$129+ 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
Dec 10 — Dec 171
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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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Mississippi to Chicago
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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 November 10, 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 November 10, 2026.
This Delta deal was found by Cheapflights users on 11/5. 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 12/54:00 pm -
1 stop6h 54m
Sat 12/124:08 pm -
1 stop4h 45m
Deal found 11/5![Delta logo]()
$331
This American Airlines deal was found by Cheapflights users on 11/5. 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 12/56:35 pm -
1 stop5h 24m
Sat 12/125:59 pm -
1 stop5h 31m
Deal found 11/5![American Airlines logo]()
$331
This American Airlines deal was found by Cheapflights users on 11/8. 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 12/212:14 pm -
1 stop7h 45m
Sat 12/511:47 am -
1 stop5h 36m
Deal found 11/8![American Airlines logo]()
$333
This Southwest deal was found by Cheapflights users on 11/8. 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 12/26:15 pm -
1 stop4h 55m
Sat 12/57:50 am -
1 stop3h 40m
Deal found 11/8![Southwest logo]()
$333
This Delta deal was found by Cheapflights users on 11/5. 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 12/54:00 pm -
1 stop4h 53m
Sat 12/129:59 am -
2 stops10h 54m
Deal found 11/5![Delta logo]()
$336
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 12/149:36 am -
1 stop19h 25m
Wed 1/134:47 pm -
2 stops40h 04m
Deal found 11/6![Multiple Airlines logo]()
$340
This Delta deal was found by Cheapflights users on 11/7. 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 stop4h 45m
Mon 12/1411:28 am -
1 stop5h 56m
Deal found 11/7![Delta logo]()
$349
This American Airlines deal was found by Cheapflights users on 11/9. 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 12/25:42 pm -
1 stop6h 17m
Sat 12/54:45 pm -
1 stop5h 58m
Deal found 11/9![American Airlines logo]()
$349
This Southwest deal was found by Cheapflights users on 11/10. 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 12/86:15 pm -
1 stop4h 55m
Tue 12/1512:45 pm -
1 stop4h 50m
Deal found 11/10![Southwest logo]()
$350
This Delta deal was found by Cheapflights users on 11/9. 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 12/26:15 am -
2 stops7h 41m
Sat 12/58:00 am -
1 stop6h 27m
Deal found 11/9![Delta logo]()
$354
This American Airlines deal was found by Cheapflights users on 11/6. 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 12/42:59 pm -
1 stop7h 33m
Tue 12/84:00 pm -
1 stop7h 12m
Deal found 11/6![American Airlines logo]()
$358
This Delta deal was found by Cheapflights users on 11/9. 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 12/73:48 pm -
1 stop5h 05m
Mon 12/146:16 pm -
1 stop4h 49m
Deal found 11/9![Delta logo]()
$363
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 November 10, 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 November 10, 2026.
This Delta deal was found by Cheapflights users on 11/5. 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 12/54:00 pm -
1 stop6h 54m
Sat 12/1210:24 am -
2 stops10h 29m
Deal found 11/5![Delta logo]()
$336
This United Airlines deal was found by Cheapflights users on 11/7. 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.
