$155+ 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 11/7. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — CHI
Oct 25 — Nov 11
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
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
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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 September 25, 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 25, 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.
Sat 11/78:00 am -
1 stop4h 13m
Mon 11/96:15 pm -
1 stop4h 50m
Deal found 9/23![Delta logo]()
$309
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 10/213:33 pm -
1 stop7h 00m
Tue 10/276:04 am -
1 stop4h 21m
Deal found 9/21![Delta logo]()
$309
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.
Wed 10/2112:55 pm -
2 stops9h 05m
Tue 10/276:25 am -
1 stop5h 50m
Deal found 9/21![Southwest logo]()
$314
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.
Sat 11/215:05 pm -
1 stop5h 49m
Tue 12/16:00 am -
1 stop7h 11m
Deal found 9/23![Delta logo]()
$321
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.
Sat 11/215:05 pm -
1 stop6h 49m
Tue 12/16:49 am -
1 stop6h 22m
Deal found 9/23![Delta logo]()
$321
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 10/304:46 pm -
1 stop5h 24m
Mon 11/23:00 pm -
1 stop5h 50m
Deal found 9/24![American Airlines logo]()
$329
This Delta deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 11/711:10 am -
1 stop4h 07m
Mon 11/95:13 pm -
1 stop5h 52m
Deal found 9/20![Delta logo]()
$329
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 11/236:04 pm -
1 stop4h 50m
Tue 12/16:00 am -
1 stop7h 11m
Deal found 9/23![Delta logo]()
$330
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 10/216:02 pm -
1 stop5h 57m
Sun 10/256:00 am -
1 stop5h 13m
Deal found 9/21![American 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.
Sun 11/226:04 pm -
1 stop5h 50m
Tue 12/17:00 am -
2 stops10h 24m
Deal found 9/23![Delta logo]()
$335
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 11/126:26 am -
1 stop5h 33m
Mon 11/166:00 am -
1 stop7h 04m
Deal found 9/23![Delta logo]()
$339
This American Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 11/126:20 am -
1 stop8h 10m
Mon 11/166:00 am -
1 stop5h 11m
Deal found 9/20![American Airlines logo]()
$339
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 25, 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 25, 2026.
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.
Thu 1/712:10 pm -
1 stop4h 27m
Wed 1/137:10 am -
1 stop4h 12m
Deal found 9/21![Delta logo]()
$309
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 1/712:55 pm -
1 stop5h 25m
Wed 1/1312:25 pm -
2 stops7h 25m
Deal found 9/21![Southwest logo]()
$314
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 11/126:20 am -
1 stop8h 10m
Mon 11/166:00 am -
1 stop5h 11m
Deal found 9/21![American Airlines logo]()
$339
This Contour 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 Contour is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/218:00 am -
2 stops27h 40m
Wed 10/2812:30 pm -
2 stops23h 40m
Deal found 9/24![Contour logo]()
$366
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 10/75:14 pm -
1 stop7h 09m
Sun 10/115:30 am -
1 stop5h 48m
Deal found 9/22![United Airlines logo]()
$369
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/68:00 am -
3 stops28h 51m
Sun 11/812:30 pm -
2 stops6h 15m
Deal found 9/24![Multiple Airlines logo]()
$411
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 11/123:50 pm -
1 stop7h 04m
Tue 11/176:00 am -
1 stop4h 29m
Deal found 9/22![Delta logo]()
$309
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.
Fri 10/3012:00 pm -
1 stop5h 55m
Mon 11/25:20 pm -
1 stop4h 45m
Deal found 9/24![Southwest 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.
Sat 11/215:05 pm -
1 stop5h 49m
Tue 12/16:00 am -
1 stop7h 11m
Deal found 9/23![Delta logo]()
$321
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.
Sat 10/106:02 pm -
1 stop5h 57m
Sat 10/176:40 pm -
1 stop5h 19m
Deal found 9/23![American Airlines logo]()
$354
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.
Tue 11/106:15 pm -
1 stop4h 55m
Sun 11/155:15 am -
1 stop5h 50m
Deal found 9/22![Southwest logo]()
$353
This Delta deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 11/711:10 am -
1 stop4h 07m
Mon 11/95:13 pm -
1 stop5h 52m
Deal found 9/20![Delta logo]()
$329
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/74:55 pm -
1 stop6h 31m
Tue 11/102:22 pm -
1 stop5h 12m
Deal found 9/24![United Airlines logo]()
$421
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.
