$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 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — CHI
Apr 12 — Apr 191
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 March 13, 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 March 13, 2026.
This United Airlines deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/86:45 pm
MEM
- ORD
Nonstop2h 03m
United Airlines
Wed 4/153:45 pm
ORD
- MEM
Nonstop2h 02m
United Airlines
Deal found 3/11![United Airlines logo]()
$157
This Southwest deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/83:00 pm
MEM
- MDW
Nonstop1h 35m
Southwest
Wed 4/89:05 pm
MDW
- MEM
Nonstop1h 45m
Southwest
Deal found 3/12![Southwest logo]()
$157
This Southwest deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” 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 5/165:00 am
MEM
- MDW
Nonstop1h 40m
Southwest
Wed 5/209:05 pm
MDW
- MEM
Nonstop1h 45m
Southwest
Deal found 3/8![Southwest logo]()
$169
This Southwest deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/86:35 am
MEM
- ORD
1 stop8h 25m
Southwest
Wed 4/1511:55 am
ORD
- MEM
1 stop5h 40m
Southwest
Deal found 3/11![Southwest logo]()
$177
This Delta deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2810:43 am
MEM
- MDW
1 stop5h 43m
Delta
Tue 5/56:00 am
MDW
- MEM
1 stop6h 39m
Delta
Deal found 3/10![Delta logo]()
$177
This Expedia deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/95:54 pm
MEM
- MDW
1 stop4h 27m
Frontier
Thu 4/166:00 am
MDW
- MEM
1 stop11h 16m
Frontier
Deal found 3/12![Frontier logo]()
$180
This Southwest deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/88:10 am
MEM
- ORD
1 stop4h 40m
Southwest
Wed 4/82:40 pm
ORD
- MEM
1 stop7h 05m
Southwest
Deal found 3/12![Southwest logo]()
$182
This American Airlines deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/137:34 pm
MEM
- ORD
Nonstop2h 05m
American Airlines
Wed 4/1510:05 pm
ORD
- MEM
Nonstop1h 54m
American Airlines
Deal found 3/10![American Airlines logo]()
$188
This Southwest deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 3/305:05 am
MEM
- MDW
Nonstop1h 35m
Southwest
Wed 4/18:40 pm
MDW
- MEM
Nonstop1h 45m
Southwest
Deal found 3/9![Southwest logo]()
$188
This Delta deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/56:10 am
MEM
- ORD
1 stop4h 09m
Delta
Tue 5/128:10 am
ORD
- MEM
1 stop5h 34m
Delta
Deal found 3/11![Delta logo]()
$197
This United Airlines deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 3/306:32 pm
MEM
- ORD
Nonstop2h 03m
United Airlines
Wed 4/18:50 am
ORD
- MEM
Nonstop2h 04m
United Airlines
Deal found 3/9![United Airlines logo]()
$198
This Southwest deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” 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 5/165:25 am
MEM
- ORD
2 stops10h 05m
Southwest
Wed 5/202:40 pm
ORD
- MEM
1 stop7h 05m
Southwest
Deal found 3/8![Southwest logo]()
$200
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 March 13, 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 March 13, 2026.
This United Airlines deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/87:30 am
MEM
- ORD
Nonstop1h 56m
United Airlines
Tue 4/143:45 pm
ORD
- MEM
Nonstop2h 02m
United Airlines
Deal found 3/12![United Airlines logo]()
$157
This Southwest deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/149:45 am
MEM
- ORD
1 stop8h 40m
Southwest
Wed 4/1511:55 am
ORD
- MEM
1 stop5h 40m
Southwest
Deal found 3/12![Southwest logo]()
$177
This Delta deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” 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 4/2512:21 pm
MEM
- ORD
1 stop7h 31m
Delta
Mon 4/275:04 pm
ORD
- MEM
1 stop4h 04m
Delta
Deal found 3/8![Delta logo]()
$220
This United Airlines deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/16:47 pm
MEM
- ORD
Nonstop2h 03m
United Airlines
Tue 4/73:45 pm
ORD
- MEM
Nonstop2h 02m
United Airlines
Deal found 3/11![United Airlines logo]()
$157
This American Airlines deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/266:45 pm
MOB
- ORD
1 stop5h 31m
American Airlines
Mon 3/305:00 pm
ORD
- MOB
1 stop6h 51m
American Airlines
Deal found 3/10![American Airlines logo]()
$319
This Southwest deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/86:35 am
MEM
- ORD
1 stop8h 25m
Southwest
Tue 4/1411:55 am
ORD
- MEM
2 stops8h 45m
Southwest
Deal found 3/12![Southwest logo]()
$182
This Southwest deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 5/128:10 am
MEM
- MDW
1 stop5h 20m
Southwest
Sat 5/166:15 pm
MDW
- MEM
Nonstop1h 45m
Southwest
Deal found 3/9![Southwest logo]()
$198
This Delta deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 4/135:59 pm
MEM
- ORD
1 stop6h 00m
Delta
Wed 4/155:15 am
ORD
- MEM
1 stop5h 57m
Delta
Deal found 3/9![Delta logo]()
$239
This Southwest deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 5/129:45 am
MEM
- ORD
1 stop8h 40m
Southwest
Sat 5/161:55 pm
ORD
- MEM
1 stop7h 50m
Southwest
Deal found 3/9![Southwest logo]()
$213
This United Airlines deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/136:48 pm
MEM
- ORD
Nonstop2h 01m
United Airlines
Sat 5/1612:40 pm
ORD
- MEM