Mon 12/75:05 pm -
1 stop5h 51m
Mon 12/1410:30 am -
1 stop5h 38m
Deal found 11/7![United Airlines logo]()
$349
This Southwest deal was found by Cheapflights users on 11/10. 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 12/86:15 pm -
1 stop4h 55m
Tue 12/1512:45 pm -
1 stop4h 50m
Deal found 11/10![Southwest logo]()
$350
This United Airlines deal was found by Cheapflights users on 11/6. 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 5/55:15 pm -
1 stop5h 21m
Sun 5/96:00 am -
1 stop7h 26m
Deal found 11/6![United Airlines logo]()
$353
This Delta deal was found by Cheapflights users on 11/7. 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 stop4h 45m
Mon 12/141:41 pm -
2 stops8h 16m
Deal found 11/7![Delta logo]()
$354
This Delta deal was found by Cheapflights users on 11/7. 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 11/245:06 pm -
1 stop6h 48m
Sat 11/285:30 am -
1 stop5h 01m
Deal found 11/7![Delta logo]()
$369
This Southwest deal was found by Cheapflights users on 11/8. 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 12/65:20 pm -
1 stop4h 50m
Deal found 11/8![Southwest logo]()
$415
This United Airlines deal was found by Cheapflights users on 11/5. 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 11/204:55 pm -
1 stop7h 50m
Mon 11/236:55 am -
1 stop6h 23m
Deal found 11/5![United Airlines logo]()
$379
This Delta deal was found by Cheapflights users on 11/6. 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 5/56:00 am -
2 stops11h 47m
Sun 5/97:10 am -
1 stop6h 25m
Deal found 11/6![Delta logo]()
$370
This Southwest deal was found by Cheapflights users on 11/5. 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 12/188:15 pm -
1 stop4h 45m
Mon 12/2112:50 pm -
2 stops9h 35m
Deal found 11/5![Southwest logo]()
$446
This Delta deal was found by Cheapflights users on 11/5. 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 11/231:31 pm -
2 stops8h 21m
Deal found 11/5![Delta logo]()
$384
This Delta deal was found by Cheapflights users on 11/6. 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 11/226:04 pm -
1 stop4h 50m
Thu 11/2612:05 pm -
2 stops8h 38m
Deal found 11/6![Delta logo]()
$384
This Southwest deal was found by Cheapflights users on 11/5. 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 12/188:15 pm -
1 stop4h 45m
Mon 12/285:10 am -
1 stop5h 45m
Deal found 11/5![Southwest logo]()
$471
This Delta deal was found by Cheapflights users on 11/6. 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 11/206:04 pm -
1 stop5h 50m
Mon 11/232:44 pm -
2 stops7h 08m
Deal found 11/6![Delta logo]()
$384
This United Airlines deal was found by Cheapflights users on 11/5. 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 12/811:58 am -
1 stop10h 57m
Fri 12/119:45 pm -
2 stops15h 35m
Deal found 11/5![United Airlines logo]()
$536
This Southwest deal was found by Cheapflights users on 11/9. 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 12/256:30 am -
1 stop5h 55m
Mon 12/2812:30 pm -
2 stops9h 55m
Deal found 11/9![Southwest logo]()
$490
This Delta deal was found by Cheapflights users on 11/8. 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 11/236:26 am -
2 stops10h 15m
Fri 11/276:00 am -
1 stop5h 09m
Deal found 11/8![Delta logo]()
$384
This Southwest deal was found by Cheapflights users on 11/7. 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 12/238:15 pm -
1 stop4h 45m
Sun 12/275:10 am -
1 stop5h 45m
Deal found 11/7![Southwest logo]()
$504
This Delta deal was found by Cheapflights users on 11/5. 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 11/206:04 pm -
1 stop4h 50m
Mon 11/231:31 pm -
2 stops8h 21m
Deal found 11/5![Delta logo]()
$404
This United Airlines deal was found by Cheapflights users on 11/6. 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 12/45:25 pm -
2 stops13h 23m
Tue 12/89:45 pm -
2 stops23h 56m
Deal found 11/6![United Airlines logo]()
$626
This Southwest deal was found by Cheapflights users on 11/8. 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 11/2311:45 am -
1 stop4h 25m
Fri 11/275:20 pm -
1 stop4h 50m
Deal found 11/8![Southwest logo]()
$527
This Delta deal was found by Cheapflights users on 11/9. 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 12/210:04 am -
2 stops7h 57m
Sat 12/54:08 pm -
1 stop4h 45m
Deal found 11/9![Delta logo]()
$409
This Southwest deal was found by Cheapflights users on 11/7. 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
