$144+ Cheap flights from Madison (MSN) to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/23. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — CHI
Sep 29 — Oct 61
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 August 30, 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 August 30, 2026.
This American Airlines deal was found by Cheapflights users on 8/25. 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.
Thu 10/85:00 am -
Nonstop1h 14m
Sun 10/186:59 am -
Nonstop1h 12m
Deal found 8/25![American Airlines logo]()
$249
This American Airlines deal was found by Cheapflights users on 8/25. 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.
Fri 10/97:05 pm -
Nonstop1h 25m
Fri 10/166:59 am -
Nonstop1h 12m
Deal found 8/25![American Airlines logo]()
$250
This American Airlines deal was found by Cheapflights users on 8/30. 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 9/248:05 pm -
Nonstop1h 25m
Sun 9/277:03 am -
Nonstop1h 11m
Deal found 8/30![American Airlines logo]()
$268
This American Airlines deal was found by Cheapflights users on 8/27. 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 12/115:00 am -
Nonstop1h 21m
Sun 12/139:59 pm -
Nonstop1h 13m
Deal found 8/27![American Airlines logo]()
$269
This American Airlines deal was found by Cheapflights users on 8/26. 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.
Sat 10/109:53 am -
Nonstop1h 17m
Sat 10/175:16 pm -
Nonstop1h 19m
Deal found 8/26![American Airlines logo]()
$270
This American Airlines deal was found by Cheapflights users on 8/25. 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.
Fri 9/118:05 pm -
Nonstop1h 25m
Sat 9/121:45 pm -
Nonstop1h 10m
Deal found 8/25![American Airlines logo]()
$279
This American Airlines deal was found by Cheapflights users on 8/28. 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 9/1712:56 pm -
Nonstop1h 24m
Sat 9/197:03 am -
Nonstop1h 11m
Deal found 8/28![American Airlines logo]()
$284
This United Airlines deal was found by Cheapflights users on 8/29. 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.
Sat 9/56:30 am -
Nonstop1h 13m
Sat 9/197:45 pm -
Nonstop1h 08m
Deal found 8/29![United Airlines logo]()
$293
This United Airlines deal was found by Cheapflights users on 8/28. 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.
Tue 9/85:00 am -
Nonstop1h 15m
Sat 9/2612:40 pm -
Nonstop0h 57m
Deal found 8/28![United Airlines logo]()
$299
This American Airlines deal was found by Cheapflights users on 8/25. 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.
Fri 9/42:45 pm -
Nonstop1h 15m
Sun 9/1311:00 pm -
Nonstop1h 17m
Deal found 8/25![American Airlines logo]()
$300
This American Airlines deal was found by Cheapflights users on 8/28. 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 9/103:25 pm -
Nonstop1h 16m
Sun 9/135:05 pm -
Nonstop1h 19m
Deal found 8/28![American Airlines logo]()
$308
This American Airlines deal was found by Cheapflights users on 8/29. 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.
Wed 9/98:05 pm -
Nonstop1h 25m
Sun 9/135:05 pm -
Nonstop1h 19m
Deal found 8/29![American Airlines logo]()
$309
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 August 30, 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 August 30, 2026.
This American Airlines deal was found by Cheapflights users on 8/26. 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 12/249:32 am -
Nonstop1h 28m
Fri 1/86:54 am -
Nonstop1h 12m
Deal found 8/26![American Airlines logo]()
$269
This United Airlines deal was found by Cheapflights users on 8/29. 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.
Sat 9/1910:46 am -
Nonstop1h 13m
Wed 9/2310:45 am -
Nonstop1h 18m
Deal found 8/29![United Airlines logo]()
$339
This Kiwi.com deal was found by Cheapflights users on 8/26. 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.
Tue 10/62:45 pm -
1 stop8h 14m
Sat 10/107:44 pm -
2 stops21h 36m
Deal found 8/26![Multiple Airlines logo]()
$462
This United Airlines deal was found by Cheapflights users on 8/25. 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.
Fri 9/112:50 pm -
1 stop18h 22m
Sat 9/1212:40 pm -
Nonstop1h 02m
Deal found 8/25![United Airlines logo]()
$409
This United Airlines deal was found by Cheapflights users on 8/27. 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.
