$154+ Cheap flights from Madison (MSN) to Illinois
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — ORD
Nov 26 — Dec 31
Round-trip
1 adult, Economy
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Find cheap flights from Madison to Illinois 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 Madison to IllinoisExplore the most affordable flight options available from Madison to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 27, 2026.
Explore the most affordable flight options available from Madison to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 27, 2026.
This American Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 12/119:43 am -
Nonstop1h 17m
Sun 12/1310:09 pm -
Nonstop1h 10m
Deal found 10/27![American Airlines logo]()
$309
This American Airlines deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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 11/256:00 am -
Nonstop1h 43m
Sun 11/297:20 am -
Nonstop1h 16m
Deal found 10/24![American Airlines logo]()
$324
This United Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 11/65:00 am -
Nonstop1h 20m
Mon 11/97:59 pm -
Nonstop1h 06m
Deal found 10/23![United Airlines logo]()
$339
This American Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 12/278:32 pm -
Nonstop1h 28m
Mon 12/2811:13 pm -
Nonstop1h 08m
Deal found 10/27![American Airlines logo]()
$359
This American Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 12/245:00 am -
Nonstop1h 21m
Fri 1/89:30 am -
Nonstop1h 16m
Deal found 10/26![American Airlines logo]()
$369
This United Airlines deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 12/246:06 am -
Nonstop1h 24m
Fri 1/88:55 am -
Nonstop1h 15m
Deal found 10/25![United Airlines logo]()
$399
This American Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/36:00 am -
Nonstop1h 28m
Tue 11/106:55 am -
Nonstop1h 15m
Deal found 10/27![American Airlines logo]()
$401
This United Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/15:00 am -
Nonstop1h 20m
Sun 11/810:45 am -
Nonstop1h 14m
Deal found 10/27![United Airlines logo]()
$419
This United Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 11/78:15 am -
1 stop5h 38m
Wed 11/112:35 pm -
1 stop4h 32m
Deal found 10/23![United Airlines logo]()
$429
This United Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 11/68:15 am -
Nonstop1h 16m
Tue 11/1012:48 pm -
Nonstop1h 12m
Deal found 10/23![United Airlines logo]()
$429
This Kiwi.com deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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 11/86:00 pm -
1 stop14h 46m
Thu 11/127:50 pm -
2 stops38h 08m
Deal found 10/24![Multiple Airlines logo]()
$434
This United Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 12/114:15 pm -
1 stop17h 25m
Sat 12/1212:40 pm -
Nonstop1h 11m
Deal found 10/23![United Airlines logo]()
$449
Best flights from Madison to IllinoisDiscover carefully curated flight deals from Madison to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 27, 2026.
Discover carefully curated flight deals from Madison to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 27, 2026.
This United Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/187:00 pm -
Nonstop1h 22m
Sat 11/215:54 pm -
Nonstop1h 13m
Deal found 10/26![United Airlines logo]()
$309
This American Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 12/119:43 am -
Nonstop1h 17m
Sun 12/1310:09 pm -
Nonstop1h 10m
Deal found 10/27![American Airlines logo]()
$309
This Kiwi.com deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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.
Wed 2/1710:38 am -
2 stops13h 08m
Sat 2/208:47 pm -
1 stop20h 33m
Deal found 10/27![Multiple Airlines logo]()
$509
This United Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/1912:30 pm -
Nonstop1h 19m
Sun 11/224:40 pm -
Nonstop1h 14m
Deal found 10/26![United Airlines logo]()
$309
This United Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/136:25 am -
Nonstop1h 19m
Sun 11/1510:05 pm -
Nonstop1h 02m
Deal found 10/22![United Airlines logo]()
$309
This United Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 12/2610:35 am -
Nonstop1h 24m
Thu 12/313:35 pm -
Nonstop1h 11m
Deal found 10/26![United Airlines logo]()
$309
This United Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 2/172:40 pm -
Nonstop1h 09m
Sat 2/208:55 am -
Nonstop1h 11m
Deal found 10/27![United Airlines logo]()
$309
This Expedia deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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.
