$119+ Cheap flights from Mississippi to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/7. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — CHI
Nov 25 — Dec 21
Round-trip
1 adult, Economy
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Find cheap flights from Mississippi to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Mississippi to ChicagoExplore the most affordable flight options available from Mississippi to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 26, 2026.
Explore the most affordable flight options available from Mississippi to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 26, 2026.
This American Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:00 am -
1 stop5h 00m
Sat 11/215:59 pm -
1 stop6h 00m
Deal found 10/22![American Airlines logo]()
$227
This American Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1412:15 pm -
1 stop6h 14m
Mon 11/164:40 pm -
1 stop6h 03m
Deal found 10/22![American Airlines logo]()
$242
This Delta deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/97:54 am -
1 stop4h 10m
Mon 12/1411:28 am -
1 stop4h 56m
Deal found 10/23![Delta logo]()
$242
This Southwest deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/76:30 am -
2 stops9h 00m
Wed 12/96:40 am -
1 stop5h 50m
Deal found 10/23![Southwest logo]()
$247
This Delta deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/93:48 pm -
1 stop5h 05m
Mon 12/146:16 pm -
1 stop4h 49m
Deal found 10/23![Delta logo]()
$248
This Southwest deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:30 am -
2 stops6h 25m
Mon 11/1612:45 pm -
1 stop4h 50m
Deal found 10/22![Southwest logo]()
$260
This Southwest deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/56:30 am -
2 stops6h 25m
Mon 12/76:40 am -
1 stop5h 50m
Deal found 10/25![Southwest logo]()
$276
This Delta deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/215:06 pm -
1 stop6h 48m
Sun 11/225:30 am -
1 stop4h 59m
Deal found 10/22![Delta logo]()
$294
This Delta deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/215:06 pm -
1 stop5h 48m
Sun 11/226:00 am -
1 stop4h 29m
Deal found 10/22![Delta logo]()
$294
This Delta deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/76:00 am -
1 stop6h 13m
Wed 11/111:30 pm -
1 stop6h 25m
Deal found 10/23![Delta logo]()
$297
This Delta deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/76:00 am -
1 stop4h 37m
Wed 11/111:05 pm -
1 stop6h 50m
Deal found 10/23![Delta logo]()
$297
This Southwest deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/46:15 pm -
1 stop4h 55m
Sun 12/67:30 am -
2 stops14h 40m
Deal found 10/23![Southwest logo]()
$300
Best flights from Mississippi to ChicagoDiscover carefully curated flight deals from Mississippi to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 26, 2026.
Discover carefully curated flight deals from Mississippi to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 26, 2026.
This Delta deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/71:24 pm -
1 stop7h 29m
Wed 12/96:16 pm -
1 stop4h 49m
Deal found 10/23![Delta logo]()
$242
This Southwest deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/76:30 am -
2 stops9h 00m
Wed 12/99:55 am -
2 stops10h 00m
Deal found 10/23![Southwest logo]()
$252
This Kiwi.com deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/137:45 pm -
2 stops39h 48m
Sat 12/198:35 pm -
1 stop22h 30m
Deal found 10/21![Multiple Airlines logo]()
$330
This United Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/64:55 pm -
1 stop6h 31m
Tue 11/1010:34 am -
1 stop5h 34m
Deal found 10/22![United Airlines logo]()
$343
This Southwest deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/51:05 pm -
1 stop6h 30m
Mon 12/712:45 pm -
1 stop4h 50m
Deal found 10/25![Southwest logo]()
$271
This Delta deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/215:06 pm -
1 stop6h 48m
Sun 11/225:30 am -
1 stop4h 59m
Deal found 10/22![Delta logo]()
$294
This Southwest deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:30 am -
2 stops6h 25m
Mon 11/167:35 am -
2 stops10h 00m
