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Cheap flights from Gulfport to Chicago from $133

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 5/4. 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

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Gulfport to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
5:31 pm - 12:23 pm
GPT
-
ORD
18h 52m
1 stop
Multiple Airlines Logo
4:05 pm - 7:10 pm
ORD
-
GPT
51h 05m
2 stops
$284Multiple Airlines
Mon, May 11 - Tue, May 19
Multiple Airlines Logo
5:31 pm - 12:23 pm
GPT
-
ORD
18h 52m
1 stop
Multiple Airlines Logo
6:55 am - 7:41 am
ORD
-
GPT
24h 46m
2 stops
$289Multiple Airlines
Fri, May 22 - Sun, May 24
Delta Logo
6:01 pm - 11:59 pm
GPT
-
ORD
5h 58m
1 stop
Delta Logo
6:40 am - 1:07 pm
ORD
-
GPT
6h 27m
1 stop
$291Delta
Wed, Jun 17 - Wed, Jun 24
Multiple Airlines Logo
5:31 pm - 7:39 pm
GPT
-
ORD
26h 08m
1 stop
Multiple Airlines Logo
7:55 am - 7:41 am
ORD
-
GPT
47h 46m
2 stops
$301Multiple Airlines
Fri, Jul 3 - Sat, Jul 11
Multiple Airlines Logo
7:50 pm - 8:03 am
GPT
-
ORD
36h 13m
2 stops
Multiple Airlines Logo
12:58 pm - 7:41 am
ORD
-
GPT
18h 43m
1 stop
$304Multiple Airlines
Sun, Jun 14 - Thu, Jun 25
American Airlines Logo
5:03 pm - 11:48 pm
GPT
-
ORD
6h 45m
1 stop
American Airlines Logo
4:17 pm - 11:26 pm
ORD
-
GPT
7h 09m
1 stop
$310American Airlines
Mon, May 11 - Tue, May 19
Multiple Airlines Logo
7:50 pm - 11:18 pm
GPT
-
ORD
27h 28m
1 stop
Multiple Airlines Logo
7:55 am - 7:41 am
ORD
-
GPT
47h 46m
2 stops
$311Multiple Airlines
Thu, Jul 2 - Sat, Jul 11
Multiple Airlines Logo
5:31 pm - 8:22 am
GPT
-
ORD
14h 51m
2 stops
Multiple Airlines Logo
12:58 pm - 7:41 am
ORD
-
GPT
18h 43m
1 stop
$312Multiple Airlines
Fri, Jun 12 - Thu, Jun 25
Delta Logo
5:55 pm - 10:28 pm
GPT
-
MDW
4h 33m
1 stop
Delta Logo
12:52 pm - 5:09 pm
MDW
-
GPT
4h 17m
1 stop
$339Delta
Fri, May 1 - Tue, May 5
Delta Logo
1:55 pm - 9:09 pm
GPT
-
MDW
7h 14m
1 stop
Delta Logo
6:36 pm - 9:21 am
MDW
-
GPT
14h 45m
2 stops
$427Delta
Fri, May 29 - Wed, Jun 3

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Delta flights from Gulfport to Chicago

Our best Delta deals on Gulfport to Chicago flight tickets
Delta
Jun 17
GPT6:01 pmGulfport Biloxi Regional
5h 58m
1 stop
ORD11:59 pmChicago O'Hare Intl
Jun 24
ORD6:40 amChicago O'Hare Intl
6h 27m
1 stop
GPT1:07 pmGulfport Biloxi Regional
$291
Delta
Jun 13
GPT3:00 pmGulfport Biloxi Regional
5h 59m
1 stop
ORD8:59 pmChicago O'Hare Intl
Jun 24
ORD6:40 amChicago O'Hare Intl
6h 27m
1 stop
GPT1:07 pmGulfport Biloxi Regional
$325
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
$329

American Airlines flights from Gulfport to Chicago

Our best American Airlines deals on Gulfport to Chicago flight tickets
American Airlines
May 11
GPT5:03 pmGulfport Biloxi Regional
6h 45m
1 stop
ORD11:48 pmChicago O'Hare Intl
May 19
ORD4:17 pmChicago O'Hare Intl
7h 09m
1 stop
GPT11:26 pmGulfport Biloxi Regional
$310
American Airlines
May 1
GPT6:09 pmGulfport Biloxi Regional
5h 45m
1 stop
ORD11:54 pmChicago O'Hare Intl
May 5
ORD9:55 amChicago O'Hare Intl
7h 24m
2 stops
GPT5:19 pmGulfport Biloxi Regional
$344
American Airlines
May 26
GPT6:38 pmGulfport Biloxi Regional
5h 21m
1 stop
ORD11:59 pmChicago O'Hare Intl
Jun 2
ORD5:10 amChicago O'Hare Intl
5h 04m
1 stop
GPT10:14 amGulfport Biloxi Regional
$373

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 April 21, 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

Cheapest round-trip

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Mon 5/11

5:31 pm-12:23 pm

1 stop18h 52m

Chicago O'Hare Intl

Tue 5/19

4:05 pm-7:10 pm

2 stops51h 05m

$284

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Fri 5/22

5:31 pm-12:23 pm

1 stop18h 52m

Chicago O'Hare Intl

Sun 5/24

6:55 am-7:41 am

2 stops24h 46m

$289

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Wed 6/17

6:01 pm-11:59 pm

1 stop5h 58m

Chicago O'Hare Intl

Wed 6/24

6:40 am-1:07 pm

1 stop6h 27m

$291

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Fri 7/3

5:31 pm-7:39 pm

1 stop26h 08m

Chicago O'Hare Intl

Sat 7/11

7:55 am-7:41 am

2 stops47h 46m

$301

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Sun 6/14

7:50 pm-8:03 am

2 stops36h 13m

Chicago O'Hare Intl

Thu 6/25

12:58 pm-7:41 am

1 stop18h 43m

$304

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Mon 5/11

5:03 pm-11:48 pm

1 stop6h 45m

Chicago O'Hare Intl

Tue 5/19

4:17 pm-11:26 pm

1 stop7h 09m

$310

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Thu 7/2

7:50 pm-11:18 pm

1 stop27h 28m

Chicago O'Hare Intl

Sat 7/11

7:55 am-7:41 am

2 stops47h 46m

$311

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Fri 6/12

5:31 pm-8:22 am

2 stops14h 51m

Chicago O'Hare Intl

Thu 6/25

12:58 pm-7:41 am

1 stop18h 43m

$312
Quickest round-trip

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Fri 5/1

5:55 pm-10:28 pm

1 stop4h 33m

Chicago Midway

Tue 5/5

12:52 pm-5:09 pm

1 stop4h 17m

$339

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Fri 5/29

1:55 pm-9:09 pm

1 stop7h 14m

Chicago Midway

Wed 6/3

6:36 pm-9:21 am

2 stops14h 45m

$427

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

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 16m

Direct flights

None
The fastest flight from Gulfport to Chicago takes 4h 16m
There are no direct flights from Gulfport to Chicago. There are no popular flight routes from Gulfport to Chicago.
Search flight deals

Frequently asked questions about flying from Gulfport to Chicago

  • 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 16m, 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
11,645 reviews
Search American Airlines flights
DeltaPriceFrom $319Free CancellationRating
7.9
8,434 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
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