$76+ 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 5/7. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — CHI
May 10 — May 171
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
Cheapest
Best
Last-minute
One-way
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 10, 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 10, 2026.
This Frontier deal was found by Cheapflights users on 4/8. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/711:59 am
MEM
- MDW
1 stop10h 03m
Frontier
Tue 6/166:00 am
MDW
- MEM
1 stop4h 55m
Frontier
Deal found 4/8![Frontier logo]()
$185
This Southwest deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/56:00 am
MEM
- ORD
2 stops9h 00m
Southwest
Tue 6/211:55 am
ORD
- MEM
2 stops8h 45m
Southwest
Deal found 4/6![Southwest logo]()
$187
This Southwest deal was found by Cheapflights users on 4/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/512:20 pm
MEM
- MDW
2 stops7h 50m
Southwest
Tue 5/1210:25 am
MDW
- MEM
2 stops7h 10m
Southwest
Deal found 4/7![Southwest logo]()
$187
This Kiwi.com deal was found by Cheapflights users on 4/8. 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 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
2 stops15h 44m
Multiple Airlines
Thu 4/301:27 pm
ORD
- MEM
1 stop28h 22m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/46:39 pm
MEM
- ORD
1 stop16h 40m
Multiple Airlines
Thu 5/73:44 pm
ORD
- MEM
1 stop26h 05m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$193
This Kiwi.com deal was found by Cheapflights users on 4/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/85:04 pm
MEM
- ORD
1 stop19h 21m
Multiple Airlines
Wed 6/107:52 am
ORD
- MEM
1 stop23h 53m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$194
This Delta deal was found by Cheapflights users on 4/8. 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.
Tue 5/51:25 pm
MEM
- ORD
1 stop5h 10m
Delta
Tue 5/126:24 am
ORD
- MEM
1 stop5h 07m
Delta
Deal found 4/8![Delta logo]()
$197
This Delta deal was found by Cheapflights users on 4/8. 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.
Tue 5/512:17 pm
MEM
- MDW
1 stop4h 09m
Delta
Tue 5/126:23 am
MDW
- MEM
1 stop5h 16m
Delta
Deal found 4/8![Delta logo]()
$197
This American Airlines deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 6/65:53 pm
MEM
- ORD
Nonstop2h 19m
American Airlines
Wed 6/108:00 am
ORD
- MEM
Nonstop1h 58m
American Airlines
Deal found 4/5![American Airlines logo]()
$198
This Southwest deal was found by Cheapflights users on 4/9. 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 5/195:15 am
MEM
- MDW
Nonstop1h 35m
Southwest
Thu 5/2110:00 am
MDW
- MEM
Nonstop1h 40m
Southwest
Deal found 4/9![Southwest logo]()
$198
This Kiwi.com deal was found by Cheapflights users on 4/9. 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.
Mon 5/49:17 pm
MEM
- ORD
2 stops25h 44m
Multiple Airlines
Wed 5/131:18 pm
ORD
- MEM
1 stop28h 37m
Multiple Airlines
Deal found 4/9![Multiple Airlines logo]()
$199
This Frontier deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 4/6![Frontier logo]()
$201
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 10, 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 10, 2026.
This Delta deal was found by Cheapflights users on 4/8. 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.
Tue 5/51:25 pm
MEM
- ORD
1 stop5h 10m
Delta
Tue 5/126:24 am
ORD
- MEM
1 stop5h 07m
Delta
Deal found 4/8![Delta logo]()
$197
This United Airlines deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 6/77:15 am
MEM
- ORD
Nonstop2h 05m
United Airlines
Wed 6/1012:40 pm
ORD
- MEM
Nonstop2h 02m
United Airlines
Deal found 4/5![United Airlines logo]()
$227
This Southwest deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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
- ORD
2 stops8h 55m
Southwest
Tue 5/262:40 pm
ORD
- MEM
1 stop7h 05m
Southwest
Deal found 4/5![Southwest logo]()
$258
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 4/307:20 pm
GPT
- ORD
1 stop17h 55m
Multiple Airlines
Sun 5/36:00 am
ORD
- GPT
1 stop12h 40m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$267
This American Airlines deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 4/206:33 pm
MOB
- ORD
1 stop5h 21m
American Airlines
Sat 4/256:41 pm
ORD
- MOB
1 stop5h 03m
American Airlines
Deal found 4/5![American Airlines logo]()
$339
This Delta deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 6/65:49 pm
MEM
- ORD
1 stop6h 19m
Delta
Tue 6/92:07 pm
ORD
- MEM
1 stop6h 57m
Delta
Deal found 4/5![Delta logo]()
$218
This Delta deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 stop4h 13m
Delta
Tue 6/165:30 am
ORD
- MEM
1 stop5h 07m
Delta
Deal found 4/5![Delta logo]()
$218
This Delta deal was found by Cheapflights users on 4/9. 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.
