$155+ Cheap flights from Chicago (CHI) to Mississippi
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 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — JAN
Oct 26 — Nov 21
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Mississippi 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 Chicago to MississippiExplore the most affordable flight options available from Chicago to Mississippi. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 26, 2026.
Explore the most affordable flight options available from Chicago to Mississippi. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 26, 2026.
This American Airlines deal was found by Cheapflights users on 9/21. 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 11/115:19 am -
1 stop6h 37m
Mon 11/164:52 pm -
1 stop6h 23m
Deal found 9/21![American Airlines logo]()
$309
This Delta deal was found by Cheapflights users on 9/22. 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 11/111:05 pm -
1 stop6h 50m
Mon 11/169:16 am -
1 stop7h 02m
Deal found 9/22![Delta logo]()
$309
This American Airlines deal was found by Cheapflights users on 9/21. 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.
Mon 10/196:40 pm -
1 stop5h 15m
Mon 10/264:46 pm -
1 stop5h 24m
Deal found 9/21![American Airlines logo]()
$329
This Delta deal was found by Cheapflights users on 9/22. 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 10/2411:33 am -
1 stop4h 44m
Thu 10/297:45 am -
1 stop4h 09m
Deal found 9/22![Delta logo]()
$329
This Delta deal was found by Cheapflights users on 9/22. 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 10/2012:49 pm -
1 stop4h 31m
Sat 10/244:00 pm -
1 stop6h 33m
Deal found 9/22![Delta logo]()
$330
This United Airlines deal was found by Cheapflights users on 9/23. 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.
Wed 10/217:30 am -
1 stop5h 55m
Sat 10/245:14 pm -
1 stop7h 09m
Deal found 9/23![United Airlines logo]()
$330
This Delta deal was found by Cheapflights users on 9/23. 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 11/182:44 pm -
2 stops7h 08m
Sun 11/226:04 pm -
1 stop5h 50m
Deal found 9/23![Delta logo]()
$335
This American Airlines deal was found by Cheapflights users on 9/26. 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 American Airlines is selected, and click “Compare selected ” under the list of providers to see comparable flight deals.
Fri 12/46:49 pm -
1 stop5h 08m
Mon 12/76:21 pm -
1 stop5h 38m
Deal found 9/26![American Airlines logo]()
$339
This Southwest deal was found by Cheapflights users on 9/24. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1812:45 pm -
1 stop4h 50m
Wed 11/258:15 pm -
1 stop4h 45m
Deal found 9/24![Southwest logo]()
$343
This Delta deal was found by Cheapflights users on 9/23. 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.
Fri 11/1310:06 am -
2 stops11h 46m
Sun 11/156:04 pm -
1 stop5h 50m
Deal found 9/23![Delta logo]()
$344
This American Airlines deal was found by Cheapflights users on 9/22. 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.
Fri 10/236:40 pm -
1 stop5h 19m
Sat 10/246:42 pm -
1 stop5h 26m
Deal found 9/22![American Airlines logo]()
$345
This Delta deal was found by Cheapflights users on 9/22. 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 10/266:08 pm -
1 stop5h 01m
Fri 10/303:33 pm -
1 stop5h 05m
Deal found 9/22![Delta logo]()
$349
Best flights from Chicago to MississippiDiscover carefully curated flight deals from Chicago to Mississippi that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 26, 2026.
Discover carefully curated flight deals from Chicago to Mississippi that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 26, 2026.
This Delta deal was found by Cheapflights users on 9/23. 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.
Thu 11/55:27 am -
1 stop4h 27m
Mon 11/91:20 pm -
1 stop7h 29m
Deal found 9/23![Delta logo]()
$309
This American Airlines deal was found by Cheapflights users on 9/21. 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.
Thu 12/246:00 am -
1 stop5h 46m
Thu 12/244:56 pm -
1 stop5h 04m
Deal found 9/21![American Airlines logo]()
$309
This United Airlines deal was found by Cheapflights users on 9/23. 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.