Thu 11/2610:10 am -
2 stops6h 20m
Deal found 11/7![Southwest logo]()
$532
This United Airlines deal was found by Cheapflights users on 11/5. 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 1/308:40 am -
1 stop14h 19m
Wed 2/32:22 pm -
1 stop20h 38m
Deal found 11/5![United Airlines logo]()
$644
This Delta deal was found by Cheapflights users on 11/7. 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 12/710:04 am -
2 stops12h 09m
Mon 12/142:41 pm -
2 stops7h 16m
Deal found 11/7![Delta logo]()
$410
This United Airlines deal was found by Cheapflights users on 11/6. 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 12/311:45 am -
2 stops18h 44m
Sun 12/610:30 am -
1 stop8h 14m
Deal found 11/6![United Airlines logo]()
$658
This Delta deal was found by Cheapflights users on 11/5. 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 12/185:11 pm -
1 stop6h 45m
Mon 12/285:25 am -
1 stop5h 46m
Deal found 11/5![Delta logo]()
$433
This United Airlines deal was found by Cheapflights users on 11/7. 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 1/3011:10 am -
1 stop10h 23m
Tue 2/27:50 pm -
1 stop18h 16m
Deal found 11/7![United Airlines logo]()
$676
This Delta deal was found by Cheapflights users on 11/7. 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 11/247:51 am -
1 stop6h 58m
Mon 11/303:59 pm -
1 stop4h 40m
Deal found 11/7![Delta logo]()
$455
This United Airlines deal was found by Cheapflights users on 11/6. 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 2/611:10 am -
1 stop11h 49m
Tue 2/98:10 pm -
2 stops17h 56m
Deal found 11/6![United Airlines logo]()
$676
Last-minute flights from Mississippi to ChicagoDiscover last-minute flight deals from Mississippi to Chicago. Data last updated November 10, 2026 and is based on user searches.
Discover last-minute flight deals from Mississippi to Chicago. Data last updated November 10, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 11/8. 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 12/212:14 pm -
1 stop7h 45m
Sat 12/511:47 am -
1 stop5h 36m
Deal found 11/8![American Airlines logo]()
$333
This Southwest deal was found by Cheapflights users on 11/8. 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 12/26:15 pm -
1 stop4h 55m
Sat 12/57:50 am -
1 stop3h 40m
Deal found 11/8![Southwest logo]()
$333
This American Airlines deal was found by Cheapflights users on 11/9. 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 12/25:42 pm -
1 stop6h 17m
Sat 12/54:45 pm -
1 stop5h 58m
Deal found 11/9![American Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 11/9. 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 12/26:15 am -
2 stops7h 41m
Sat 12/58:00 am -
1 stop6h 27m
Deal found 11/9![Delta logo]()
$354
This American Airlines deal was found by Cheapflights users on 11/6. 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 12/42:59 pm -
1 stop7h 33m
Tue 12/84:00 pm -
1 stop7h 12m
Deal found 11/6![American Airlines logo]()
$358
This Delta deal was found by Cheapflights users on 11/5. 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 12/54:00 pm -
1 stop6h 54m
Sat 12/124:08 pm -
1 stop4h 45m
Deal found 11/5![Delta logo]()
$331
This American Airlines deal was found by Cheapflights users on 11/5. 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 12/56:35 pm -
1 stop5h 24m
Sat 12/125:59 pm -
1 stop5h 31m
Deal found 11/5![American Airlines logo]()
$331
This Delta deal was found by Cheapflights users on 11/5. 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 12/54:00 pm -
1 stop4h 53m
Sat 12/129:59 am -
2 stops10h 54m
Deal found 11/5![Delta logo]()
$336
This Delta deal was found by Cheapflights users on 11/7. 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 stop4h 45m
Mon 12/1411:28 am -
1 stop5h 56m
Deal found 11/7![Delta logo]()
$349
This Delta deal was found by Cheapflights users on 11/9. 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 12/73:48 pm -
1 stop5h 05m
Mon 12/146:16 pm -
1 stop4h 49m
Deal found 11/9![Delta logo]()
$363
This Southwest deal was found by Cheapflights users on 11/10. 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 12/86:15 pm -
1 stop4h 55m
Tue 12/1512:45 pm -
1 stop4h 50m
Deal found 11/10![Southwest logo]()
$350
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 12/149:36 am -
1 stop19h 25m
Wed 1/134:47 pm -
2 stops40h 04m
Deal found 11/6![Multiple Airlines logo]()
$340
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 November 10, 2026.
