$139+ Cheap flights from Madison (MSN) to Chicago (CHI)
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 — CHI
Oct 10 — Oct 171
Round-trip
1 adult, Economy
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Find cheap flights from Madison 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 Madison to Chicago
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Cheapest flights from Madison to ChicagoExplore the most affordable flight options available from Madison to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 10, 2026.
Explore the most affordable flight options available from Madison to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 10, 2026.
This American Airlines deal was found by Cheapflights users on 9/9. 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.
Wed 12/165:00 am -
Nonstop1h 21m
Wed 3/176:54 am -
Nonstop1h 12m
Deal found 9/9![American Airlines logo]()
$268
This American Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/242:19 pm -
Nonstop1h 23m
Fri 1/89:33 am -
Nonstop1h 27m
Deal found 9/10![American Airlines logo]()
$269
This American Airlines deal was found by Cheapflights users on 9/6. 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.
Mon 12/218:32 pm -
Nonstop1h 28m
Tue 12/227:15 am -
Nonstop1h 13m
Deal found 9/6![American Airlines logo]()
$270
This American Airlines deal was found by Cheapflights users on 9/6. 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.
Fri 9/258:05 pm -
Nonstop1h 25m
Mon 9/2811:00 pm -
Nonstop1h 17m
Deal found 9/6![American Airlines logo]()
$284
This United Airlines deal was found by Cheapflights users on 9/7. 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 11/256:25 am -
Nonstop1h 19m
Sun 11/2910:05 pm -
Nonstop1h 02m
Deal found 9/7![United Airlines logo]()
$289
This American Airlines deal was found by Cheapflights users on 9/9. 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.
Wed 9/239:40 am -
Nonstop1h 15m
Sun 9/278:52 pm -
Nonstop1h 18m
Deal found 9/9![American Airlines logo]()
$299
This American Airlines deal was found by Cheapflights users on 9/9. 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.
Sat 9/1912:56 pm -
Nonstop1h 24m
Sun 9/277:03 am -
Nonstop1h 11m
Deal found 9/9![American Airlines logo]()
$314
This American Airlines deal was found by Cheapflights users on 9/9. 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.
Thu 12/178:32 pm -
Nonstop1h 28m
Sun 1/172:00 pm -
Nonstop1h 08m
Deal found 9/9![American Airlines logo]()
$330
This United Airlines deal was found by Cheapflights users on 9/9. 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 10/216:35 pm -
Nonstop1h 20m
Sun 10/257:59 pm -
Nonstop1h 06m
Deal found 9/9![United Airlines logo]()
$339
This United Airlines deal was found by Cheapflights users on 9/9. 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.
Sat 9/264:10 pm -
Nonstop1h 19m
Wed 9/308:45 am -
Nonstop1h 09m
Deal found 9/9![United Airlines logo]()
$354
This American Airlines deal was found by Cheapflights users on 9/6. 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.
Wed 9/93:25 pm -
Nonstop1h 16m
Sun 9/1311:17 am -
Nonstop1h 09m
Deal found 9/6![American Airlines logo]()
$360
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/176:32 am -
1 stop5h 27m
Sun 1/175:35 pm -
1 stop5h 20m
Deal found 9/10![Delta logo]()
$1,143
Best flights from Madison to ChicagoDiscover carefully curated flight deals from Madison to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 10, 2026.
Discover carefully curated flight deals from Madison to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 10, 2026.
This United Airlines deal was found by Cheapflights users on 9/10. 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 10/84:10 pm -
Nonstop1h 19m
Thu 10/152:00 pm -
Nonstop1h 04m
Deal found 9/10![United Airlines logo]()
$269
This American Airlines deal was found by Cheapflights users on 9/5. 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.
Tue 10/205:00 am -
Nonstop1h 14m
Sat 10/249:40 am -
Nonstop1h 12m
Deal found 9/5![American Airlines logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Tue 10/2010:30 am -
1 stop21h 21m
Fri 11/68:00 am -
2 stops25h 58m
Deal found 9/9![Multiple Airlines logo]()
$433
This United Airlines deal was found by Cheapflights users on 9/7. 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 11/256:25 am -
Nonstop1h 19m
Sun 11/2910:05 pm -
Nonstop1h 02m
Deal found 9/7![United Airlines logo]()
$289
This United Airlines deal was found by Cheapflights users on 9/9. 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.