Sat 9/1212:41 pm -
Nonstop1h 19m
Wed 9/161:55 pm -
Nonstop1h 04m
Deal found 8/27![United Airlines logo]()
$479
This Delta deal was found by Cheapflights users on 8/28. 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.
Sat 10/107:59 am -
1 stop3h 48m
Sat 10/175:31 pm -
1 stop3h 52m
Deal found 8/28![Delta logo]()
$1,183
This United Airlines deal was found by Cheapflights users on 8/29. 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.
Sat 10/176:39 pm -
Nonstop1h 21m
Sat 10/179:30 pm -
Nonstop1h 05m
Deal found 8/29![United Airlines logo]()
$492
This United Airlines deal was found by Cheapflights users on 8/29. 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.
Tue 11/37:00 pm -
Nonstop1h 22m
Tue 11/310:05 pm -
Nonstop1h 02m
Deal found 8/29![United Airlines logo]()
$492
This Delta deal was found by Cheapflights users on 8/29. 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.
Sat 9/269:02 am -
1 stop4h 18m
Sat 10/39:59 am -
1 stop4h 08m
Deal found 8/29![Delta logo]()
$1,183
This Delta deal was found by Cheapflights users on 8/27. 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.
Fri 9/2512:00 pm -
1 stop6h 19m
Wed 9/309:59 am -
1 stop4h 08m
Deal found 8/27![Delta logo]()
$1,183
This Delta deal was found by Cheapflights users on 8/26. 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.
Fri 10/910:53 am -
1 stop5h 54m
Fri 10/165:31 pm -
1 stop3h 24m
Deal found 8/26![Delta logo]()
$1,183
This Delta deal was found by Cheapflights users on 8/28. 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 10/96:00 am -
1 stop5h 47m
Fri 10/95:31 pm -
1 stop3h 24m
Deal found 8/28![Delta logo]()
$1,303
This Delta deal was found by Cheapflights users on 8/26. 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 10/610:53 am -
1 stop5h 54m
Sat 10/1012:27 pm -
1 stop6h 39m
Deal found 8/26![Delta logo]()
$1,343
This Delta deal was found by Cheapflights users on 8/27. 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.
Fri 9/119:02 am -
1 stop4h 18m
Tue 9/157:13 pm -
1 stop3h 48m
Deal found 8/27![Delta logo]()
$1,405
This Delta deal was found by Cheapflights users on 8/28. 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 9/1112:00 pm -
1 stop6h 19m
Sat 9/124:48 pm -
1 stop4h 42m
Deal found 8/28![Delta logo]()
$1,405
This Delta deal was found by Cheapflights users on 8/29. 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.
Wed 9/92:47 pm -
1 stop3h 32m
Sun 9/139:59 am -
1 stop4h 08m
Deal found 8/29![Delta logo]()
$1,455
This Delta deal was found by Cheapflights users on 8/29. 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.
Sun 9/139:02 am -
1 stop4h 18m
Thu 9/179:29 am -
1 stop3h 06m
Deal found 8/29![Delta logo]()
$1,468
This Delta deal was found by Cheapflights users on 8/25. 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.
Thu 9/249:02 am -
1 stop4h 18m
Thu 10/17:13 pm -
1 stop3h 48m
Deal found 8/25![Delta logo]()
$1,503
This Delta deal was found by Cheapflights users on 8/29. 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.
Mon 9/147:05 am -
1 stop5h 34m
Fri 9/187:13 pm -
1 stop3h 48m
Deal found 8/29![Delta logo]()
$1,507
Last-minute flights from Madison to ChicagoDiscover last-minute flight deals from Madison to Chicago. Data last updated August 30, 2026 and is based on user searches.
Discover last-minute flight deals from Madison to Chicago. Data last updated August 30, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 8/25. 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.
Wed 9/210:43 am -
Nonstop1h 16m
Wed 9/97:45 pm -
Nonstop1h 08m
Deal found 8/25![United Airlines logo]()
$314
This United Airlines deal was found by Cheapflights users on 8/29. 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.
Wed 9/25:00 am -
Nonstop1h 15m
Sat 10/1710:35 am -
Nonstop1h 19m
Deal found 8/29![United Airlines logo]()
$330
This American Airlines deal was found by Cheapflights users on 8/25. 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.
