$89+ 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 10/13. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — CHI
Oct 15 — Oct 221
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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
Cheapest
Best
Last-minute
One-way
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 September 15, 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 September 15, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Tue 10/136:11 pm -
1 stop21h 19m
Thu 11/128:00 am -
1 stop11h 04m
Deal found 9/14![Multiple Airlines logo]()
$206
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/146:41 am -
Nonstop2h 06m
Tue 10/2011:50 am -
Nonstop1h 57m
Deal found 9/14![American Airlines logo]()
$219
This Southwest deal was found by Cheapflights users on 9/14. 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 10/135:10 am -
Nonstop1h 35m
Tue 10/208:40 pm -
Nonstop1h 40m
Deal found 9/14![Southwest logo]()
$219
This Southwest deal was found by Cheapflights users on 9/14. 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 10/145:10 am -
Nonstop1h 35m
Tue 10/208:40 pm -
Nonstop1h 40m
Deal found 9/14![Southwest logo]()
$221
This Southwest deal was found by Cheapflights users on 9/14. 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 10/145:10 am -
Nonstop1h 35m
Wed 10/218:10 am -
1 stop6h 30m
Deal found 9/14![Southwest logo]()
$231
This Southwest deal was found by Cheapflights users on 9/13. 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 11/113:10 pm -
Nonstop1h 45m
Sat 11/1410:20 am -
Nonstop1h 40m
Deal found 9/13![Southwest logo]()
$233
This American Airlines deal was found by Cheapflights users on 9/15. 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 10/216:41 am -
Nonstop2h 06m
Mon 10/268:10 am -
Nonstop1h 58m
Deal found 9/15![American Airlines logo]()
$235
This Delta deal was found by Cheapflights users on 9/14. 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 11/146:00 am -
1 stop6h 20m
Tue 11/1710:32 am -
1 stop5h 21m
Deal found 9/14![Delta logo]()
$239
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/146:41 am -
Nonstop2h 06m
Mon 10/196:40 pm -
1 stop5h 15m
Deal found 9/14![American Airlines logo]()
$245
This Southwest deal was found by Cheapflights users on 9/14. 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 11/75:00 am -
Nonstop1h 40m
Mon 11/95:55 am -
1 stop7h 45m
Deal found 9/14![Southwest logo]()
$245
This Southwest deal was found by Cheapflights users on 9/14. 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 10/1712:30 pm -
1 stop7h 30m
Sat 10/248:40 am -
1 stop6h 05m
Deal found 9/14![Southwest logo]()
$246
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
Thu 10/297:54 pm -
1 stop28h 27m
Sun 11/16:30 am -
1 stop12h 39m
Deal found 9/11![Frontier logo]()
$248
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 September 15, 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 September 15, 2026.
This Southwest deal was found by Cheapflights users on 9/14. 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 10/133:15 pm -
Nonstop1h 35m
Tue 10/201:05 pm -
2 stops8h 10m
Deal found 9/14![Southwest logo]()
$234
This Delta deal was found by Cheapflights users on 9/14. 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 10/133:35 pm -
1 stop5h 03m
Tue 10/208:05 am -
1 stop6h 25m
Deal found 9/14![Delta logo]()
$239
This American Airlines deal was found by Cheapflights users on 9/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/102:29 pm -
1 stop6h 09m
Sat 10/178:14 am -
1 stop5h 45m
Deal found 9/10![American Airlines logo]()
$314
This United Airlines deal was found by Cheapflights users on 9/11. 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 11/196:15 pm -
1 stop6h 30m
Mon 11/235:30 am -
1 stop5h 51m
Deal found 9/11![United Airlines logo]()
$319
This Southwest deal was found by Cheapflights users on 9/13. 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 11/116:25 am -
2 stops10h 40m
Sat 11/1410:20 am -
Nonstop1h 40m
Deal found 9/13![Southwest logo]()
$249
This Delta deal was found by Cheapflights users on 9/15. 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 10/2110:41 am -
1 stop6h 17m
Mon 10/265:27 am -
1 stop4h 09m
Deal found 9/15![Delta logo]()
$255
This Southwest deal was found by Cheapflights users on 9/14. 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 10/1712:30 pm -
2 stops7h 05m
Sat 10/246:55 am -
2 stops7h 50m
Deal found 9/14![Southwest logo]()
$257
This United Airlines deal was found by Cheapflights users on 9/14. 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 11/207:00 am -
Nonstop2h 00m
Mon 11/238:43 am -
Nonstop2h 07m
Deal found 9/14![United Airlines logo]()
$326
This Delta deal was found by Cheapflights users on 9/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:20 am -
1 stop6h 00m
Sun 11/156:49 am -
1 stop6h 16m
Deal found 9/10![Delta logo]()
$310
This Southwest deal was found by Cheapflights users on 9/10. 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.