Wed 10/217:30 am -
1 stop5h 55m
Sat 10/245:14 pm -
1 stop7h 09m
Deal found 9/23![United Airlines logo]()
$330
This Southwest deal was found by Cheapflights users on 9/21. 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.
Thu 12/246:40 am -
1 stop5h 50m
Thu 12/246:15 pm -
1 stop4h 50m
Deal found 9/21![Southwest logo]()
$361
This Delta deal was found by Cheapflights users on 9/21. 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 11/116:00 am -
1 stop4h 29m
Mon 11/165:06 pm -
1 stop5h 48m
Deal found 9/21![Delta logo]()
$309
This Delta deal was found by Cheapflights users on 9/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/36:49 am -
1 stop6h 20m
Tue 12/810:04 am -
1 stop6h 58m
Deal found 9/25![Delta logo]()
$330
This Southwest deal was found by Cheapflights users on 9/23. 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.
Tue 12/2212:50 pm -
2 stops9h 30m
Fri 12/256:30 am -
2 stops10h 35m
Deal found 9/23![Southwest logo]()
$379
This American Airlines deal was found by Cheapflights users on 9/21. 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 10/312:09 pm -
1 stop5h 43m
Mon 10/56:02 pm -
1 stop5h 57m
Deal found 9/21![American Airlines logo]()
$395
This Southwest deal was found by Cheapflights users on 9/25. 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.
Thu 10/2211:50 am -
1 stop8h 00m
Thu 10/295:55 am -
2 stops9h 40m
Deal found 9/25![Southwest logo]()
$380
This United Airlines deal was found by Cheapflights users on 9/22. 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.
Sat 10/317:29 am -
1 stop5h 49m
Wed 11/44:55 pm -
1 stop6h 31m
Deal found 9/22![United Airlines logo]()
$421
This Delta deal was found by Cheapflights users on 9/23. 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 11/181:05 pm -
1 stop4h 14m
Sun 11/226:04 pm -
1 stop4h 50m
Deal found 9/23![Delta logo]()
$350
This American Airlines deal was found by Cheapflights users on 9/21. 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 10/179:40 am -
1 stop5h 49m
Wed 10/213:59 pm -
1 stop8h 00m
Deal found 9/21![American Airlines logo]()
$398
This Southwest deal was found by Cheapflights users on 9/23. 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.
Tue 10/202:10 pm -
1 stop3h 50m
Thu 10/225:55 am -
2 stops9h 10m
Deal found 9/23![Southwest logo]()
$385
This Delta deal was found by Cheapflights users on 9/22. 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.
Thu 12/35:30 am -
1 stop4h 59m
Sun 12/65:20 am -
1 stop7h 06m
Deal found 9/22![Delta logo]()
$353
This American Airlines deal was found by Cheapflights users on 9/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/179:16 am -
1 stop6h 09m
Sun 12/203:55 pm -
1 stop8h 04m
Deal found 9/26![American Airlines logo]()
$422
This Southwest deal was found by Cheapflights users on 9/21. 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.
Mon 10/193:45 pm -
1 stop6h 10m
Mon 10/265:55 am -
2 stops9h 10m
Deal found 9/21![Southwest logo]()
$386
This Delta deal was found by Cheapflights users on 9/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/108:05 am -
1 stop6h 16m
Wed 10/146:05 pm -
1 stop5h 52m
Deal found 9/25![Delta logo]()
$369
This Southwest deal was found by Cheapflights users on 9/23. 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.
Tue 10/2012:00 pm -
2 stops8h 00m
Mon 10/265:55 am -
2 stops7h 55m
Deal found 9/23![Southwest logo]()
$399
This American Airlines deal was found by Cheapflights users on 9/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/308:14 am -
1 stop7h 15m
Sun 11/13:59 pm -
1 stop8h 00m
Deal found 9/24![American Airlines logo]()
$442
This Delta deal was found by Cheapflights users on 9/24. 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.
