$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 9/6. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — CHI
Aug 21 — Aug 281
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 July 22, 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 July 22, 2026.
This Southwest deal was found by Cheapflights users on 7/21. 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 8/134:55 pm
MEM
- MDW
1 stop6h 25m
Southwest
Mon 8/178:45 pm
MDW
- MEM
Nonstop1h 40m
Southwest
Deal found 7/21![Southwest logo]()
$167
This Delta deal was found by Cheapflights users on 7/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/511:45 am
MEM
- ORD
1 stop7h 14m
Delta
Sun 9/65:30 am
ORD
- MEM
1 stop7h 13m
Delta
Deal found 7/17![Delta logo]()
$177
This Delta deal was found by Cheapflights users on 7/20. 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 9/510:26 am
MEM
- MDW
1 stop5h 18m
Delta
Sun 9/66:05 am
MDW
- MEM
1 stop4h 34m
Delta
Deal found 7/20![Delta logo]()
$177
This Delta deal was found by Cheapflights users on 7/21. 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 8/206:30 am
MEM
- ORD
1 stop6h 28m
Delta
Thu 8/279:54 am
ORD
- MEM
1 stop4h 13m
Delta
Deal found 7/21![Delta logo]()
$187
This Southwest deal was found by Cheapflights users on 7/21. 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.
Tue 8/119:55 am
MEM
- MDW
2 stops6h 55m
Southwest
Sat 8/156:50 am
MDW
- MEM
1 stop9h 45m
Southwest
Deal found 7/21![Southwest logo]()
$188
This American Airlines deal was found by Cheapflights users on 7/19. 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.
Thu 9/36:32 am
MEM
- ORD
Nonstop2h 13m
American Airlines
Sun 9/68:05 am
ORD
- MEM
Nonstop1h 51m
American Airlines
Deal found 7/19![American Airlines logo]()
$201
This Southwest deal was found by Cheapflights users on 7/21. 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 10/85:20 am
MEM
- MDW
Nonstop1h 35m
Southwest
Sat 10/107:30 pm
MDW
- MEM
Nonstop1h 35m
Southwest
Deal found 7/21![Southwest logo]()
$201
This American Airlines deal was found by Cheapflights users on 7/20. 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 9/55:32 am
MEM
- ORD
1 stop6h 43m
American Airlines
Sun 9/68:05 am
ORD
- MEM
Nonstop1h 51m
American Airlines
Deal found 7/20![American Airlines logo]()
$211
This Southwest deal was found by Cheapflights users on 7/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/512:40 pm
MEM
- MDW
Nonstop1h 35m
Southwest
Mon 9/75:55 am
MDW
- MEM
1 stop3h 05m
Southwest
Deal found 7/17![Southwest logo]()
$211
This Southwest deal was found by Cheapflights users on 7/18. 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 10/305:20 am
MEM
- MDW
Nonstop1h 35m
Southwest
Mon 11/22:30 pm
MDW
- MEM
2 stops9h 10m
Southwest
Deal found 7/18![Southwest logo]()
$216
This Delta deal was found by Cheapflights users on 7/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:01 pm
MEM
- ORD
1 stop5h 58m
Delta
Mon 9/145:30 am
ORD
- MEM
1 stop7h 02m
Delta
Deal found 7/17![Delta logo]()
$218
This Delta deal was found by Cheapflights users on 7/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:00 pm
MEM
- ORD
1 stop5h 57m
Delta
Sun 9/65:30 am
ORD
- MEM
1 stop5h 09m
Delta
Deal found 7/17![Delta logo]()
$221
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 July 22, 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 July 22, 2026.
This Southwest deal was found by Cheapflights users on 7/21. 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 8/2711:20 am
MEM
- MDW
1 stop6h 55m
Southwest
Mon 8/3110:05 am
MDW
- MEM
Nonstop1h 35m
Southwest
Deal found 7/21![Southwest logo]()
$167
This Delta deal was found by Cheapflights users on 7/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/511:45 am
MEM
- ORD
1 stop7h 14m
Delta
Sun 9/65:30 am
ORD
- MEM
1 stop7h 13m
Delta
Deal found 7/17![Delta logo]()
$177
This United Airlines deal was found by Cheapflights users on 7/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/117:15 am
MEM
- ORD
Nonstop2h 06m
United Airlines
Thu 8/138:47 am
ORD
- MEM
Nonstop2h 16m
United Airlines
Deal found 7/21![United Airlines logo]()
$227
This American Airlines deal was found by Cheapflights users on 7/20. 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.
