$70+ 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 5/14. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — CHI
May 23 — May 301
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 April 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 April 23, 2026.
This Frontier deal was found by Cheapflights users on 4/18. 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 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
Tue 6/96:00 am
MDW
- MEM
1 stop5h 14m
Frontier
Deal found 4/18![Frontier logo]()
$202
This American Airlines deal was found by Cheapflights users on 4/18. 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.
Sat 6/62:43 pm
MEM
- ORD
1 stop7h 37m
American Airlines
Wed 6/109:04 pm
ORD
- MEM
Nonstop1h 52m
American Airlines
Deal found 4/18![American Airlines logo]()
$208
This Delta deal was found by Cheapflights users on 4/20. 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 5/126:35 am
MEM
- ORD
1 stop3h 54m
Delta
Tue 5/122:59 pm
ORD
- MEM
1 stop5h 24m
Delta
Deal found 4/20![Delta logo]()
$209
This Delta deal was found by Cheapflights users on 4/20. 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 5/125:30 am
MEM
- MDW
1 stop4h 30m
Delta
Tue 5/125:10 pm
MDW
- MEM
1 stop6h 02m
Delta
Deal found 4/20![Delta logo]()
$209
This Southwest deal was found by Cheapflights users on 4/17. 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 5/95:25 am
MEM
- ORD
1 stop6h 05m
Southwest
Sat 5/92:05 pm
ORD
- MEM
1 stop5h 00m
Southwest
Deal found 4/17![Southwest logo]()
$217
This Delta deal was found by Cheapflights users on 4/17. 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 5/95:30 am
MEM
- ORD
1 stop4h 08m
Delta
Tue 5/126:24 am
ORD
- MEM
1 stop5h 07m
Delta
Deal found 4/17![Delta logo]()
$218
This Southwest deal was found by Cheapflights users on 4/21. 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 6/65:00 am
MEM
- MDW
Nonstop1h 35m
Southwest
Wed 6/109:40 pm
MDW
- MEM
Nonstop1h 40m
Southwest
Deal found 4/21![Southwest logo]()
$226
This United Airlines deal was found by Cheapflights users on 4/17. 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 8/259:46 am
MEM
- ORD
Nonstop2h 09m
United Airlines
Wed 8/269:40 pm
ORD
- MEM
Nonstop2h 06m
United Airlines
Deal found 4/17![United Airlines logo]()
$227
This Southwest deal was found by Cheapflights users on 4/19. 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 6/35:15 am
MEM
- MDW
Nonstop1h 35m
Southwest
Sat 6/66:40 pm
MDW
- MEM
Nonstop1h 35m
Southwest
Deal found 4/19![Southwest logo]()
$227
This American Airlines deal was found by Cheapflights users on 4/21. 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 5/205:05 am
MEM
- ORD
1 stop7h 31m
American Airlines
Wed 5/279:00 pm
ORD
- MEM
Nonstop1h 55m
American Airlines
Deal found 4/21![American Airlines logo]()
$228
This Orbitz deal was found by Cheapflights users on 4/21. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/2511:51 am
MEM
- MDW
1 stop10h 20m
Frontier
Sun 6/286:00 am
MDW
- MEM
1 stop4h 55m
Frontier
Deal found 4/21![Frontier logo]()
$230
This Southwest deal was found by Cheapflights users on 4/19. 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.
Mon 5/184:10 pm
MEM
- MDW
Nonstop1h 35m
Southwest
Wed 5/209:05 pm
MDW
- MEM
Nonstop1h 45m
Southwest
Deal found 4/19![Southwest logo]()
$231
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 April 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 April 23, 2026.
This Delta deal was found by Cheapflights users on 4/20. 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 5/125:49 pm
MEM
- ORD
1 stop4h 38m
Delta
Wed 5/135:30 am
ORD
- MEM
1 stop5h 05m
Delta
Deal found 4/20![Delta logo]()
$209
This Southwest deal was found by Cheapflights users on 4/21. 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 5/123:00 pm
MEM
- MDW
Nonstop1h 35m
Southwest
Thu 5/149:40 pm
MDW
- MEM
Nonstop1h 45m
Southwest
Deal found 4/21![Southwest logo]()
$277
This United Airlines deal was found by Cheapflights users on 4/19. 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.
