$89+ Cheap flights from Mississippi to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/30. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — CHI
Jul 8 — Jul 151
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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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 June 8, 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 June 8, 2026.
This American Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2711:21 am
MEM
- ORD
1 stop5h 29m
American Airlines
Sat 8/298:03 am
ORD
- MEM
Nonstop1h 51m
American Airlines
Deal found 6/4![American Airlines logo]()
$255
This Southwest deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:15 pm
MEM
- MDW
1 stop5h 30m
Southwest
Sat 8/299:55 am
MDW
- MEM
Nonstop1h 35m
Southwest
Deal found 6/4![Southwest logo]()
$255
This Booking.com deal was found by Cheapflights users on 6/6. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/127:48 pm
MEM
- ORD
1 stop25h 04m
Frontier
Sat 8/155:13 pm
ORD
- MEM
1 stop25h 12m
Frontier
Deal found 6/6![Frontier logo]()
$256
This Kiwi.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/34:49 pm
MEM
- ORD
1 stop19h 26m
Multiple Airlines
Tue 8/49:57 pm
ORD
- MEM
1 stop21h 06m
Multiple Airlines
Deal found 6/3![Multiple Airlines logo]()
$257
This American Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 7/1810:33 am
MEM
- ORD
Nonstop2h 02m
American Airlines
Wed 7/223:40 pm
ORD
- MEM
Nonstop1h 56m
American Airlines
Deal found 6/4![American Airlines logo]()
$258
This Southwest deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 7/15:20 am
MEM
- MDW
Nonstop1h 35m
Southwest
Sat 7/410:25 am
MDW
- MEM
Nonstop1h 35m
Southwest
Deal found 6/4![Southwest logo]()
$258
This Booking.com deal was found by Cheapflights users on 6/5. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/37:48 pm
MEM
- ORD
1 stop25h 04m
Frontier
Wed 8/55:13 pm
ORD
- MEM
1 stop25h 12m
Frontier
Deal found 6/5![Frontier logo]()
$261
This Southwest deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/85:00 am
MEM
- MDW
Nonstop1h 35m
Southwest
Mon 10/125:00 am
MDW
- MEM
1 stop10h 00m
Southwest
Deal found 6/3![Southwest logo]()
$261
This Booking.com deal was found by Cheapflights users on 6/5. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/27:10 pm
MEM
- ORD
1 stop14h 01m
Frontier
Wed 8/55:13 pm
ORD
- MEM
1 stop25h 12m
Frontier
Deal found 6/5![Frontier logo]()
$262
This United Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 7/297:25 am
MEM
- ORD
Nonstop2h 05m
United Airlines
Fri 7/3112:40 pm
ORD
- MEM
Nonstop2h 02m
United Airlines
Deal found 6/4![United Airlines logo]()
$264
This Southwest deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/295:20 am
MEM
- MDW
Nonstop1h 35m
Southwest
Sun 8/29:55 pm
MDW
- MEM
Nonstop1h 45m
Southwest
Deal found 6/3![Southwest logo]()
$264
This Kiwi.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 7/208:39 am
MEM
- MDW
1 stop11h 51m
Multiple Airlines
Wed 7/224:45 pm
MDW
- MEM
2 stops20h 28m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$265
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 June 8, 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 June 8, 2026.
This United Airlines deal was found by Cheapflights users on 6/5. 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 8/39:46 am
MEM
- ORD
Nonstop2h 11m
United Airlines
Wed 8/59:20 pm
ORD
- MEM
Nonstop2h 01m
United Airlines
Deal found 6/5![United Airlines logo]()
$264
This Southwest deal was found by Cheapflights users on 6/7. 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.
Wed 8/56:30 am
MEM
- MDW
2 stops9h 30m
Southwest
Wed 8/126:00 am
MDW
- MEM
2 stops7h 40m
Southwest
Deal found 6/7![Southwest logo]()
$274
This Delta deal was found by Cheapflights users on 6/7. 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.