Sat 11/76:00 am -
1 stop10h 47m
Wed 11/1112:30 pm -
1 stop8h 47m
Deal found 10/25![Delta logo]()
$931
This United Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 11/65:00 am -
Nonstop1h 20m
Mon 11/97:59 pm -
Nonstop1h 06m
Deal found 10/23![United Airlines logo]()
$339
This American Airlines deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/97:09 pm -
1 stop4h 54m
Fri 11/135:37 pm -
1 stop6h 06m
Deal found 10/25![American Airlines logo]()
$637
This United Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 1/306:35 am -
Nonstop1h 23m
Sun 1/318:55 am -
Nonstop1h 15m
Deal found 10/23![United Airlines logo]()
$399
This Kiwi.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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.
Wed 11/1810:38 am -
2 stops13h 09m
Sat 11/218:42 pm -
1 stop20h 38m
Deal found 10/26![Multiple Airlines logo]()
$659
This United Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 11/78:15 am -
1 stop5h 38m
Wed 11/112:35 pm -
1 stop4h 32m
Deal found 10/23![United Airlines logo]()
$429
This United Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/105:43 pm -
1 stop5h 30m
Sat 11/145:30 pm -
1 stop3h 35m
Deal found 10/26![United Airlines logo]()
$429
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/246:30 am -
1 stop5h 20m
Tue 12/15:30 pm -
1 stop3h 59m
Deal found 10/26![Delta logo]()
$1,059
This Delta deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/156:30 am -
1 stop5h 20m
Sun 11/225:29 pm -
1 stop3h 48m
Deal found 10/25![Delta logo]()
$1,145
This United Airlines deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/97:00 pm -
1 stop3h 58m
Fri 11/135:30 pm -
2 stops30h 07m
Deal found 10/25![United Airlines logo]()
$688
This Delta deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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 11/256:30 am -
1 stop5h 20m
Sun 11/295:29 pm -
1 stop3h 48m
Deal found 10/24![Delta logo]()
$1,272
This Delta deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 4/196:15 am -
1 stop5h 36m
Fri 4/235:35 pm -
1 stop5h 20m
Deal found 10/27![Delta logo]()
$1,453
This Delta deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1110:59 am -
1 stop5h 40m
Fri 11/135:29 pm -
1 stop3h 48m
Deal found 10/22![Delta logo]()
$1,469
This Delta deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 12/1110:59 am -
1 stop5h 51m
Sat 12/125:30 pm -
1 stop3h 59m
Deal found 10/23![Delta logo]()
$1,483
This Delta deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 2/176:15 am -
1 stop5h 36m
Sat 2/205:35 pm -
1 stop5h 20m
Deal found 10/27![Delta logo]()
$1,483
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/186:30 am -
1 stop5h 20m
Sat 11/2112:30 pm -
1 stop6h 37m
Deal found 10/26![Delta logo]()
$1,483
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 12/96:32 am -
1 stop5h 27m
Sat 12/1210:24 am -
1 stop3h 46m
Deal found 10/26![Delta logo]()
$1,483
Last-minute flights from Madison to IllinoisDiscover last-minute flight deals from Madison to Illinois. Data last updated October 27, 2026 and is based on user searches.
Discover last-minute flight deals from Madison to Illinois. Data last updated October 27, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 10/305:00 am -
Nonstop1h 20m
Sun 11/18:44 am -
Nonstop1h 16m
Deal found 10/26![United Airlines logo]()
$469
This United Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/15:00 am -
Nonstop1h 20m
Sun 11/810:45 am -
Nonstop1h 14m
Deal found 10/27![United Airlines logo]()
$419
This American Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/36:00 am -
Nonstop1h 28m
Tue 11/106:55 am -
Nonstop1h 15m
Deal found 10/27![American Airlines logo]()
$401
This Kiwi.com deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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.