Fri 8/216:34 pm
GPT
- ORD
1 stop5h 44m
American Airlines
Tue 8/255:00 am
ORD
- GPT
1 stop5h 41m
American Airlines
Deal found 7/20![American Airlines logo]()
$300
This Kiwi.com deal was found by Cheapflights users on 7/21. 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 8/207:25 pm
GPT
- ORD
1 stop17h 55m
Multiple Airlines
Thu 8/278:05 am
ORD
- GPT
2 stops23h 36m
Multiple Airlines
Deal found 7/21![Multiple Airlines logo]()
$317
This Delta deal was found by Cheapflights users on 7/21. 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 8/177:26 pm
MEM
- ORD
1 stop4h 31m
Delta
Mon 8/241:59 pm
ORD
- MEM
1 stop7h 12m
Delta
Deal found 7/21![Delta logo]()
$187
This United Airlines deal was found by Cheapflights users on 7/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:15 am
MEM
- ORD
Nonstop2h 06m
United Airlines
Thu 10/229:10 pm
ORD
- MEM
Nonstop1h 56m
United Airlines
Deal found 7/21![United Airlines logo]()
$227
This Southwest deal was found by Cheapflights users on 7/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/195:10 am
MEM
- MDW
Nonstop1h 35m
Southwest
Mon 9/218:45 pm
MDW
- MEM
Nonstop1h 40m
Southwest
Deal found 7/17![Southwest logo]()
$245
This United Airlines deal was found by Cheapflights users on 7/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/137:15 am
MEM
- ORD
Nonstop2h 06m
United Airlines
Mon 8/179:20 pm
ORD
- MEM
Nonstop1h 58m
United Airlines
Deal found 7/21![United Airlines logo]()
$228
This Southwest deal was found by Cheapflights users on 7/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/155:10 am
MEM
- MDW
Nonstop1h 35m
Southwest
Sat 8/226:15 pm
MDW
- MEM
Nonstop1h 40m
Southwest
Deal found 7/17![Southwest logo]()
$245
This Delta deal was found by Cheapflights users on 7/20. 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 10/1510:33 am
MEM
- ORD
1 stop5h 51m
Delta
Thu 10/2211:19 am
ORD
- MEM
1 stop5h 54m
Delta
Deal found 7/20![Delta logo]()
$265
This United Airlines deal was found by Cheapflights users on 7/18. 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 8/157:15 am
MEM
- ORD
Nonstop2h 06m
United Airlines
Sat 8/2212:42 pm
ORD
- MEM
Nonstop2h 04m
United Airlines
Deal found 7/18![United Airlines logo]()
$245
This Southwest deal was found by Cheapflights users on 7/20. 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 10/315:30 am
MEM
- MDW
Nonstop1h 35m
Southwest
Mon 11/29:35 pm
MDW
- MEM
Nonstop1h 45m
Southwest
Deal found 7/20![Southwest logo]()
$245
This American Airlines deal was found by Cheapflights users on 7/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/145:16 pm
BTR
- ORD
1 stop7h 02m
American Airlines
Sun 8/165:00 am
ORD
- BTR
1 stop5h 42m
American Airlines
Deal found 7/17![American Airlines logo]()
$309
This Delta deal was found by Cheapflights users on 7/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1710:34 am
MEM
- ORD
1 stop5h 40m
Delta
Tue 9/226:40 am
ORD
- MEM
1 stop4h 07m
Delta
Deal found 7/17![Delta logo]()
$265
This American Airlines deal was found by Cheapflights users on 7/21. 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 8/205:45 pm
GPT
- ORD
1 stop6h 07m
American Airlines
Thu 8/276:49 am
ORD
- GPT
1 stop6h 28m
American Airlines
Deal found 7/21![American Airlines logo]()
$309
This United Airlines deal was found by Cheapflights users on 7/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/207:15 am
MEM
- ORD
Nonstop2h 06m
United Airlines
Sun 8/239:20 pm
ORD
- MEM
Nonstop1h 58m
United Airlines
Deal found 7/21![United Airlines logo]()
$259
This Delta deal was found by Cheapflights users on 7/18. 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.
