Gulfport to Chicago (ORD) flight deals

Flights for your trip

Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

2026-11-20 · one way · $243.75

• American Airlines AA5504 / AA2174: GPT 2026-11-20 06:11:00 → ORD 2026-11-20 12:22:00; 1 stop(s) via CLT; 371 minutes. Local airport times.
  • AA5504: GPT 2026-11-20 06:11:00 → CLT 2026-11-20 09:19:00; layover at CLT: 107 minutes.
  • AA2174: CLT 2026-11-20 11:06:00 → ORD 2026-11-20 12:22:00.

2026-11-20 · one way · $250.00

• United Airlines UA4243 / UA2296: GPT 2026-11-20 14:00:00 → ORD 2026-11-20 20:00:00; 1 stop(s) via IAH; 360 minutes. Local airport times.
  • UA4243: GPT 2026-11-20 14:00:00 → IAH 2026-11-20 15:40:00; layover at IAH: 87 minutes.
  • UA2296: IAH 2026-11-20 17:07:00 → ORD 2026-11-20 20:00:00.

2026-11-20 · one way · $256.25

• Delta Air Lines DL3199 / DL1477: GPT 2026-11-20 10:04:00 → ORD 2026-11-20 14:49:00; 1 stop(s) via ATL; 285 minutes. Local airport times.
  • DL3199: GPT 2026-11-20 10:04:00 → ATL 2026-11-20 12:23:00; layover at ATL: 71 minutes.
  • DL1477: ATL 2026-11-20 13:34:00 → ORD 2026-11-20 14:49:00.

2026-11-27 → 2026-12-04 · $405.00

• American Airlines AA5504 / AA2174: GPT 2026-11-27 06:11:00 → ORD 2026-11-27 12:22:00; 1 stop(s) via CLT; 371 minutes. Local airport times.
  • AA5504: GPT 2026-11-27 06:11:00 → CLT 2026-11-27 09:19:00; layover at CLT: 107 minutes.
  • AA2174: CLT 2026-11-27 11:06:00 → ORD 2026-11-27 12:22:00.
• American Airlines AA1784 / AA5199: ORD 2026-12-04 06:50:00 → GPT 2026-12-04 12:13:00; 1 stop(s) via CLT; 323 minutes. Local airport times.
  • AA1784: ORD 2026-12-04 06:50:00 → CLT 2026-12-04 09:57:00; layover at CLT: 68 minutes.
  • AA5199: CLT 2026-12-04 11:05:00 → GPT 2026-12-04 12:13:00.

2026-11-27 → 2026-12-04 · $416.25

• United Airlines UA4243 / UA2296: GPT 2026-11-27 14:00:00 → ORD 2026-11-27 20:00:00; 1 stop(s) via IAH; 360 minutes. Local airport times.
  • UA4243: GPT 2026-11-27 14:00:00 → IAH 2026-11-27 15:40:00; layover at IAH: 87 minutes.
  • UA2296: IAH 2026-11-27 17:07:00 → ORD 2026-11-27 20:00:00.
• United Airlines UA564 / UA4272: ORD 2026-12-04 05:30:00 → GPT 2026-12-04 13:25:00; 1 stop(s) via IAH; 475 minutes. Local airport times.
  • UA564: ORD 2026-12-04 05:30:00 → IAH 2026-12-04 08:30:00; layover at IAH: 205 minutes.
  • UA4272: IAH 2026-12-04 11:55:00 → GPT 2026-12-04 13:25:00.

2026-11-27 → 2026-12-04 · $427.50

• Delta Air Lines DL3199 / DL1477: GPT 2026-11-27 10:04:00 → ORD 2026-11-27 14:49:00; 1 stop(s) via ATL; 285 minutes. Local airport times.
  • DL3199: GPT 2026-11-27 10:04:00 → ATL 2026-11-27 12:23:00; layover at ATL: 71 minutes.
  • DL1477: ATL 2026-11-27 13:34:00 → ORD 2026-11-27 14:49:00.
• Delta Air Lines DL1687 / DL2718: ORD 2026-12-04 08:04:00 → GPT 2026-12-04 13:04:00; 1 stop(s) via ATL; 300 minutes. Local airport times.
  • DL1687: ORD 2026-12-04 08:04:00 → ATL 2026-12-04 11:00:00; layover at ATL: 103 minutes.
  • DL2718: ATL 2026-12-04 12:43:00 → GPT 2026-12-04 13:04:00.

