--- title: "CA $524 Cheap Flights from Gulfport (GPT) to Chicago (CHI)" description: "Cheap Flights from Gulfport (GPT) to Chicago (CHI) start at CA $524 for one-way and CA $630 for round trip. Earn your airline miles on top of our rewards!" canonical: "https://www.expedia.ca/lp/flights/gpt/chi/gulfport-to-chicago" language: en-CA market: CA currency: CAD prices_as_of: 2026-11-14T10:49:41Z --- # CA $524 Cheap Flights from Gulfport (GPT) to Chicago (CHI) ![A river with a yellow boat, surrounded by tall buildings and a bridge.](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=500&q=medium) [View CA $524 flight on Thu, Nov 19, 2026](https://www.expedia.ca/Flights-Search?leg1=from:GPT,to:ORD,departure:19/11/2026TANYT&trip=oneway&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:523.61&airProductToken=AQpnCjIIwYIBEgQ2MDA0GOabASDimgEotc6dAzCzz50DOFNAAFgBagRNQUlOcghTMEFaWk5OMQoxCMGCARIEMTAzORjimgEgrhwooNCdAzCn0Z0DOFNAAVgBagRNQUlOcghTMEFaWk5OMRIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAE) ## Popular airlines from Gulfport - Biloxi Intl. Airport (GPT) to Chicago [Delta](https://www.expedia.ca/Flights-Search?leg1=from:GPT,to:CHI,departure:28/11/2026TANYT&leg2=from:CHI,to:GPT,departure:05/12/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) [American Airlines](https://www.expedia.ca/Flights-Search?leg1=from:GPT,to:CHI,departure:28/11/2026TANYT&leg2=from:CHI,to:GPT,departure:05/12/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) [United](https://www.expedia.ca/Flights-Search?leg1=from:GPT,to:CHI,departure:28/11/2026TANYT&leg2=from:CHI,to:GPT,departure:05/12/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) ### Be in the know Get alerts if flight prices drop or rise\* ### Book smarter Save up to 30% on select hotels after you book a flight\* ### Earn twice Earn your airline miles on top of our rewards [Sign in](https://www.expedia.ca/login) ## Cheap Flights from Gulfport to Chicago (GPT-CHI) Prices were available within the past 7 days and start at CA $524 for one-way flights and CA $630 for roundtrip, for the period specified. Prices and availability are subject to change. All deals One way Roundtrip [Select Delta flight, departing Tue, Nov 17 from Gulfport to Chicago, returning Mon, Nov 23, priced at CA $630 Found 1 day ago](https://www.expedia.ca/Flights-Search?leg1=from:GPT,to:ORD,departure:17/11/2026TANYT&leg2=from:ORD,to:GPT,departure:23/11/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:629.30&airProductToken=AQpFCiEIxJgBEgQzMTk5GOabASDgXCiktJ0DMPW0nQM4RUAAWAEKIAjEmAESBDE0NzcY4FwgrhwovrWdAzDBtp0DOEVAAVgBCkUKIAjEmAESBDE0NzcYrhwg4Fwox%5FqdAzC6-50DOEVAAFgBCiEIxJgBEgQzMTc4GOBcIOabASjV%5FJ0DMKj9nQM4RUABWAESCggBEAEYASoCREwYASIECAEQASgEMAE) Tue, Nov 17 - Mon, Nov 23 · GPT · ORD · Roundtrip [Select Delta flight, departing Tue, Nov 17 from Gulfport to Chicago, returning Sat, Nov 21, priced at CA $631 Found 1 day