Fri 9/42:45 pm -
Nonstop1h 15m
Sun 9/1311:00 pm -
Nonstop1h 17m
Deal found 8/25![American Airlines logo]()
$300
This United Airlines deal was found by Cheapflights users on 8/29. 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.
Sat 9/56:30 am -
Nonstop1h 13m
Sat 9/197:45 pm -
Nonstop1h 08m
Deal found 8/29![United Airlines logo]()
$293
This American Airlines deal was found by Cheapflights users on 8/27. 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.
Sat 9/52:45 pm -
Nonstop1h 15m
Wed 9/911:00 pm -
Nonstop1h 17m
Deal found 8/27![American Airlines logo]()
$323
This United Airlines deal was found by Cheapflights users on 8/28. 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.
Tue 9/85:00 am -
Nonstop1h 15m
Sat 9/2612:40 pm -
Nonstop0h 57m
Deal found 8/28![United Airlines logo]()
$299
This American Airlines deal was found by Cheapflights users on 8/29. 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.
Wed 9/98:05 pm -
Nonstop1h 25m
Sun 9/135:05 pm -
Nonstop1h 19m
Deal found 8/29![American Airlines logo]()
$309
This American Airlines deal was found by Cheapflights users on 8/28. 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 9/103:25 pm -
Nonstop1h 16m
Sun 9/135:05 pm -
Nonstop1h 19m
Deal found 8/28![American Airlines logo]()
$308
This American Airlines deal was found by Cheapflights users on 8/25. 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.
Fri 9/118:05 pm -
Nonstop1h 25m
Sat 9/121:45 pm -
Nonstop1h 10m
Deal found 8/25![American Airlines logo]()
$279
This American Airlines deal was found by Cheapflights users on 8/28. 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 9/1712:56 pm -
Nonstop1h 24m
Sat 9/197:03 am -
Nonstop1h 11m
Deal found 8/28![American Airlines logo]()
$284
This American Airlines deal was found by Cheapflights users on 8/30. 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 9/248:05 pm -
Nonstop1h 25m
Sun 9/277:03 am -
Nonstop1h 11m
Deal found 8/30![American Airlines logo]()
$268
This American Airlines deal was found by Cheapflights users on 8/27. 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 9/255:00 am -
Nonstop1h 25m
Wed 9/301:45 pm -
Nonstop1h 10m
Deal found 8/27![American Airlines logo]()
$269
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 August 30, 2026.
Search for one-way flight options from Madison to Chicago. Find affordable one-way fares based on user searches. Data last updated August 30, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/25. 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.
Wed 9/2310:33 am -
2 stops28h 12m
Deal found 8/25![Multiple Airlines logo]()
$144
This American Airlines deal was found by Cheapflights users on 8/28. 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.
Sat 9/267:15 am -
Nonstop1h 31m
Deal found 8/28![American Airlines logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 8/28. 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.
Wed 9/1610:33 am -
2 stops28h 12m
Deal found 8/28![Multiple Airlines logo]()
$181
This Kiwi.com deal was found by Cheapflights users on 8/27. 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 9/276:00 pm -
1 stop28h 59m
Deal found 8/27![Multiple Airlines logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 8/28. 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.
Tue 9/2912:15 pm -
1 stop10h 44m
Deal found 8/28![Multiple Airlines logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 8/25. 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.
Thu 9/248:00 pm -
1 stop28h 23m
Deal found 8/25![Frontier logo]()
$187
This Kiwi.com deal was found by Cheapflights users on 8/29. 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.
Wed 9/3010:33 am -
2 stops28h 12m
Deal found 8/29![Multiple Airlines logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 8/28. 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.
Sun 10/256:00 pm -
1 stop13h 31m
Deal found 8/28![Multiple Airlines logo]()
$193
This Kiwi.com deal was found by Cheapflights users on 8/27. 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 10/2810:33 am -
2 stops29h 04m
Deal found 8/27![Multiple Airlines logo]()
$195
This Kiwi.com deal was found by Cheapflights users on 8/25. 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.
Wed 10/2110:33 am -
2 stops13h 10m
Deal found 8/25![Multiple Airlines logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 8/29. 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.
Wed 10/2810:33 am -
2 stops13h 14m
Deal found 8/29![Multiple Airlines logo]()
$224
This Kiwi.com deal was found by Cheapflights users on 8/29. 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.