Thu 12/36:30 am -
2 stops9h 00m
Sun 12/65:15 am -
1 stop5h 50m
Deal found 9/24![Southwest logo]()
$358
This Contour 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 Contour is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/88:00 am -
2 stops27h 40m
Mon 10/1212:30 pm -
2 stops23h 40m
Deal found 9/23![Contour logo]()
$436
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 11/236:04 pm -
1 stop4h 50m
Tue 12/16:00 am -
1 stop7h 11m
Deal found 9/23![Delta logo]()
$330
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2112:55 pm -
1 stop11h 31m
Wed 10/2810:40 am -
1 stop8h 25m
Deal found 9/21![Multiple Airlines logo]()
$474
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.
Thu 12/241:10 pm -
1 stop5h 55m
Thu 12/3112:45 pm -
1 stop4h 50m
Deal found 9/22![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.
Fri 11/136:04 pm -
1 stop4h 50m
Mon 11/1611:27 am -
1 stop5h 52m
Deal found 9/21![Delta logo]()
$339
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.
Sun 10/258:25 pm -
1 stop4h 35m
Thu 10/292:30 pm -
1 stop5h 20m
Deal found 9/21![Southwest logo]()
$363
This Contour 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 Contour is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/78:00 am -
2 stops27h 40m
Sun 10/1112:30 pm -
2 stops23h 40m
Deal found 9/22![Contour logo]()
$485
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.
Thu 3/42:15 pm -
1 stop6h 55m
Sun 3/75:55 pm -
1 stop4h 12m
Deal found 9/24![Delta logo]()
$339
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/71:20 pm -
1 stop5h 03m
Sun 10/1110:26 am -
1 stop5h 54m
Deal found 9/22![Multiple Airlines logo]()
$524
This United Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 10/158:20 am -
1 stop8h 21m
Mon 10/195:30 am -
1 stop5h 53m
Deal found 9/20![United Airlines logo]()
$552
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.
Thu 11/126:26 am -
1 stop5h 33m
Mon 11/1612:30 pm -
2 stops9h 22m
Deal found 9/21![Delta logo]()
$344
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/69:00 am -
2 stops30h 20m
Sat 10/106:00 am -
1 stop10h 20m
Deal found 9/21![Multiple Airlines logo]()
$540
This Delta deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 stop5h 15m
Mon 11/166:23 am -
2 stops10h 56m
Deal found 9/20![Delta logo]()
$344
This United Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/25:20 pm -
2 stops17h 40m
Wed 2/34:35 pm -
2 stops18h 38m
Deal found 9/20![United Airlines logo]()
$556
This United Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 11/76:50 am -
2 stops13h 29m
Mon 11/92:12 pm -
2 stops23h 07m
Deal found 9/20![United Airlines logo]()
$556
This Delta deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1210:04 am -
2 stops10h 13m
Mon 11/168:29 am -
2 stops8h 50m
Deal found 9/20![Delta logo]()
$349
Last-minute flights from Mississippi to ChicagoDiscover last-minute flight deals from Mississippi to Chicago. Data last updated September 25, 2026 and is based on user searches.
Discover last-minute flight deals from Mississippi to Chicago. Data last updated September 25, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 10/106:02 pm -
1 stop5h 57m
Sat 10/176:40 pm -
1 stop5h 19m
Deal found 9/20![American Airlines logo]()
$354
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.
Sat 10/1712:30 pm -
1 stop7h 30m
Mon 12/2112:50 pm -
2 stops9h 30m
Deal found 9/23![Southwest logo]()
$346
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 10/211:04 pm -
1 stop6h 07m
Tue 10/275:27 am -
1 stop6h 47m
Deal found 9/21![Delta logo]()
$309
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 10/213:33 pm -
1 stop7h 00m
Tue 10/276:04 am -
1 stop4h 21m
Deal found 9/21![Delta logo]()
$309
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.
Wed 10/2112:55 pm -
2 stops9h 05m
Tue 10/276:25 am -
1 stop5h 50m
Deal found 9/21![Southwest logo]()
$314
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 10/216:02 pm -
1 stop5h 57m
Sun 10/256:00 am -
1 stop5h 13m
Deal found 9/21![American Airlines logo]()
$330
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.
Thu 10/225:14 pm -
1 stop7h 09m
Thu 10/299:15 am -
1 stop6h 53m
Deal found 9/22![United Airlines logo]()
$339
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 10/227:29 pm -
1 stop4h 28m
Sun 10/255:27 am -
1 stop6h 47m
Deal found 9/22![Delta logo]()
$353
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.
Sun 10/257:29 pm -
1 stop4h 28m
Thu 10/295:27 am -
1 stop6h 47m
Deal found 9/21![Delta logo]()
$363
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 10/304:46 pm -
1 stop5h 24m
Mon 11/23:00 pm -
1 stop5h 50m
Deal found 9/24![American Airlines logo]()
$329
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.
Fri 10/3012:00 pm -
1 stop5h 55m
Mon 11/25:20 pm -
1 stop4h 45m
Deal found 9/24![Southwest logo]()
$349
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.