Fri 12/116:15 pm -
1 stop4h 50m
Sun 12/137:24 pm -
1 stop4h 28m
Deal found 9/24![Delta logo]()
$373
This United Airlines deal was found by Cheapflights users on 9/25. 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 10/312:22 pm -
1 stop6h 04m
Tue 11/35:23 pm -
2 stops14h 13m
Deal found 9/25![United Airlines logo]()
$560
This United Airlines deal was found by Cheapflights users on 9/23. 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.
Thu 11/55:30 am -
1 stop5h 45m
Mon 11/95:23 pm -
2 stops15h 37m
Deal found 9/23![United Airlines logo]()
$560
This Southwest deal was found by Cheapflights users on 9/22. 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.
Fri 10/234:30 pm -
1 stop3h 20m
Sat 10/2412:30 pm -
2 stops7h 05m
Deal found 9/22![Southwest logo]()
$429
This Delta deal was found by Cheapflights users on 9/23. 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.
Thu 11/58:36 am -
2 stops12h 10m
Fri 11/136:04 pm -
1 stop5h 50m
Deal found 9/23![Delta logo]()
$394
This United Airlines deal was found by Cheapflights users on 9/23. 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 10/166:25 am -
1 stop7h 55m
Sat 10/1710:40 am -
1 stop7h 50m
Deal found 9/23![United Airlines logo]()
$562
This Delta deal was found by Cheapflights users on 9/22. 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 11/238:04 am -
1 stop5h 57m
Thu 11/266:00 am -
1 stop6h 23m
Deal found 9/22![Delta logo]()
$398
This Southwest deal was found by Cheapflights users on 9/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2211:05 am -
2 stops8h 45m
Sun 10/258:25 pm -
1 stop4h 35m
Deal found 9/26![Southwest logo]()
$456
This United Airlines deal was found by Cheapflights users on 9/23. 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.
Thu 10/85:30 am -
1 stop5h 53m
Mon 10/1211:58 am -
1 stop6h 32m
Deal found 9/23![United Airlines logo]()
$565
This Delta deal was found by Cheapflights users on 9/21. 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.
Sat 10/177:00 am -
2 stops6h 42m
Wed 10/212:23 pm -
1 stop4h 48m
Deal found 9/21![Delta logo]()
$404
This United Airlines deal was found by Cheapflights users on 9/22. 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.
Wed 11/44:35 pm -
2 stops18h 26m
Sun 11/811:40 am -
2 stops19h 19m
Deal found 9/22![United Airlines logo]()
$595
Last-minute flights from Chicago to MississippiDiscover last-minute flight deals from Chicago to Mississippi. Data last updated September 26, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Mississippi. Data last updated September 26, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 9/21. 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.
Mon 10/196:40 pm -
1 stop5h 15m
Mon 10/264:46 pm -
1 stop5h 24m
Deal found 9/21![American Airlines logo]()
$329
This Delta deal was found by Cheapflights users on 9/22. 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 10/2012:49 pm -
1 stop4h 31m
Sat 10/244:00 pm -
1 stop6h 33m
Deal found 9/22![Delta logo]()
$330
This United Airlines deal was found by Cheapflights users on 9/23. 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.
Wed 10/217:30 am -
1 stop5h 55m
Sat 10/245:14 pm -
1 stop7h 09m
Deal found 9/23![United Airlines logo]()
$330
This American Airlines deal was found by Cheapflights users on 9/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:00 am -
1 stop5h 13m
Sat 10/246:11 am -
1 stop8h 09m
Deal found 9/26![American Airlines logo]()
$339
This American Airlines deal was found by Cheapflights users on 9/22. 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.
