$79+ Cheap flights from Mississippi to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/17. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — CHI
Jun 22 — Jun 291
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 May 23, 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 May 23, 2026.
This United Airlines deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 8/189:47 am
MEM
- ORD
Nonstop2h 12m
United Airlines
Wed 8/199:00 pm
ORD
- MEM
Nonstop1h 58m
United Airlines
Deal found 5/17![United Airlines logo]()
$247
This Southwest deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 9/129:20 am
MEM
- MDW
2 stops9h 05m
Southwest
Mon 9/148:45 pm
MDW
- MEM
Nonstop1h 40m
Southwest
Deal found 5/18![Southwest logo]()
$254
This Southwest deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 10/85:00 am
MEM
- MDW
Nonstop1h 35m
Southwest
Mon 10/125:00 am
MDW
- MEM
1 stop10h 00m
Southwest
Deal found 5/18![Southwest logo]()
$255
This American Airlines deal was found by Cheapflights users on 5/20. 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.
Wed 5/276:10 am
MEM
- ORD
Nonstop2h 10m
American Airlines
Wed 6/1011:53 am
ORD
- MEM
Nonstop1h 51m
American Airlines
Deal found 5/20![American Airlines logo]()
$258
This Southwest deal was found by Cheapflights users on 5/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/103:35 pm
MEM
- MDW
Nonstop1h 35m
Southwest
Sat 6/131:00 pm
MDW
- MEM
Nonstop1h 40m
Southwest
Deal found 5/20![Southwest logo]()
$258
This American Airlines deal was found by Cheapflights users on 5/20. 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 8/2710:41 am
MEM
- ORD
1 stop6h 58m
American Airlines
Sat 8/292:57 pm
ORD
- MEM
1 stop5h 20m
American Airlines
Deal found 5/20![American Airlines logo]()
$259
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 8/2711:46 am
MEM
- MDW
1 stop4h 29m
Delta
Sat 8/291:27 pm
MDW
- MEM
1 stop5h 25m
Delta
Deal found 5/18![Delta logo]()
$259
This Delta deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 8/1212:06 pm
MOB
- MDW
1 stop4h 09m
Delta
Tue 8/1810:54 am
MDW
- MOB
1 stop4h 56m
Delta
Deal found 5/19![Delta logo]()
$261
This Delta deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 8/126:55 pm
MOB
- ORD
1 stop5h 03m
Delta
Tue 8/185:28 am
ORD
- MOB
1 stop5h 52m
Delta
Deal found 5/19![Delta logo]()
$261
This Kiwi.com deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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.
Fri 7/248:39 am
MEM
- MDW
1 stop11h 52m
Multiple Airlines
Tue 7/286:00 am
MDW
- MEM
1 stop4h 55m
Multiple Airlines
Deal found 5/19![Multiple Airlines logo]()
$261
This Booking.com deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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.
Fri 7/107:51 pm
MEM
- ORD
1 stop25h 01m
Frontier
Mon 7/135:13 pm
ORD
- MEM
1 stop25h 02m
Frontier
Deal found 5/18![Frontier logo]()
$262
This American Airlines deal was found by Cheapflights users on 5/20. 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.
Tue 7/282:56 pm
MEM
- ORD
1 stop4h 55m
American Airlines
Tue 8/46:47 pm
ORD
- MEM
1 stop4h 58m
American Airlines
Deal found 5/20![American Airlines logo]()
$263
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 May 23, 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 May 23, 2026.
This Southwest deal was found by Cheapflights users on 5/22. 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 7/1412:25 pm
MEM
- MDW
1 stop6h 05m
Southwest
Sat 7/186:40 pm
MDW
- MEM
Nonstop1h 40m
Southwest
Deal found 5/22![Southwest logo]()
$258
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 5/272:30 pm
MEM
- ORD
1 stop7h 23m
Delta
Wed 6/106:35 am
ORD
- MEM
1 stop7h 22m
Delta
Deal found 5/18![Delta logo]()
$278
This United Airlines deal was found by Cheapflights users on 5/22. 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 7/96:09 pm
BTR
- ORD
1 stop6h 36m
United Airlines
Sun 7/125:30 am
ORD
- BTR
1 stop5h 50m
United Airlines
Deal found 5/22![United Airlines logo]()
$335
This American Airlines deal was found by Cheapflights users on 5/22. 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.
