$107+ Cheap flights from Chicago (CHI) to Madison (MSN)
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 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MSN
Sep 9 — Sep 161
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Madison with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Chicago to MadisonExplore the most affordable flight options available from Chicago to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 10, 2026.
Explore the most affordable flight options available from Chicago to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 10, 2026.
This United Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/169:30 pm -
Nonstop1h 05m
Sun 11/13:49 pm -
Nonstop1h 16m
Deal found 8/7![United Airlines logo]()
$249
This American Airlines deal was found by Cheapflights users on 8/6. 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 9/38:10 am -
Nonstop1h 07m
Thu 9/103:25 pm -
Nonstop1h 16m
Deal found 8/6![American Airlines logo]()
$250
This American Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2111:00 pm -
Nonstop1h 10m
Sun 8/309:48 am -
Nonstop1h 13m
Deal found 8/5![American Airlines logo]()
$265
This United Airlines deal was found by Cheapflights users on 8/5. 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.
Wed 8/191:55 pm -
Nonstop1h 04m
Sat 8/222:23 pm -
Nonstop1h 15m
Deal found 8/5![United Airlines logo]()
$279
This American Airlines deal was found by Cheapflights users on 8/5. 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 8/189:09 pm -
Nonstop1h 09m
Sat 8/226:53 pm -
Nonstop1h 37m
Deal found 8/5![American Airlines logo]()
$294
This American Airlines deal was found by Cheapflights users on 8/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/158:19 am -
Nonstop1h 07m
Sat 8/226:53 pm -
Nonstop1h 37m
Deal found 8/8![American Airlines logo]()
$295
This Kiwi.com deal was found by Cheapflights users on 8/10. 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 9/227:11 am -
2 stops26h 42m
Tue 9/2912:15 pm -
1 stop10h 44m
Deal found 8/10![Multiple Airlines logo]()
$315
This United Airlines deal was found by Cheapflights users on 8/5. 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.
Tue 8/255:52 pm -
Nonstop1h 04m
Wed 9/212:40 pm -
Nonstop1h 19m
Deal found 8/5![United Airlines logo]()
$316
This United Airlines deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/28:50 am -
Nonstop1h 14m
Sun 9/66:30 am -
Nonstop1h 13m
Deal found 8/6![United Airlines logo]()
$319
This American Airlines deal was found by Cheapflights users on 8/6. 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 8/78:10 am -
Nonstop1h 07m
Thu 9/109:40 am -
Nonstop1h 15m
Deal found 8/6![American Airlines logo]()
$330
This American Airlines deal was found by Cheapflights users on 8/10. 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 8/119:09 pm -
Nonstop1h 09m
Tue 8/187:47 am -
Nonstop1h 21m
Deal found 8/10![American Airlines logo]()
$340
This Delta deal was found by Cheapflights users on 8/9. 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.
Fri 9/117:13 pm -
1 stop16h 07m
Tue 9/156:00 am -
1 stop12h 19m
Deal found 8/9![Delta logo]()
$450
Best flights from Chicago to MadisonDiscover carefully curated flight deals from Chicago to Madison that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 10, 2026.
Discover carefully curated flight deals from Chicago to Madison that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 10, 2026.
This United Airlines deal was found by Cheapflights users on 8/5. 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 9/1910:45 am -
Nonstop1h 18m
Sun 9/208:05 am -
Nonstop1h 13m
Deal found 8/5![United Airlines logo]()
$249
This American Airlines deal was found by Cheapflights users on 8/9. 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 9/2311:00 pm -
Nonstop1h 17m
Wed 9/3012:56 pm -
Nonstop1h 24m
Deal found 8/9![American Airlines logo]()
$249
This Kiwi.com deal was found by Cheapflights users on 8/7. 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.
Thu 9/106:30 am -
1 stop12h 45m
Sun 9/208:00 pm -
1 stop28h 23m
Deal found 8/7![Frontier logo]()
$394
This Delta deal was found by Cheapflights users on 8/9. 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.
Fri 9/117:13 pm -
1 stop13h 09m
Tue 9/156:00 am -
2 stops12h 33m
Deal found 8/9![Delta logo]()
$455
This United Airlines deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/271:55 pm -
Nonstop1h 04m
Sun 8/303:55 pm -
Nonstop1h 16m
Deal found 8/6![United Airlines logo]()
$249
This United Airlines deal was found by Cheapflights users on 8/9. 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 9/121:55 pm -
Nonstop1h 04m
Tue 9/156:30 am -
Nonstop1h 13m
Deal found 8/9![United Airlines logo]()
$319
This United Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/281:55 pm -
Nonstop1h 04m
Sun 8/303:55 pm -
Nonstop1h 16m
Deal found 8/7![United Airlines logo]()
$319
This United Airlines deal was found by Cheapflights users on 8/7. 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 9/28:50 am -
Nonstop1h 14m
Sun 9/66:30 am -
Nonstop1h 13m
Deal found 8/7![United Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 8/9. 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.
Sat 9/129:59 am -
1 stop11h 31m
Tue 9/156:00 am -
1 stop12h 19m
Deal found 8/9![Delta logo]()
$505
This United Airlines deal was found by Cheapflights users on 8/8. 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.