Thu 10/15:20 am -
Nonstop1h 35m
Mon 10/510:20 pm -
Nonstop1h 35m
Deal found 9/10![Southwest logo]()
$293
This United Airlines deal was found by Cheapflights users on 9/11. 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 11/177:00 am -
Nonstop2h 00m
Wed 11/188:43 am -
Nonstop2h 07m
Deal found 9/11![United Airlines logo]()
$327
This American Airlines deal was found by Cheapflights users on 9/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:17 pm -
1 stop5h 42m
Fri 11/276:41 am -
1 stop5h 32m
Deal found 9/10![American Airlines logo]()
$371
This Delta deal was found by Cheapflights users on 9/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1011:59 am -
1 stop7h 06m
Sat 11/148:04 am -
1 stop6h 31m
Deal found 9/10![Delta logo]()
$313
This Southwest deal was found by Cheapflights users on 9/14. 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 10/2912:00 pm -
2 stops7h 55m
Thu 11/512:25 pm -
1 stop9h 45m
Deal found 9/14![Southwest logo]()
$304
This United Airlines deal was found by Cheapflights users on 9/11. 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 12/22:35 pm -
Nonstop2h 05m
Thu 12/38:40 am -
Nonstop2h 08m
Deal found 9/11![United Airlines logo]()
$341
This Delta deal was found by Cheapflights users on 9/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/96:04 pm -
1 stop5h 50m
Sun 11/156:49 am -
1 stop6h 16m
Deal found 9/10![Delta logo]()
$319
This United Airlines deal was found by Cheapflights users on 9/14. 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 10/307:00 am -
Nonstop2h 00m
Sun 11/112:40 pm -
Nonstop2h 04m
Deal found 9/14![United Airlines logo]()
$342
This Southwest deal was found by Cheapflights users on 9/14. 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 12/315:25 am -
Nonstop1h 40m
Tue 1/510:15 am -
Nonstop1h 40m
Deal found 9/14![Southwest logo]()
$311
This Delta deal was found by Cheapflights users on 9/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/96:04 pm -
1 stop5h 50m
Mon 11/162:44 pm -
2 stops7h 08m
Deal found 9/10![Delta logo]()
$324
This American Airlines deal was found by Cheapflights users on 9/13. 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 10/212:17 pm -
1 stop8h 13m
Mon 10/54:45 pm -
1 stop7h 10m
Deal found 9/13![American Airlines logo]()
$447
This United Airlines deal was found by Cheapflights users on 9/12. 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 11/102:40 pm -
Nonstop2h 08m
Tue 11/249:44 pm -
Nonstop2h 00m
Deal found 9/12![United Airlines logo]()
$347
This Delta deal was found by Cheapflights users on 9/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/131:50 pm -
1 stop6h 59m
Mon 11/166:00 am -
2 stops11h 19m
Deal found 9/10![Delta logo]()
$324
This Southwest deal was found by Cheapflights users on 9/10. 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.