ago](https://www.expedia.ca/Flights-Search?leg1=from:GPT,to:ORD,departure:17/11/2026TANYT&leg2=from:ORD,to:GPT,departure:21/11/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:630.40&airProductToken=AQpFCiEIxJgBEgQzMTk5GOabASDgXCiktJ0DMPW0nQM4RUAAWAEKIAjEmAESBDE0NzcY4FwgrhwovrWdAzDBtp0DOEVAAVgBCmcKIAjEmAESBDE3MTcYrhwgzHwoxN-dAzCi4J0DOEVAAFgBCiAIxJgBEgQxMDQ2GMx8IOBcKK%5FhnQMwv-KdAzhFQAFYAQohCMSYARIEMjcxOBjgXCDmmwEox-OdAzCa5J0DOEVAAVgBEgoIARABGAEqAkRMGAEiBAgBEAEoBDAB) Tue, Nov 17 - Sat, Nov 21 · GPT · ORD · Roundtrip [Select Delta flight, departing Thu, Nov 19 from Gulfport to Chicago, returning Sat, Nov 21, priced at CA $637 Found 1 day ago](https://www.expedia.ca/Flights-Search?leg1=from:GPT,to:ORD,departure:19/11/2026TANYT&leg2=from:ORD,to:GPT,departure:21/11/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:636.80&airProductToken=AQpFCiEIxJgBEgQyNzE4GOabASDgXCjGzJ0DMJrNnQM4RUAAWAEKIAjEmAESBDI4NzkY4Fwgrhwo9c2dAzCBz50DOEVAAVgBCmcKIAjEmAESBDE3MTcYrhwgzHwoxN-dAzCi4J0DOEVAAFgBCiAIxJgBEgQxMDQ2GMx8IOBcKK%5FhnQMwv-KdAzhFQAFYAQohCMSYARIEMjcxOBjgXCDmmwEox-OdAzCa5J0DOEVAAVgBEgoIARABGAEqAkRMGAEiBAgBEAEoBDAB) Thu, Nov 19 - Sat, Nov 21 · GPT · ORD · Roundtrip [Select Delta flight, departing Thu, Nov 19 from Gulfport to Chicago, returning Sun, Nov 22, priced at CA $660 Found 11 hours ago](https://www.expedia.ca/Flights-Search?leg1=from:GPT,to:ORD,departure:19/11/2026TANYT&leg2=from:ORD,to:GPT,departure:22/11/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:659.60&airProductToken=AQpvCjYIxJgBEgQyNzE4GOabASDgXCjGzJ0DMJrNnQM4RUAAWAFqCU1BSU5CQVNJQ3IIWEYwTkEwQlEKNQjEmAESBDI4NzkY4Fwgrhwo9c2dAzCBz50DOEVAAVgBaglNQUlOQkFTSUNyCFhGME5BMEJRCm8KNQjEmAESBDEyNDcYrhwg4FwogeudAzD%5F650DOEVAAFgBaglNQUlOQkFTSUNyCFZGN05BMEJRCjYIxJgBEgQyNzE4GOBcIOabASin7Z0DMPjtnQM4RUABWAFqCU1BSU5CQVNJQ3IIVkY3TkEwQlESCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) Thu, Nov 19 - Sun, Nov 22 · GPT · ORD · Roundtrip [Select Delta flight, departing Thu, Nov 19 from Gulfport to Chicago, returning Sun, Nov 22, priced at CA $759 Found 11 hours ago](https://www.expedia.ca/Flights-Search?leg1=from:GPT,to:ORD,departure:19/11/2026TANYT&leg2=from:ORD,to:GPT,departure:22/11/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:758.50&airProductToken=AQpvCjYIxJgBEgQzMTk5GOabASDgXCjkyp0DMLXLnQM4RUAAWAFqCU1BSU5CQVNJQ3IIVEYwT0EwQlEKNQjEmAESBDE0NzcY4Fwgrhwo%5FsudAzCBzZ0DOEVAAVgBaglNQUlOQkFTSUNyCFRGME9BMEJRCm8KNQjEmAESBDEyNDcYrhwg4FwogeudAzD%5F650DOEVAAFgBaglNQUlOQkFTSUNyCFZGN05BMEJRCjYIxJgBEgQyNzE4GOBcIOabASin7Z0DMPjtnQM4RUABWAFqCU1BSU5CQVNJQ3IIVkY3TkEwQlESCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) Thu, Nov 19 - Sun, Nov 22 · GPT · ORD · Roundtrip [Select American Airlines flight, departing Tue, Nov 17 from Gulfport to Chicago, returning Tue, Nov 24, priced at CA $765 Found 1 day