Deal found 10/22![Southwest logo]()
$271
This Delta deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/215:06 pm -
1 stop5h 48m
Sun 11/226:00 am -
1 stop4h 29m
Deal found 10/22![Delta logo]()
$294
This Delta deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/172:43 pm -
1 stop4h 22m
Wed 11/183:59 pm -
1 stop6h 18m
Deal found 10/22![Delta logo]()
$316
This United Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/194:55 pm -
1 stop7h 50m
Thu 11/266:55 am -
1 stop6h 23m
Deal found 10/21![United Airlines logo]()
$419
This Delta deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/1310:30 am -
1 stop5h 55m
Tue 2/165:25 pm -
1 stop4h 42m
Deal found 10/22![Delta logo]()
$317
This Southwest deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/46:15 pm -
1 stop4h 55m
Sun 12/67:30 am -
2 stops14h 40m
Deal found 10/25![Southwest logo]()
$375
This United Airlines deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/61:59 pm -
1 stop7h 34m
Sat 1/92:22 pm -
1 stop5h 11m
Deal found 10/24![United Airlines logo]()
$421
This Delta deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1210:04 am -
1 stop6h 14m
Mon 11/165:13 pm -
1 stop4h 39m
Deal found 10/21![Delta logo]()
$319
This Delta deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/111:50 pm -
1 stop5h 15m
Mon 11/162:44 pm -
2 stops7h 08m
Deal found 10/21![Delta logo]()
$323
This Southwest deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/106:30 am -
2 stops9h 00m
Sat 12/195:20 am -
2 stops9h 35m
Deal found 10/23![Southwest logo]()
$397
This Delta deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:26 am -
2 stops9h 52m
Mon 11/163:59 pm -
1 stop5h 53m
Deal found 10/21![Delta logo]()
$324
This Southwest deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/712:05 pm -
2 stops7h 35m
Wed 11/1110:55 am -
2 stops9h 00m
Deal found 10/23![Southwest logo]()
$427
This Delta deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/235:59 pm -
1 stop6h 00m
Mon 12/286:25 am -
1 stop6h 58m
Deal found 10/22![Delta logo]()
$332
This United Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/2911:43 am -
1 stop23h 32m
Tue 2/27:50 pm -
1 stop22h 52m
Deal found 10/23![United Airlines logo]()
$556
This Southwest deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/101:10 pm -
2 stops7h 35m
Fri 2/1211:00 am -
2 stops9h 50m
Deal found 10/21![Southwest logo]()
$442
This Delta deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/136:04 pm -
1 stop4h 50m
Mon 11/161:31 pm -
2 stops8h 21m
Deal found 10/21![Delta logo]()
$334
This United Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1211:10 am -
1 stop11h 46m
Mon 12/149:21 am -
1 stop24h 09m
Deal found 10/23![United Airlines logo]()
$566
This Delta deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/25:59 pm -
1 stop4h 23m
Tue 1/56:00 am -
1 stop5h 22m
Deal found 10/23![Delta logo]()
$337
This United Airlines deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/26:50 am -
1 stop13h 13m
Wed 2/38:10 pm -
2 stops15h 16m
Deal found 10/25![United Airlines logo]()
$571
This Delta deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/156:15 am -
2 stops12h 08m
Fri 12/186:49 am -
1 stop6h 17m
Deal found 10/23![Delta logo]()
$345
This United Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/181:57 pm -
1 stop9h 29m
Wed 11/258:10 pm -
2 stops20h 24m
Deal found 10/21![United Airlines logo]()
$596
This Delta deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/215:05 pm -
1 stop5h 49m
Mon 11/2310:34 am -
2 stops6h 45m
Deal found 10/24![Delta logo]()
$354
This United Airlines deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/51:55 pm -
2 stops16h 34m
Mon 12/79:45 pm -
2 stops13h 38m
Deal found 10/25![United Airlines logo]()
$604
This Delta deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/105:45 am -
1 stop4h 22m
Fri 2/127:00 pm -
1 stop4h 23m
Deal found 10/21![Delta logo]()
$372
Last-minute flights from Mississippi to ChicagoDiscover last-minute flight deals from Mississippi to Chicago. Data last updated October 26, 2026 and is based on user searches.