Tue 5/512:21 pm
MEM
- ORD
1 stop7h 31m
Delta
Sat 5/91:44 pm
ORD
- MEM
1 stop7h 12m
Delta
Deal found 4/9![Delta logo]()
$218
This Southwest deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/125:15 am
MEM
- MDW
Nonstop1h 35m
Southwest
Wed 6/178:10 am
MDW
- MEM
1 stop6h 50m
Southwest
Deal found 4/6![Southwest logo]()
$264
This United Airlines deal was found by Cheapflights users on 4/7. 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.
Wed 4/292:45 pm
MEM
- ORD
Nonstop2h 03m
United Airlines
Mon 5/48:03 pm
ORD
- MEM
Nonstop2h 01m
United Airlines
Deal found 4/7![United Airlines logo]()
$268
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/45:59 pm
MEM
- ORD
1 stop6h 00m
Delta
Wed 5/66:25 am
ORD
- MEM
1 stop5h 15m
Delta
Deal found 4/6![Delta logo]()
$218
This United Airlines deal was found by Cheapflights users on 4/9. 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.
Wed 5/69:02 am
MEM
- ORD
Nonstop1h 58m
United Airlines
Sat 5/93:45 pm
ORD
- MEM
Nonstop2h 00m
United Airlines
Deal found 4/9![United Airlines logo]()
$268
This Southwest deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 4/305:05 am
MEM
- MDW
Nonstop1h 35m
Southwest
Sun 5/35:00 am
MDW
- MEM
2 stops6h 40m
Southwest
Deal found 4/5![Southwest logo]()
$283
This United Airlines deal was found by Cheapflights users on 4/7. 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.
Wed 5/1311:10 am
MEM
- ORD
Nonstop2h 05m
United Airlines
Sat 5/168:50 am
ORD
- MEM
Nonstop2h 04m
United Airlines
Deal found 4/7![United Airlines logo]()
$268
This American Airlines deal was found by Cheapflights users on 4/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/86:30 pm
GPT
- ORD
1 stop5h 18m
American Airlines
Sat 9/127:02 am
ORD
- GPT
1 stop5h 10m
American Airlines
Deal found 4/7![American Airlines logo]()
$341
This Southwest deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/237:50 am
MEM
- MDW
1 stop6h 50m
Southwest
Thu 5/289:40 pm
MDW
- MEM
Nonstop1h 45m
Southwest
Deal found 4/6![Southwest logo]()
$284
This Delta deal was found by Cheapflights users on 4/7. 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.
Wed 4/296:10 am
MEM
- MDW
1 stop6h 33m
Delta
Sat 5/25:40 am
MDW
- MEM
1 stop5h 40m
Delta
Deal found 4/7![Delta logo]()
$238
This Southwest deal was found by Cheapflights users on 4/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/85:05 am
MEM
- MDW
Nonstop1h 35m
Southwest
Sun 5/1010:00 am
MDW
- MEM
Nonstop1h 40m
Southwest
Deal found 4/7![Southwest logo]()
$297
This Delta deal was found by Cheapflights users on 4/7. 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.
Fri 5/15:59 pm
MEM
- ORD
1 stop6h 00m
Delta
Tue 5/58:15 am
ORD
- MEM
1 stop6h 12m
Delta
Deal found 4/7![Delta logo]()
$267
This United Airlines deal was found by Cheapflights users on 4/9. 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.
Fri 6/56:09 pm
BTR
- ORD
1 stop6h 36m
United Airlines
Sun 7/55:30 am
ORD
- BTR
1 stop5h 50m
United Airlines
Deal found 4/9![United Airlines logo]()
$329
This Delta deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/106:32 am
MEM
- MDW
1 stop6h 04m
Delta
Sat 6/136:05 am
MDW
- MEM
1 stop4h 32m
Delta
Deal found 4/5![Delta logo]()
$274
This Southwest deal was found by Cheapflights users on 4/9. 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 5/412:15 pm
JAN
- MDW
1 stop8h 45m
Southwest
Tue 5/1211:35 am
MDW
- JAN
2 stops8h 45m
Southwest
Deal found 4/9![Southwest logo]()
$344
This United Airlines deal was found by Cheapflights users on 4/10. 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.
Thu 8/206:14 pm
BTR
- ORD
1 stop5h 03m
United Airlines
Mon 8/2410:32 am
ORD
- BTR
1 stop7h 00m
United Airlines
Deal found 4/10![United Airlines logo]()
$350
This Delta deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/910:36 am
MEM
- MDW
1 stop5h 40m
Delta
Mon 6/156:05 am
MDW
- MEM
1 stop4h 32m
Delta
Deal found 4/5![Delta logo]()
$274
This Delta deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/106:32 am
MEM
- MDW
1 stop6h 04m
Delta
Mon 6/156:05 am
MDW
- MEM
1 stop4h 32m
Delta
Deal found 4/5![Delta logo]()
$274
This Southwest deal was found by Cheapflights users on 4/9. 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.
