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Cheap flights from Gulfport to Chicago from $179

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 1/4. 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.
Multiple Airlines Logo
6:54 pm - 4:58 pm
GPT
-
ORD
22h 04m1 stop
Multiple Airlines Logo
4:41 pm - 9:00 am
ORD
-
GPT
40h 19m2 stops
$244Multiple Airlines
Fri, Jan 9 - Sat, Jan 17
Delta Logo
6:05 am - 1:40 pm
GPT
-
ORD
7h 35m1 stop
Delta Logo
8:00 am - 3:09 pm
ORD
-
GPT
7h 09m1 stop
$249Delta
Fri, Jan 9 - Sat, Jan 17
American Airlines Logo
1:45 pm - 10:34 pm
GPT
-
ORD
8h 49m2 stops
American Airlines Logo
5:46 pm - 10:41 pm
ORD
-
GPT
4h 55m1 stop
$254American Airlines
Wed, Jan 7 - Wed, Jan 14
American Airlines Logo
6:32 am - 1:22 pm
GPT
-
ORD
6h 50m1 stop
American Airlines Logo
3:21 pm - 10:41 pm
ORD
-
GPT
7h 20m1 stop
$294American Airlines
Thu, Jan 8 - Thu, Jan 15
United Airlines Logo
5:13 pm - 12:28 am
GPT
-
ORD
7h 15m1 stop
United Airlines Logo
7:35 am - 2:07 pm
ORD
-
GPT
6h 32m1 stop
$319United Airlines
Fri, Jan 9 - Tue, Jan 13
United Airlines Logo
4:55 pm - 12:26 am
GPT
-
ORD
7h 31m1 stop
United Airlines Logo
7:35 am - 1:20 pm
ORD
-
GPT
5h 45m1 stop
$364United Airlines
Sat, Feb 14 - Wed, Feb 18
Multiple Airlines Logo
10:05 am - 10:18 am
GPT
-
ORD
24h 13m1 stop
Multiple Airlines Logo
6:10 am - 7:10 pm
ORD
-
GPT
37h 00m2 stops
$371Multiple Airlines
Tue, Dec 23 - Sat, Dec 27
United Airlines Logo
7:00 am - 1:00 pm
GPT
-
ORD
6h 00m1 stop
United Airlines Logo
2:12 pm - 7:48 pm
ORD
-
GPT
5h 36m1 stop
$398United Airlines
Tue, Jan 6 - Tue, Jan 13
United Airlines Logo
1:57 pm - 9:26 pm
GPT
-
ORD
7h 29m1 stop
United Airlines Logo
8:54 am - 4:03 pm
ORD
-
GPT
7h 09m1 stop
$409United Airlines
Thu, Dec 18 - Mon, Dec 22
Delta Logo
6:05 am - 11:59 am
GPT
-
MDW
5h 54m1 stop
Delta Logo
10:48 am - 5:15 pm
MDW
-
GPT
6h 27m1 stop
$457Delta
Wed, Jan 28 - Thu, Jan 29

American Airlines flights from Gulfport to Chicago

Our best American Airlines deals on Gulfport to Chicago flight tickets
American Airlines
Jan 7
GPT1:45 pmGulfport Biloxi Regional
8h 49m
2 stops
ORD10:34 pmChicago O'Hare Intl
Jan 14
ORD5:46 pmChicago O'Hare Intl
4h 55m
1 stop
GPT10:41 pmGulfport Biloxi Regional
$254
Find similar
American Airlines
Jan 8
GPT6:32 amGulfport Biloxi Regional
6h 50m
1 stop
ORD1:22 pmChicago O'Hare Intl
Jan 15
ORD3:21 pmChicago O'Hare Intl
7h 20m
1 stop
GPT10:41 pmGulfport Biloxi Regional
$294
Find similar
American Airlines
Dec 12
GPT5:32 pmGulfport Biloxi Regional
6h 07m
1 stop
ORD11:39 pmChicago O'Hare Intl
Dec 14
ORD8:20 amChicago O'Hare Intl
7h 48m
1 stop
GPT4:08 pmGulfport Biloxi Regional
$354
Find similar

Delta flights from Gulfport to Chicago

Our best Delta deals on Gulfport to Chicago flight tickets
Delta
Jan 9
GPT6:05 amGulfport Biloxi Regional
7h 35m
1 stop
ORD1:40 pmChicago O'Hare Intl
Jan 17
ORD8:00 amChicago O'Hare Intl
7h 09m
1 stop
GPT3:09 pmGulfport Biloxi Regional
$249
Find similar
Delta
Feb 25
GPT3:00 pmGulfport Biloxi Regional
4h 19m
1 stop
ORD7:19 pmChicago O'Hare Intl
Mar 1
ORD9:48 amChicago O'Hare Intl
7h 27m
1 stop
GPT5:15 pmGulfport Biloxi Regional
$444
Find similar
Delta
Jan 28
GPT3:00 pmGulfport Biloxi Regional
4h 21m
1 stop
ORD7:21 pmChicago O'Hare Intl
Jan 29
ORD11:15 amChicago O'Hare Intl
6h 00m
1 stop
GPT5:15 pmGulfport Biloxi Regional
$457
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 December 10, 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 1/9

6:54 pm-4:58 pm

1 stop22h 04m

Chicago O'Hare Intl

Sat 1/17

4:41 pm-9:00 am

2 stops40h 19m

$244

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Fri 1/9

6:05 am-1:40 pm

1 stop7h 35m

Chicago O'Hare Intl

Sat 1/17

8:00 am-3:09 pm

1 stop7h 09m

$249

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Wed 1/7

1:45 pm-10:34 pm

2 stops8h 49m

Chicago O'Hare Intl

Wed 1/14

5:46 pm-10:41 pm

1 stop4h 55m

$254

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Thu 1/8

6:32 am-1:22 pm

1 stop6h 50m

Chicago O'Hare Intl

Thu 1/15

3:21 pm-10:41 pm

1 stop7h 20m

$294

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Fri 1/9

5:13 pm-12:28 am

1 stop7h 15m

Chicago O'Hare Intl

Tue 1/13

7:35 am-2:07 pm

1 stop6h 32m

$319

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Sat 2/14

4:55 pm-12:26 am

1 stop7h 31m

Chicago O'Hare Intl

Wed 2/18

7:35 am-1:20 pm

1 stop5h 45m

$364

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Tue 12/23

10:05 am-10:18 am

1 stop24h 13m

Chicago O'Hare Intl

Sat 12/27

6:10 am-7:10 pm

2 stops37h 00m

$371

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Tue 1/6

7:00 am-1:00 pm

1 stop6h 00m

Chicago O'Hare Intl

Tue 1/13

2:12 pm-7:48 pm

1 stop5h 36m

$398

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Thu 12/18

1:57 pm-9:26 pm

1 stop7h 29m

Chicago O'Hare Intl

Mon 12/22

8:54 am-4:03 pm

1 stop7h 09m

$409

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Wed 1/28

6:05 am-11:59 am

1 stop5h 54m

Chicago Midway

Thu 1/29

10:48 am-5:15 pm

1 stop6h 27m

$457

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 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

Fastest flight time

4h 22m

Direct flights

None
The fastest flight from Gulfport to Chicago takes 4h 22m
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 22m, 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
7.2
11,048 reviews
Search American Airlines flights
DeltaPriceFrom $327Free CancellationRating
7.9
8,007 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
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