Discover last-minute flight deals from Mississippi to Chicago. Data last updated October 26, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/76:00 am -
1 stop6h 13m
Wed 11/111:30 pm -
1 stop6h 25m
Deal found 10/23![Delta logo]()
$297
This Delta deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/76:00 am -
1 stop4h 37m
Wed 11/111:05 pm -
1 stop6h 50m
Deal found 10/23![Delta logo]()
$297
This American Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:21 pm -
1 stop5h 38m
Mon 11/164:53 pm -
1 stop6h 42m
Deal found 10/21![American Airlines logo]()
$318
This American Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:00 am -
1 stop5h 00m
Sat 11/215:59 pm -
1 stop6h 00m
Deal found 10/22![American Airlines logo]()
$227
This American Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1412:15 pm -
1 stop6h 14m
Mon 11/164:40 pm -
1 stop6h 03m
Deal found 10/22![American Airlines logo]()
$242
This Southwest deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:30 am -
2 stops6h 25m
Mon 11/1612:45 pm -
1 stop4h 50m
Deal found 10/22![Southwest logo]()
$260
This Delta deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/143:50 pm -
1 stop7h 04m
Sat 11/216:00 am -
1 stop4h 29m
Deal found 10/22![Delta logo]()
$303
This Delta deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/143:50 pm -
1 stop7h 04m
Mon 11/165:13 pm -
1 stop5h 52m
Deal found 10/22![Delta logo]()
$312
This American Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/142:02 pm -
1 stop6h 09m
Sat 11/214:58 pm -
1 stop7h 03m
Deal found 10/21![American Airlines logo]()
$317
This Delta deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/172:43 pm -
1 stop4h 22m
Wed 11/183:59 pm -
1 stop6h 18m
Deal found 10/22![Delta logo]()
$316
This Delta deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/215:06 pm -
1 stop6h 48m
Sun 11/225:30 am -
1 stop4h 59m
Deal found 10/22![Delta logo]()
$294
This Delta deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/215:06 pm -
1 stop5h 48m
Sun 11/226:00 am -
1 stop4h 29m
Deal found 10/22![Delta logo]()
$294
One-way flights from Mississippi to ChicagoSearch for one-way flight options from Mississippi to Chicago. Find affordable one-way fares based on user searches. Data last updated October 26, 2026.
Search for one-way flight options from Mississippi to Chicago. Find affordable one-way fares based on user searches. Data last updated October 26, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/76:46 pm -
2 stops19h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Multiple Airlines logo]()
$119
This Delta deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/215:59 pm -
1 stop6h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Delta logo]()
$129
This Delta deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2611:14 am -
1 stop4h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Delta logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/76:46 pm -
2 stops40h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Multiple Airlines logo]()
$130
This Southwest deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/228:15 pm -
1 stop4h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Southwest logo]()
$145
This Delta deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/195:20 pm -
1 stop6h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Delta logo]()
$159
This Delta deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/76:09 pm -
1 stop5h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Delta logo]()
$160
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/203:50 pm -
1 stop7h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Delta logo]()
$163
This Delta deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/56:00 am -
2 stops10h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Delta logo]()
$164
This American Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/256:30 pm -
1 stop5h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![American Airlines logo]()
$164
This American Airlines deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/245:30 am -
1 stop5h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![American Airlines logo]()
$174
This Delta deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/205:30 am -
1 stop6h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Delta logo]()
$180
Find flight deals from Mississippi to Chicago
Keep the following information in mind while searching for Mississippi to Chicago flight deals. Data was last updated October 26, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $227 (Kiwi.com) |
One-way from | $119 (Kiwi.com) |
Popular in | June |
Cheapest in | April |
Average price | $442 |
Cheapflights Fare Finder
Customize your flight search to find flights from Mississippi 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, Cheapflights users made 7,457,451 searches. Data last updated October 26, 2026.