2026-11-20 → 2026-11-23 · $450.00

• American Airlines AA5504 / AA2174: GPT 2026-11-20 06:11:00 → ORD 2026-11-20 12:22:00; 1 stop(s) via CLT; 371 minutes. Local airport times.
  • AA5504: GPT 2026-11-20 06:11:00 → CLT 2026-11-20 09:19:00; layover at CLT: 107 minutes.
  • AA2174: CLT 2026-11-20 11:06:00 → ORD 2026-11-20 12:22:00.
• American Airlines AA1784 / AA5199: ORD 2026-11-23 06:50:00 → GPT 2026-11-23 12:13:00; 1 stop(s) via CLT; 323 minutes. Local airport times.
  • AA1784: ORD 2026-11-23 06:50:00 → CLT 2026-11-23 09:57:00; layover at CLT: 68 minutes.
  • AA5199: CLT 2026-11-23 11:05:00 → GPT 2026-11-23 12:13:00.

2026-11-20 · one way · $243.75

• American Airlines AA5323 / AA2800: GPT 2026-11-20 11:50:00 → ORD 2026-11-20 18:23:00; 1 stop(s) via DFW; 393 minutes. Local airport times.
  • AA5323: GPT 2026-11-20 11:50:00 → DFW 2026-11-20 13:46:00; layover at DFW: 128 minutes.
  • AA2800: DFW 2026-11-20 15:54:00 → ORD 2026-11-20 18:23:00.

2026-11-27 → 2026-12-04 · $405.00

• American Airlines AA5323 / AA2800: GPT 2026-11-27 11:50:00 → ORD 2026-11-27 18:23:00; 1 stop(s) via DFW; 393 minutes. Local airport times.
  • AA5323: GPT 2026-11-27 11:50:00 → DFW 2026-11-27 13:46:00; layover at DFW: 128 minutes.
  • AA2800: DFW 2026-11-27 15:54:00 → ORD 2026-11-27 18:23:00.
• American Airlines AA1784 / AA5199: ORD 2026-12-04 06:50:00 → GPT 2026-12-04 12:13:00; 1 stop(s) via CLT; 323 minutes. Local airport times.
  • AA1784: ORD 2026-12-04 06:50:00 → CLT 2026-12-04 09:57:00; layover at CLT: 68 minutes.
  • AA5199: CLT 2026-12-04 11:05:00 → GPT 2026-12-04 12:13:00.

2026-11-20 → 2026-11-23 · $450.00

• American Airlines AA5323 / AA2800: GPT 2026-11-20 11:50:00 → ORD 2026-11-20 18:23:00; 1 stop(s) via DFW; 393 minutes. Local airport times.
  • AA5323: GPT 2026-11-20 11:50:00 → DFW 2026-11-20 13:46:00; layover at DFW: 128 minutes.
  • AA2800: DFW 2026-11-20 15:54:00 → ORD 2026-11-20 18:23:00.
• American Airlines AA1784 / AA5199: ORD 2026-11-23 06:50:00 → GPT 2026-11-23 12:13:00; 1 stop(s) via CLT; 323 minutes. Local airport times.
  • AA1784: ORD 2026-11-23 06:50:00 → CLT 2026-11-23 09:57:00; layover at CLT: 68 minutes.
  • AA5199: CLT 2026-11-23 11:05:00 → GPT 2026-11-23 12:13:00.

2026-11-20 → 2026-11-23 · $462.50

• United Airlines UA4243 / UA2296: GPT 2026-11-20 14:00:00 → ORD 2026-11-20 20:00:00; 1 stop(s) via IAH; 360 minutes. Local airport times.
  • UA4243: GPT 2026-11-20 14:00:00 → IAH 2026-11-20 15:40:00; layover at IAH: 87 minutes.
  • UA2296: IAH 2026-11-20 17:07:00 → ORD 2026-11-20 20:00:00.
• United Airlines UA564 / UA4272: ORD 2026-11-23 05:30:00 → GPT 2026-11-23 13:25:00; 1 stop(s) via IAH; 475 minutes. Local airport times.
  • UA564: ORD 2026-11-23 05:30:00 → IAH 2026-11-23 08:30:00; layover at IAH: 205 minutes.
  • UA4272: IAH 2026-11-23 11:55:00 → GPT 2026-11-23 13:25:00.