Tue 7/1410:25 am
BTR
- MDW
1 stop5h 50m
Delta
Tue 7/215:10 pm
MDW
- BTR
1 stop4h 46m
Delta
Deal found 6/7![Delta logo]()
$303
This American Airlines deal was found by Cheapflights users on 6/7. 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 7/712:42 pm
MOB
- ORD
1 stop7h 09m
American Airlines
Tue 7/145:00 am
ORD
- MOB
1 stop6h 16m
American Airlines
Deal found 6/7![American Airlines logo]()
$313
This Southwest deal was found by Cheapflights users on 6/5. 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.
Sun 9/63:40 pm
MEM
- MDW
Nonstop1h 35m
Southwest
Thu 9/108:45 pm
MDW
- MEM
Nonstop1h 40m
Southwest
Deal found 6/5![Southwest logo]()
$292
This United Airlines deal was found by Cheapflights users on 6/7. 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.
Tue 7/76:35 pm
MEM
- ORD
Nonstop2h 05m
United Airlines
Tue 7/1412:40 pm
ORD
- MEM
Nonstop2h 02m
United Airlines
Deal found 6/7![United Airlines logo]()
$297
This Delta deal was found by Cheapflights users on 6/7. 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.
Tue 7/147:06 pm
BTR
- ORD
1 stop4h 47m
Delta
Sat 7/185:30 am
ORD
- BTR
1 stop4h 09m
Delta
Deal found 6/7![Delta logo]()
$303
This Southwest deal was found by Cheapflights users on 6/7. 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 7/75:20 am
MEM
- MDW
Nonstop1h 35m
Southwest
Tue 7/149:40 pm
MDW
- MEM
Nonstop1h 45m
Southwest
Deal found 6/7![Southwest logo]()
$297
This Delta deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 6/216:30 am
MEM
- MDW
1 stop6h 16m
Delta
Tue 6/306:00 am
MDW
- MEM
1 stop4h 37m
Delta
Deal found 6/3![Delta logo]()
$304
This Southwest deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 8/165:35 am
MEM
- MDW
Nonstop1h 35m
Southwest
Thu 8/208:45 pm
MDW
- MEM
Nonstop1h 40m
Southwest
Deal found 6/4![Southwest logo]()
$298
This Delta deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 6/275:17 pm
MOB
- ORD
1 stop6h 47m
Delta
Tue 6/306:35 am
ORD
- MOB
1 stop5h 22m
Delta
Deal found 6/3![Delta logo]()
$309
This American Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 7/186:35 pm
GPT
- ORD
1 stop5h 26m
American Airlines
Sun 7/195:07 am
ORD
- GPT
1 stop5h 04m
American Airlines
Deal found 6/4![American Airlines logo]()
$390
This United Airlines deal was found by Cheapflights users on 6/7. 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.
Fri 6/269:46 am
MEM
- ORD
Nonstop2h 11m
United Airlines
Tue 6/309:00 am
ORD
- MEM
Nonstop2h 05m
United Airlines
Deal found 6/7![United Airlines logo]()
$365
This Delta deal was found by Cheapflights users on 6/6. 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.
Fri 11/207:00 pm
BTR
- ORD
1 stop4h 50m
Delta
Mon 11/233:35 pm
ORD
- BTR
1 stop6h 26m
Delta
Deal found 6/6![Delta logo]()
$319
This Southwest deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 7/15:20 am
MEM
- MDW
Nonstop1h 35m
Southwest
Sun 7/56:10 am
MDW
- MEM
2 stops7h 35m
Southwest
Deal found 6/4![Southwest logo]()
$336
This United Airlines deal was found by Cheapflights users on 6/7. 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.