Nonstop1h 59m
United Airlines
Deal found 3/12![United Airlines logo]()
$248
This Southwest deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” 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 4/95:05 am
MEM
- MDW
Nonstop1h 35m
Southwest
Mon 4/139:40 pm
MDW
- MEM
Nonstop1h 45m
Southwest
Deal found 3/8![Southwest logo]()
$219
This Delta deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/106:48 pm
MOB
- ORD
1 stop5h 06m
Delta
Tue 4/145:15 am
ORD
- MOB
1 stop6h 48m
Delta
Deal found 3/11![Delta logo]()
$280
This Southwest deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/115:00 am
MEM
- MDW
Nonstop1h 40m
Southwest
Mon 4/139:40 pm
MDW
- MEM
Nonstop1h 45m
Southwest
Deal found 3/10![Southwest logo]()
$219
This United Airlines deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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 5/711:10 am
MEM
- ORD
Nonstop2h 05m
United Airlines
Sun 5/108:03 pm
ORD
- MEM
Nonstop2h 01m
United Airlines
Deal found 3/7![United Airlines logo]()
$275
This Delta deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” 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 5/131:36 pm
BTR
- MDW
1 stop7h 33m
Delta
Tue 5/196:23 am
MDW
- BTR
1 stop6h 28m
Delta
Deal found 3/8![Delta logo]()
$289
This American Airlines deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” 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 4/176:33 pm
MOB
- ORD
1 stop5h 21m
American Airlines
Tue 4/219:55 am
ORD
- MOB
2 stops7h 24m
American Airlines
Deal found 3/8![American Airlines logo]()
$354
This United Airlines deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” 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.
Sun 4/267:30 am
MEM
- ORD
Nonstop1h 56m
United Airlines
Wed 4/293:45 pm
ORD
- MEM
Nonstop2h 02m
United Airlines
Deal found 3/8![United Airlines logo]()
$275
This Southwest deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/235:05 am
MEM
- MDW
Nonstop1h 35m
Southwest
Mon 4/274:00 pm
MDW
- MEM
2 stops7h 00m
Southwest
Deal found 3/11![Southwest logo]()
$234
This Delta deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” 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 5/131:36 pm
BTR
- MDW
1 stop7h 33m
Delta
Thu 5/216:23 am
MDW
- BTR
1 stop6h 28m
Delta
Deal found 3/8![Delta logo]()
$289
This Kiwi.com deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 3/279:40 am
GPT
- MDW
2 stops13h 59m
Multiple Airlines
Sun 3/299:30 am
MDW
- GPT
1 stop9h 10m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$842
This Delta deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” 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 5/131:36 pm
BTR
- MDW
1 stop7h 33m
Delta
Sat 5/165:10 pm
MDW
- BTR
1 stop4h 53m
Delta
Deal found 3/8![Delta logo]()
$289
This United Airlines deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/275:15 pm
GPT
- ORD
1 stop7h 33m
United Airlines
Sun 8/305:30 am
ORD
- GPT
1 stop7h 56m
United Airlines
Deal found 3/11![United Airlines logo]()
$309
This Southwest deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” 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 4/265:10 am
MEM
- MDW
Nonstop1h 35m
Southwest
Wed 4/292:35 pm
MDW
- MEM
2 stops7h 10m
Southwest
Deal found 3/8![Southwest logo]()
$259
This Delta deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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 4/167:08 pm
BTR
- ORD
1 stop4h 51m
Delta
Sun 4/195:15 am
ORD
- BTR
1 stop4h 31m
Delta
Deal found 3/7![Delta logo]()
$289
This Southwest deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/95:40 am
MEM
- ORD
2 stops9h 50m
Southwest
Thu 4/166:00 am
ORD
- MEM
1 stop9h 30m
Southwest
Deal found 3/12![Southwest logo]()
$260
This KAYAK deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/125:10 am
MOB
- ORD
1 stop5h 34m
American Airlines
Tue 4/145:00 am
ORD
- MOB
1 stop5h 06m
American Airlines
Deal found 3/12![American Airlines logo]()
$464
This Delta deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” 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 5/157:04 pm
BTR
- ORD
1 stop4h 55m
Delta
Tue 5/198:10 am
ORD
- BTR
1 stop4h 41m
Delta
Deal found 3/8![Delta logo]()
$289
This Delta deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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 4/164:00 pm
BTR
- ORD
1 stop5h 25m
Delta
Mon 4/209:48 am
ORD
- BTR
1 stop5h 27m
Delta
Deal found 3/7![Delta logo]()
$289
This Southwest deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” 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 5/87:45 am
MEM
- ORD
1 stop5h 05m
Southwest
Tue 5/1210:30 am
ORD
- MEM
1 stop11h 15m
Southwest
Deal found 3/8![Southwest logo]()
$269
This United Airlines deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” 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 5/135:00 am
BTR
- ORD
1 stop5h 55m
United Airlines
Sun 5/175:30 am
ORD
- BTR
1 stop7h 53m
United Airlines
Deal found 3/8![United Airlines logo]()
$359
Last-minute flights from Mississippi to ChicagoDiscover last-minute flight deals from Mississippi to Chicago. Data last updated March 13, 2026 and is based on user searches.