Tue 11/310:30 am -
1 stop30h 37m
Mon 11/97:50 pm -
2 stops38h 08m
Deal found 10/23![Multiple Airlines logo]()
$450
This United Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 11/65:00 am -
Nonstop1h 20m
Mon 11/97:59 pm -
Nonstop1h 06m
Deal found 10/23![United Airlines logo]()
$339
This United Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 11/68:15 am -
Nonstop1h 16m
Tue 11/1012:48 pm -
Nonstop1h 12m
Deal found 10/23![United Airlines logo]()
$429
This United Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 11/78:15 am -
1 stop5h 38m
Wed 11/112:35 pm -
1 stop4h 32m
Deal found 10/23![United Airlines logo]()
$429
This Kiwi.com deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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 11/86:00 pm -
1 stop14h 46m
Thu 11/127:50 pm -
2 stops38h 08m
Deal found 10/24![Multiple Airlines logo]()
$434
This American Airlines deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/97:09 pm -
1 stop4h 54m
Fri 11/135:37 pm -
1 stop6h 06m
Deal found 10/25![American Airlines logo]()
$637
This United Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/1912:30 pm -
Nonstop1h 19m
Sun 11/224:40 pm -
Nonstop1h 14m
Deal found 10/27![United Airlines logo]()
$309
This Mytrip deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/192:40 pm -
2 stops14h 33m
Sun 11/226:40 am -
2 stops30h 56m
Deal found 10/27![Multiple Airlines logo]()
$480
This American Airlines deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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 11/256:00 am -
Nonstop1h 43m
Sun 11/297:20 am -
Nonstop1h 16m
Deal found 10/24![American Airlines logo]()
$324
One-way flights from Madison to IllinoisSearch for one-way flight options from Madison to Illinois. Find affordable one-way fares based on user searches. Data last updated October 27, 2026.
Search for one-way flight options from Madison to Illinois. Find affordable one-way fares based on user searches. Data last updated October 27, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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.
Wed 12/910:38 am -
2 stops33h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Multiple Airlines logo]()
$154
This Kiwi.com deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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.
Tue 12/1510:30 am -
1 stop14h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Multiple Airlines logo]()
$170
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 12/2310:58 am -
1 stop6h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Delta logo]()
$183
This Mytrip deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/192:40 pm -
2 stops14h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Multiple Airlines logo]()
$187
This Kiwi.com deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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.
Tue 12/1510:30 am -
2 stops23h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Multiple Airlines logo]()
$190
This American Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 12/272:19 pm -
Nonstop1h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![American Airlines logo]()
$205
This Delta deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 12/216:40 am -
1 stop4h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Delta logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 1/106:00 pm -
2 stops18h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Multiple Airlines logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 1/106:00 pm -
2 stops22h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Multiple Airlines logo]()
$224
This Kiwi.com deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 12/206:10 pm -
2 stops28h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Multiple Airlines logo]()
$250
This Kiwi.com deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 11/196:00 pm -
1 stop25h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Multiple Airlines logo]()
$253
This Kiwi.com deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 12/206:10 pm -
1 stop25h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Multiple Airlines logo]()
$262
Find flight deals from Madison to Illinois
Keep the following information in mind while searching for Madison to Illinois flight deals. Data was last updated October 27, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $309 (American Airlines) |
One-way from | $154 (Kiwi.com) |
Popular in | April |
Cheapest in | March |
Average price | $440 |
Good round-trip deal | $395 or less |
Good one-way deal | $284 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Madison to Illinois 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 7,457,451 searches. Data last updated October 27, 2026.