Fri 6/269:46 am
MEM
- ORD
Nonstop2h 11m
United Airlines
Mon 6/299:20 pm
ORD
- MEM
Nonstop2h 01m
United Airlines
Deal found 6/7![United Airlines logo]()
$371
This American Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/176:35 pm
GPT
- ORD
1 stop5h 26m
American Airlines
Sun 7/195:07 am
ORD
- GPT
1 stop5h 04m
American Airlines
Deal found 6/3![American Airlines logo]()
$409
This Delta deal was found by Cheapflights users on 6/7. 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 9/106:00 pm
GPT
- ORD
1 stop5h 57m
Delta
Mon 9/146:40 am
ORD
- GPT
1 stop6h 19m
Delta
Deal found 6/7![Delta logo]()
$334
This United Airlines deal was found by Cheapflights users on 6/7. 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 6/257:25 am
MEM
- ORD
Nonstop2h 05m
United Airlines
Sun 6/289:00 am
ORD
- MEM
Nonstop2h 05m
United Airlines
Deal found 6/7![United Airlines logo]()
$371
This Southwest deal was found by Cheapflights users on 6/5. 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.
Fri 7/175:10 pm
MEM
- MDW
1 stop7h 05m
Southwest
Sun 7/199:55 pm
MDW
- MEM
Nonstop1h 45m
Southwest
Deal found 6/5![Southwest logo]()
$361
This Delta deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 11/203:20 pm
BTR
- MDW
1 stop6h 25m
Delta
Mon 11/236:00 am
MDW
- BTR
1 stop6h 50m
Delta
Deal found 6/4![Delta logo]()
$344
This United Airlines deal was found by Cheapflights users on 6/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/294:10 pm
BTR
- ORD
1 stop7h 16m
United Airlines
Tue 9/17:30 am
ORD
- BTR
1 stop8h 00m
United Airlines
Deal found 6/6![United Airlines logo]()
$383
This American Airlines deal was found by Cheapflights users on 6/5. 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.
Fri 7/36:32 pm
GPT
- ORD
1 stop5h 29m
American Airlines
Mon 7/65:07 am
ORD
- GPT
1 stop5h 04m
American Airlines
Deal found 6/5![American Airlines logo]()
$480
This Southwest deal was found by Cheapflights users on 6/5. 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.
Wed 9/307:05 am
JAN
- MDW
1 stop5h 10m
Southwest
Sun 10/46:55 am
MDW
- JAN
1 stop4h 30m
Southwest
Deal found 6/5![Southwest logo]()
$363
This Delta deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/36:55 pm
MOB
- ORD
1 stop5h 07m
Delta
Mon 9/75:28 am
ORD
- MOB
1 stop5h 52m
Delta
Deal found 6/3![Delta logo]()
$354
This United Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 10/205:04 pm
GPT
- ORD
1 stop7h 19m
United Airlines
Sat 10/242:10 pm
ORD
- GPT
1 stop5h 30m
United Airlines
Deal found 6/3![United Airlines logo]()
$390
This Southwest deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1312:40 pm
JAN
- MDW
2 stops6h 50m
Southwest
Tue 8/187:50 am
MDW
- JAN
1 stop5h 00m
Southwest
Deal found 6/4![Southwest logo]()
$364
This Delta deal was found by Cheapflights users on 6/7. 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.
Tue 7/1410:25 am
BTR
- MDW
1 stop5h 50m
Delta
Sat 7/186:00 am
MDW
- BTR
1 stop6h 47m
Delta
Deal found 6/7![Delta logo]()
$361
This Southwest deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/112:20 pm
JAN
- MDW
1 stop4h 45m
Southwest
Tue 7/712:00 pm
MDW
- JAN
1 stop8h 45m
Southwest
Deal found 6/3![Southwest logo]()
$374
This United Airlines deal was found by Cheapflights users on 6/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/57:25 am
MEM
- ORD
Nonstop2h 05m
United Airlines
Sat 7/119:00 am
ORD
- MEM
Nonstop2h 05m
United Airlines
Deal found 6/6![United Airlines logo]()
$415
Last-minute flights from Mississippi to ChicagoDiscover last-minute flight deals from Mississippi to Chicago. Data last updated June 8, 2026 and is based on user searches.