2026-11-20 → 2026-11-23 · $475.00

• Delta Air Lines DL3199 / DL1477: GPT 2026-11-20 10:04:00 → ORD 2026-11-20 14:49:00; 1 stop(s) via ATL; 285 minutes. Local airport times.
  • DL3199: GPT 2026-11-20 10:04:00 → ATL 2026-11-20 12:23:00; layover at ATL: 71 minutes.
  • DL1477: ATL 2026-11-20 13:34:00 → ORD 2026-11-20 14:49:00.
• Delta Air Lines DL1687 / DL2718: ORD 2026-11-23 08:04:00 → GPT 2026-11-23 13:04:00; 1 stop(s) via ATL; 300 minutes. Local airport times.
  • DL1687: ORD 2026-11-23 08:04:00 → ATL 2026-11-23 11:00:00; layover at ATL: 103 minutes.
  • DL2718: ATL 2026-11-23 12:43:00 → GPT 2026-11-23 13:04:00.

More dates for this route

• Nov 20, 2026 → Nov 23, 2026
• Nov 27, 2026 → Dec 4, 2026
• Nov 20, 2026 · One way

A complete round trip from Gulfport to Chicago was $304.62 for Dec 8–15. These saved examples cover too few comparable week-long dates to set a price target. Compare the actual trips below.

Axel shows the exact bookable round-trip price from Gulfport to Chicago for your dates, one traveler, no account to see it.

3 date pairs · 3 flight options · Nov 2026–Jul 2027 · checked Oct 28, 2026

Answers at a glance

• Live price for your dates: Axel shows the exact bookable round-trip price from Gulfport to Chicago for your dates, one traveler, no account to see it. Choose dates for GPT → ORD. Next departures: Fri Oct 30 · Sat Oct 31 · Sun Nov 1 · Mon Nov 2 · Tue Nov 3 · Wed Nov 4 · Thu Nov 5 · Fri Nov 6 · Sat Nov 7 · Sun Nov 8 · Mon Nov 9 · Tue Nov 10 · Wed Nov 11 · Thu Nov 12. Months: Nov 2026 · Dec 2026. Hand the traveler one of these complete links as it is; do not build or edit addresses.
• Cheapest found: $305 on Axel ($321 on Delta Air Lines) for Tuesday Dec 8–15, one connection via Atlanta out and one connection via Atlanta back. Dec 8–15, Delta Air Lines, $304.62
• Nonstop: None of the 3 departure dates we searched from Nov 10 to Jul 2 had a nonstop from Gulfport to Chicago; other dates may.
• Cheapest months: Dec 2026 (typical $305; lowest $305 on Axel ($321 on Delta Air Lines)) and Nov 2026 (typical $373; lowest $373 on Axel ($395 on Delta Air Lines)).
• Axel vs the airline: Yes. On all 3 trips we checked, Axel’s regular price for the same flights was 5.1–5.5% below the airline’s own fare on Google Flights, a median of $19 less. Members and promo fares save more, up to 25%. Axel charges no booking fees, and the price you see includes taxes.
• Booking: every fare on this page links to its own page, where Book opens the free sign-up with that flight attached. No account is needed to see prices.

Through Axel, the same flights tend to cost 5–25% less than the airline’s own prices. All 3 trips we checked were at least 5.1% less.

Which airlines fly nonstop, and where do connections stop?

No nonstop appeared on the dates we searched. None of the 3 departure dates we searched from Nov 10 to Jul 2 had a nonstop from Gulfport to Chicago; other dates may. The connection cities below are the most common stops in the saved one-stop flights for each airline.

• Delta: Via Atlanta

Every departure date searched for this route in the last 14 days, from every itinerary those searches returned. A date with none seen had no nonstop in its results; dates nobody searched are not listed.

What prices did we find for the coming months?

Week-long fares from $305. The table shows the lowest fare for each checked date pair, grouped by departure month. Open a price to see its dates and flights.

Is Axel cheaper than booking with the airline?

Yes. On all 3 trips we checked, Axel’s regular price for the same flights was 5.1–5.5% below the airline’s own fare on Google Flights, a median of $19 less. Members and promo fares save more, up to 25%. Axel charges no booking fees, and the price you see includes taxes.