Thu 6/186:21 am
MEM
- ORD
Nonstop2h 08m
American Airlines
Mon 6/226:29 am
ORD
- MEM
1 stop7h 38m
American Airlines
Deal found 5/22![American Airlines logo]()
$361
This Kiwi.com deal was found by Cheapflights users on 5/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/248:21 am
GPT
- ORD
1 stop21h 16m
Multiple Airlines
Tue 7/289:57 pm
ORD
- GPT
2 stops45h 13m
Multiple Airlines
Deal found 5/20![Multiple Airlines logo]()
$525
This Southwest deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 7/216:45 pm
MEM
- MDW
1 stop5h 05m
Southwest
Mon 7/279:25 pm
MDW
- MEM
Nonstop1h 40m
Southwest
Deal found 5/19![Southwest logo]()
$274
This Delta deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/166:30 am
MEM
- MDW
1 stop6h 16m
Delta
Sat 6/206:00 am
MDW
- MEM
1 stop4h 37m
Delta
Deal found 5/21![Delta logo]()
$278
This Delta deal was found by Cheapflights users on 5/20. 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.
Wed 6/106:30 am
MEM
- ORD
1 stop6h 34m
Delta
Fri 6/129:48 am
ORD
- MEM
1 stop4h 09m
Delta
Deal found 5/20![Delta logo]()
$284
This Delta deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/1610:29 am
MEM
- ORD
1 stop5h 57m
Delta
Fri 6/195:30 am
ORD
- MEM
1 stop5h 07m
Delta
Deal found 5/21![Delta logo]()
$284
This United Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 5/287:22 am
MEM
- ORD
Nonstop2h 05m
United Airlines
Sat 5/304:00 pm
ORD
- MEM
Nonstop1h 59m
United Airlines
Deal found 5/19![United Airlines logo]()
$357
This Southwest deal was found by Cheapflights users on 5/22. 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 7/87:15 pm
JAN
- MDW
1 stop4h 40m
Southwest
Tue 7/143:10 pm
MDW
- JAN
1 stop3h 35m
Southwest
Deal found 5/22![Southwest logo]()
$329
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 6/612:15 pm
MEM
- ORD
1 stop4h 14m
Delta
Tue 6/95:30 am
ORD
- MEM
1 stop7h 05m
Delta
Deal found 5/18![Delta logo]()
$296
This United Airlines deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/82:05 pm
BTR
- ORD
1 stop7h 35m
United Airlines
Wed 8/126:30 am
ORD
- BTR
1 stop4h 43m
United Airlines
Deal found 5/22![United Airlines logo]()
$383
This Southwest deal was found by Cheapflights users on 5/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/42:55 pm
MEM
- MDW
1 stop5h 45m
Southwest
Sat 7/111:00 pm
MDW
- MEM
Nonstop1h 40m
Southwest
Deal found 5/20![Southwest logo]()
$349
This Delta deal was found by Cheapflights users on 5/20. 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.