Search for one-way flight options from Mississippi to Chicago. Find affordable one-way fares based on user searches. Data last updated November 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/7. 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 11/7![Multiple Airlines logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 11/8. 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 12/216:46 pm -
2 stops22h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![Multiple Airlines logo]()
$163
This Delta deal was found by Cheapflights users on 11/5. 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 12/15:20 am -
1 stop5h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Delta logo]()
$164
This American Airlines deal was found by Cheapflights users on 11/8. 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 11/246:30 pm -
1 stop5h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![American Airlines logo]()
$178
This American Airlines deal was found by Cheapflights users on 11/5. 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 11/215:01 pm -
1 stop6h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![American Airlines logo]()
$179
This Delta deal was found by Cheapflights users on 11/9. 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 11/255:30 am -
1 stop6h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Delta logo]()
$179
This Delta deal was found by Cheapflights users on 11/9. 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 12/711:14 am -
1 stop5h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Delta logo]()
$182
This Southwest deal was found by Cheapflights users on 11/9. 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 12/146:15 pm -
1 stop4h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Southwest logo]()
$182
This Southwest deal was found by Cheapflights users on 11/5. 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 11/213:35 pm -
1 stop8h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Southwest logo]()
$184
This Delta deal was found by Cheapflights users on 11/8. 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 11/251:20 pm -
1 stop5h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![Delta logo]()
$185
This Delta deal was found by Cheapflights users on 11/8. 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 11/245:06 pm -
1 stop6h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![Delta logo]()
$186
This Delta deal was found by Cheapflights users on 11/8. 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 11/245:30 am -
1 stop4h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![Delta logo]()
$186
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 November 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $331 (Delta) |
One-way from | $129 (Kiwi.com) |
Popular in | June |
Cheapest in | April |
Average price | $396 |
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 November 10, 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-10:00 pm
3 stops27h 14m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$158
GulfportChicago
GPT Gulfport Biloxi Regional - ORD Chicago O'Hare Intl
GPTORD
Gulfport Biloxi Regional
Mon 12/21
6:46 pm-4:52 pm
2 stops22h 06m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$163
JacksonChicago
JAN Jackson-Evers Intl - ORD Chicago O'Hare Intl
JANORD
Jackson-Evers Intl
Tue 11/24
5:01 pm-12:20 am
1 stop7h 19m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$178
JacksonChicago
JAN Jackson-Evers Intl - MDW Chicago Midway
JANMDW
Jackson-Evers Intl
Mon 12/14
6:15 pm-11:10 pm
1 stop4h 55m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$182
JacksonChicago
JAN Jackson-Evers Intl - MDW Chicago Midway
JANMDW
Jackson-Evers Intl
Sat 11/21
3:35 pm-12:25 am
1 stop8h 50m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$184
JacksonChicago
JAN Jackson-Evers Intl - ORD Chicago O'Hare Intl
JANORD
Jackson-Evers Intl
Tue 11/24
5:06 pm-11:54 pm
1 stop6h 48m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$186
JacksonChicago
JAN Jackson-Evers Intl - ORD Chicago O'Hare Intl
JANORD
Jackson-Evers Intl
Wed 11/25
1:20 pm-7:05 pm
1 stop5h 45m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$186
JacksonChicago
JAN Jackson-Evers Intl - MDW Chicago Midway
JANMDW
Jackson-Evers Intl
Tue 11/24
5:30 am-10:24 am
1 stop4h 54m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$186
JacksonChicago
JAN Jackson-Evers Intl - ORD Chicago O'Hare Intl
JANORD
Jackson-Evers Intl
Thu 12/24
4:05 pm-11:07 pm
1 stop7h 02m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$191
JacksonChicago
JAN Jackson-Evers Intl - ORD Chicago O'Hare Intl
JANORD
Jackson-Evers Intl
Mon 12/14
5:20 am-10:25 am
1 stop5h 05m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$191
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.
GPT-MDW
GPT-ORD
JAN-ORD
JAN-MDW
MEI-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
GPT-MDW
GPT-ORD
JAN-ORD
JAN-MDW
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 $345 and $566 in December.The cheapest round-trip price found within the last 5 days was $333 on American Airlines (Dec 2-Dec 5).
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
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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 November 10, 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 November 10, 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 November 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$286 | Average$409 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$296 | Average$502 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$308 | Average$489 | FlexibilityNo cancel fee | On-time63% |