Tue 9/1512:40 pm -
Nonstop1h 02m
Thu 9/174:04 pm -
Nonstop1h 16m
Deal found 8/8![United Airlines logo]()
$477
This Delta deal was found by Cheapflights users on 8/7. 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.
Sun 9/64:52 pm -
1 stop4h 37m
Sun 9/139:02 am -
1 stop4h 18m
Deal found 8/7![Delta logo]()
$989
This Delta deal was found by Cheapflights users on 8/9. 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 9/109:59 am -
1 stop4h 08m
Sun 9/2012:00 pm -
1 stop6h 19m
Deal found 8/9![Delta logo]()
$1,163
This Delta deal was found by Cheapflights users on 8/5. 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.
Sat 9/199:59 am -
1 stop4h 08m
Sat 9/2612:00 pm -
1 stop5h 59m
Deal found 8/5![Delta logo]()
$1,163
This Delta deal was found by Cheapflights users on 8/9. 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 9/237:13 pm -
1 stop3h 48m
Wed 9/309:02 am -
1 stop4h 18m
Deal found 8/9![Delta logo]()
$1,163
This Delta deal was found by Cheapflights users on 8/7. 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.
Sat 9/199:59 am -
1 stop4h 08m
Sun 9/202:47 pm -
1 stop3h 32m
Deal found 8/7![Delta logo]()
$1,163
This Delta deal was found by Cheapflights users on 8/8. 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.
Sat 9/54:52 pm -
1 stop4h 37m
Sat 9/1212:00 pm -
1 stop4h 00m
Deal found 8/8![Delta logo]()
$1,163
This Delta deal was found by Cheapflights users on 8/7. 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.
Fri 8/287:25 pm -
1 stop3h 35m
Sun 8/3012:10 pm -
1 stop5h 51m
Deal found 8/7![Delta logo]()
$1,163
Last-minute flights from Chicago to MadisonDiscover last-minute flight deals from Chicago to Madison. Data last updated August 10, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Madison. Data last updated August 10, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 8/6. 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 8/78:10 am -
Nonstop1h 07m
Thu 9/109:40 am -
Nonstop1h 15m
Deal found 8/6![American Airlines logo]()
$330
This American Airlines deal was found by Cheapflights users on 8/10. 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 8/119:09 pm -
Nonstop1h 09m
Tue 8/187:47 am -
Nonstop1h 21m
Deal found 8/10![American Airlines logo]()
$340
This American Airlines deal was found by Cheapflights users on 8/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/158:19 am -
Nonstop1h 07m
Sat 8/226:53 pm -
Nonstop1h 37m
Deal found 8/8![American Airlines logo]()
$295
This American Airlines deal was found by Cheapflights users on 8/5. 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 8/189:09 pm -
Nonstop1h 09m
Sat 8/226:53 pm -
Nonstop1h 37m
Deal found 8/5![American Airlines logo]()
$294
This United Airlines deal was found by Cheapflights users on 8/5. 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.
Wed 8/191:55 pm -
Nonstop1h 04m
Sat 8/222:23 pm -
Nonstop1h 15m
Deal found 8/5![United Airlines logo]()
$279
This American Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2111:00 pm -
Nonstop1h 10m
Sun 8/309:48 am -
Nonstop1h 13m
Deal found 8/5![American Airlines logo]()
$265
This United Airlines deal was found by Cheapflights users on 8/5. 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.
Tue 8/255:52 pm -
Nonstop1h 04m
Wed 9/212:40 pm -
Nonstop1h 19m
Deal found 8/5![United Airlines logo]()
$316
This United Airlines deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/28:50 am -
Nonstop1h 14m
Sun 9/66:30 am -
Nonstop1h 13m
Deal found 8/6![United Airlines logo]()
$319
This American Airlines deal was found by Cheapflights users on 8/6. 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 9/38:10 am -
Nonstop1h 07m
Thu 9/103:25 pm -
Nonstop1h 16m
Deal found 8/6![American Airlines logo]()
$250
This Delta deal was found by Cheapflights users on 8/9. 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.
Fri 9/117:13 pm -
1 stop16h 07m
Tue 9/156:00 am -
1 stop12h 19m
Deal found 8/9![Delta logo]()
$450
This United Airlines deal was found by Cheapflights users on 8/7. 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.
Sat 9/1910:45 am -
Nonstop1h 18m
Sun 9/208:05 am -
Nonstop1h 13m
Deal found 8/7![United Airlines logo]()
$249
This Kiwi.com deal was found by Cheapflights users on 8/10. 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 9/227:11 am -
2 stops26h 42m
Tue 9/2912:15 pm -
1 stop10h 44m
Deal found 8/10![Multiple Airlines logo]()
$315
One-way flights from Chicago to MadisonSearch for one-way flight options from Chicago to Madison. Find affordable one-way fares based on user searches. Data last updated August 10, 2026.
Search for one-way flight options from Chicago to Madison. Find affordable one-way fares based on user searches. Data last updated August 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/5. 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.
