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Cheap flights from Gulfport to Chicago from $152

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 7/10. 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
1 adult, Economy, 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.
American Airlines Logo
6:38 pm - 11:58 pm
GPT
-
ORD
5h 20m
1 stop
American Airlines Logo
3:50 pm - 11:01 pm
ORD
-
GPT
7h 11m
1 stop
$309American Airlines
Tue, Jun 23 - Sat, Jun 27
Multiple Airlines Logo
7:25 pm - 9:11 am
GPT
-
ORD
13h 46m
1 stop
Multiple Airlines Logo
5:13 pm - 6:45 pm
ORD
-
GPT
25h 32m
1 stop
$316Multiple Airlines
Sun, Jul 5 - Wed, Jul 8
Multiple Airlines Logo
7:25 pm - 5:37 am
GPT
-
ORD
34h 12m
2 stops
Multiple Airlines Logo
5:13 pm - 6:45 pm
ORD
-
GPT
25h 32m
1 stop
$332Multiple Airlines
Sun, Jul 5 - Wed, Jul 8
American Airlines Logo
6:35 pm - 12:01 am
GPT
-
ORD
5h 26m
1 stop
American Airlines Logo
5:00 am - 10:54 am
ORD
-
GPT
5h 54m
1 stop
$334American Airlines
Thu, Jul 16 - Sat, Jul 18
Delta Logo
10:01 am - 4:15 pm
GPT
-
MDW
6h 14m
1 stop
Delta Logo
6:05 am - 1:03 pm
MDW
-
GPT
6h 58m
1 stop
$344Delta
Thu, Aug 27 - Sun, Aug 30
American Airlines Logo
6:35 pm - 12:01 am
GPT
-
ORD
5h 26m
1 stop
American Airlines Logo
5:00 am - 10:54 am
ORD
-
GPT
5h 54m
1 stop
$344American Airlines
Thu, Jul 16 - Sat, Jul 18
Delta Logo
5:56 pm - 11:59 pm
GPT
-
ORD
6h 03m
1 stop
Delta Logo
6:35 am - 1:07 pm
ORD
-
GPT
6h 32m
1 stop
$359Delta
Tue, Jun 16 - Mon, Jun 22
American Airlines Logo
7:04 am - 2:23 pm
GPT
-
ORD
7h 19m
1 stop
American Airlines Logo
5:45 pm - 11:56 pm
ORD
-
GPT
6h 11m
1 stop
$368American Airlines
Wed, Jul 1 - Tue, Jul 7
American Airlines Logo
6:35 pm - 12:01 am
GPT
-
ORD
5h 26m
1 stop
American Airlines Logo
5:45 pm - 11:56 pm
ORD
-
GPT
6h 11m
1 stop
$370American Airlines
Wed, Jul 15 - Mon, Jul 20
Delta Logo
10:01 am - 4:51 pm
GPT
-
ORD
6h 50m
1 stop
Delta Logo
6:40 am - 1:03 pm
ORD
-
GPT
6h 23m
1 stop
$379Delta
Fri, Aug 21 - Sun, Aug 23

Delta flights from Gulfport to Chicago

Our best Delta deals on Gulfport to Chicago flight tickets
Delta
Aug 27
GPT10:01 amGulfport Biloxi Regional
6h 14m
1 stop
MDW4:15 pmChicago Midway
Aug 30
MDW6:05 amChicago Midway
6h 58m
1 stop
GPT1:03 pmGulfport Biloxi Regional
$344
Delta
Jun 16
GPT5:56 pmGulfport Biloxi Regional
6h 03m
1 stop
ORD11:59 pmChicago O'Hare Intl
Jun 22
ORD6:35 amChicago O'Hare Intl
6h 32m
1 stop
GPT1:07 pmGulfport Biloxi Regional
$359
Delta
Jun 9
GPT1:53 pmGulfport Biloxi Regional
4h 49m
1 stop
ORD6:42 pmChicago O'Hare Intl
Jun 19
ORD6:35 amChicago O'Hare Intl
6h 32m
1 stop
GPT1:07 pmGulfport Biloxi Regional
$365