ago](https://www.expedia.ca/Flights-Search?leg1=from:GPT,to:ORD,departure:17/11/2026TANYT&leg2=from:ORD,to:GPT,departure:24/11/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:764.80&airProductToken=AQpHCiIIwYIBEgQ1MTk5GOabASDimgEohLadAzD6tp0DOFFAAFgBCiEIwYIBEgQyNTc2GOKaASCuHCjJt50DMOC4nQM4UUABWAEKRwohCMGCARIEMTYwNhiuHCDimgEo54CeAzDigZ4DOFNAAFgBCiIIwYIBEgQ1MTk5GOKaASDmmwEojYKeAzCQg54DOFNAAVgBEgoIARABGAEqAkFBGAEiBAgBEAEoCCgEMAE) Tue, Nov 17 - Tue, Nov 24 · GPT · ORD · Roundtrip [Select Delta flight, departing Thu, Nov 19 from Gulfport to Chicago, returning Sun, Nov 22, priced at CA $767 Found 11 hours ago](https://www.expedia.ca/Flights-Search?leg1=from:GPT,to:ORD,departure:19/11/2026TANYT&leg2=from:ORD,to:GPT,departure:22/11/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:766.10&airProductToken=AQpvCjYIxJgBEgQyNzE4GOabASDgXCjGzJ0DMJrNnQM4RUAAWAFqCU1BSU5CQVNJQ3IIWEYwTkEwQlEKNQjEmAESBDExMzkY4Fwgrhwo486dAzDpz50DOEVAAVgBaglNQUlOQkFTSUNyCFhGME5BMEJRCm8KNQjEmAESBDE2ODcYrhwg4FwozOudAzDA7J0DOEVAAFgBaglNQUlOQkFTSUNyCFRGN09BMEJRCjYIxJgBEgQyNzE4GOBcIOabASin7Z0DMPjtnQM4RUABWAFqCU1BSU5CQVNJQ3IIVEY3T0EwQlESCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) Thu, Nov 19 - Sun, Nov 22 · GPT · ORD · Roundtrip [Select American Airlines flight, departing Fri, Nov 20 from Gulfport to Chicago, returning Tue, Nov 24, priced at CA $771 Found 1 day ago](https://www.expedia.ca/Flights-Search?leg1=from:GPT,to:ORD,departure:20/11/2026TANYT&leg2=from:ORD,to:GPT,departure:24/11/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:770.20&airProductToken=AQpGCiIIwYIBEgQ1MjA5GOabASCjsQEo%5FNmdAzD22p0DOFFAAFgBCiAIwYIBEgM4ODIYo7EBIK4cKMTbnQMw3NydAzhRQAFYAQpHCiEIwYIBEgQxNjA2GK4cIOKaASjngJ4DMOKBngM4U0AAWAEKIgjBggESBDUxOTkY4poBIOabASiNgp4DMJCDngM4U0ABWAESCggBEAEYASoCQUEYASIECAEQASgIKAQwAQ) Fri, Nov 20 - Tue, Nov 24 · GPT · ORD · Roundtrip [Select American Airlines flight, departing Mon, Nov 16 from Gulfport to Chicago, returning Sat, Nov 21, priced at CA $778 Found 1 day ago](https://www.expedia.ca/Flights-Search?leg1=from:GPT,to:ORD,departure:16/11/2026TANYT&leg2=from:ORD,to:GPT,departure:21/11/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:777.70&airProductToken=AQpHCiIIwYIBEgQ2MDA0GOabASDimgEoxKydAzDDrZ0DOFFAAFgBCiEIwYIBEgQxMDM5GOKaASCuHCjFrp0DMMmvnQM4UUABWAEKRgogCMGCARIDOTIyGK4cIOKaASix5Z0DMK%5FmnQM4UUAAWAEKIgjBggESBDU1MzMY4poBIOabASjm5p0DMOnnnQM4UUABWAESCggBEAEYASoCQUEYASIECAEQASgIKAQwAQ) Mon, Nov 16 - Sat, Nov 21 · GPT · ORD · Roundtrip [Select United flight, departing Thu, Nov 19 from Gulfport to Chicago, returning Sun, Nov 22, priced at CA $802 Found 11 hours ago](https://www.expedia.ca/Flights-Search?leg1=from:GPT,to:ORD,departure:19/11/2026TANYT&leg2=from:ORD,to:GPT,departure:22/11/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:801.50&airProductToken=AQpnCjII1YIBEgQ0MjQ2GOabASCIOCj%5FzZ0DMOnOnQM4VEAAWAFqBTJfZWNvcghURkEwUEZETgoxCNWCARIEMTMyNhiIOCCuHCi10J0DMNXRnQM4VEAAWAFqBTJfZWNvcghURkEwUEZETgpnCjEI1YIBEgQxOTgyGK4cIIg4KLLqnQMw4uudAzhUQABYAWoFMl9lY29yCFRGQTdQRkROCjII1YIBEgQ0MjcyGIg4IOabASiz7Z0DMIbunQM4VEAAWAFqBTJfZWNvcghURkE3UEZEThIKCAEQARgBKgJVQRgBIgQIARABKAIoAygEMAs) Thu, Nov 