Fri 5/812:15 pm
JAN
- MDW
2 stops9h 00m
Southwest
Sat 5/165:00 am
MDW
- JAN
1 stop6h 45m
Southwest
Deal found 4/9![Southwest logo]()
$377
This United Airlines deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 6/154:09 pm
BTR
- ORD
1 stop7h 05m
United Airlines
Sun 6/286:30 am
ORD
- BTR
1 stop4h 50m
United Airlines
Deal found 4/5![United Airlines logo]()
$385
This Southwest deal was found by Cheapflights users on 4/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/812:15 pm
JAN
- MDW
1 stop4h 45m
Southwest
Mon 5/116:55 am
MDW
- JAN
1 stop4h 45m
Southwest
Deal found 4/7![Southwest logo]()
$377
This American Airlines deal was found by Cheapflights users on 4/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/134:49 pm
MOB
- ORD
1 stop6h 59m
American Airlines
Thu 4/165:00 am
ORD
- MOB
1 stop5h 06m
American Airlines
Deal found 4/9![American Airlines logo]()
$614
This United Airlines deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 5/24:06 pm
BTR
- ORD
1 stop5h 45m
United Airlines
Tue 5/512:40 pm
ORD
- BTR
1 stop4h 54m
United Airlines
Deal found 4/5![United Airlines logo]()
$396
Last-minute flights from Mississippi to ChicagoDiscover last-minute flight deals from Mississippi to Chicago. Data last updated April 10, 2026 and is based on user searches.
Discover last-minute flight deals from Mississippi to Chicago. Data last updated April 10, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 4/125:54 pm
MEM
- MDW
1 stop4h 27m
Frontier
Thu 4/236:00 am
MDW
- MEM
1 stop11h 16m
Frontier
Deal found 4/5![Frontier logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 4/9. 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.
Sun 4/197:44 pm
MEM
- ORD
2 stops37h 56m
Multiple Airlines
Wed 4/221:27 pm
ORD
- MEM
1 stop28h 28m
Multiple Airlines
Deal found 4/9![Multiple Airlines logo]()
$231
This Kiwi.com deal was found by Cheapflights users on 4/9. 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.
Mon 4/206:39 pm
MEM
- ORD
1 stop26h 38m
Multiple Airlines
Wed 4/227:15 pm
ORD
- MEM
1 stop22h 40m
Multiple Airlines
Deal found 4/9![Multiple Airlines logo]()
$205
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 4/206:39 pm
MEM
- ORD
1 stop26h 38m
Multiple Airlines
Fri 4/245:05 am
ORD
- MEM
1 stop12h 44m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$239
This Southwest deal was found by Cheapflights users on 4/9. 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.
Sun 5/35:10 am
MEM
- MDW
Nonstop1h 35m
Southwest
Wed 5/610:05 am
MDW
- MEM
Nonstop1h 40m
Southwest
Deal found 4/9![Southwest logo]()
$227
This Southwest deal was found by Cheapflights users on 4/8. 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.
Mon 5/44:25 pm
MEM
- MDW
2 stops6h 20m
Southwest
Wed 5/61:55 pm
MDW
- MEM
2 stops6h 45m
Southwest
Deal found 4/8![Southwest logo]()
$228
This Southwest deal was found by Cheapflights users on 4/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/512:20 pm
MEM
- MDW
2 stops7h 50m
Southwest
Tue 5/1210:25 am
MDW
- MEM
2 stops7h 10m
Southwest
Deal found 4/7![Southwest logo]()
$187
This Delta deal was found by Cheapflights users on 4/8. 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.
Tue 5/512:17 pm
MEM
- MDW
1 stop4h 09m
Delta
Tue 5/126:23 am
MDW
- MEM
1 stop5h 16m
Delta
Deal found 4/8![Delta logo]()
$197
This Frontier deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 4/6![Frontier logo]()
$201
This Delta deal was found by Cheapflights users on 4/8. 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 5/166:35 am
MEM
- MDW
1 stop6h 07m
Delta
Wed 5/206:23 am
MDW
- MEM
1 stop5h 16m
Delta
Deal found 4/8![Delta logo]()
$218
This Southwest deal was found by Cheapflights users on 4/9. 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 5/195:15 am
MEM
- MDW
Nonstop1h 35m
Southwest
Thu 5/2110:00 am
MDW
- MEM
Nonstop1h 40m
Southwest
Deal found 4/9![Southwest logo]()
$198
This Southwest deal was found by Cheapflights users on 4/8. 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 5/234:25 pm
MEM
- MDW
1 stop4h 40m
Southwest
Wed 5/2710:05 am
MDW
- MEM
Nonstop1h 40m
Southwest
Deal found 4/8![Southwest logo]()
$237
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 10, 2026.