Tue 9/110:33 am
MEM
- ORD
1 stop6h 18m
Delta
Tue 9/87:05 am
ORD
- MEM
1 stop4h 08m
Delta
Deal found 7/18![Delta logo]()
$265
This Southwest deal was found by Cheapflights users on 7/21. 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 8/1912:25 pm
MEM
- MDW
1 stop4h 45m
Southwest
Fri 8/2110:05 am
MDW
- MEM
Nonstop1h 35m
Southwest
Deal found 7/21![Southwest logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 7/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/149:36 am
GPT
- ORD
1 stop20h 06m
Multiple Airlines
Thu 9/177:45 am
ORD
- GPT
2 stops25h 06m
Multiple Airlines
Deal found 7/17![Multiple Airlines logo]()
$382
This Delta deal was found by Cheapflights users on 7/18. 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 10/159:37 am
MEM
- ORD
1 stop7h 20m
Delta
Mon 10/192:00 pm
ORD
- MEM
1 stop7h 05m
Delta
Deal found 7/18![Delta logo]()
$265
This Southwest deal was found by Cheapflights users on 7/20. 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 8/121:30 pm
JAN
- MDW
1 stop6h 40m
Southwest
Sat 8/151:45 pm
MDW
- JAN
1 stop5h 20m
Southwest
Deal found 7/20![Southwest logo]()
$303
This United Airlines deal was found by Cheapflights users on 7/17. 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.
Fri 8/144:10 pm
BTR
- ORD
1 stop5h 22m
United Airlines
Sat 8/152:16 pm
ORD
- BTR
1 stop7h 12m
United Airlines
Deal found 7/17![United Airlines logo]()
$309
This Delta deal was found by Cheapflights users on 7/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/194:00 pm
GPT
- ORD
1 stop4h 55m
Delta
Wed 9/238:05 am
ORD
- GPT
1 stop5h 06m
Delta
Deal found 7/17![Delta logo]()
$291
This Southwest deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 9/1112:40 pm
JAN
- MDW
2 stops6h 50m
Southwest
Mon 9/145:25 am
MDW
- JAN
1 stop6h 35m
Southwest
Deal found 7/16![Southwest logo]()
$308
This Delta deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 9/115:03 pm
JAN
- MDW
1 stop5h 42m
Delta
Mon 9/146:05 am
MDW
- JAN
1 stop4h 18m
Delta
Deal found 7/16![Delta logo]()
$303
This Southwest deal was found by Cheapflights users on 7/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/286:55 am
MEM
- MDW
2 stops10h 10m
Southwest
Mon 8/3110:30 am
MDW
- MEM
1 stop7h 20m
Southwest
Deal found 7/17![Southwest logo]()
$323
This United Airlines deal was found by Cheapflights users on 7/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/46:14 pm
BTR
- ORD
1 stop5h 12m
United Airlines
Mon 9/75:30 am
ORD
- BTR
1 stop5h 43m
United Airlines
Deal found 7/21![United Airlines logo]()
$359
This Delta deal was found by Cheapflights users on 7/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:00 pm
GPT
- ORD
1 stop5h 57m
Delta
Tue 8/257:05 am
ORD
- GPT
2 stops10h 10m
Delta
Deal found 7/17![Delta logo]()
$305
This Southwest deal was found by Cheapflights users on 7/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/188:30 am
MEM
- MDW
1 stop4h 25m
Southwest
Sun 11/225:15 am
MDW
- MEM
2 stops10h 05m
Southwest
Deal found 7/17![Southwest logo]()
$323
Last-minute flights from Mississippi to ChicagoDiscover last-minute flight deals from Mississippi to Chicago. Data last updated July 22, 2026 and is based on user searches.
Discover last-minute flight deals from Mississippi to Chicago. Data last updated July 22, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 7/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/66:30 am
MEM
- ORD
1 stop6h 38m
Delta
Sat 8/82:30 pm
ORD
- MEM
1 stop4h 22m
Delta
Deal found 7/17![Delta logo]()
$177
This Southwest deal was found by Cheapflights users on 7/21. 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.