Sat 9/264:10 pm -
Nonstop1h 19m
Wed 9/308:45 am -
Nonstop1h 09m
Deal found 9/9![United Airlines logo]()
$354
This United Airlines deal was found by Cheapflights users on 9/5. 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 9/1910:46 am -
Nonstop1h 13m
Wed 9/2310:45 am -
Nonstop1h 18m
Deal found 9/5![United Airlines logo]()
$389
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/86:00 pm -
1 stop13h 31m
Thu 10/1512:26 pm -
2 stops45h 32m
Deal found 9/10![Multiple Airlines logo]()
$481
This Delta deal was found by Cheapflights users on 9/9. 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.
Thu 12/176:32 am -
1 stop5h 27m
Wed 3/179:55 am -
1 stop4h 00m
Deal found 9/9![Delta logo]()
$1,143
This United Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/234:14 pm -
Nonstop1h 16m
Sun 9/272:00 pm -
Nonstop1h 04m
Deal found 9/8![United Airlines logo]()
$479
This United Airlines deal was found by Cheapflights users on 9/9. 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.
Tue 10/208:50 am -
1 stop10h 40m
Fri 11/610:05 pm -
Nonstop1h 02m
Deal found 9/9![United Airlines logo]()
$508
This Delta deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/156:15 am -
1 stop5h 36m
Sat 1/169:55 am -
1 stop4h 00m
Deal found 9/8![Delta logo]()
$1,143
This Delta deal was found by Cheapflights users on 9/9. 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.
Thu 12/176:32 am -
1 stop5h 27m
Sun 1/175:35 pm -
1 stop5h 20m
Deal found 9/9![Delta logo]()
$1,143
This Delta deal was found by Cheapflights users on 9/7. 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 11/410:53 am -
1 stop5h 54m
Fri 11/65:31 pm -
1 stop3h 52m
Deal found 9/7![Delta logo]()
$1,163
This Delta deal was found by Cheapflights users on 9/7. 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 10/287:59 am -
1 stop3h 48m
Sat 10/3112:27 pm -
1 stop6h 47m
Deal found 9/7![Delta logo]()
$1,163
This Delta deal was found by Cheapflights users on 9/6. 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 10/2310:53 am -
1 stop5h 54m
Sun 10/2512:27 pm -
1 stop6h 39m
Deal found 9/6![Delta logo]()
$1,173
This KAYAK deal was found by Cheapflights users on 9/5. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2112:00 pm -
1 stop6h 19m
Thu 9/242:00 pm -
1 stop3h 57m
Deal found 9/5![Delta logo]()
$1,245
This Delta deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1610:53 am -
1 stop5h 54m
Sun 10/1810:12 am -
1 stop3h 59m
Deal found 9/8![Delta logo]()
$1,325
This Delta deal was found by Cheapflights users on 9/6. 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 9/2512:00 pm -
1 stop6h 19m
Mon 9/289:59 am -
1 stop4h 08m
Deal found 9/6![Delta logo]()
$1,380
This Delta deal was found by Cheapflights users on 9/9. 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.
Wed 9/232:47 pm -
1 stop3h 32m
Sun 9/272:00 pm -
1 stop3h 57m
Deal found 9/9![Delta logo]()
$1,405
This Delta deal was found by Cheapflights users on 9/5. 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.
Sun 9/2012:00 pm -
1 stop6h 19m
Thu 9/242:00 pm -
1 stop3h 57m
Deal found 9/5![Delta logo]()
$1,463
Last-minute flights from Madison to ChicagoDiscover last-minute flight deals from Madison to Chicago. Data last updated September 10, 2026 and is based on user searches.
Discover last-minute flight deals from Madison to Chicago. Data last updated September 10, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 9/6. 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.
Thu 9/107:15 am -
Nonstop1h 31m
Sat 9/125:05 pm -
Nonstop1h 19m
Deal found 9/6![American Airlines logo]()
$410
This American Airlines deal was found by Cheapflights users on 9/9. 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.