Sat 9/1210:33 am -
3 stops31h 13m
Deal found 8/29![Multiple Airlines logo]()
$231
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 August 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $249 (American Airlines) |
One-way from | $144 (Kiwi.com) |
Popular in | April |
Cheapest in | November |
Average price | $249 |
Good round-trip deal | $359 or less |
Good one-way deal | $288 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 August 30, 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 - ORD Chicago O'Hare Intl
MSNORD
Madison Truax Field
Thu 12/24
9:32 am-11:00 am
Nonstop1h 28m
Chicago O'Hare Intl
Fri 1/8
6:54 am-8:06 am
Nonstop1h 12m
$269
MadisonChicago
MSN Madison Truax Field - ORD Chicago O'Hare Intl
MSNORD
Madison Truax Field
Sat 9/19
10:46 am-11:59 am
Nonstop1h 13m
Chicago O'Hare Intl
Wed 9/23
10:45 am-12:03 pm
Nonstop1h 18m
$339
MadisonChicago
MSN Madison Truax Field - ORD Chicago O'Hare Intl
MSNORD
Madison Truax Field
Fri 9/11
2:50 pm-9:12 am
1 stop18h 22m
Chicago O'Hare Intl
Sat 9/12
12:40 pm-1:42 pm
Nonstop1h 02m
$409
MadisonChicago
MSN Madison Truax Field - ORD Chicago O'Hare Intl
MSNORD
Madison Truax Field
Tue 10/6
2:45 pm-10:59 pm
1 stop8h 14m
Chicago O'Hare Intl
Sat 10/10
7:44 pm-5:20 pm
2 stops21h 36m
$462
Quickest round-trip
MadisonChicago
MSN Madison Truax Field - ORD Chicago O'Hare Intl
MSNORD
Madison Truax Field
Sat 9/12
12:41 pm-2:00 pm
Nonstop1h 19m
Chicago O'Hare Intl
Wed 9/16
1:55 pm-2:59 pm
Nonstop1h 04m
$479
MadisonChicago
MSN Madison Truax Field - ORD Chicago O'Hare Intl
MSNORD
Madison Truax Field
Sat 10/17
6:39 pm-8:00 pm
Nonstop1h 21m
Chicago O'Hare Intl
Sat 10/17
9:30 pm-10:35 pm
Nonstop1h 05m
$492
MadisonChicago
MSN Madison Truax Field - ORD Chicago O'Hare Intl
MSNORD
Madison Truax Field
Tue 11/3
7:00 pm-8:22 pm
Nonstop1h 22m
Chicago O'Hare Intl
Tue 11/3
10:05 pm-11:07 pm
Nonstop1h 02m
$492
MadisonChicago
MSN Madison Truax Field - MDW Chicago Midway
MSNMDW
Madison Truax Field
Sat 10/10
7:59 am-11:47 am
1 stop3h 48m
Chicago Midway
Sat 10/17
5:31 pm-9:23 pm
1 stop3h 52m
$1,183
MadisonChicago
MSN Madison Truax Field - MDW Chicago Midway
MSNMDW
Madison Truax Field
Sat 9/26
9:02 am-1:20 pm
1 stop4h 18m
Chicago Midway
Sat 10/3
9:59 am-2:07 pm
1 stop4h 08m
$1,183
MadisonChicago
MSN Madison Truax Field - MDW Chicago Midway
MSNMDW
Madison Truax Field
Fri 9/25
12:00 pm-6:19 pm
1 stop6h 19m
Chicago Midway
Wed 9/30
9:59 am-2:07 pm
1 stop4h 08m
$1,183
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 August.
| 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 August 30, 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 August 30, 2026.
The most flights from MSN to CHI are scheduled on a Friday (46 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (28 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 August 22, 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 August 30, 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.
Food
6.7
Boarding
7.7
Entertainment
7.1
Overall
7.4
Comfort
7.3
Crew
8.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Food
6.7
Boarding
7.7
Entertainment
7.1
Overall
7.4
Comfort
7.3
Crew
8.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Food
6.7
Boarding
7.7
Entertainment
7.1
Overall
7.4
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
Lansing
Merrillville
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 August 30, 2026.
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Madison and Chicago flights
Browse other Madison and Chicago flight options. Last updated on August 30, 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 August 30, 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 August 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$179 | Average$231 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$179 | Average$345 | FlexibilityNo cancel fee | On-time69% |