Sat 10/3112:15 pm -
1 stop4h 30m
Sun 11/15:15 am -
1 stop5h 50m
Deal found 9/21![Southwest logo]()
$353
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 25, 2026.
Search for one-way flight options from Mississippi to Chicago. Find affordable one-way fares based on user searches. Data last updated September 25, 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 10/227:29 pm -
1 stop4h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Delta 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.
Wed 10/286:40 am -
1 stop4h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Southwest logo]()
$155
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/78:00 am -
2 stops27h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Contour logo]()
$162
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.
Fri 10/161:04 pm -
1 stop7h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Delta logo]()
$175
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 11/2311:45 am -
2 stops8h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Southwest logo]()
$180
This Contour 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 Contour is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/113:20 pm -
2 stops20h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Contour logo]()
$180
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:45 pm -
3 stops46h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Multiple Airlines logo]()
$183
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 11/77:42 am -
1 stop8h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![American Airlines logo]()
$188
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 10/286:05 pm -
1 stop4h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Delta logo]()
$196
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 10/286:05 pm -
1 stop5h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Delta logo]()
$196
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:45 pm -
2 stops41h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Multiple Airlines logo]()
$197
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.
Thu 10/295:40 am -
1 stop5h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![American Airlines logo]()
$199
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 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $246 (Kiwi.com) |
One-way from | $155 (Delta) |
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 25, 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
JacksonChicago
JAN Jackson-Evers Intl - MDW Chicago Midway
JANMDW
Jackson-Evers Intl
Sat 11/7
1:05 pm-7:40 pm
1 stop6h 35m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$155
JacksonChicago
JAN Jackson-Evers Intl - MDW Chicago Midway
JANMDW
Jackson-Evers Intl
Mon 11/23
8:15 pm-1:10 am
1 stop4h 55m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$155
JacksonChicago
JAN Jackson-Evers Intl - MDW Chicago Midway
JANMDW
Jackson-Evers Intl
Wed 10/28
12:55 pm-10:00 pm
2 stops9h 05m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$160
TupeloChicago
TUP Tupelo Lemons Municipal - ORD Chicago O'Hare Intl
TUPORD
Tupelo Lemons Municipal
Wed 10/7
8:00 am-11:40 am
2 stops27h 40m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$162
JacksonChicago
JAN Jackson-Evers Intl - ORD Chicago O'Hare Intl
JANORD
Jackson-Evers Intl
Fri 10/16
1:04 pm-8:38 pm
1 stop7h 34m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$175
TupeloChicago
TUP Tupelo Lemons Municipal - ORD Chicago O'Hare Intl
TUPORD
Tupelo Lemons Municipal
Sun 10/11
3:20 pm-11:40 am
2 stops20h 20m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$180
GulfportChicago
GPT Gulfport Biloxi Regional - ORD Chicago O'Hare Intl
GPTORD
Gulfport Biloxi Regional
Tue 11/17
6:45 am-12:19 pm
1 stop5h 34m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$196
Quickest round-trip
GulfportChicago
GPT Gulfport Biloxi Regional - MDW Chicago Midway
GPTMDW
Gulfport Biloxi Regional
Wed 10/28
6:05 pm-10:33 pm
1 stop4h 28m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$196
GulfportChicago
GPT Gulfport Biloxi Regional - ORD Chicago O'Hare Intl
GPTORD
Gulfport Biloxi Regional
Wed 10/28
6:05 pm-11:57 pm
1 stop5h 52m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$196
GulfportChicago
GPT Gulfport Biloxi Regional - ORD Chicago O'Hare Intl
GPTORD
Gulfport Biloxi Regional
Sun 11/8
10:00 am-12:21 am
2 stops38h 21m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$201
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Mississippi to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Mississippi with our price prediction graph.
JAN-ORD
JAN-MDW
GPT-ORD
TUP-ORD
GPT-MDW
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Mississippi to Chicago
USMS-CHI
JAN-ORD
JAN-MDW
GPT-ORD
TUP-ORD
What is the cheapest month to book a flight from Mississippi to Chicago?
Currently, January is the cheapest month in which you can book a flight from Mississippi to Chicago (average of $358). Flying from Mississippi to Chicago in June is currently the most expensive (average of $674). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
How much does it cost to fly round-trip from Mississippi to Chicago?
Airfare is below average for this route at the moment.
Mississippi to Chicago flights typically cost between $375 and $456 in November.The cheapest round-trip price found within the last 5 days was $309 on Delta (Nov 7-Nov 9).
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
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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 September 25, 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 25, 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 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$248 | Average$502 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$254 | Average$481 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$308 | Average$428 | FlexibilityNo cancel fee | On-time63% |