Search for one-way flight options from Mississippi to Chicago. Find affordable one-way fares based on user searches. Data last updated April 10, 2026.
This Frontier deal was found by Cheapflights users on 4/10. 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 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
Deal found 4/10![Frontier logo]()
$76
This American Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 10m
American Airlines
Deal found 4/6![American Airlines logo]()
$79
This Southwest deal was found by Cheapflights users on 4/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/55:15 am
MEM
- MDW
Nonstop1h 35m
Southwest
Deal found 4/7![Southwest logo]()
$79
This Kiwi.com deal was found by Cheapflights users on 4/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/206:39 pm
MEM
- ORD
1 stop26h 38m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$87
This Southwest deal was found by Cheapflights users on 4/7. 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 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
Deal found 4/7![Southwest logo]()
$89
This Frontier deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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
- ORD
1 stop7h 52m
Frontier
Deal found 4/6![Frontier logo]()
$90
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/46:39 pm
MEM
- ORD
1 stop28h 36m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$94
This Kiwi.com deal was found by Cheapflights users on 4/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/55:04 pm
MEM
- ORD
1 stop19h 33m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$95
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/85:04 pm
MEM
- ORD
1 stop19h 21m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$96
This Frontier deal was found by Cheapflights users on 4/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/711:59 am
MEM
- MDW
1 stop10h 03m
Frontier
Deal found 4/10![Frontier logo]()
$96
This American Airlines deal was found by Cheapflights users on 4/10. 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.
Wed 5/66:40 am
MEM
- ORD
Nonstop2h 09m
American Airlines
Deal found 4/10![American Airlines logo]()
$98
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/510:34 am
MEM
- ORD
1 stop5h 44m
Delta
Deal found 4/6![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 April 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $185 (Frontier) |
One-way from | $76 (Frontier) |
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 10, 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 5/5
1:25 pm-6:35 pm
1 stop5h 10m
Chicago O'Hare Intl
Tue 5/12
6:24 am-11:31 am
1 stop5h 07m
$197
MemphisChicago
MEM - ORD
MEMORD
Memphis
Sat 6/6
5:49 pm-12:08 am
1 stop6h 19m
Chicago O'Hare Intl
Tue 6/9
2:07 pm-9:04 pm
1 stop6h 57m
$218
MemphisChicago
MEM - ORD
MEMORD
Memphis
Sat 6/6
4:11 pm-8:24 pm
1 stop4h 13m
Chicago O'Hare Intl
Tue 6/16
5:30 am-10:37 am
1 stop5h 07m
$218
MemphisChicago
MEM - ORD
MEMORD
Memphis
Tue 5/5
12:21 pm-7:52 pm
1 stop7h 31m
Chicago O'Hare Intl
Sat 5/9
1:44 pm-8:56 pm
1 stop7h 12m
$218
MemphisChicago
MEM - ORD
MEMORD
Memphis
Mon 5/4
5:59 pm-11:59 pm
1 stop6h 00m
Chicago O'Hare Intl
Wed 5/6
6:25 am-11:40 am
1 stop5h 15m
$218
MemphisChicago
MEM - ORD
MEMORD
Memphis
Sun 6/7
7:15 am-9:20 am
Nonstop2h 05m
Chicago O'Hare Intl
Wed 6/10
12:40 pm-2:42 pm
Nonstop2h 02m
$227
MemphisChicago
MEM - MDW
MEMMDW
Memphis
Wed 4/29
6:10 am-12:43 pm
1 stop6h 33m
Chicago Midway
Sat 5/2
5:40 am-11:20 am
1 stop5h 40m
$238
MemphisChicago
MEM - ORD
MEMORD
Memphis
Sat 5/23
5:25 am-2:20 pm
2 stops8h 55m
Chicago O'Hare Intl
Tue 5/26
2:40 pm-9:45 pm
1 stop7h 05m
$258
MemphisChicago
MEM - MDW
MEMMDW
Memphis
Fri 6/12
5:15 am-6:50 am
Nonstop1h 35m
Chicago Midway
Wed 6/17
8:10 am-3:00 pm
1 stop6h 50m
$264
GulfportChicago
GPT - ORD
GPTORD
Gulfport Biloxi Regional
Thu 4/30
7:20 pm-1:15 pm
1 stop17h 55m
Chicago O'Hare Intl
Sun 5/3
6:00 am-6:40 pm
1 stop12h 40m
$267
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
MOB-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-MDW
MEM-ORD
GPT-ORD
MOB-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 $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
Flights by cabin class
Other flight options
Popular flights
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 10, 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 10, 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 10, 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$450 | FlexibilityNo cancel fee | On-time71% |