19 - Sun, Nov 22 · GPT · Gulfp · ort · ORD · Roundtrip ## Find the cheapest month to fly from Gulfport (GPT) to Chicago (CHI) ### April is typically the cheapest month to fly From CA $353 - CA $665 per traveller. View flights in April Insights are based on prices from searches for economy trips of 10 days or less on our sites in the last 12 months. Insights are informative only and current prices may differ. ## Book with confidence ### Gulfport to Chicago Flights #### The easy way to book your flights from Gulfport to Chicago With Expedia, it’s simple to find and book flights to Chicago from Gulfport whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 3 airlines that cover this route. There are nonstop flights to CHI-All Airports, too. Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from Gulfport to Chicago today, tomorrow, or this week. #### Save dollars with cheap flights from Gulfport - Biloxi Intl., GPT to CHI-All Airports, CHI Sort your search results by price to find great deals on your flight from Gulfport to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Gulfport currently is just CA $630 rising to CA $802\. Here are more money-saving tips: - Fly in November when flight prices are normally at their lowest - Book about a month to 6 weeks before you travel for the best prices to Chicago - Avoid peak season and weekends when flights can cost more - Early morning and late-night flights are sometimes cheaper, so try varying your travel times - One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free! #### Reasons to choose Expedia for your flight to Chicago from Gulfport Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to Chicago with Expedia today. ## Travel information | Origin airport | Gulfport - Biloxi Intl. Airport | | ------------------- | ------------------------------- | | Destination airport | Chicago, IL | | Distance | 1,305 km away | | Roundtrip price | CA $630 | ## Explore a world of travel with Expedia - [Flights](?equalTargetTab=tab-0) - [Flights from Chatham (XCM) to Chicago (CHI)](https://www.expedia.ca/lp/flights/xcm/chi/chatham-to-chicago) - [Flights from Singapore (SIN) to Chicago (CHI)](https://www.expedia.ca/lp/flights/sin/chi/singapore-to-chicago) - [Flights from Boston (BOS) to Chicago (CHI)](https://www.expedia.ca/lp/flights/bos/chi/boston-to-chicago) - [Flights from St. John's (YYT) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yyt/chi/st-johns-to-chicago) - [Flights from Little Rock (LIT) to Chicago (CHI)](https://www.expedia.ca/lp/flights/lit/chi/little-rock-to-chicago) - [Flights from Gary (GYY) to Chicago (CHI)](https://www.expedia.ca/lp/flights/gyy/chi/gary-to-chicago) - [Flights from Manhattan (MHK) to Chicago (CHI)](https://www.expedia.ca/lp/flights/mhk/chi/manhattan-to-chicago) - 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Airport (EWR) to Chicago (CHI)](https://www.expedia.ca/lp/flights/ewr/chi/newark-liberty-intl-airport-to-chicago) - [Flights from Myrtle Beach (MYR) to Chicago (CHI)](https://www.expedia.ca/lp/flights/myr/chi/myrtle-beach-to-chicago) - [Flights from Hartford (BDL) to Chicago (CHI)](https://www.expedia.ca/lp/flights/bdl/chi/hartford-to-chicago) - [Flights from Debrecen (DEB) to Chicago (CHI)](https://www.expedia.ca/lp/flights/deb/chi/debrecen-to-chicago) - [Flights from Detroit (DTW) to Chicago (ORD)](https://www.expedia.ca/lp/flights/dtw/ord/detroit-to-chicago) - [Flights from Fort Frances (YAG) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yag/chi/fort-frances-to-chicago) - [Flights from Whitehorse (YXY) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yxy/chi/whitehorse-to-chicago) - [Flights from Phoenix (PHX) to Chicago (CHI)](https://www.expedia.ca/lp/flights/phx/chi/phoenix-to-chicago) - [Flights from Peoria (PIA) to Chicago (CHI)](https://www.expedia.ca/lp/flights/pia/chi/peoria-to-chicago) - [Flights from Carlsbad (CNM) to Chicago (CHI)](https://www.expedia.ca/lp/flights/cnm/chi/carlsbad-to-chicago) - [Flights from Toronto (YTO) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yto/chi/toronto-to-chicago) - [Flights from Salt Lake City (SLC) to Chicago (CHI)](https://www.expedia.ca/lp/flights/slc/chi/salt-lake-city-to-chicago) - [Flights from Nanaimo (YCD) to Chicago (CHI)](https://www.expedia.ca/lp/flights/ycd/chi/nanaimo-to-chicago) - [Flights from Halifax (YHZ) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yhz/chi/halifax-to-chicago) - [Flights from Sept-Iles (YZV) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yzv/chi/sept-iles-to-chicago) - [Flights from San Antonio (SAT) to Chicago (CHI)](https://www.expedia.ca/lp/flights/sat/chi/san-antonio-to-chicago) - [Flights from Detroit (DTW) to Chicago (CHI)](https://www.expedia.ca/lp/flights/dtw/chi/detroit-to-chicago) - [Flights from New Orleans (MSY) to Chicago (CHI)](https://www.expedia.ca/lp/flights/msy/chi/new-orleans-to-chicago) - [Flights from Terrace (YXT) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yxt/chi/terrace-to-chicago) - [Flights from San Diego (SAN) to Chicago (CHI)](https://www.expedia.ca/lp/flights/san/chi/san-diego-to-chicago) \*Available to Expedia members. ## Other language versions ```yaml hreflang: x-default: https://www.expedia.com/lp/flights/gpt/chi/gulfport-to-chicago en-CA: https://www.expedia.ca/lp/flights/gpt/chi/gulfport-to-chicago es: https://www.expedia.com/es/lp/vuelos/gpt/chi/gulfport-a-todos-los-aeropuertos-de-chicago en-GB: https://www.expedia.co.uk/lp/flights/gpt/chi/gulfport-to-chicago en-US: https://www.expedia.com/lp/flights/gpt/chi/gulfport-to-chicago en-IN: https://www.expedia.co.in/lp/flights/gpt/chi/gulfport-to-chicago nb-NO: https://www.expedia.no/lp/fly/gpt/chi/gulfport-til-chicago en-PH: https://www.expedia.com.ph/lp/flights/gpt/chi/gulfport-to-chicago ar: https://www.expedia.sa/lp/flights/gpt/chi/gulfport-to-chicago ```