Discover last-minute flight deals from Mississippi to Chicago. Data last updated March 13, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 3/305:05 am
MEM
- MDW
Nonstop1h 35m
Southwest
Wed 4/18:40 pm
MDW
- MEM
Nonstop1h 45m
Southwest
Deal found 3/9![Southwest logo]()
$188
This United Airlines deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 3/306:32 pm
MEM
- ORD
Nonstop2h 03m
United Airlines
Wed 4/18:50 am
ORD
- MEM
Nonstop2h 04m
United Airlines
Deal found 3/9![United Airlines logo]()
$198
This United Airlines deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/86:45 pm
MEM
- ORD
Nonstop2h 03m
United Airlines
Wed 4/153:45 pm
ORD
- MEM
Nonstop2h 02m
United Airlines
Deal found 3/11![United Airlines logo]()
$157
This Southwest deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/83:00 pm
MEM
- MDW
Nonstop1h 35m
Southwest
Tue 4/149:05 pm
MDW
- MEM
Nonstop1h 45m
Southwest
Deal found 3/11![Southwest logo]()
$157
This Southwest deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/85:15 am
MEM
- MDW
Nonstop1h 35m
Southwest
Wed 4/811:35 am
MDW
- MEM
1 stop6h 00m
Southwest
Deal found 3/12![Southwest logo]()
$167
This Southwest deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/88:10 am
MEM
- ORD
1 stop4h 40m
Southwest
Tue 4/1411:55 am
ORD
- MEM
1 stop5h 40m
Southwest
Deal found 3/11![Southwest logo]()
$177
This Southwest deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/88:10 am
MEM
- ORD
1 stop4h 40m
Southwest
Wed 4/82:40 pm
ORD
- MEM
1 stop7h 05m
Southwest
Deal found 3/12![Southwest logo]()
$182
This Expedia deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/95:54 pm
MEM
- MDW
1 stop4h 27m
Frontier
Thu 4/166:00 am
MDW
- MEM
1 stop11h 16m
Frontier
Deal found 3/12![Frontier logo]()
$180
This American Airlines deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/137:34 pm
MEM
- ORD
Nonstop2h 05m
American Airlines
Wed 4/1510:05 pm
ORD
- MEM
Nonstop1h 54m
American Airlines
Deal found 3/10![American Airlines logo]()
$188
This Delta deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/156:29 am
MEM
- MDW
1 stop6h 14m
Delta
Tue 4/216:00 am
MDW
- MEM
1 stop5h 12m
Delta
Deal found 3/12![Delta logo]()
$197
This American Airlines deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” 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 4/257:34 pm
MEM
- ORD
Nonstop2h 05m
American Airlines
Mon 4/2710:05 pm
ORD
- MEM
Nonstop1h 54m
American Airlines
Deal found 3/8![American Airlines logo]()
$200
This Delta deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2810:43 am
MEM
- MDW
1 stop5h 43m
Delta
Tue 5/56:00 am
MDW
- MEM
1 stop6h 39m
Delta
Deal found 3/10![Delta logo]()
$177
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 March 13, 2026.
Search for one-way flight options from Mississippi to Chicago. Find affordable one-way fares based on user searches. Data last updated March 13, 2026.
This United Airlines deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/66:48 pm
MEM
- ORD
Nonstop2h 01m
United Airlines
Deal found 3/10![United Airlines logo]()
$79
This Southwest deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/153:00 pm
MEM
- MDW
Nonstop1h 35m
Southwest
Deal found 3/10![Southwest logo]()
$79
This Priceline deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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.