Thu 10/2212:00 pm -
1 stop3h 55m
Tue 11/36:40 am -
1 stop5h 50m
Deal found 9/10![Southwest logo]()
$332
This United Airlines deal was found by Cheapflights users on 9/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/62:40 pm -
Nonstop2h 08m
Sun 11/89:44 pm -
Nonstop2h 00m
Deal found 9/10![United Airlines logo]()
$355
This Southwest deal was found by Cheapflights users on 9/13. 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 2/135:30 am -
2 stops11h 15m
Mon 2/1511:00 am -
2 stops9h 55m
Deal found 9/13![Southwest logo]()
$332
This Delta deal was found by Cheapflights users on 9/11. 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 11/186:00 am -
1 stop5h 59m
Wed 11/251:05 pm -
1 stop5h 24m
Deal found 9/11![Delta logo]()
$333
This Delta deal was found by Cheapflights users on 9/12. 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 10/174:26 pm -
1 stop7h 31m
Sat 10/246:30 am -
1 stop6h 26m
Deal found 9/12![Delta logo]()
$333
This United Airlines deal was found by Cheapflights users on 9/13. 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 11/119:51 am -
Nonstop2h 08m
Sat 11/1412:40 pm -
Nonstop2h 04m
Deal found 9/13![United Airlines logo]()
$368
This Southwest deal was found by Cheapflights users on 9/10. 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.
Wed 11/183:10 pm -
Nonstop1h 45m
Sat 11/215:50 pm -
2 stops6h 00m
Deal found 9/10![Southwest logo]()
$346
This Delta deal was found by Cheapflights users on 9/14. 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 10/146:26 am -
2 stops6h 33m
Mon 10/196:30 am -
1 stop6h 31m
Deal found 9/14![Delta logo]()
$335
Last-minute flights from Mississippi to ChicagoDiscover last-minute flight deals from Mississippi to Chicago. Data last updated September 15, 2026 and is based on user searches.
Discover last-minute flight deals from Mississippi to Chicago. Data last updated September 15, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Tue 10/136:11 pm -
1 stop21h 19m
Thu 11/128:00 am -
1 stop11h 04m
Deal found 9/14![Multiple Airlines logo]()
$206
This Southwest deal was found by Cheapflights users on 9/15. 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 10/133:15 pm -
Nonstop1h 35m
Wed 10/148:40 pm -
Nonstop1h 40m
Deal found 9/15![Southwest logo]()
$219
This Southwest deal was found by Cheapflights users on 9/14. 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 10/133:15 pm -
Nonstop1h 35m
Tue 10/206:25 am -
1 stop6h 10m
Deal found 9/14![Southwest logo]()
$229
This Delta deal was found by Cheapflights users on 9/14. 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 10/133:35 pm -
1 stop5h 03m
Tue 10/208:05 am -
1 stop6h 25m
Deal found 9/14![Delta logo]()
$239
This Delta deal was found by Cheapflights users on 9/15. 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 10/133:35 pm -
1 stop6h 58m
Wed 10/146:04 am -
1 stop6h 49m
Deal found 9/15![Delta logo]()
$239
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/146:41 am -
Nonstop2h 06m
Tue 10/2011:50 am -
Nonstop1h 57m
Deal found 9/14![American Airlines logo]()
$219
This Southwest deal was found by Cheapflights users on 9/14. 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 10/145:10 am -
Nonstop1h 35m
Tue 10/208:40 pm -
Nonstop1h 40m
Deal found 9/14![Southwest logo]()
$221
This Southwest deal was found by Cheapflights users on 9/14. 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 10/145:10 am -
Nonstop1h 35m
Wed 10/218:10 am -
1 stop6h 30m
Deal found 9/14![Southwest logo]()
$231
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/146:41 am -
Nonstop2h 06m
Mon 10/196:40 pm -
1 stop5h 15m
Deal found 9/14![American Airlines logo]()
$245
This Southwest deal was found by Cheapflights users on 9/14. 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 10/1712:30 pm -
1 stop7h 30m
Sat 10/248:40 am -
1 stop6h 05m
Deal found 9/14![Southwest logo]()
$246
This American Airlines deal was found by Cheapflights users on 9/15. 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 10/216:41 am -
Nonstop2h 06m
Mon 10/268:10 am -
Nonstop1h 58m
Deal found 9/15![American Airlines logo]()
$235
This Southwest deal was found by Cheapflights users on 9/15. 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 10/215:10 am -
Nonstop1h 35m
Thu 10/2210:20 pm -
Nonstop1h 35m
Deal found 9/15![Southwest logo]()
$235
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 September 15, 2026.