Tue 7/74:00 pm
BTR
- MDW
1 stop6h 15m
Delta
Sat 7/1110:55 am
MDW
- BTR
1 stop4h 14m
Delta
Deal found 5/20![Delta logo]()
$303
This Southwest deal was found by Cheapflights users on 5/22. 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 5/275:15 am
MEM
- MDW
Nonstop1h 35m
Southwest
Wed 6/310:05 am
MDW
- MEM
Nonstop1h 40m
Southwest
Deal found 5/22![Southwest logo]()
$357
This American Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 7/76:35 pm
GPT
- ORD
1 stop5h 26m
American Airlines
Thu 7/93:49 pm
ORD
- GPT
1 stop7h 08m
American Airlines
Deal found 5/18![American Airlines logo]()
$484
This Delta deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/66:11 am
BTR
- MDW
1 stop5h 54m
Delta
Sat 7/1110:55 am
MDW
- BTR
1 stop4h 14m
Delta
Deal found 5/21![Delta logo]()
$306
This Southwest deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 6/185:15 am
MEM
- MDW
Nonstop1h 35m
Southwest
Thu 6/1810:05 am
MDW
- MEM
Nonstop1h 35m
Southwest
Deal found 5/18![Southwest logo]()
$358
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 7/241:27 pm
BTR
- ORD
1 stop5h 18m
Delta
Sat 8/15:30 am
ORD
- BTR
1 stop4h 09m
Delta
Deal found 5/18![Delta logo]()
$306
This United Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 6/2312:10 pm
BTR
- ORD
2 stops18h 18m
United Airlines
Tue 6/305:30 am
ORD
- BTR
1 stop5h 50m
United Airlines
Deal found 5/19![United Airlines logo]()
$475
This Southwest deal was found by Cheapflights users on 5/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/125:10 pm
MEM
- MDW
1 stop7h 00m
Southwest
Sun 6/149:55 pm
MDW
- MEM
Nonstop1h 40m
Southwest
Deal found 5/20![Southwest logo]()
$361
This deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/317:15 am
MOB
- ORD
1 stop7h 05m
American Airlines
Thu 6/115:00 am
ORD
- MOB
1 stop6h 25m
American Airlines
Deal found 5/19![American Airlines logo]()
$533
This Delta deal was found by Cheapflights users on 5/22. 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 7/167:06 pm
BTR
- ORD
1 stop4h 47m
Delta
Tue 7/215:30 am
ORD
- BTR
1 stop7h 17m
Delta
Deal found 5/22![Delta logo]()
$306
This Southwest deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 6/195:00 pm
MEM
- MDW
1 stop4h 55m
Southwest
Sun 6/289:55 pm
MDW
- MEM
Nonstop1h 40m
Southwest
Deal found 5/18![Southwest logo]()
$361
This United Airlines deal was found by Cheapflights users on 5/20. 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.
Fri 6/1212:10 pm
BTR
- ORD
2 stops18h 18m
United Airlines
Wed 6/176:30 am
ORD
- BTR
1 stop4h 50m
United Airlines
Deal found 5/20![United Airlines logo]()
$493
This Delta deal was found by Cheapflights users on 5/21. 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 8/147:13 pm
BTR
- ORD
1 stop4h 45m
Delta
Sun 8/165:28 am
ORD
- BTR
1 stop4h 12m
Delta
Deal found 5/21![Delta logo]()
$309
This Southwest deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 8/79:35 am
MEM
- MDW
1 stop8h 25m
Southwest
Sun 8/99:40 pm
MDW
- MEM
Nonstop1h 35m
Southwest
Deal found 5/19![Southwest logo]()
$361
This Delta deal was found by Cheapflights users on 5/21. 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 8/196:55 pm
MOB
- ORD
1 stop5h 03m
Delta
Sun 8/235:28 am
ORD
- MOB
1 stop5h 52m
Delta
Deal found 5/21![Delta logo]()
$310
This Southwest deal was found by Cheapflights users on 5/22. 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 7/95:15 am
MEM
- MDW
Nonstop1h 35m
Southwest
Mon 7/137:50 am
MDW
- MEM
2 stops6h 00m
Southwest
Deal found 5/22![Southwest logo]()
$366
Last-minute flights from Mississippi to ChicagoDiscover last-minute flight deals from Mississippi to Chicago. Data last updated May 23, 2026 and is based on user searches.
Discover last-minute flight deals from Mississippi to Chicago. Data last updated May 23, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 5/20. 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.
Wed 5/276:10 am
MEM
- ORD
Nonstop2h 10m
American Airlines
Wed 6/1011:53 am
ORD
- MEM
Nonstop1h 51m
American Airlines
Deal found 5/20![American Airlines logo]()
$258
This Frontier deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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.