Wed 7/17:15 am
MEM
- ORD
Nonstop2h 05m
United Airlines
Wed 7/812:40 pm
ORD
- MEM
Nonstop2h 02m
United Airlines
Deal found 4/19![United Airlines logo]()
$297
This Kiwi.com deal was found by Cheapflights users on 4/18. 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.
Sun 5/37:20 pm
GPT
- ORD
2 stops36h 35m
Multiple Airlines
Thu 5/710:22 am
ORD
- GPT
1 stop21h 19m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$346
This Delta deal was found by Cheapflights users on 4/20. 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 6/64:11 pm
MEM
- ORD
1 stop5h 42m
Delta
Wed 6/105:30 am
ORD
- MEM
1 stop7h 05m
Delta
Deal found 4/20![Delta logo]()
$245
This Southwest deal was found by Cheapflights users on 4/20. 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.
Tue 6/98:25 am
MEM
- MDW
2 stops6h 45m
Southwest
Sat 6/136:30 am
MDW
- MEM
1 stop5h 55m
Southwest
Deal found 4/20![Southwest logo]()
$290
This Delta deal was found by Cheapflights users on 4/18. 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 8/127:15 pm
MOB
- ORD
1 stop4h 42m
Delta
Sat 8/153:35 pm
ORD
- MOB
1 stop7h 20m
Delta
Deal found 4/18![Delta logo]()
$275
This United Airlines deal was found by Cheapflights users on 4/22. 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.
Tue 7/146:40 pm
MEM
- ORD
Nonstop2h 05m
United Airlines
Sat 7/188:55 am
ORD
- MEM
Nonstop2h 10m
United Airlines
Deal found 4/22![United Airlines logo]()
$318
This Southwest deal was found by Cheapflights users on 4/18. 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.
Tue 5/193:00 pm
MEM
- MDW
Nonstop1h 35m
Southwest
Tue 5/199:05 pm
MDW
- MEM
Nonstop1h 45m
Southwest
Deal found 4/18![Southwest logo]()
$297
This Delta deal was found by Cheapflights users on 4/18. 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 7/314:26 pm
MOB
- MDW
1 stop5h 49m
Delta
Tue 8/411:05 am
MDW
- MOB
1 stop7h 05m
Delta
Deal found 4/18![Delta logo]()
$290
This United Airlines deal was found by Cheapflights users on 4/21. 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 7/29:46 am
MEM
- ORD
Nonstop2h 11m
United Airlines
Tue 7/78:05 pm
ORD
- MEM
Nonstop2h 01m
United Airlines
Deal found 4/21![United Airlines logo]()
$324
This Southwest deal was found by Cheapflights users on 4/22. 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 5/56:35 am
MEM
- ORD
1 stop8h 25m
Southwest
Wed 5/2711:55 am
ORD
- MEM
2 stops9h 50m
Southwest
Deal found 4/22![Southwest logo]()
$308
This United Airlines deal was found by Cheapflights users on 4/18. 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.
Mon 6/294:09 pm
BTR
- ORD
1 stop5h 31m
United Airlines
Fri 7/36:30 am
ORD
- BTR
1 stop6h 59m
United Airlines
Deal found 4/18![United Airlines logo]()
$329
This Delta deal was found by Cheapflights users on 4/22. 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.
Sun 5/37:26 pm
MEM
- ORD
1 stop4h 33m
Delta
Wed 5/277:07 am
ORD
- MEM
1 stop6h 37m
Delta
Deal found 4/22![Delta logo]()
$302
This Southwest deal was found by Cheapflights users on 4/22. 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.
Sun 5/37:45 am
MEM
- ORD
1 stop5h 05m
Southwest
Wed 5/2711:55 am
ORD
- MEM
2 stops9h 50m
Southwest
Deal found 4/22![Southwest logo]()
$308
This Delta deal was found by Cheapflights users on 4/21. 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 5/302:55 pm
JAN
- ORD
1 stop6h 58m
Delta
Mon 6/15:30 am
ORD
- JAN
1 stop4h 34m
Delta
Deal found 4/21![Delta logo]()
$303
This Southwest deal was found by Cheapflights users on 4/18. 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.