Discover last-minute flight deals from Mississippi to Chicago. Data last updated June 8, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 6/236:30 am
MEM
- ORD
1 stop6h 34m
Delta
Tue 6/306:35 am
ORD
- MEM
1 stop7h 22m
Delta
Deal found 6/4![Delta logo]()
$267
This Frontier deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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
Thu 6/256:00 am
MDW
- MEM
1 stop4h 55m
Frontier
Deal found 6/3![Frontier logo]()
$269
This United Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/232:22 pm
MEM
- ORD
Nonstop2h 07m
United Airlines
Wed 6/249:20 pm
ORD
- MEM
Nonstop2h 01m
United Airlines
Deal found 6/3![United Airlines logo]()
$276
This Southwest deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 7/15:20 am
MEM
- MDW
Nonstop1h 35m
Southwest
Sat 7/410:25 am
MDW
- MEM
Nonstop1h 35m
Southwest
Deal found 6/4![Southwest logo]()
$258
This Delta deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 7/35:54 pm
MEM
- ORD
1 stop6h 05m
Delta
Tue 7/75:30 am
ORD
- MEM
1 stop3h 57m
Delta
Deal found 6/4![Delta logo]()
$277
This American Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/56:30 pm
MEM
- ORD
1 stop6h 20m
American Airlines
Wed 7/810:30 pm
ORD
- MEM
Nonstop1h 48m
American Airlines
Deal found 6/3![American Airlines logo]()
$274
This Delta deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 7/1112:07 pm
MEM
- ORD
1 stop4h 16m
Delta
Tue 7/142:07 pm
ORD
- MEM
1 stop6h 54m
Delta
Deal found 6/4![Delta logo]()
$278
This American Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 7/1810:33 am
MEM
- ORD
Nonstop2h 02m
American Airlines
Wed 7/223:40 pm
ORD
- MEM
Nonstop1h 56m
American Airlines
Deal found 6/4![American Airlines logo]()
$258
This Kiwi.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 7/208:39 am
MEM
- MDW
1 stop11h 51m
Multiple Airlines
Wed 7/224:45 pm
MDW
- MEM
2 stops20h 28m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$265
This Kiwi.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/208:39 am
MEM
- MDW
1 stop11h 51m
Multiple Airlines
Sat 7/256:41 pm
MDW
- MEM
2 stops18h 32m
Multiple Airlines
Deal found 6/3![Multiple Airlines logo]()
$277
This United Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 7/297:25 am
MEM
- ORD
Nonstop2h 05m
United Airlines
Fri 7/3112:40 pm
ORD
- MEM
Nonstop2h 02m
United Airlines
Deal found 6/4![United Airlines logo]()
$264
This Southwest deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/295:20 am
MEM
- MDW
Nonstop1h 35m
Southwest
Sun 8/29:55 pm
MDW
- MEM
Nonstop1h 45m
Southwest
Deal found 6/3![Southwest logo]()
$264
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 June 8, 2026.
Search for one-way flight options from Mississippi to Chicago. Find affordable one-way fares based on user searches. Data last updated June 8, 2026.
