfport Biloxi Regional
$444
Find similar
United Airlines
Nov 21
GPT5:15 pmGulfport Biloxi Regional
7h 00m
1 stop
ORD12:15 amChicago O'Hare Intl
Nov 24
ORD9:05 pmChicago O'Hare Intl
16h 15m
2 stops
GPT1:20 pmGulfport Biloxi Regional
$451
Find similar

American Airlines flights from Gulfport to Chicago

Our best American Airlines deals on Gulfport to Chicago flight tickets
American Airlines
Nov 21
GPT5:20 amGulfport Biloxi Regional
5h 16m
1 stop
ORD10:36 amChicago O'Hare Intl
Nov 24
ORD6:46 amChicago O'Hare Intl
6h 34m
1 stop
GPT1:20 pmGulfport Biloxi Regional
$344
Find similar
American Airlines
Dec 24
GPT7:05 amGulfport Biloxi Regional
8h 22m
2 stops
ORD3:27 pmChicago O'Hare Intl
Dec 27
ORD8:03 amChicago O'Hare Intl
8h 05m
1 stop
GPT4:08 pmGulfport Biloxi Regional
$618
Find similar
American Airlines
Sep 18
GPT12:52 pmGulfport Biloxi Regional
6h 41m
2 stops
ORD7:33 pmChicago O'Hare Intl
Sep 22
ORD3:02 pmChicago O'Hare Intl
7h 40m
2 stops
GPT10:42 pmGulfport Biloxi Regional
$1,067
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Gulfport to Chicago 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 September 15, 2025.
Use the filters below to find and compare flights from Gulfport to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Fri 10/3

6:51 pm-10:17 am

1 stop15h 26m

Chicago O'Hare Intl

Sun 10/5

8:05 am-8:59 am

1 stop24h 54m

$228

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Mon 10/13

6:51 pm-10:08 am

1 stop15h 17m

Chicago O'Hare Intl

Wed 10/15

6:58 pm-7:15 pm

1 stop24h 17m

$236

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Sat 11/15

3:30 pm-9:53 pm

1 stop6h 23m

Chicago O'Hare Intl

Tue 11/18

1:09 pm-5:13 pm

1 stop4h 04m

$249

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Mon 10/13

6:51 pm-10:08 am

1 stop15h 17m

Chicago O'Hare Intl

Wed 10/15

11:00 am-7:15 pm

2 stops32h 15m

$262

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Fri 10/3

6:51 pm-10:17 am

1 stop15h 26m

Chicago O'Hare Intl

Sun 10/5

11:36 am-8:59 am

2 stops21h 23m

$264

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Fri 9/26

6:04 pm-11:54 pm

1 stop5h 50m

Chicago O'Hare Intl

Tue 9/30

1:05 pm-5:19 pm

1 stop4h 14m

$284

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Fri 9/26

2:00 pm-9:36 pm

1 stop7h 36m

Chicago O'Hare Intl

Mon 9/29

10:35 am-4:12 pm

1 stop5h 37m

$312

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Fri 11/21

5:20 am-10:36 am

1 stop5h 16m

Chicago O'Hare Intl

Mon 11/24

6:46 am-1:20 pm

1 stop6h 34m

$344

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Thu 9/25

11:57 am-5:09 pm

1 stop5h 12m

Chicago O'Hare Intl

Sun 9/28

7:10 am-1:25 pm

1 stop6h 15m

$444

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Wed 12/24

7:05 am-3:27 pm

2 stops8h 22m

Chicago O'Hare Intl

Sat 12/27

8:03 am-4:08 pm

1 stop8h 05m

$618

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Gulfport to Chicago

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 typical price of a round-trip flight between Gulfport and Chicago?

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Monday when prices can be found for as low as $297. This is often the case because there is less demand to fly during this day of the week. When flying out on a Wednesday, the most expensive travel day of the week, you can expect to see flight prices from Gulfport to Chicago for around $587.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Gulfport to Chicago during this time can be as low as $263. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $381.

When to book flights from Gulfport to Chicago

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

Cheap Gulfport to Chicago (GPT to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Gulfport to Chicago

Direct flights

None
There are no direct flights from Gulfport to Chicago. There are no popular flight routes from Gulfport to Chicago.
Search flight deals

  • How far is Gulfport Biloxi Regional to Chicago by plane?

    There are 798.7 mi between Gulfport Biloxi Regional and Chicago. Flights usually cover this in 4h 09m, depending on flying conditions and air traffic around both airports.

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

    Prices for flights from Gulfport Biloxi Regional Airport to Chicago are updated daily.

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

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

    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.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Gulfport to Chicago?

Best airlines flying from Gulfport to Chicago

Compare and see reviews for airlines that fly from Gulfport to Chicago with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $116Free CancellationRating
7.9
7,956 reviews
Search Delta flights
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
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Gulfport to Chicago. momondo saves you time and could save you money on your trip.

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

Flights from Gulfport to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

Once you have performed a search for Gulfport to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Price alerts on flights to Chicago from Gulfport are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport