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Cheap flights from Gulfport to Chicago from $142

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 8/28. 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

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.
American Airlines Logo
11:12 am - 7:42 pmGPT  Gulfport Biloxi Regional-ORD Chicago O'Hare Intl
8h 30m1 stop Dallas/Fort Worth
American Airlines Logo
4:53 pm - 10:30 pmORD  Chicago O'Hare Intl-GPT Gulfport Biloxi Regional
5h 37m1 stop Charlotte Douglas
$301American Airlines
Tue, Sep 1 - Tue, Sep 8
American Airlines Logo
11:12 am - 7:42 pmGPT  Gulfport Biloxi Regional-ORD Chicago O'Hare Intl
8h 30m1 stop Dallas/Fort Worth
American Airlines Logo
5:00 am - 10:41 amORD  Chicago O'Hare Intl-GPT Gulfport Biloxi Regional
5h 41m1 stop Dallas/Fort Worth
$301American Airlines
Sat, Sep 5 - Tue, Sep 8
American Airlines Logo
6:34 pm - 12:18 amGPT  Gulfport Biloxi Regional-ORD Chicago O'Hare Intl
5h 44m1 stop Dallas/Fort Worth
American Airlines Logo
5:00 am - 10:40 amORD  Chicago O'Hare Intl-GPT Gulfport Biloxi Regional
5h 40m1 stop Dallas/Fort Worth
$303American Airlines
Sat, Sep 5 - Fri, Sep 11
American Airlines Logo
5:42 pm - 12:01 amGPT  Gulfport Biloxi Regional-ORD Chicago O'Hare Intl
6h 19m1 stop Charlotte Douglas
American Airlines Logo
5:00 am - 10:40 amORD  Chicago O'Hare Intl-GPT Gulfport Biloxi Regional
5h 40m1 stop Dallas/Fort Worth
$303American Airlines
Sat, Sep 26 - Wed, Sep 30
Delta Logo
6:04 pm - 10:56 pmGPT  Gulfport Biloxi Regional-MDW Chicago Midway
4h 52m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:00 am - 1:08 pmMDW  Chicago Midway-GPT Gulfport Biloxi Regional
7h 08m1 stop Atlanta Hartsfield-Jackson
$319Delta
Fri, Dec 11 - Mon, Dec 14
Delta Logo
6:04 pm - 10:56 pmGPT  Gulfport Biloxi Regional-MDW Chicago Midway
4h 52m1 stop Atlanta Hartsfield-Jackson
Delta Logo
9:30 am - 5:19 pmMDW  Chicago Midway-GPT Gulfport Biloxi Regional
7h 49m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
$324Delta
Fri, Dec 11 - Mon, Dec 14
Delta Logo
4:00 pm - 10:36 pmGPT  Gulfport Biloxi Regional-MDW Chicago Midway
6h 36m1 stop Atlanta Hartsfield-Jackson
Delta Logo
4:30 pm - 8:49 pmMDW  Chicago Midway-GPT Gulfport Biloxi Regional
4h 19m1 stop Atlanta Hartsfield-Jackson
$328Delta
Sat, Sep 5 - Tue, Sep 8
Multiple Airlines Logo
6:46 pm - 11:51 amGPT  Gulfport Biloxi Regional-ORD Chicago O'Hare Intl
17h 05m2 stops Tampa Atlanta Hartsfield-Jackson
Multiple Airlines Logo
6:05 am - 7:05 pmORD  Chicago O'Hare Intl-GPT Gulfport Biloxi Regional
13h 00m1 stop Orlando
$352Multiple Airlines
Fri, Oct 2 - Sun, Oct 18
United Airlines Logo
5:15 pm - 12:15 amGPT  Gulfport Biloxi Regional-ORD Chicago O'Hare Intl
7h 00m1 stop Houston George Bush Intcntl
United Airlines Logo
10:42 am - 4:02 pmORD  Chicago O'Hare Intl-GPT Gulfport Biloxi Regional
5h 20m1 stop Houston George Bush Intcntl
$390United Airlines
Thu, Dec 3 - Sat, Dec 5
United Airlines Logo
4:59 pm - 11:26 pmGPT  Gulfport Biloxi Regional-ORD Chicago O'Hare Intl
6h 27m1 stop Houston George Bush Intcntl
United Airlines Logo
10:40 am - 4:12 pmORD  Chicago O'Hare Intl-GPT Gulfport Biloxi Regional
5h 32m1 stop Houston George Bush Intcntl
$390United Airlines
Sat, Aug 29 - Sat, Sep 5

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United Airlines flights from Gulfport to Chicago

Our best United Airlines deals on Gulfport to Chicago flight tickets
United Airlines
Aug 29
GPT4:59 pmGulfport Biloxi Regional
6h 27m
1 stop
ORD11:26 pmChicago O'Hare Intl
Sep 5
ORD10:40 amChicago O'Hare Intl
5h 32m
1 stop
GPT4:12 pmGulfport Biloxi Regional
$390
United Airlines
Aug 6
GPT9:25 amGulfport Biloxi Regional
7h 14m
1 stop
ORD4:39 pmChicago O'Hare Intl
Aug 12
ORD6:30 amChicago O'Hare Intl
6h 54m
1 stop
GPT1:24 pmGulfport Biloxi Regional
$420
United Airlines
Aug 7
GPT5:19 pmGulfport Biloxi Regional
5h 56m
1 stop
ORD11:15 pmChicago O'Hare Intl
Aug 9
ORD6:29 amChicago O'Hare Intl
6h 56m
1 stop
GPT1:25 pmGulfport Biloxi Regional
$443