American Airlines flights from Gulfport to Chicago

Our best American Airlines deals on Gulfport to Chicago flight tickets
American Airlines
Jun 23
GPT6:38 pmGulfport Biloxi Regional
5h 20m
1 stop
ORD11:58 pmChicago O'Hare Intl
Jun 27
ORD3:50 pmChicago O'Hare Intl
7h 11m
1 stop
GPT11:01 pmGulfport Biloxi Regional
$309
American Airlines
Jul 16
GPT6:35 pmGulfport Biloxi Regional
5h 26m
1 stop
ORD12:01 amChicago O'Hare Intl
Jul 18
ORD5:00 amChicago O'Hare Intl
5h 54m
1 stop
GPT10:54 amGulfport Biloxi Regional
$334
American Airlines
Jul 16
GPT6:35 pmGulfport Biloxi Regional
5h 26m
1 stop
ORD12:01 amChicago O'Hare Intl
Jul 18
ORD5:00 amChicago O'Hare Intl
5h 54m
1 stop
GPT10:54 amGulfport Biloxi Regional
$344

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 June 4, 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

Tue 6/23

6:38 pm-11:58 pm

1 stop5h 20m

Chicago O'Hare Intl

Sat 6/27

3:50 pm-11:01 pm

1 stop7h 11m

$309

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Sun 7/5

7:25 pm-9:11 am

1 stop13h 46m

Chicago O'Hare Intl

Wed 7/8

5:13 pm-6:45 pm

1 stop25h 32m

$316

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Sun 7/5

7:25 pm-5:37 am

2 stops34h 12m

Chicago O'Hare Intl

Wed 7/8

5:13 pm-6:45 pm

1 stop25h 32m

$332
Quickest round-trip

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Thu 7/16

6:35 pm-12:01 am

1 stop5h 26m

Chicago O'Hare Intl

Sat 7/18

5:00 am-10:54 am

1 stop5h 54m

$334

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Thu 8/27

10:01 am-4:15 pm

1 stop6h 14m

Chicago Midway

Sun 8/30

6:05 am-1:03 pm

1 stop6h 58m

$344

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Thu 7/16

6:35 pm-12:01 am

1 stop5h 26m

Chicago O'Hare Intl

Sat 7/18

5:00 am-10:54 am

1 stop5h 54m

$344

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Tue 6/16

5:56 pm-11:59 pm

1 stop6h 03m

Chicago O'Hare Intl

Mon 6/22

6:35 am-1:07 pm

1 stop6h 32m

$359

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Wed 7/1

7:04 am-2:23 pm

1 stop7h 19m

Chicago O'Hare Intl

Tue 7/7

5:45 pm-11:56 pm

1 stop6h 11m

$368

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Wed 7/15

6:35 pm-12:01 am

1 stop5h 26m

Chicago O'Hare Intl

Mon 7/20

5:45 pm-11:56 pm

1 stop6h 11m

$370

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Fri 8/21

10:01 am-4:51 pm

1 stop6h 50m

Chicago O'Hare Intl

Sun 8/23

6:40 am-1:03 pm

1 stop6h 23m

$379

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?

What is the cheapest month to fly to Chicago?

The month of February is, on average, the cheapest month to fly to Chicago from Gulfport, with most prices found around $0. If you’re not able to fly to Chicago in February, then January is your next best option. Flight prices from Gulfport to Chicago during January average around $0.

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 18m

Direct flights

None
The fastest flight from Gulfport to Chicago takes 4h 18m
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 18m, 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.

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
11,641 reviews
Search American Airlines flights
DeltaPriceFrom $319Free CancellationRating
7.8
8,395 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
Portage
Benton Harbor
Lansing
Valparaiso
Schererville
Munster
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