This United Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/302:22 pm
MEM
- ORD
Nonstop2h 07m
United Airlines
Deal found 6/3![United Airlines logo]()
$89
This Southwest deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 6/305:20 am
MEM
- MDW
Nonstop1h 35m
Southwest
Deal found 6/4![Southwest logo]()
$89
This Kiwi.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/39:28 pm
MEM
- ORD
1 stop32h 09m
Multiple Airlines
Deal found 6/3![Multiple Airlines logo]()
$93
This Southwest deal was found by Cheapflights users on 6/7. 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 8/43:25 pm
MEM
- MDW
Nonstop1h 35m
Southwest
Deal found 6/7![Southwest logo]()
$96
This Delta deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 6/306:30 am
MEM
- ORD
1 stop6h 34m
Delta
Deal found 6/3![Delta logo]()
$99
This Delta deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/14:46 pm
MEM
- MDW
1 stop5h 50m
Delta
Deal found 6/3![Delta logo]()
$99
This Kiwi.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/208:39 am
MEM
- MDW
1 stop11h 51m
Allegiant Air
Deal found 6/3![Allegiant Air logo]()
$103
This Kiwi.com deal was found by Cheapflights users on 6/7. 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 8/75:04 pm
MEM
- ORD
1 stop19h 11m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$111
This Frontier deal was found by Cheapflights users on 6/7. 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 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 stop7h 59m
Frontier
Deal found 6/7![Frontier logo]()
$115
This Kiwi.com deal was found by Cheapflights users on 6/6. 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 8/38:39 am
MEM
- MDW
1 stop11h 51m
Allegiant Air
Deal found 6/6![Allegiant Air logo]()
$118
This Kiwi.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/314:49 pm
MEM
- ORD
1 stop19h 26m
Multiple Airlines
Deal found 6/3![Multiple Airlines logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/248:39 am
MEM
- MDW
1 stop11h 52m
Allegiant Air
Deal found 6/3![Allegiant Air logo]()
$121
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 June 8, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $255 (American Airlines) |
One-way from | $89 (United Airlines) |
Popular in | March |
Cheapest in | September |
Average price | $476 |
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 June 8, 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
Mon 8/3
9:46 am-11:57 am
Nonstop2h 11m
Chicago O'Hare Intl
Wed 8/5
9:20 pm-11:21 pm
Nonstop2h 01m
$264
MemphisChicago
MEM - MDW
MEMMDW
Memphis
Wed 8/5
6:30 am-4:00 pm
2 stops9h 30m
Chicago Midway
Wed 8/12
6:00 am-1:40 pm
2 stops7h 40m
$274
Quickest round-trip
MemphisChicago
MEM - MDW
MEMMDW
Memphis
Sun 9/6
3:40 pm-5:15 pm
Nonstop1h 35m
Chicago Midway
Thu 9/10
8:45 pm-10:25 pm
Nonstop1h 40m
$292
MemphisChicago
MEM - ORD
MEMORD
Memphis
Tue 7/7
6:35 pm-8:40 pm
Nonstop2h 05m
Chicago O'Hare Intl
Tue 7/14
12:40 pm-2:42 pm
Nonstop2h 02m
$297
MemphisChicago
MEM - MDW
MEMMDW
Memphis
Tue 7/7
5:20 am-6:55 am
Nonstop1h 35m
Chicago Midway
Tue 7/14
9:40 pm-11:25 pm
Nonstop1h 45m
$297
MemphisChicago
MEM - MDW
MEMMDW
Memphis
Sun 8/16
5:35 am-7:10 am
Nonstop1h 35m
Chicago Midway
Thu 8/20
8:45 pm-10:25 pm
Nonstop1h 40m
$298
Baton RougeChicago
BTR - MDW
BTRMDW
Baton Rouge Ryan
Tue 7/14
10:25 am-4:15 pm
1 stop5h 50m
Chicago Midway
Tue 7/21
5:10 pm-9:56 pm
1 stop4h 46m
$303
Baton RougeChicago
BTR - ORD
BTRORD
Baton Rouge Ryan
Tue 7/14
7:06 pm-11:53 pm
1 stop4h 47m
Chicago O'Hare Intl
Sat 7/18
5:30 am-9:39 am
1 stop4h 09m
$303
MemphisChicago
MEM - MDW
MEMMDW
Memphis
Sun 6/21
6:30 am-12:46 pm
1 stop6h 16m
Chicago Midway
Tue 6/30
6:00 am-10:37 am
1 stop4h 37m
$304
MobileChicago
MOB - ORD
MOBORD
Mobile
Sat 6/27
5:17 pm-12:04 am
1 stop6h 47m
Chicago O'Hare Intl
Tue 6/30
6:35 am-11:57 am
1 stop5h 22m
$309
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-MDW
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-MDW
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 May is currently the most expensive (average of $372). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
How much does it cost to fly round-trip from Mississippi to Chicago?
Related info for your journey
Find useful and relevant information for your journey from Mississippi to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Chicago flight routes
Complete your trip
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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 June 8, 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 June 8, 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 June 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$196 | Average$443 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$234 | Average$417 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$248 | Average$463 | FlexibilityNo cancel fee | On-time71% |