Use the filters below to find and compare flights from Mississippi to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
GulfportChicago
GPT Gulfport Biloxi Regional - ORD Chicago O'Hare Intl
GPTORD
Gulfport Biloxi Regional
Mon 12/7
6:46 pm-2:30 pm
2 stops19h 44m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$119
JacksonChicago
JAN Jackson-Evers Intl - ORD Chicago O'Hare Intl
JANORD
Jackson-Evers Intl
Thu 11/26
1:20 pm-7:05 pm
1 stop5h 45m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$129
JacksonChicago
JAN Jackson-Evers Intl - ORD Chicago O'Hare Intl
JANORD
Jackson-Evers Intl
Mon 12/21
5:59 pm-11:59 pm
1 stop6h 00m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$129
GulfportChicago
GPT Gulfport Biloxi Regional - MDW Chicago Midway
GPTMDW
Gulfport Biloxi Regional
Mon 12/7
6:46 pm-11:33 am
2 stops40h 47m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$130
JacksonChicago
JAN Jackson-Evers Intl - MDW Chicago Midway
JANMDW
Jackson-Evers Intl
Sun 11/22
8:15 pm-1:10 am
1 stop4h 55m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$145
JacksonChicago
JAN Jackson-Evers Intl - MDW Chicago Midway
JANMDW
Jackson-Evers Intl
Sun 12/6
8:15 pm-1:10 am
1 stop4h 55m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$145
GulfportChicago
GPT Gulfport Biloxi Regional - ORD Chicago O'Hare Intl
GPTORD
Gulfport Biloxi Regional
Sat 12/19
5:20 pm-11:59 pm
1 stop6h 39m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$159
JacksonChicago
JAN Jackson-Evers Intl - MDW Chicago Midway
JANMDW
Jackson-Evers Intl
Fri 11/20
3:50 pm-10:54 pm
1 stop7h 04m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$163
GulfportChicago
GPT Gulfport Biloxi Regional - ORD Chicago O'Hare Intl
GPTORD
Gulfport Biloxi Regional
Tue 1/5
6:00 am-4:12 pm
2 stops10h 12m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$164
JacksonChicago
JAN Jackson-Evers Intl - ORD Chicago O'Hare Intl
JANORD
Jackson-Evers Intl
Tue 11/24
5:30 am-11:02 am
1 stop5h 32m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$174
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Mississippi to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Mississippi with our price prediction graph.
JAN-ORD
JAN-MDW
GPT-MDW
GPT-ORD
GTR-ORD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Mississippi to Chicago
USMS-CHI
JAN-ORD
JAN-MDW
GPT-MDW
GPT-ORD
What is the cheapest month to book a flight from Mississippi to Chicago?
Currently, January is the cheapest month in which you can book a flight from Mississippi to Chicago (average of $358). Flying from Mississippi to Chicago in June is currently the most expensive (average of $674). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
How much does it cost to fly round-trip from Mississippi to Chicago?
Airfare is below average for this route at the moment.
Mississippi to Chicago flights typically cost between $359 and $548 in November.The cheapest round-trip price found within the last 5 days was $227 on American Airlines (Nov 14-Nov 21).
Related info for your journey
Find useful and relevant information for your journey from Mississippi to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Chicago flight routes
Complete your trip
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Alternative routes for Mississippi to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 26, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Mississippi to Chicago by cabin class
Find flights from Mississippi to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Mississippi and Chicago flights
Browse other Mississippi and Chicago flight options. Last updated on October 26, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Mississippi to Chicago flights
Consider these flights traveling from Mississippi to Chicago.
Top 3 airlines flying from Mississippi to Chicago
Discover the top 3 airlines that operate flights from Mississippi to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 26, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$286 | Average$409 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$296 | Average$500 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$308 | Average$462 | FlexibilityNo cancel fee | On-time63% |