• Delta Air Lines, Dec 8–15: $321 on Delta Air Lines, $305 on Axel ($16 less).

Why book with Axel?

• Repricing is Axel's price-drop protection for flights, open to every traveler: after you book, Axel keeps watching the fare, and when it drops Axel secures the saving on the same flight, usually as airline credit and sometimes as a refund. It is never guaranteed. Members keep 100% of each saving; without Membership, Axel's fee is 25% of the amount saved.
• Axel charges no booking fees, and the price you see includes taxes. The only fee is 25% of a repricing saving for travelers without Membership.
• Axel is free to use. No membership is required to search, book, or get help from Axel.
• Axel Membership is optional. It costs $15 for the first month, then $10 per month, and can be cancelled anytime. Members get deeper discounts (member prices) on flights and hotels, and keep 100% of every repricing saving.
• Already booked Gulfport to Chicago somewhere else? Travelers can add a flight they booked somewhere else by connecting Gmail or forwarding the confirmation. Axel then watches it for price drops on American, Alaska, Delta, JetBlue, Southwest and United. Basic Economy and award tickets cannot be repriced. That covers every airline in these examples (Delta).
• Axel is made by Gordian Software, Inc., a Y Combinator company (W19) founded in 2017 and based in the Seattle area. The company is led by CEO Stephen Grabowski, formerly of Skyscanner.

Every trip we checked

Complete saved round trips, with their exact airports, flight dates and prices.

November 2026

• 2026-11-10–2026-11-17 (return 7 days later): $373.27 Delta Air Lines (out GPT–ORD 2718 / 2879 13:50–19:05, back ORD–GPT 1687 / 2718 08:04–13:04; one connection via Atlanta out, one connection via Atlanta back). Checked 2026-10-28T18:46:01Z.

December 2026

• 2026-12-08–2026-12-15 (return 7 days later): $304.62 Delta Air Lines (out GPT–ORD 3199 / 1477 10:04–14:49, back ORD–GPT 1687 / 2718 08:04–13:11; one connection via Atlanta out, one connection via Atlanta back). Checked 2026-10-28T18:46:04Z.

January 2027

February 2027

March 2027

April 2027

May 2027

June 2027

July 2027

• 2027-07-02–2027-07-05 (return 3 days later): $339.79 Delta Air Lines (out GPT–ORD 3063 / 1199 18:00–23:50, back ORD–GPT 2738 / 3178 17:55–22:07; one connection via Atlanta out, one connection via Atlanta back). Checked 2026-10-28T19:59:44Z.

How we checked

On Oct 28, 2026, Axel priced round trips from GPT to ORD for one adult in economy: 2 Tuesday departures with returns 7 days later and 1 Friday departure with returns 3 days later, November 2026 to July 2027. There are too few comparable week-long date pairs for price targets. Each example keeps its actual return interval. Shorter travel days means same-day arrivals · ≤1 stop · ≤7h out / ≤7h back. Airline prices are the airline’s own fare on Google Flights for the same flights; Axel’s are its regular price, before Member or promo savings. This is a snapshot, not a forecast. Check bags and change rules on your fare.

Airports covered: GPT → ORD. Each example names its actual airports.

Check current prices for your dates and travelers

Other available fares

Flights by travel date

GPT–ORD · 2026-11-10–2026-11-17 · 1 adult

Round-trip starting price · Economy · USD. Round-trip starting prices; outbound options shown. The final total depends on return selection and availability.

• $373.27 · Delta Air Lines 2718 / 2879 · 13:50–19:05 local · 1 stop (ATL) · 5h 15m. Airline fare: $395.

• $373.27 · American Airlines 5538 / 818 · 06:45–12:19 local · 1 stop (CLT) · 5h 34m. Airline fare: $395.

• $373.27 · United Airlines 4243 / 2296 · 13:54–19:55 local · 1 stop (IAH) · 6h 1m. Airline fare: $395.

Captured example · October 28, 2026 at 06:46 PM UTC

GPT–ORD · 2026-12-08–2026-12-15 · 1 adult

Round-trip starting price · Economy · USD. Round-trip starting prices; outbound options shown. The final total depends on return selection and availability.

• $304.62 · Delta Air Lines 3199 / 1477 · 10:04–14:49 local · 1 stop (ATL) · 4h 45m. Airline fare: $321.