Tue 8/119:55 am
MEM
- MDW
2 stops6h 55m
Southwest
Sat 8/156:50 am
MDW
- MEM
1 stop9h 45m
Southwest
Deal found 7/21![Southwest logo]()
$188
This United Airlines deal was found by Cheapflights users on 7/20. 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 8/112:37 pm
MEM
- ORD
Nonstop2h 09m
United Airlines
Thu 8/138:47 am
ORD
- MEM
Nonstop2h 16m
United Airlines
Deal found 7/20![United Airlines logo]()
$227
This Southwest deal was found by Cheapflights users on 7/21. 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 8/134:55 pm
MEM
- MDW
1 stop6h 25m
Southwest
Mon 8/178:45 pm
MDW
- MEM
Nonstop1h 40m
Southwest
Deal found 7/21![Southwest logo]()
$167
This American Airlines deal was found by Cheapflights users on 7/22. 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 8/138:15 am
MEM
- ORD
1 stop7h 45m
American Airlines
Sat 8/159:20 pm
ORD
- MEM
Nonstop1h 56m
American Airlines
Deal found 7/22![American Airlines logo]()
$211
This United Airlines deal was found by Cheapflights users on 7/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/137:15 am
MEM
- ORD
Nonstop2h 06m
United Airlines
Mon 8/179:20 pm
ORD
- MEM
Nonstop1h 58m
United Airlines
Deal found 7/21![United Airlines logo]()
$228
This CheapOair deal was found by Cheapflights users on 7/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/137:10 pm
MEM
- ORD
1 stop28h 00m
Frontier
Wed 8/195:59 pm
ORD
- MEM
1 stop19h 56m
Frontier
Deal found 7/19![Frontier logo]()
$243
This Southwest deal was found by Cheapflights users on 7/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/155:10 am
MEM
- MDW
Nonstop1h 35m
Southwest
Sat 8/226:15 pm
MDW
- MEM
Nonstop1h 40m
Southwest
Deal found 7/17![Southwest logo]()
$245
This Delta deal was found by Cheapflights users on 7/21. 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 8/206:30 am
MEM
- ORD
1 stop6h 28m
Delta
Thu 8/279:54 am
ORD
- MEM
1 stop4h 13m
Delta
Deal found 7/21![Delta logo]()
$187
This American Airlines deal was found by Cheapflights users on 7/19. 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.
Thu 8/205:44 pm
MEM
- ORD
Nonstop2h 24m
American Airlines
Tue 8/259:20 pm
ORD
- MEM
Nonstop1h 56m
American Airlines
Deal found 7/19![American Airlines logo]()
$245
This Kiwi.com deal was found by Cheapflights users on 7/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/247:03 pm
MEM
- ORD
2 stops41h 47m
Multiple Airlines
Thu 9/247:45 am
ORD
- MEM
1 stop7h 24m
Multiple Airlines
Deal found 7/17![Multiple Airlines logo]()
$249
This American Airlines deal was found by Cheapflights users on 7/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/316:32 am
MEM
- ORD
Nonstop2h 13m
American Airlines
Mon 9/711:00 pm
ORD
- MEM
Nonstop1h 53m
American Airlines
Deal found 7/17![American Airlines logo]()
$246
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 July 22, 2026.
Search for one-way flight options from Mississippi to Chicago. Find affordable one-way fares based on user searches. Data last updated July 22, 2026.
This American Airlines deal was found by Cheapflights users on 7/20. 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.
