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Cheap flights from Gulfport to Chicago from $172

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 3/19. 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

Enter your travel dates to find the best prices.
Delta Logo
5:57 pm - 11:54 pm
GPT
-
ORD
5h 57m
1 stop
Delta Logo
5:59 pm - 10:15 pm
ORD
-
GPT
4h 16m
1 stop
$269Delta
Tue, Mar 24 - Tue, Mar 31
Multiple Airlines Logo
7:20 pm - 8:17 am
GPT
-
ORD
12h 57m
1 stop
Multiple Airlines Logo
11:25 am - 9:00 am
ORD
-
GPT
21h 35m
1 stop
$303Multiple Airlines
Thu, Apr 9 - Sun, Apr 12
Delta Logo
5:57 pm - 11:54 pm
GPT
-
ORD
5h 57m
1 stop
Delta Logo
5:59 pm - 10:15 pm
ORD
-
GPT
4h 16m
1 stop
$304Delta
Tue, Mar 24 - Mon, Mar 30
American Airlines Logo
4:29 pm - 12:16 am
GPT
-
ORD
7h 47m
1 stop
American Airlines Logo
6:44 pm - 11:49 pm
ORD
-
GPT
5h 05m
1 stop
$309American Airlines
Fri, Mar 13 - Tue, Mar 17
Delta Logo
6:00 pm - 11:56 pm
GPT
-
ORD
5h 56m
1 stop
Delta Logo
5:59 pm - 10:15 pm
ORD
-
GPT
4h 16m
1 stop
$319Delta
Thu, Mar 5 - Tue, Apr 7
Multiple Airlines Logo
7:20 pm - 8:17 am
GPT
-
ORD
12h 57m
1 stop
Multiple Airlines Logo
12:00 pm - 9:00 am
ORD
-
GPT
21h 00m
2 stops
$321Multiple Airlines
Thu, Apr 9 - Sun, Apr 12
Delta Logo
5:57 pm - 10:31 pm
GPT
-
MDW
4h 34m
1 stop
Delta Logo
12:47 pm - 5:11 pm
MDW
-
GPT
4h 24m
1 stop
$324Delta
Tue, Mar 24 - Tue, Mar 31
Delta Logo
5:57 pm - 11:54 pm
GPT
-
ORD
5h 57m
1 stop
Delta Logo
5:59 pm - 10:15 pm
ORD
-
GPT
4h 16m
1 stop
$324Delta
Mon, Mar 23 - Tue, Mar 31
Delta Logo
6:00 am - 6:41 pm
GPT
-
ORD
12h 41m
2 stops
Delta Logo
5:59 pm - 10:15 pm
ORD
-
GPT
4h 16m
1 stop
$353Delta
Wed, Mar 25 - Tue, Mar 31
United Airlines Logo
4:55 pm - 11:08 pm
GPT
-
ORD
6h 13m
1 stop
United Airlines Logo
12:45 pm - 7:45 pm
ORD
-
GPT
7h 00m
1 stop
$369United Airlines
Thu, Mar 5 - Sat, Mar 7

Delta flights from Gulfport to Chicago

Our best Delta deals on Gulfport to Chicago flight tickets
Delta
Aug 27
GPT2:15 pmGulfport Biloxi Regional
6h 02m
1 stop
ORD8:17 pmChicago O'Hare Intl
Aug 30
ORD7:10 amChicago O'Hare Intl
6h 23m
1 stop
GPT1:33 pmGulfport Biloxi Regional
$269
Delta
Apr 1
GPT5:57 pmGulfport Biloxi Regional
5h 57m
1 stop
ORD11:54 pmChicago O'Hare Intl
Apr 8
ORD11:10 amChicago O'Hare Intl
6h 01m
1 stop
GPT5:11 pmGulfport Biloxi Regional
$304
Delta
Mar 5
GPT6:00 pmGulfport Biloxi Regional
5h 56m
1 stop
ORD11:56 pmChicago O'Hare Intl
Apr 7
ORD5:59 pmChicago O'Hare Intl
4h 16m
1 stop
GPT10:15 pmGulfport Biloxi Regional
$319