Sat 9/1912:56 pm -
Nonstop1h 24m
Sun 9/277:03 am -
Nonstop1h 11m
Deal found 9/9![American Airlines logo]()
$314
This United Airlines deal was found by Cheapflights users on 9/5. 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 9/1910:46 am -
Nonstop1h 13m
Wed 9/2310:45 am -
Nonstop1h 18m
Deal found 9/5![United Airlines logo]()
$389
This American Airlines deal was found by Cheapflights users on 9/9. 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.
Wed 9/239:40 am -
Nonstop1h 15m
Sun 9/278:52 pm -
Nonstop1h 18m
Deal found 9/9![American Airlines logo]()
$299
This United Airlines deal was found by Cheapflights users on 9/9. 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.
Thu 9/2412:39 pm -
Nonstop1h 19m
Mon 9/289:30 pm -
Nonstop1h 05m
Deal found 9/9![United Airlines logo]()
$369
This American Airlines deal was found by Cheapflights users on 9/6. 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.
Fri 9/258:05 pm -
Nonstop1h 25m
Mon 9/2811:00 pm -
Nonstop1h 17m
Deal found 9/6![American Airlines logo]()
$284
This United Airlines deal was found by Cheapflights users on 9/9. 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.
Sat 9/264:10 pm -
Nonstop1h 19m
Wed 9/308:45 am -
Nonstop1h 09m
Deal found 9/9![United Airlines logo]()
$354
This United Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/22:49 pm -
Nonstop1h 11m
Fri 10/27:50 pm -
1 stop17h 28m
Deal found 9/8![United Airlines logo]()
$409
This Delta deal was found by Cheapflights users on 9/7. 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.
Mon 10/59:02 am -
1 stop4h 18m
Mon 10/125:31 pm -
1 stop3h 24m
Deal found 9/7![Delta logo]()
$1,163
This American Airlines deal was found by Cheapflights users on 9/10. 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.
Tue 10/205:00 am -
Nonstop1h 14m
Sat 10/249:40 am -
Nonstop1h 12m
Deal found 9/10![American Airlines logo]()
$269
This United Airlines deal was found by Cheapflights users on 9/9. 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 10/216:35 pm -
Nonstop1h 20m
Sun 10/257:59 pm -
Nonstop1h 06m
Deal found 9/9![United Airlines logo]()
$339
This Delta deal was found by Cheapflights users on 9/6. 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 10/2310:53 am -
1 stop5h 54m
Sun 10/2512:27 pm -
1 stop6h 39m
Deal found 9/6![Delta logo]()
$1,173
One-way flights from Madison to ChicagoSearch for one-way flight options from Madison to Chicago. Find affordable one-way fares based on user searches. Data last updated September 10, 2026.
Search for one-way flight options from Madison to Chicago. Find affordable one-way fares based on user searches. Data last updated September 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/910:38 am -
1 stop23h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Multiple Airlines logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 9/5. 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.
Wed 10/2110:38 am -
2 stops28h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Multiple Airlines logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 9/8. 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.
Tue 10/62:45 pm -
2 stops27h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Multiple Airlines logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1010:30 am -
2 stops26h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Multiple Airlines logo]()
$175
This American Airlines deal was found by Cheapflights users on 9/6. 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.
Mon 10/511:22 am -
Nonstop1h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![American Airlines logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 9/7. 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.
Wed 10/710:38 am -
2 stops28h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 9/5. 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.
Wed 10/2110:38 am -
3 stops31h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Multiple Airlines logo]()
$193
This Kiwi.com deal was found by Cheapflights users on 9/6. 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.
Tue 10/62:45 pm -
2 stops27h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Multiple Airlines logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 9/7. 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.
Sun 10/116:00 pm -
2 stops29h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 9/7. 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.
Wed 10/1410:38 am -
3 stops31h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$226
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/186:00 pm -
3 stops44h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Tue 10/1310:30 am -
2 stops37h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$230
Find flight deals from Madison to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Madison (MSN) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $268 (American Airlines) |
One-way from | $139 (Kiwi.com) |
Popular in | April |
Cheapest in | November |
Average price | $209 |
Good round-trip deal | $364 or less |
Good one-way deal | $287 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Madison 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 7,457,451 searches. Data last updated September 10, 2026.