Tue 5/198:10 am
MEM
- MDW
2 stops7h 35m
Southwest
Tue 5/269:05 pm
MDW
- MEM
Nonstop1h 45m
Southwest
Deal found 4/18![Southwest logo]()
$312
This United Airlines deal was found by Cheapflights users on 4/18. 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 8/295:15 pm
GPT
- ORD
1 stop6h 02m
United Airlines
Wed 9/27:30 am
ORD
- GPT
1 stop5h 56m
United Airlines
Deal found 4/18![United Airlines logo]()
$371
This Delta deal was found by Cheapflights users on 4/21. 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 5/235:10 pm
MOB
- ORD
1 stop4h 36m
Delta
Tue 5/265:30 am
ORD
- MOB
1 stop6h 35m
Delta
Deal found 4/21![Delta logo]()
$307
This Southwest deal was found by Cheapflights users on 4/19. 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 7/14:15 pm
MEM
- MDW
1 stop4h 55m
Southwest
Wed 7/810:15 am
MDW
- MEM
2 stops7h 15m
Southwest
Deal found 4/19![Southwest logo]()
$322
This Delta deal was found by Cheapflights users on 4/20. 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 5/293:48 pm
BTR
- MDW
1 stop5h 21m
Delta
Mon 6/110:59 am
MDW
- BTR
1 stop7h 25m
Delta
Deal found 4/20![Delta logo]()
$316
This Southwest deal was found by Cheapflights users on 4/20. 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.
Sun 5/105:40 am
MEM
- ORD
2 stops9h 50m
Southwest
Wed 5/1311:55 am
ORD
- MEM
1 stop5h 35m
Southwest
Deal found 4/20![Southwest logo]()
$324
This Delta deal was found by Cheapflights users on 4/18. 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 7/167:06 pm
BTR
- ORD
1 stop4h 47m
Delta
Tue 7/218:03 am
ORD
- BTR
1 stop7h 06m
Delta
Deal found 4/18![Delta logo]()
$316
This Southwest deal was found by Cheapflights users on 4/20. 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.
Thu 5/215:05 am
MEM
- MDW
Nonstop1h 35m
Southwest
Sun 5/2411:10 am
MDW
- MEM
Nonstop1h 40m
Southwest
Deal found 4/20![Southwest logo]()
$324
This Delta deal was found by Cheapflights users on 4/20. 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 5/293:48 pm
BTR
- ORD
1 stop4h 38m
Delta
Mon 6/15:30 am
ORD
- BTR
1 stop7h 19m
Delta
Deal found 4/20![Delta logo]()
$316
This United Airlines deal was found by Cheapflights users on 4/20. 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 6/126:09 pm
BTR
- ORD
1 stop6h 36m
United Airlines
Sun 6/146:30 am
ORD
- BTR
1 stop4h 50m
United Airlines
Deal found 4/20![United Airlines logo]()
$483
This Southwest deal was found by Cheapflights users on 4/18. 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 5/235:25 am
MEM
- MDW
2 stops9h 15m
Southwest
Sun 5/2411:10 am
MDW
- MEM
Nonstop1h 40m
Southwest
Deal found 4/18![Southwest logo]()
$333
This Delta deal was found by Cheapflights users on 4/22. 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.
Fri 6/52:30 pm
MEM
- MDW
1 stop6h 39m
Delta
Wed 6/105:11 pm
MDW
- MEM
1 stop6h 15m
Delta
Deal found 4/22![Delta logo]()
$324
This United Airlines deal was found by Cheapflights users on 4/19. 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.
Fri 5/86:15 pm
BTR
- ORD
2 stops12h 28m
United Airlines
Sun 5/107:30 am
ORD
- BTR
1 stop8h 01m
United Airlines
Deal found 4/19![United Airlines logo]()
$503
This Delta deal was found by Cheapflights users on 4/19. 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.
Fri 7/33:00 pm
GPT
- ORD
1 stop5h 32m
Delta
Sat 7/115:15 am
ORD
- GPT
1 stop4h 04m
Delta
Deal found 4/19![Delta logo]()
$325
Last-minute flights from Mississippi to ChicagoDiscover last-minute flight deals from Mississippi to Chicago. Data last updated April 23, 2026 and is based on user searches.
Discover last-minute flight deals from Mississippi to Chicago. Data last updated April 23, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 4/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/711:59 am
MEM
- MDW
1 stop10h 03m
Frontier
Sun 5/106:00 am
MDW
- MEM
1 stop4h 59m
Frontier
Deal found 4/22![Frontier logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 4/17. 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.