Use the filters below to find and compare flights from Madison to Illinois that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
MadisonChicago
MSN Madison Truax Field - ORD Chicago O'Hare Intl
MSNORD
Madison Truax Field
Wed 12/9
10:38 am-4:04 pm
3 stops29h 26m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$157
MadisonChicago
MSN Madison Truax Field - ORD Chicago O'Hare Intl
MSNORD
Madison Truax Field
Tue 12/15
10:30 am-1:08 am
1 stop14h 38m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$170
MadisonChicago
MSN Madison Truax Field - MDW Chicago Midway
MSNMDW
Madison Truax Field
Thu 12/24
6:40 am-11:01 am
1 stop4h 21m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$183
MadisonChicago
MSN Madison Truax Field - MDW Chicago Midway
MSNMDW
Madison Truax Field
Wed 12/23
10:58 am-5:24 pm
1 stop6h 26m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$183
MadisonChicago
MSN Madison Truax Field - MDW Chicago Midway
MSNMDW
Madison Truax Field
Tue 12/15
10:30 am-9:45 am
2 stops23h 15m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$190
MadisonChicago
MSN Madison Truax Field - MDW Chicago Midway
MSNMDW
Madison Truax Field
Mon 12/21
6:40 am-11:01 am
1 stop4h 21m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$213
MadisonChicago
MSN Madison Truax Field - ORD Chicago O'Hare Intl
MSNORD
Madison Truax Field
Sun 1/10
6:00 pm-12:10 pm
2 stops18h 10m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$221
MadisonChicago
MSN Madison Truax Field - MDW Chicago Midway
MSNMDW
Madison Truax Field
Sun 1/10
6:00 pm-4:26 pm
2 stops22h 26m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$224
MadisonChicago
MSN Madison Truax Field - ORD Chicago O'Hare Intl
MSNORD
Madison Truax Field
Thu 11/19
6:00 pm-12:43 am
1 stop30h 43m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$253
Quickest round-trip
MadisonChicago
MSN Madison Truax Field - ORD Chicago O'Hare Intl
MSNORD
Madison Truax Field
Thu 11/19
3:52 pm-5:05 pm
Nonstop1h 13m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$269
Showing 1-10 of 44 resultsSorted by cheapest first
Best time to book a flight from Madison to Illinois
Have a flexible travel schedule? Discover the best time to fly to Illinois from Madison with our price prediction graph.
MSN-ORD
MSN-PIA
MSN-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 Madison to Illinois
MSN-USIL
MSN-ORD
MSN-PIA
MSN-MDW
What is the cheapest month to book a flight from Madison to Illinois?
Currently, March is the cheapest month in which you can book a flight from Madison to Illinois (average of $239). Flying from Madison to Illinois in April is currently the most expensive (average of $490). 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.
What is the cheapest time of day to fly from MSN to IL?
Find hourly flight availability from Madison to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 27, 2026.
When flying from Madison to Illinois, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 23% versus a flight in the evening.
What is the cheapest day to fly from Madison to Illinois?
Use this chart to determine the cheapest time to fly round-trip from Madison to Illinois. Price data was last updated on October 24, 2026.
Travelers seeking maximum savings on their Madison to Illinois flight should consider departing on Saturday mornings when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Illinois
Get insights into the airlines that provide service to Illinois. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Illinois. Reviews last updated October 27, 2026.
Get a feel of what it's like to fly with United Airlines and American Airlines from Madison to Illinois by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
7.3
Boarding
7.7
Comfort
7.3
Entertainment
7.1
Food
6.7
Crew
8.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Overall
7.3
Boarding
7.7
Comfort
7.3
Entertainment
7.1
Food
6.7
Crew
8.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Overall
7.3
Boarding
7.7
Comfort
7.3
Entertainment
7.1
Food
6.7
Crew
8.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Related info for your journey
Find useful and relevant information for your journey from Madison to Illinois. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Madison to Illinois
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Complete your trip
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Madison and Illinois flights
Browse other Madison and Illinois flight options. Last updated on October 27, 2026.
Popular flight searches
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Madison to Illinois flights
Consider these flights traveling from Madison to Illinois.
Top 2 airlines flying from Madison to Illinois
Discover the top 2 airlines that operate flights from Madison to Illinois. 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 7,457,451 searches. Data last updated October 27, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$179 | Average$389 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$219 | Average$363 | FlexibilityNo cancel fee | On-time71% |