Tue 6/211:59 am
MEM
- MDW
1 stop10h 03m
Frontier
Thu 6/116:00 am
MDW
- MEM
1 stop4h 55m
Frontier
Deal found 5/19![Frontier logo]()
$269
This Expedia deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/411:59 am
MEM
- MDW
1 stop10h 03m
Frontier
Tue 6/96:00 am
MDW
- MEM
1 stop5h 14m
Frontier
Deal found 5/19![Frontier logo]()
$270
This United Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 6/66:35 pm
MEM
- ORD
Nonstop2h 05m
United Airlines
Tue 6/99:20 pm
ORD
- MEM
Nonstop2h 01m
United Airlines
Deal found 5/18![United Airlines logo]()
$276
This Kiwi.com deal was found by Cheapflights users on 5/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/85:04 pm
MEM
- ORD
1 stop19h 20m
Multiple Airlines
Thu 6/117:52 am
ORD
- MEM
1 stop23h 41m
Multiple Airlines
Deal found 5/20![Multiple Airlines logo]()
$275
This American Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 6/95:00 am
MEM
- ORD
1 stop6h 00m
American Airlines
Tue 6/95:34 pm
ORD
- MEM
1 stop5h 51m
American Airlines
Deal found 5/19![American Airlines logo]()
$267
This Southwest deal was found by Cheapflights users on 5/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/103:35 pm
MEM
- MDW
Nonstop1h 35m
Southwest
Sat 6/131:00 pm
MDW
- MEM
Nonstop1h 40m
Southwest
Deal found 5/20![Southwest logo]()
$258
This United Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 6/106:35 pm
MEM
- ORD
Nonstop2h 05m
United Airlines
Mon 6/159:20 pm
ORD
- MEM
Nonstop2h 01m
United Airlines
Deal found 5/18![United Airlines logo]()
$264
This Southwest deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 6/103:35 pm
MEM
- MDW
Nonstop1h 35m
Southwest
Mon 6/159:25 pm
MDW
- MEM
Nonstop1h 40m
Southwest
Deal found 5/18![Southwest logo]()
$264
This American Airlines deal was found by Cheapflights users on 5/20. 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.
Wed 6/106:10 am
MEM
- ORD
Nonstop2h 08m
American Airlines
Sat 6/139:30 am
ORD
- MEM
1 stop4h 50m
American Airlines
Deal found 5/20![American Airlines logo]()
$274
This Southwest deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 6/178:25 am
MEM
- MDW
2 stops6h 45m
Southwest
Wed 6/243:55 pm
MDW
- MEM
2 stops6h 50m
Southwest
Deal found 5/18![Southwest logo]()
$267
This Southwest deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 6/175:20 am
MEM
- MDW
Nonstop1h 35m
Southwest
Sun 6/219:55 pm
MDW
- MEM
Nonstop1h 40m
Southwest
Deal found 5/18![Southwest logo]()
$271
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 May 23, 2026.
Search for one-way flight options from Mississippi to Chicago. Find affordable one-way fares based on user searches. Data last updated May 23, 2026.
This United Airlines deal was found by Cheapflights users on 5/22. 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 6/179:48 am
MEM
- ORD
Nonstop2h 11m
United Airlines
Deal found 5/22![United Airlines logo]()
$79
This Southwest deal was found by Cheapflights users on 5/22. 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 8/183:25 pm
MEM
- MDW
Nonstop1h 35m
Southwest
Deal found 5/22![Southwest logo]()
$79
This American Airlines deal was found by Cheapflights users on 5/22. 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.
Tue 6/305:48 pm
MEM
- ORD
Nonstop2h 22m
American Airlines
Deal found 5/22![American Airlines logo]()
$89
This Southwest deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 6/173:35 pm
MEM
- MDW
Nonstop1h 35m
Southwest
Deal found 5/19![Southwest logo]()
$89
This Priceline deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/1411:51 am
MEM
- ORD
1 stop8h 02m
Frontier
Deal found 5/18![Frontier logo]()
$95
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 6/1710:36 am
MEM
- ORD
1 stop6h 28m
Delta
Deal found 5/18![Delta logo]()
$99
This Delta deal was found by Cheapflights users on 5/20. 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.
Wed 7/156:32 am
MEM
- MDW
1 stop6h 06m
Delta
Deal found 5/20![Delta logo]()
$99
This Kiwi.com deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 6/15:04 pm
MEM
- ORD
1 stop19h 20m
Multiple Airlines
Deal found 5/18![Multiple Airlines logo]()
$100
This Kiwi.com deal was found by Cheapflights users on 5/21. 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.