Sun 9/65:44 pm
MEM
- ORD
Nonstop2h 24m
American Airlines
Deal found 7/20![American Airlines logo]()
$79
This Southwest deal was found by Cheapflights users on 7/21. 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 8/205:15 am
MEM
- MDW
Nonstop1h 35m
Southwest
Deal found 7/21![Southwest logo]()
$79
This Delta deal was found by Cheapflights users on 7/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/81:54 pm
MEM
- ORD
1 stop7h 01m
Delta
Deal found 7/17![Delta logo]()
$89
This Southwest deal was found by Cheapflights users on 7/21. 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 9/64:40 pm
MEM
- MDW
1 stop4h 40m
Southwest
Deal found 7/21![Southwest logo]()
$89
This Delta deal was found by Cheapflights users on 7/21. 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 8/171:49 pm
MEM
- ORD
1 stop7h 06m
Delta
Deal found 7/21![Delta logo]()
$94
This Delta deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/196:10 pm
MEM
- MDW
1 stop4h 34m
Delta
Deal found 7/21![Delta logo]()
$94
This United Airlines deal was found by Cheapflights users on 7/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/177:15 am
MEM
- ORD
Nonstop2h 06m
United Airlines
Deal found 7/21![United Airlines logo]()
$114
This Kiwi.com deal was found by Cheapflights users on 7/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/175:04 pm
MEM
- ORD
1 stop19h 46m
Multiple Airlines
Deal found 7/17![Multiple Airlines logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 7/18. 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 8/38:39 am
MEM
- MDW
1 stop11h 51m
Allegiant Air
Deal found 7/18![Allegiant Air logo]()
$116
This Frontier deal was found by Cheapflights users on 7/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/272:50 pm
MEM
- ORD
1 stop8h 18m
Frontier
Deal found 7/21![Frontier logo]()
$120
This Frontier deal was found by Cheapflights users on 7/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/232:30 pm
MEM
- ORD
1 stop8h 38m
Frontier
Deal found 7/21![Frontier logo]()
$121
This Southwest deal was found by Cheapflights users on 7/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/175:15 am
MEM
- MDW
Nonstop1h 35m
Southwest
Deal found 7/17![Southwest logo]()
$123
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 July 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $167 (Southwest) |
One-way from | $79 (American Airlines) |
Popular in | June |
Cheapest in | April |
Average price | $541 |
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 July 22, 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
Thu 8/27
11:20 am-6:15 pm
1 stop6h 55m
Chicago Midway
Mon 8/31
10:05 am-11:40 am
Nonstop1h 35m
$167
MemphisChicago
MEM - ORD
MEMORD
Memphis
Sat 9/5
11:45 am-6:59 pm
1 stop7h 14m
Chicago O'Hare Intl
Sun 9/6
5:30 am-12:43 pm
1 stop7h 13m
$177
MemphisChicago
MEM - ORD
MEMORD
Memphis
Mon 8/17
7:26 pm-11:57 pm
1 stop4h 31m
Chicago O'Hare Intl
Mon 8/24
1:59 pm-9:11 pm
1 stop7h 12m
$187
MemphisChicago
MEM - ORD
MEMORD
Memphis
Tue 8/11
7:15 am-9:21 am
Nonstop2h 06m
Chicago O'Hare Intl
Thu 8/13
8:47 am-11:03 am
Nonstop2h 16m
$227
MemphisChicago
MEM - ORD
MEMORD
Memphis
Thu 10/15
7:15 am-9:21 am
Nonstop2h 06m
Chicago O'Hare Intl
Thu 10/22
9:10 pm-11:06 pm
Nonstop1h 56m
$227
MemphisChicago
MEM - ORD
MEMORD
Memphis
Thu 8/13
7:15 am-9:21 am
Nonstop2h 06m
Chicago O'Hare Intl
Mon 8/17
9:20 pm-11:18 pm
Nonstop1h 58m
$228
Quickest round-trip
MemphisChicago
MEM - MDW
MEMMDW
Memphis
Sat 9/19
5:10 am-6:45 am
Nonstop1h 35m
Chicago Midway
Mon 9/21
8:45 pm-10:25 pm
Nonstop1h 40m
$245
MemphisChicago
MEM - MDW
MEMMDW
Memphis
Sat 8/15
5:10 am-6:45 am
Nonstop1h 35m
Chicago Midway
Sat 8/22
6:15 pm-7:55 pm
Nonstop1h 40m
$245
MemphisChicago
MEM - ORD
MEMORD
Memphis
Sat 8/15
7:15 am-9:21 am
Nonstop2h 06m
Chicago O'Hare Intl
Sat 8/22
12:42 pm-2:46 pm
Nonstop2h 04m
$245
MemphisChicago
MEM - MDW
MEMMDW
Memphis
Sat 10/31
5:30 am-7:05 am
Nonstop1h 35m
Chicago Midway
Mon 11/2
9:35 pm-11:20 pm
Nonstop1h 45m
$245
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
GPT-ORD
BTR-ORD
JAN-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
MEM-MDW
MEM-ORD
GPT-ORD
BTR-ORD
What is the cheapest month to book a flight from Mississippi to Chicago?
Currently, August is the cheapest month in which you can book a flight from Mississippi to Chicago (average of $323). Flying from Mississippi to Chicago in June is currently the most expensive (average of $629). 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
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
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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 July 22, 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 July 22, 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 July 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$236 | Average$428 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$248 | Average$481 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$249 | Average$424 | FlexibilityNo cancel fee | On-timeN/A |