Fri 5/87:03 pm
MEM
- ORD
1 stop17h 20m
Multiple Airlines
Sat 5/99:37 pm
ORD
- MEM
2 stops21h 29m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 4/17. 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.
Fri 5/87:03 pm
MEM
- ORD
1 stop17h 20m
Multiple Airlines
Tue 5/124:05 pm
ORD
- MEM
2 stops48h 27m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$238
This Southwest deal was found by Cheapflights users on 4/17. 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 5/95:25 am
MEM
- ORD
1 stop6h 05m
Southwest
Sat 5/92:05 pm
ORD
- MEM
1 stop5h 00m
Southwest
Deal found 4/17![Southwest logo]()
$217
This Delta deal was found by Cheapflights users on 4/17. 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 5/95:30 am
MEM
- ORD
1 stop4h 08m
Delta
Tue 5/126:24 am
ORD
- MEM
1 stop5h 07m
Delta
Deal found 4/17![Delta logo]()
$218
This American Airlines deal was found by Cheapflights users on 4/17. 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.
Sat 5/99:45 am
MEM
- ORD
Nonstop2h 05m
American Airlines
Sat 5/95:06 pm
ORD
- MEM
Nonstop1h 58m
American Airlines
Deal found 4/17![American Airlines logo]()
$239
This American Airlines deal was found by Cheapflights users on 4/20. 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.
Mon 5/117:34 pm
MEM
- ORD
Nonstop2h 05m
American Airlines
Wed 5/1310:05 pm
ORD
- MEM
Nonstop1h 54m
American Airlines
Deal found 4/20![American Airlines logo]()
$225
This Delta deal was found by Cheapflights users on 4/20. 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.
Mon 5/114:11 pm
MEM
- ORD
1 stop4h 15m
Delta
Wed 5/1311:26 am
ORD
- MEM
1 stop5h 33m
Delta
Deal found 4/20![Delta logo]()
$245
This Delta deal was found by Cheapflights users on 4/20. 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 5/125:49 pm
MEM
- ORD
1 stop4h 38m
Delta
Wed 5/135:30 am
ORD
- MEM
1 stop5h 05m
Delta
Deal found 4/20![Delta logo]()
$209
This Delta deal was found by Cheapflights users on 4/20. 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 5/125:30 am
MEM
- MDW
1 stop4h 30m
Delta
Tue 5/125:10 pm
MDW
- MEM
1 stop6h 02m
Delta
Deal found 4/20![Delta logo]()
$209
This Southwest deal was found by Cheapflights users on 4/19. 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.
Mon 5/184:10 pm
MEM
- MDW
Nonstop1h 35m
Southwest
Wed 5/209:05 pm
MDW
- MEM
Nonstop1h 45m
Southwest
Deal found 4/19![Southwest logo]()
$231
This American Airlines deal was found by Cheapflights users on 4/21. 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 5/205:05 am
MEM
- ORD
1 stop7h 31m
American Airlines
Wed 5/279:00 pm
ORD
- MEM
Nonstop1h 55m
American Airlines
Deal found 4/21![American Airlines logo]()
$228
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 April 23, 2026.
Search for one-way flight options from Mississippi to Chicago. Find affordable one-way fares based on user searches. Data last updated April 23, 2026.
This Priceline deal was found by Cheapflights users on 4/22. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/1411:59 am
MEM
- ORD
1 stop7h 52m
Frontier
Deal found 4/22![Frontier logo]()
$70
This American Airlines deal was found by Cheapflights users on 4/18. 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 6/306:10 am
MEM
- ORD
Nonstop2h 08m
American Airlines
Deal found 4/18![American Airlines logo]()
$79
This Delta deal was found by Cheapflights users on 4/18. 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 5/195:49 pm
MEM
- ORD
1 stop4h 38m
Delta
Deal found 4/18![Delta logo]()
$89
This Expedia deal was found by Cheapflights users on 4/22. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/711:59 am
MEM
- ORD
1 stop7h 52m
Frontier
Deal found 4/22![Frontier logo]()
$90
This Frontier deal was found by Cheapflights users on 4/19. 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 6/3011:51 am
MEM
- ORD
1 stop8h 02m
Frontier
Deal found 4/19![Frontier logo]()
$95
This Southwest deal was found by Cheapflights users on 4/21. 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 5/205:15 am
MEM
- MDW
Nonstop1h 35m
Southwest
Deal found 4/21![Southwest logo]()
$95
This Frontier deal was found by Cheapflights users on 4/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/1411:59 am
MEM
- MDW
1 stop10h 03m
Frontier
Deal found 4/18![Frontier logo]()
$96
This Expedia deal was found by Cheapflights users on 4/22. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/1011:59 am
MEM
- MDW
1 stop10h 03m
Frontier
Deal found 4/22![Frontier logo]()
$98
This Kiwi.com deal was found by Cheapflights users on 4/19. 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.