American Airlines flights from Gulfport to Chicago

Our best American Airlines deals on Gulfport to Chicago flight tickets
American Airlines
Sep 5
GPT11:12 amGulfport Biloxi Regional
8h 30m
1 stop
ORD7:42 pmChicago O'Hare Intl
Sep 8
ORD5:00 amChicago O'Hare Intl
5h 41m
1 stop
GPT10:41 amGulfport Biloxi Regional
$301
American Airlines
Sep 5
GPT6:34 pmGulfport Biloxi Regional
5h 44m
1 stop
ORD12:18 amChicago O'Hare Intl
Sep 11
ORD5:00 amChicago O'Hare Intl
5h 40m
1 stop
GPT10:40 amGulfport Biloxi Regional
$303
American Airlines
Sep 4
GPT6:34 pmGulfport Biloxi Regional
5h 44m
1 stop
ORD12:18 amChicago O'Hare Intl
Sep 8
ORD5:00 amChicago O'Hare Intl
5h 41m
1 stop
GPT10:41 amGulfport Biloxi Regional
$310

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 August 6, 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 Gulfport Biloxi Regional - ORD Chicago O'Hare Intl

GPTORD

Gulfport Biloxi Regional

Tue 9/1

11:12 am-7:42 pm

1 stop8h 30m

Chicago O'Hare Intl

Tue 9/8

4:53 pm-10:30 pm

1 stop5h 37m

$301

GulfportChicago

GPT Gulfport Biloxi Regional - ORD Chicago O'Hare Intl

GPTORD

Gulfport Biloxi Regional

Sat 9/5

11:12 am-7:42 pm

1 stop8h 30m

Chicago O'Hare Intl

Tue 9/8

5:00 am-10:41 am

1 stop5h 41m

$301

GulfportChicago

GPT Gulfport Biloxi Regional - ORD Chicago O'Hare Intl

GPTORD

Gulfport Biloxi Regional

Sat 9/5

6:34 pm-12:18 am

1 stop5h 44m

Chicago O'Hare Intl

Fri 9/11

5:00 am-10:40 am

1 stop5h 40m

$303

GulfportChicago

GPT Gulfport Biloxi Regional - ORD Chicago O'Hare Intl

GPTORD

Gulfport Biloxi Regional

Sat 9/26

5:42 pm-12:01 am

1 stop6h 19m

Chicago O'Hare Intl

Wed 9/30

5:00 am-10:40 am

1 stop5h 40m

$303

GulfportChicago

GPT Gulfport Biloxi Regional - MDW Chicago Midway

GPTMDW

Gulfport Biloxi Regional

Fri 12/11

6:04 pm-10:56 pm

1 stop4h 52m

Chicago Midway

Mon 12/14

6:00 am-1:08 pm

1 stop7h 08m

$319

GulfportChicago

GPT Gulfport Biloxi Regional - MDW Chicago Midway

GPTMDW

Gulfport Biloxi Regional

Fri 12/11

6:04 pm-10:56 pm

1 stop4h 52m

Chicago Midway

Mon 12/14

9:30 am-5:19 pm

2 stops7h 49m

$324
Quickest round-trip

GulfportChicago

GPT Gulfport Biloxi Regional - MDW Chicago Midway

GPTMDW

Gulfport Biloxi Regional

Sat 9/5

4:00 pm-10:36 pm

1 stop6h 36m

Chicago Midway

Tue 9/8

4:30 pm-8:49 pm

1 stop4h 19m

$328

GulfportChicago

GPT Gulfport Biloxi Regional - ORD Chicago O'Hare Intl

GPTORD

Gulfport Biloxi Regional

Fri 10/2

6:46 pm-11:51 am

2 stops17h 05m

Chicago O'Hare Intl

Sun 10/18

6:05 am-7:05 pm

1 stop13h 00m

$352

GulfportChicago

GPT Gulfport Biloxi Regional - ORD Chicago O'Hare Intl

GPTORD

Gulfport Biloxi Regional

Thu 12/3

5:15 pm-12:15 am

1 stop7h 00m

Chicago O'Hare Intl

Sat 12/5

10:42 am-4:02 pm

1 stop5h 20m

$390

GulfportChicago

GPT Gulfport Biloxi Regional - ORD Chicago O'Hare Intl

GPTORD

Gulfport Biloxi Regional

Sat 8/29

4:59 pm-11:26 pm

1 stop6h 27m

Chicago O'Hare Intl

Sat 9/5

10:40 am-4:12 pm

1 stop5h 32m

$390

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 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.

Can stopping save me money on Gulfport to Chicago flights?

You could potentially save up to 25% on your flight if you consider stops on a Gulfport to Chicago flight.

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 36m

Direct flights

None
The fastest flight from Gulfport to Chicago takes 4h 36m
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 36m, 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
11,848 reviews
Search American Airlines flights
DeltaPriceFrom $319Free CancellationRating
7.8
8,490 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
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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