Fri 10/236:40 pm -
1 stop5h 19m
Sat 10/246:42 pm -
1 stop5h 26m
Deal found 9/22![American Airlines logo]()
$345
This Delta deal was found by Cheapflights users on 9/22. 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 10/241:23 pm -
1 stop5h 21m
Mon 10/267:29 pm -
1 stop4h 28m
Deal found 9/22![Delta logo]()
$309
This Delta deal was found by Cheapflights users on 9/22. 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 10/2411:33 am -
1 stop4h 44m
Thu 10/297:45 am -
1 stop4h 09m
Deal found 9/22![Delta logo]()
$329
This Delta deal was found by Cheapflights users on 9/22. 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 10/265:09 pm -
1 stop6h 00m
Tue 10/2711:10 am -
1 stop5h 04m
Deal found 9/22![Delta logo]()
$309
This Delta deal was found by Cheapflights users on 9/22. 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 10/266:08 pm -
1 stop5h 01m
Fri 10/303:33 pm -
1 stop5h 05m
Deal found 9/22![Delta logo]()
$349
This Delta deal was found by Cheapflights users on 9/23. 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.
Thu 10/296:30 am -
1 stop5h 44m
Sun 11/11:04 pm -
1 stop7h 34m
Deal found 9/23![Delta logo]()
$353
This Delta deal was found by Cheapflights users on 9/23. 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.
Thu 10/296:04 am -
1 stop4h 21m
Sun 11/13:33 pm -
1 stop7h 00m
Deal found 9/23![Delta logo]()
$353
This American Airlines deal was found by Cheapflights users on 9/22. 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.
Fri 10/306:00 am -
1 stop5h 13m
Sun 11/16:21 pm -
1 stop5h 38m
Deal found 9/22![American Airlines logo]()
$354
One-way flights from Chicago to MississippiSearch for one-way flight options from Chicago to Mississippi. Find affordable one-way fares based on user searches. Data last updated September 26, 2026.
Search for one-way flight options from Chicago to Mississippi. Find affordable one-way fares based on user searches. Data last updated September 26, 2026.
This American Airlines deal was found by Cheapflights users on 9/22. 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 11/143:00 pm -
1 stop8h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![American Airlines logo]()
$155
This Southwest deal was found by Cheapflights users on 9/22. 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 11/147:50 am -
1 stop3h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Southwest logo]()
$155
This Southwest deal was found by Cheapflights users on 9/24. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/235:15 am -
1 stop5h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Southwest logo]()
$187
This American Airlines deal was found by Cheapflights users on 9/21. 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.
Mon 11/234:58 pm -
1 stop5h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![American Airlines logo]()
$199
This Delta deal was found by Cheapflights users on 9/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/156:00 am -
1 stop4h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Delta logo]()
$199
This Southwest deal was found by Cheapflights users on 9/25. 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.
Sun 11/1511:10 am -
2 stops8h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Southwest logo]()
$204
This Southwest deal was found by Cheapflights users on 9/25. 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.
Thu 10/2211:50 am -
1 stop8h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Southwest logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 9/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/148:04 am -
3 stops35h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Multiple Airlines logo]()
$215
This Delta deal was found by Cheapflights users on 9/23. 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 10/126:30 am -
1 stop5h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Delta logo]()
$249
This Delta deal was found by Cheapflights users on 9/23. 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 10/126:04 am -
1 stop6h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Delta logo]()
$249
This American Airlines deal was found by Cheapflights users on 9/23. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:40 pm -
1 stop5h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![American Airlines logo]()
$260
This Kiwi.com deal was found by Cheapflights users on 9/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/116:00 am -
3 stops26h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/26![Multiple Airlines logo]()
$261
Find flight deals from Chicago to Mississippi
Keep the following information in mind while searching for Chicago to Mississippi flight deals. Data was last updated September 26, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $309 (American Airlines) |
One-way from | $155 (American Airlines) |
Popular in | December |
Cheapest in | August |
Average price | $588 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Mississippi 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 September 26, 2026.