Search for one-way flight options from Mississippi to Chicago. Find affordable one-way fares based on user searches. Data last updated September 15, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Tue 10/136:11 pm -
1 stop21h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Multiple Airlines logo]()
$89
This American Airlines deal was found by Cheapflights users on 9/15. 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 10/145:52 pm -
Nonstop2h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![American Airlines logo]()
$110
This Southwest deal was found by Cheapflights users on 9/15. 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 10/133:15 pm -
Nonstop1h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Southwest logo]()
$110
This Southwest deal was found by Cheapflights users on 9/14. 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 10/145:10 am -
Nonstop1h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Southwest logo]()
$111
This Delta deal was found by Cheapflights users on 9/15. 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 10/174:43 pm -
1 stop7h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Delta logo]()
$120
This Delta deal was found by Cheapflights users on 9/14. 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 10/285:02 pm -
1 stop6h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Delta logo]()
$123
This Delta deal was found by Cheapflights users on 9/14. 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 10/289:18 am -
1 stop6h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Delta logo]()
$123
This Southwest deal was found by Cheapflights users on 9/14. 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 10/171:35 pm -
Nonstop1h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Southwest logo]()
$123
This American Airlines deal was found by Cheapflights users on 9/15. 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 10/125:52 pm -
Nonstop2h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![American Airlines logo]()
$126
This Southwest deal was found by Cheapflights users on 9/14. 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 10/2812:55 pm -
2 stops9h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Southwest logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/127:58 pm -
2 stops43h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Multiple Airlines logo]()
$130
This Frontier deal was found by Cheapflights users on 9/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/116:51 pm -
1 stop12h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$136
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 September 15, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $206 (Kiwi.com) |
One-way from | $89 (Kiwi.com) |
Popular in | June |
Cheapest in | April |
Average price | $470 |
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 September 15, 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
MemphisChicago
MEM Memphis - ORD Chicago O'Hare Intl
MEMORD
Memphis
Wed 10/14
11:55 am-4:58 pm
1 stop5h 03m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$120
MemphisChicago
MEM Memphis - MDW Chicago Midway
MEMMDW
Memphis
Sat 10/17
4:43 pm-10:33 pm
1 stop5h 50m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$120
MemphisChicago
MEM Memphis - MDW Chicago Midway
MEMMDW
Memphis
Mon 10/12
6:08 pm-10:33 pm
1 stop4h 25m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$136
MemphisChicago
MEM Memphis - MDW Chicago Midway
MEMMDW
Memphis
Sat 11/14
8:15 am-2:50 pm
2 stops6h 35m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$138
JacksonChicago
JAN Jackson-Evers Intl - MDW Chicago Midway
JANMDW
Jackson-Evers Intl
Wed 10/7
12:55 pm-9:25 pm
2 stops8h 30m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$141
MemphisChicago
MEM Memphis - ORD Chicago O'Hare Intl
MEMORD
Memphis
Mon 10/5
6:25 pm-8:34 pm
Nonstop2h 09m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$147
MemphisChicago
MEM Memphis - ORD Chicago O'Hare Intl
MEMORD
Memphis
Tue 10/13
9:48 am-11:59 am
Nonstop2h 11m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$147
JacksonChicago
JAN Jackson-Evers Intl - MDW Chicago Midway
JANMDW
Jackson-Evers Intl
Thu 10/29
12:00 pm-3:55 pm
1 stop3h 55m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$147
Quickest round-trip
MemphisChicago
MEM Memphis - MDW Chicago Midway
MEMMDW
Memphis
Thu 12/10
3:10 pm-4:55 pm
Nonstop1h 45m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$147
MemphisChicago
MEM Memphis - MDW Chicago Midway
MEMMDW
Memphis
Fri 11/13
4:53 pm-10:54 pm
1 stop6h 01m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$152
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.
MEM-MDW
MEM-ORD
BTR-ORD
JAN-MDW
GPT-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
MEM-MDW
MEM-ORD
BTR-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 $345). 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.
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
Lansing
Merrillville
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
Flights by cabin class
Other flight options
Popular flights
Top destinations
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 September 15, 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 September 15, 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 September 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$248 | Average$469 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$254 | Average$467 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$308 | Average$428 | FlexibilityNo cancel fee | On-time63% |