Sun 5/178:30 pm
MEM
- ORD
1 stop10h 17m
Frontier
Deal found 3/9![Frontier logo]()
$80
This Priceline deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” 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 4/95:54 pm
MEM
- MDW
1 stop4h 27m
Frontier
Deal found 3/8![Frontier logo]()
$80
This Expedia deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 4/164:36 pm
MEM
- ORD
1 stop17h 14m
Frontier
Deal found 3/9![Frontier logo]()
$86
This Delta deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/126:35 am
MEM
- ORD
1 stop6h 26m
Delta
Deal found 3/10![Delta logo]()
$89
This Delta deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/56:20 am
MEM
- MDW
1 stop5h 47m
Delta
Deal found 3/10![Delta logo]()
$89
This Frontier deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier 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 3/11![Frontier logo]()
$90
This United Airlines deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” 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 4/46:47 pm
MEM
- ORD
Nonstop2h 03m
United Airlines
Deal found 3/8![United Airlines logo]()
$91
This Southwest deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 5/165:00 am
MEM
- MDW
Nonstop1h 40m
Southwest
Deal found 3/9![Southwest logo]()
$91
This Southwest deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/95:50 am
MEM
- ORD
2 stops12h 00m
Southwest
Deal found 3/10![Southwest logo]()
$94
This Delta deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/76:22 am
MEM
- ORD
1 stop6h 55m
Delta
Deal found 3/10![Delta logo]()
$99
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 March 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $157 (United Airlines) |
One-way from | $79 (United Airlines) |
Popular in | July |
Cheapest in | September |
Average price | $533 |
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 March 13, 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
Wed 4/8
7:30 am-9:26 am
Nonstop1h 56m
Chicago O'Hare Intl
Tue 4/14
3:45 pm-5:47 pm
Nonstop2h 02m
$157
MemphisChicago
MEM - ORD
MEMORD
Memphis
Wed 4/1
6:47 pm-8:50 pm
Nonstop2h 03m
Chicago O'Hare Intl
Tue 4/7
3:45 pm-5:47 pm
Nonstop2h 02m
$157
MemphisChicago
MEM - ORD
MEMORD
Memphis
Tue 4/14
9:45 am-6:25 pm
1 stop8h 40m
Chicago O'Hare Intl
Wed 4/15
11:55 am-5:35 pm
1 stop5h 40m
$177
MemphisChicago
MEM - ORD
MEMORD
Memphis
Wed 4/8
6:35 am-3:00 pm
1 stop8h 25m
Chicago O'Hare Intl
Tue 4/14
11:55 am-8:40 pm
2 stops8h 45m
$182
MemphisChicago
MEM - MDW
MEMMDW
Memphis
Tue 5/12
8:10 am-1:30 pm
1 stop5h 20m
Chicago Midway
Sat 5/16
6:15 pm-8:00 pm
Nonstop1h 45m
$198
MemphisChicago
MEM - ORD
MEMORD
Memphis
Tue 5/12
9:45 am-6:25 pm
1 stop8h 40m
Chicago O'Hare Intl
Sat 5/16
1:55 pm-9:45 pm
1 stop7h 50m
$213
Quickest round-trip
MemphisChicago
MEM - MDW
MEMMDW
Memphis
Thu 4/9
5:05 am-6:40 am
Nonstop1h 35m
Chicago Midway
Mon 4/13
9:40 pm-11:25 pm
Nonstop1h 45m
$219
MemphisChicago
MEM - MDW
MEMMDW
Memphis
Sat 4/11
5:00 am-6:40 am
Nonstop1h 40m
Chicago Midway
Mon 4/13
9:40 pm-11:25 pm
Nonstop1h 45m
$219
MemphisChicago
MEM - ORD
MEMORD
Memphis
Sat 4/25
12:21 pm-7:52 pm
1 stop7h 31m
Chicago O'Hare Intl
Mon 4/27
5:04 pm-9:08 pm
1 stop4h 04m
$220
MemphisChicago
MEM - MDW
MEMMDW
Memphis
Thu 4/23
5:05 am-6:40 am
Nonstop1h 35m
Chicago Midway
Mon 4/27
4:00 pm-11:00 pm
2 stops7h 00m
$234
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
MOB-ORD
MEM-MDW
BTR-MDW
GPT-MDW
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Mississippi to Chicago
USMS-CHI
MEM-ORD
MOB-ORD
MEM-MDW
BTR-MDW
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 $196). Flying from Mississippi to Chicago in March is currently the most expensive (average of $337). 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 locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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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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 March 13, 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 March 13, 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 March 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$196 | Average$465 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$234 | Average$406 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$248 | Average$447 | FlexibilityNo cancel fee | On-time71% |