Use the filters below to find and compare flights from Chicago to Mississippi that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoJackson
ORD Chicago O'Hare Intl - JAN Jackson-Evers Intl
ORDJAN
Chicago O'Hare Intl
Sat 11/14
3:00 pm-11:12 pm
1 stop8h 12m
Jackson-Evers Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$155
ChicagoJackson
MDW Chicago Midway - JAN Jackson-Evers Intl
MDWJAN
Chicago Midway
Sat 11/14
10:15 am-7:15 pm
2 stops9h 00m
Jackson-Evers Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$180
ChicagoJackson
MDW Chicago Midway - JAN Jackson-Evers Intl
MDWJAN
Chicago Midway
Sun 11/15
6:00 am-10:29 am
1 stop4h 29m
Jackson-Evers Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$199
ChicagoJackson
MDW Chicago Midway - JAN Jackson-Evers Intl
MDWJAN
Chicago Midway
Thu 10/22
11:50 am-7:50 pm
1 stop8h 00m
Jackson-Evers Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$214
ChicagoJackson
ORD Chicago O'Hare Intl - JAN Jackson-Evers Intl
ORDJAN
Chicago O'Hare Intl
Thu 10/22
5:00 am-11:45 am
1 stop6h 45m
Jackson-Evers Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$249
ChicagoJackson
ORD Chicago O'Hare Intl - JAN Jackson-Evers Intl
ORDJAN
Chicago O'Hare Intl
Mon 10/12
6:30 am-12:14 pm
1 stop5h 44m
Jackson-Evers Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$249
ChicagoJackson
MDW Chicago Midway - JAN Jackson-Evers Intl
MDWJAN
Chicago Midway
Mon 11/23
11:10 am-7:45 pm
2 stops8h 35m
Jackson-Evers Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$254
ChicagoGulfport
ORD Chicago O'Hare Intl - GPT Gulfport Biloxi Regional
ORDGPT
Chicago O'Hare Intl
Fri 10/23
6:40 pm-11:59 pm
1 stop5h 19m
Gulfport Biloxi Regional
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$260
ChicagoGulfport
ORD Chicago O'Hare Intl - GPT Gulfport Biloxi Regional
ORDGPT
Chicago O'Hare Intl
Sun 10/11
6:00 am-8:51 am
3 stops26h 51m
Gulfport Biloxi Regional
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$261
ChicagoGulfport
MDW Chicago Midway - GPT Gulfport Biloxi Regional
MDWGPT
Chicago Midway
Wed 10/14
3:30 pm-7:05 pm
3 stops27h 35m
Gulfport Biloxi Regional
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$265
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Chicago to Mississippi
Have a flexible travel schedule? Discover the best time to fly to Mississippi from Chicago with our price prediction graph.
ORD-JAN
MDW-JAN
ORD-GPT
MDW-GPT
ORD-GTR
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 Chicago to Mississippi
CHI-USMS
ORD-JAN
MDW-JAN
ORD-GPT
MDW-GPT
What is the cheapest month to book a flight from Chicago to Mississippi?
Currently, August is the cheapest month in which you can book a flight from Chicago to Mississippi (average of $306). Flying from Chicago to Mississippi in September is currently the most expensive (average of $588). 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 Chicago to Mississippi?
Airfare is below average for this route at the moment.
Chicago to Mississippi flights typically cost between $402 and $592 in November.The cheapest round-trip price found within the last 5 days was $309 on American Airlines (Nov 11-Nov 16).
Reviews of airlines servicing Mississippi
Get insights into the airlines that provide service to Mississippi. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Mississippi. Reviews last updated September 26, 2026.
See what other customers who have flown with Southwest,Delta, andAmerican Airlines from Chicago to Mississippi have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Boarding
8.1
Overall
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Comfort
8.0
Boarding
8.1
Overall
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Comfort
8.0
Boarding
8.1
Overall
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Comfort
8.0
Boarding
8.1
Overall
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Related info for your journey
Find useful and relevant information for your journey from Chicago to Mississippi. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chicago to Mississippi
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Mississippi by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Mississippi by cabin class
Find flights from Chicago to Mississippi, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Mississippi flights
Browse other Chicago and Mississippi flight options. Last updated on September 26, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Chicago to Mississippi flights
Consider these flights traveling from Chicago to Mississippi.
Top 3 airlines flying from Chicago to Mississippi
Discover the top 3 airlines that operate flights from Chicago to Mississippi. 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 September 26, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$268 | Average$530 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$293 | Average$511 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$308 | Average$562 | FlexibilityNo cancel fee | On-time63% |