Fri 7/318:39 am
MEM
- MDW
1 stop11h 52m
Allegiant Air
Deal found 5/21![Allegiant Air logo]()
$102
This Kiwi.com deal was found by Cheapflights users on 5/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/248:39 am
MEM
- MDW
1 stop11h 52m
Allegiant Air
Deal found 5/20![Allegiant Air logo]()
$107
This Delta deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/305:54 pm
MEM
- ORD
1 stop6h 05m
Delta
Deal found 5/22![Delta logo]()
$109
This Delta deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/166:30 am
MEM
- MDW
1 stop6h 16m
Delta
Deal found 5/21![Delta logo]()
$109
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 May 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $254 (Southwest) |
One-way from | $79 (United Airlines) |
Popular in | March |
Cheapest in | September |
Average price | $519 |
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 2,558,603 searches. Data last updated May 23, 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 - MDW
MEMMDW
Memphis
Tue 7/14
12:25 pm-6:30 pm
1 stop6h 05m
Chicago Midway
Sat 7/18
6:40 pm-8:20 pm
Nonstop1h 40m
$258
MemphisChicago
MEM - MDW
MEMMDW
Memphis
Tue 7/21
6:45 pm-11:50 pm
1 stop5h 05m
Chicago Midway
Mon 7/27
9:25 pm-11:05 pm
Nonstop1h 40m
$274
MemphisChicago
MEM - ORD
MEMORD
Memphis
Wed 5/27
2:30 pm-9:53 pm
1 stop7h 23m
Chicago O'Hare Intl
Wed 6/10
6:35 am-1:57 pm
1 stop7h 22m
$278
MemphisChicago
MEM - MDW
MEMMDW
Memphis
Tue 6/16
6:30 am-12:46 pm
1 stop6h 16m
Chicago Midway
Sat 6/20
6:00 am-10:37 am
1 stop4h 37m
$278
MemphisChicago
MEM - ORD
MEMORD
Memphis
Wed 6/10
6:30 am-1:04 pm
1 stop6h 34m
Chicago O'Hare Intl
Fri 6/12
9:48 am-1:57 pm
1 stop4h 09m
$284
MemphisChicago
MEM - ORD
MEMORD
Memphis
Tue 6/16
10:29 am-4:26 pm
1 stop5h 57m
Chicago O'Hare Intl
Fri 6/19
5:30 am-10:37 am
1 stop5h 07m
$284
MemphisChicago
MEM - ORD
MEMORD
Memphis
Sat 6/6
12:15 pm-4:29 pm
1 stop4h 14m
Chicago O'Hare Intl
Tue 6/9
5:30 am-12:35 pm
1 stop7h 05m
$296
Baton RougeChicago
BTR - MDW
BTRMDW
Baton Rouge Ryan
Tue 7/7
4:00 pm-10:15 pm
1 stop6h 15m
Chicago Midway
Sat 7/11
10:55 am-3:09 pm
1 stop4h 14m
$303
Baton RougeChicago
BTR - MDW
BTRMDW
Baton Rouge Ryan
Mon 7/6
6:11 am-12:05 pm
1 stop5h 54m
Chicago Midway
Sat 7/11
10:55 am-3:09 pm
1 stop4h 14m
$306
Baton RougeChicago
BTR - ORD
BTRORD
Baton Rouge Ryan
Fri 7/24
1:27 pm-6:45 pm
1 stop5h 18m
Chicago O'Hare Intl
Sat 8/1
5:30 am-9:39 am
1 stop4h 09m
$306
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-ORD
MEM-MDW
GPT-ORD
JAN-ORD
MOB-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-ORD
MEM-MDW
GPT-ORD
JAN-ORD
What is the cheapest month to book a flight from Mississippi to Chicago?
Currently, September is the cheapest month in which you can book a flight from Mississippi to Chicago (average of $191). Flying from Mississippi to Chicago in June is currently the most expensive (average of $346). 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?
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
Hammond
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Chicago flight routes
Complete your trip
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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 May 23, 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 May 23, 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 2,558,603 searches. Data last updated May 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$196 | Average$455 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$234 | Average$417 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$248 | Average$454 | FlexibilityNo cancel fee | On-time71% |