$155+ 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 12/22. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — CHI
Nov 30 — Dec 71
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 October 31, 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 October 31, 2026.
This American Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 10/28![American Airlines logo]()
$309
This American Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 11/159:15 am -
Nonstop1h 25m
Sun 11/2211:09 pm -
Nonstop1h 16m
Deal found 10/28![American Airlines logo]()
$324
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 11/113:00 pm -
Nonstop1h 19m
Sun 11/155:54 pm -
Nonstop1h 13m
Deal found 10/27![United Airlines logo]()
$339
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 11/65:00 am -
Nonstop1h 20m
Mon 11/97:59 pm -
Nonstop1h 06m
Deal found 10/26![United Airlines logo]()
$354
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 United Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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
Sun 11/87:59 pm -
Nonstop1h 06m
Deal found 10/28![United Airlines logo]()
$369
This United Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 12/125:38 pm -
Nonstop1h 21m
Sat 12/129:20 pm -
Nonstop1h 03m
Deal found 10/28![United Airlines logo]()
$392
This American Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 11/45:00 am -
Nonstop1h 21m
Wed 11/117:00 pm -
Nonstop1h 07m
Deal found 10/30![American Airlines logo]()
$400
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 10/28. Clicking the “Pick Dates” 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 11/128:15 am -
Nonstop1h 16m
Mon 11/167:59 pm -
Nonstop1h 06m
Deal found 10/28![United Airlines logo]()
$429
This United Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 10/29![United Airlines logo]()
$449
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 October 31, 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 October 31, 2026.
This United Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 12/35:38 pm -
Nonstop1h 22m
Sun 12/61:45 pm -
Nonstop1h 05m
Deal found 10/29![United Airlines logo]()
$309
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.
Tue 11/248:41 pm -
Nonstop1h 14m
Tue 12/111:00 pm -
Nonstop1h 16m
Deal found 10/26![American 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.
Thu 11/1912:30 pm -
Nonstop1h 19m
Sun 11/224:40 pm -
Nonstop1h 14m
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 10/26. 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 10/26. 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 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 10/30. Clicking the “Pick Dates” 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 11/275:43 pm -
Nonstop1h 22m
Fri 12/49:20 pm -
Nonstop1h 03m
Deal found 10/30![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 10/27. 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 11/113:00 pm -
Nonstop1h 19m
Sun 11/155:54 pm -
Nonstop1h 13m
Deal found 10/27![United Airlines logo]()
$339
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 11/65:00 am -
Nonstop1h 20m
Mon 11/97:59 pm -
Nonstop1h 06m
Deal found 10/26![United Airlines logo]()
$354
This United Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 12/125:38 pm -
Nonstop1h 21m
Sat 12/129:20 pm -
Nonstop1h 03m
Deal found 10/28![United Airlines logo]()
$392
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 10/28. Clicking the “Pick Dates” 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 11/1910:59 am -
1 stop5h 40m
Sun 11/2210:34 am -
1 stop3h 16m
Deal found 10/28![Delta logo]()
$1,079
This Delta deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 10/28![Delta logo]()
$1,159
This Delta deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 12/46:32 am -
1 stop5h 27m
Fri 6/45:35 pm -
1 stop3h 25m
Deal found 10/28![Delta logo]()
$1,393
This Delta deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 12/36:32 am -
1 stop5h 27m
Sun 12/65:30 pm -
1 stop3h 59m
Deal found 10/29![Delta logo]()
$1,453
This Delta deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 10/29![Delta logo]()
$1,453
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
Last-minute flights from Madison to ChicagoDiscover last-minute flight deals from Madison to Chicago. Data last updated October 31, 2026 and is based on user searches.
Discover last-minute flight deals from Madison to Chicago. Data last updated October 31, 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 American Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 11/45:00 am -
Nonstop1h 21m
Wed 11/117:00 pm -
Nonstop1h 07m
Deal found 10/30![American Airlines logo]()
$400
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 11/65:00 am -
Nonstop1h 20m
Mon 11/97:59 pm -
Nonstop1h 06m
Deal found 10/26![United Airlines logo]()
$354
This United Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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
Sun 11/87:59 pm -
Nonstop1h 06m
Deal found 10/28![United Airlines logo]()
$369
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 11/113:00 pm -
Nonstop1h 19m
Sun 11/155:54 pm -
Nonstop1h 13m
Deal found 10/27![United Airlines logo]()
$339
This United Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 11/128:15 am -
Nonstop1h 16m
Mon 11/167:59 pm -
Nonstop1h 06m
Deal found 10/28![United Airlines logo]()
$429
This American Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 11/159:15 am -
Nonstop1h 25m
Sun 11/2211:09 pm -
Nonstop1h 16m
Deal found 10/28![American Airlines logo]()
$324
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 10/28. Clicking the “Pick Dates” 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 10/28![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
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 October 31, 2026.
Search for one-way flight options from Madison to Chicago. Find affordable one-way fares based on user searches. Data last updated October 31, 2026.
This American Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 12/228:32 pm -
Nonstop1h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![American Airlines logo]()
$155
This Delta deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 12/246:40 am -
1 stop4h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Delta logo]()
$183
This American Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![American Airlines logo]()
$185
This American Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 12/175:51 am -
Nonstop1h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![American Airlines logo]()
$199
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 10/29. Clicking the “Pick Dates” 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 12/1710:40 am -
2 stops13h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Multiple Airlines logo]()
$223
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 10/28. Clicking the “Pick Dates” 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 12/33:55 pm -
1 stop30h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Multiple Airlines logo]()
$228
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 10/25. 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 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 October 31, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $309 (American Airlines) |
One-way from | $155 (American Airlines) |
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 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 October 31, 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
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
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 12/17
10:40 am-12:26 am
2 stops13h 46m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$226
Quickest round-trip
MadisonChicago
MSN Madison Truax Field - ORD Chicago O'Hare Intl
MSNORD
Madison Truax Field
Sun 1/10
4:01 pm-5:14 pm
Nonstop1h 13m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$269
MadisonChicago
MSN Madison Truax Field - ORD Chicago O'Hare Intl
MSNORD
Madison Truax Field
Mon 12/21
6:05 am-7:29 am
Nonstop1h 24m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$269
MadisonChicago
MSN Madison Truax Field - ORD Chicago O'Hare Intl
MSNORD
Madison Truax Field
Tue 12/1
5:38 pm-7:00 pm
Nonstop1h 22m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$269
MadisonChicago
MSN Madison Truax Field - ORD Chicago O'Hare Intl
MSNORD
Madison Truax Field
Wed 12/23
8:10 am-9:33 am
Nonstop1h 23m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$269
Showing 1-10 of 36 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 October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 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, March is the cheapest month in which you can book a flight from Madison to Chicago (average of $239). 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 October 31, 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 23% on your trip compared to booking a flight in the evening.
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 October 24, 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. Monday at noon 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 October 31, 2026.
See what other customers who have flown with United Airlines and American 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.
Boarding
7.7
Food
6.7
Entertainment
7.1
Overall
7.3
Comfort
7.3
Crew
8.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Boarding
7.7
Food
6.7
Entertainment
7.1
Overall
7.3
Comfort
7.3
Crew
8.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Boarding
7.7
Food
6.7
Entertainment
7.1
Overall
7.3
Comfort
7.3
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 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
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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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 October 31, 2026.
Complete your trip
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Madison and Chicago flights
Browse other Madison and Chicago flight options. Last updated on October 31, 2026.
Other flights from Madison
Browse through other flights departing from Madison. Flights are based on user searches made on Cheapflights and were last updated on October 31, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 October 31, 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% |