Mon 4/276:39 pm
MEM
- ORD
1 stop26h 38m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$100
This Frontier deal was found by Cheapflights users on 4/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/2311:51 am
MEM
- MDW
1 stop10h 20m
Frontier
Deal found 4/20![Frontier logo]()
$101
This Delta deal was found by Cheapflights users on 4/20. 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 5/202:30 pm
MEM
- MDW
1 stop6h 39m
Delta
Deal found 4/20![Delta logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 4/18. 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 6/158:41 am
MEM
- MDW
1 stop11h 52m
Allegiant Air
Deal found 4/18![Allegiant Air logo]()
$110
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 April 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $202 (Frontier) |
One-way from | $70 (Priceline) |
Popular in | July |
Cheapest in | September |
Average price | $346 |
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 April 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 - ORD
MEMORD
Memphis
Tue 5/12
5:49 pm-10:27 pm
1 stop4h 38m
Chicago O'Hare Intl
Wed 5/13
5:30 am-10:35 am
1 stop5h 05m
$209
MemphisChicago
MEM - ORD
MEMORD
Memphis
Sat 6/6
4:11 pm-9:53 pm
1 stop5h 42m
Chicago O'Hare Intl
Wed 6/10
5:30 am-12:35 pm
1 stop7h 05m
$245
MobileChicago
MOB - ORD
MOBORD
Mobile
Wed 8/12
7:15 pm-11:57 pm
1 stop4h 42m
Chicago O'Hare Intl
Sat 8/15
3:35 pm-10:55 pm
1 stop7h 20m
$275
MemphisChicago
MEM - MDW
MEMMDW
Memphis
Tue 5/12
3:00 pm-4:35 pm
Nonstop1h 35m
Chicago Midway
Thu 5/14
9:40 pm-11:25 pm
Nonstop1h 45m
$277
MemphisChicago
MEM - MDW
MEMMDW
Memphis
Tue 6/9
8:25 am-3:10 pm
2 stops6h 45m
Chicago Midway
Sat 6/13
6:30 am-12:25 pm
1 stop5h 55m
$290
MobileChicago
MOB - MDW
MOBMDW
Mobile
Fri 7/31
4:26 pm-10:15 pm
1 stop5h 49m
Chicago Midway
Tue 8/4
11:05 am-6:10 pm
1 stop7h 05m
$290
MemphisChicago
MEM - ORD
MEMORD
Memphis
Wed 7/1
7:15 am-9:20 am
Nonstop2h 05m
Chicago O'Hare Intl
Wed 7/8
12:40 pm-2:42 pm
Nonstop2h 02m
$297
MemphisChicago
MEM - MDW
MEMMDW
Memphis
Tue 5/19
3:00 pm-4:35 pm
Nonstop1h 35m
Chicago Midway
Tue 5/19
9:05 pm-10:50 pm
Nonstop1h 45m
$297
MemphisChicago
MEM - ORD
MEMORD
Memphis
Sun 5/3
7:26 pm-11:59 pm
1 stop4h 33m
Chicago O'Hare Intl
Wed 5/27
7:07 am-1:44 pm
1 stop6h 37m
$302
JacksonChicago
JAN - ORD
JANORD
Jackson-Evers Intl
Sat 5/30
2:55 pm-9:53 pm
1 stop6h 58m
Chicago O'Hare Intl
Mon 6/1
5:30 am-10:04 am
1 stop4h 34m
$303
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
BTR-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 April is currently the most expensive (average of $314). 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
Flights by cabin class
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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 April 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 April 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 April 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$196 | Average$460 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$234 | Average$406 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$248 | Average$445 | FlexibilityNo cancel fee | On-time71% |