Use the filters below to find and compare flights from Madison to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
MadisonChicago
MSN Madison Truax Field - MDW Chicago Midway
MSNMDW
Madison Truax Field
Wed 10/21
10:38 am-5:45 pm
3 stops31h 07m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$193
MadisonChicago
MSN Madison Truax Field - MDW Chicago Midway
MSNMDW
Madison Truax Field
Tue 10/6
2:45 pm-5:51 pm
2 stops27h 06m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$201
MadisonChicago
MSN Madison Truax Field - ORD Chicago O'Hare Intl
MSNORD
Madison Truax Field
Fri 11/6
3:00 pm-8:53 am
1 stop17h 53m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$208
MadisonChicago
MSN Madison Truax Field - MDW Chicago Midway
MSNMDW
Madison Truax Field
Wed 10/14
10:38 am-5:45 pm
3 stops31h 07m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$226
MadisonChicago
MSN Madison Truax Field - ORD Chicago O'Hare Intl
MSNORD
Madison Truax Field
Fri 12/18
6:00 am-7:24 am
Nonstop1h 24m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$259
MadisonChicago
MSN Madison Truax Field - ORD Chicago O'Hare Intl
MSNORD
Madison Truax Field
Mon 11/9
7:49 pm-11:48 am
1 stop15h 59m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$267
MadisonChicago
MSN Madison Truax Field - ORD Chicago O'Hare Intl
MSNORD
Madison Truax Field
Wed 11/11
2:30 pm-9:33 pm
1 stop7h 03m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$267
MadisonChicago
MSN Madison Truax Field - ORD Chicago O'Hare Intl
MSNORD
Madison Truax Field
Mon 12/7
2:50 pm-9:04 am
1 stop18h 14m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$267
MadisonChicago
MSN Madison Truax Field - ORD Chicago O'Hare Intl
MSNORD
Madison Truax Field
Sat 10/10
7:59 am-9:27 pm
1 stop13h 28m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$267
MadisonChicago
MSN Madison Truax Field - ORD Chicago O'Hare Intl
MSNORD
Madison Truax Field
Thu 10/8
4:10 pm-5:29 pm
Nonstop1h 19m
Chicago O'Hare Intl
Thu 10/15
2:00 pm-3:04 pm
Nonstop1h 04m
$269
Showing 1-10 of 40 resultsSorted by cheapest first
Compare providers for flights from Madison to Chicago
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Madison to Chicago in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Madison-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Madison-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Madison-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Madison-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Madison-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Madison to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Madison with our price prediction graph.
MSN-CHI
MSN-ORD
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 Chicago
MSN-CHI
MSN-ORD
MSN-MDW
What is the cheapest month to book a flight from Madison to Chicago?
Currently, October is the cheapest month in which you can book a flight from Madison to Chicago (average of $182). Flying from Madison to Chicago 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 CHI?
Find hourly flight availability from Madison to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 10, 2026.
A simple way to save on the total cost of your ticket is to fly from Madison to Chicago in the morning. If you’re flexible enough to do this you can expect to save up to 26% on your trip compared to booking a flight in the evening.
Weekly flight availability from Madison to Chicago
Explore weekly flight availability from Madison to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 10, 2026.
The most flights from MSN to CHI are scheduled on a Wednesday (49 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (22 on average).
What is the cheapest day to fly from Madison to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Madison to Chicago. Price data was last updated on September 5, 2026.
Travelers seeking maximum savings on their Madison to Chicago flight should consider departing on Saturday mornings when fares are most often at their lowest. Wednesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated September 10, 2026.
See what other customers who have flown with United Airlines from Madison to Chicago have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
7.4
Boarding
7.7
Crew
8.1
Entertainment
7.1
Comfort
7.3
Food
6.7
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Overall
7.4
Boarding
7.7
Crew
8.1
Entertainment
7.1
Comfort
7.3
Food
6.7
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 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
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Top 2 airlines flying from Madison to Chicago
Discover the top 2 airlines that operate flights from Madison 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 7,457,451 searches. Data last updated September 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$179 | Average$259 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$179 | Average$345 | FlexibilityNo cancel fee | On-time69% |