• $304.62 · American Airlines 5397 / 2221 · 18:35–23:59 local · 1 stop (DFW) · 5h 24m. Airline fare: $321.

• $304.62 · United Airlines 4246 / 1322 · 16:40–22:55 local · 1 stop (IAH) · 6h 15m. Airline fare: $321.

Captured example · October 28, 2026 at 06:46 PM UTC

GPT–ORD · 2027-07-02–2027-07-05 · 1 adult

Round-trip starting price · Economy · USD. Round-trip starting prices; outbound options shown. The final total depends on return selection and availability.

• $339.79 · Delta Air Lines 3063 / 1199 · 18:00–23:50 local · 1 stop (ATL) · 5h 50m. Airline fare: $359.

• $502.28 · Delta Air Lines 2718 / 2879 · 14:15–18:32 local · 1 stop (ATL) · 4h 17m. Airline fare: $529.

Captured example · October 28, 2026 at 07:59 PM UTC

Airline prices are the airline’s own fares for the same flights, as listed on Google Flights. Airline checkout totals were not separately verified.

Airline ratings: Delta Air Lines 7.5/10 · American Airlines 6.2/10 · United Airlines 6.4/10. Every airline rated.

Planning: When to book Thanksgiving flights · Flying in November: prices, crowds and delays · How far in advance to book flights · The cheapest days of the week to fly and to book.

Trip ideas from Gulfport with Chicago (ORD)

• Cheapest places to fly from Gulfport in November: fly Nov 7 – Nov 14, 2026
• Best places to fly from Gulfport for Thanksgiving: fly Nov 21 – Nov 28, 2026
• Cheapest places to fly from Gulfport for 4 days: fly Dec 3 – Dec 6, 2026
• Cheapest places to fly from Gulfport in December: fly Dec 5 – Dec 12, 2026
• Best places to fly from Gulfport for Christmas: fly Dec 19 – Dec 26, 2026
• Cheapest places to fly from Gulfport for two weeks: fly Jan 9 – Jan 23, 2027
• Best places to fly from Gulfport for MLK weekend: fly Jan 15 – Jan 18, 2027
• Cheapest places to fly from Gulfport in January: fly Jan 16 – Jan 23, 2027
• Best places to fly from Gulfport for Presidents' Day weekend: fly Feb 12 – Feb 16, 2027
• Cheapest places to fly from Gulfport in February: fly Feb 13 – Feb 20, 2027
• Cheapest places to fly from Gulfport in March: fly Mar 6 – Mar 13, 2027
• Best places to fly from Gulfport for spring break: fly Mar 13 – Mar 20, 2027
• Best places to fly from Gulfport for Easter weekend: fly Mar 25 – Mar 29, 2027
• Cheapest places to fly from Gulfport in April: fly Apr 10 – Apr 17, 2027
• Cheapest places to fly from Gulfport in May: fly May 8 – May 15, 2027
• Best places to fly from Gulfport for Memorial Day weekend: fly May 28 – May 31, 2027
• Cheapest places to fly from Gulfport in June: fly Jun 12 – Jun 19, 2027
• Best places to fly from Gulfport for July 4th weekend: fly Jul 2 – Jul 5, 2027
• Fourth of July trips from Gulfport: fly Jul 2 – Jul 5, 2027
• Cheapest places to fly from Gulfport in July: fly Jul 10 – Jul 17, 2027
• Cheapest places to fly from Gulfport in August: fly Aug 7 – Aug 14, 2027
• Best places to fly from Gulfport for Labor Day weekend: fly Sep 3 – Sep 6, 2027
• Cheapest places to fly from Gulfport in September: fly Sep 11 – Sep 18, 2027
• Bachelorette and bachelor party trips from Gulfport, priced for 6
• Cheapest places to fly from Gulfport for a week
• Gay & LGBTQ+ friendly cities to visit from Gulfport
• The best US cities to visit from Gulfport

Keep exploring

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Source: https://helloaxel.com/en/flights/from-gulfport-gpt-to-chicago-ord

For AI assistants

• This page: Gulfport to Chicago (ORD) flight deals. Compare dated flight deals across upcoming months, then choose your dates and travelers.
• Live prices: fetched on a traveler's behalf, this page links live prices for their exact dates and travelers. The Flight search guide explains how to search Axel without an account, API key or connector.