United Airlines flights from Gulfport to Chicago

Our best United Airlines deals on Gulfport to Chicago flight tickets
United Airlines
Aug 27
GPT5:15 pmGulfport Biloxi Regional
6h 55m
1 stop
ORD12:10 amChicago O'Hare Intl
Aug 31
ORD6:30 amChicago O'Hare Intl
6h 56m
1 stop
GPT1:26 pmGulfport Biloxi Regional
$287
United Airlines
Mar 5
GPT4:55 pmGulfport Biloxi Regional
6h 13m
1 stop
ORD11:08 pmChicago O'Hare Intl
Mar 7
ORD12:45 pmChicago O'Hare Intl
7h 00m
1 stop
GPT7:45 pmGulfport Biloxi Regional
$369
United Airlines
Apr 1
GPT2:05 pmGulfport Biloxi Regional
17h 55m
2 stops
ORD8:00 amChicago O'Hare Intl
Apr 8
ORD8:51 amChicago O'Hare Intl
7h 22m
1 stop
GPT4:13 pmGulfport Biloxi Regional
$451

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 March 2, 2026.
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

Tue 3/24

5:57 pm-11:54 pm

1 stop5h 57m

Chicago O'Hare Intl

Tue 3/31

5:59 pm-10:15 pm

1 stop4h 16m

$269

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Thu 4/9

7:20 pm-8:17 am

1 stop12h 57m

Chicago O'Hare Intl

Sun 4/12

11:25 am-9:00 am

1 stop21h 35m

$303

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Tue 3/24

5:57 pm-11:54 pm

1 stop5h 57m

Chicago O'Hare Intl

Mon 3/30

5:59 pm-10:15 pm

1 stop4h 16m

$304

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Fri 3/13

4:29 pm-12:16 am

1 stop7h 47m

Chicago O'Hare Intl

Tue 3/17

6:44 pm-11:49 pm

1 stop5h 05m

$309

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Thu 3/5

6:00 pm-11:56 pm

1 stop5h 56m

Chicago O'Hare Intl

Tue 4/7

5:59 pm-10:15 pm

1 stop4h 16m

$319

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Thu 4/9

7:20 pm-8:17 am

1 stop12h 57m

Chicago O'Hare Intl

Sun 4/12

12:00 pm-9:00 am

2 stops21h 00m

$321

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Tue 3/24

5:57 pm-10:31 pm

1 stop4h 34m

Chicago Midway

Tue 3/31

12:47 pm-5:11 pm

1 stop4h 24m

$324

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Mon 3/23

5:57 pm-11:54 pm

1 stop5h 57m

Chicago O'Hare Intl

Tue 3/31

5:59 pm-10:15 pm

1 stop4h 16m

$324

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Wed 3/25

6:00 am-6:41 pm

2 stops12h 41m

Chicago O'Hare Intl

Tue 3/31

5:59 pm-10:15 pm

1 stop4h 16m

$353

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Thu 3/5

4:55 pm-11:08 pm

1 stop6h 13m

Chicago O'Hare Intl

Sat 3/7

12:45 pm-7:45 pm

1 stop7h 00m

$369

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 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 cheapest airline that flies from Gulfport Biloxi Regional to Chicago?

Delta is the most popular carrier operating from Gulfport Biloxi Regional to Chicago

What airlines fly to Chicago?

American Airlines, United Airlines and Spirit Airlines are the top three most popular airlines that fly to Chicago from Gulfport according to our data. American Airlines is the first choice among our users, with 34% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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

Fastest flight time

4h 19m

Direct flights

None
The fastest flight from Gulfport to Chicago takes 4h 19m
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 19m, 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
American AirlinesPriceFrom $248Free CancellationRating
7.1
11,369 reviews
Search American Airlines flights
DeltaPriceFrom $319Free CancellationRating
7.9
8,237 reviews
Search Delta 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
Portage
Lansing
Valparaiso
Schererville
Munster
Crown Point
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