Tue 9/297:11 am -
2 stops26h 42m
Deal found 8/5![Multiple Airlines logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 8/9. 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.
Fri 9/117:11 am -
2 stops26h 42m
Deal found 8/9![Multiple Airlines logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 8/8. 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 9/18:05 am -
2 stops25h 42m
Deal found 8/8![Multiple Airlines logo]()
$136
This Kiwi.com deal was found by Cheapflights users on 8/8. 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 9/88:05 am -
2 stops25h 48m
Deal found 8/8![Multiple Airlines logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 8/6. 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.
Fri 11/67:50 am -
2 stops26h 03m
Deal found 8/6![Multiple Airlines logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 8/8. 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 9/227:11 am -
2 stops26h 42m
Deal found 8/8![Multiple Airlines logo]()
$145
This American Airlines deal was found by Cheapflights users on 8/5. 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.
Mon 9/281:45 pm -
Nonstop1h 10m
Deal found 8/5![American Airlines logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 8/6. 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 10/139:20 am -
2 stops24h 33m
Deal found 8/6![Multiple Airlines logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 8/9. 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.
Wed 10/76:20 am -
2 stops35h 00m
Deal found 8/9![Multiple Airlines logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 8/8. 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.
Fri 9/116:25 am -
2 stops27h 28m
Deal found 8/8![Multiple Airlines logo]()
$187
This Kiwi.com deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2111:50 am -
2 stops21h 57m
Deal found 8/7![Multiple Airlines logo]()
$258
This Kiwi.com deal was found by Cheapflights users on 8/5. 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.
Thu 8/206:05 am -
2 stops13h 05m
Deal found 8/5![Frontier logo]()
$269
Find flight deals from Chicago to Madison
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Madison (MSN). 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 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $249 (United Airlines) |
One-way from | $107 (Kiwi.com) |
Popular in | June |
Cheapest in | December |
Average price | $470 |
Good round-trip deal | $470 or less |
Good one-way deal | $281 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Madison that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 10, 2026.
Use the filters below to find and compare flights from Chicago to Madison that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoMadison
ORD Chicago O'Hare Intl - MSN Madison Truax Field
ORDMSN
Chicago O'Hare Intl
Sat 9/19
10:45 am-12:03 pm
Nonstop1h 18m
Madison Truax Field
Sun 9/20
8:05 am-9:18 am
Nonstop1h 13m
$249
ChicagoMadison
ORD Chicago O'Hare Intl - MSN Madison Truax Field
ORDMSN
Chicago O'Hare Intl
Wed 9/23
11:00 pm-12:17 am
Nonstop1h 17m
Madison Truax Field
Wed 9/30
12:56 pm-2:20 pm
Nonstop1h 24m
$249
ChicagoMadison
ORD Chicago O'Hare Intl - MSN Madison Truax Field
ORDMSN
Chicago O'Hare Intl
Thu 8/27
1:55 pm-2:59 pm
Nonstop1h 04m
Madison Truax Field
Sun 8/30
3:55 pm-5:11 pm
Nonstop1h 16m
$249
Quickest round-trip
ChicagoMadison
ORD Chicago O'Hare Intl - MSN Madison Truax Field
ORDMSN
Chicago O'Hare Intl
Sat 9/12
1:55 pm-2:59 pm
Nonstop1h 04m
Madison Truax Field
Tue 9/15
6:30 am-7:43 am
Nonstop1h 13m
$319
ChicagoMadison
ORD Chicago O'Hare Intl - MSN Madison Truax Field
ORDMSN
Chicago O'Hare Intl
Fri 8/28
1:55 pm-2:59 pm
Nonstop1h 04m
Madison Truax Field
Sun 8/30
3:55 pm-5:11 pm
Nonstop1h 16m
$319
ChicagoMadison
ORD Chicago O'Hare Intl - MSN Madison Truax Field
ORDMSN
Chicago O'Hare Intl
Wed 9/2
8:50 am-10:04 am
Nonstop1h 14m
Madison Truax Field
Sun 9/6
6:30 am-7:43 am
Nonstop1h 13m
$319
ChicagoMadison
ORD Chicago O'Hare Intl - MSN Madison Truax Field
ORDMSN
Chicago O'Hare Intl
Thu 9/10
6:30 am-7:15 pm
1 stop12h 45m
Madison Truax Field
Sun 9/20
8:00 pm-12:23 am
1 stop28h 23m
$394
ChicagoMadison
MDW Chicago Midway - MSN Madison Truax Field
MDWMSN
Chicago Midway
Fri 9/11
7:13 pm-8:22 am
1 stop13h 09m
Madison Truax Field
Tue 9/15
6:00 am-6:33 pm
2 stops12h 33m
$455
ChicagoMadison
ORD Chicago O'Hare Intl - MSN Madison Truax Field
ORDMSN
Chicago O'Hare Intl
Tue 9/15
12:40 pm-1:42 pm
Nonstop1h 02m
Madison Truax Field
Thu 9/17
4:04 pm-5:20 pm
Nonstop1h 16m
$477
ChicagoMadison
MDW Chicago Midway - MSN Madison Truax Field
MDWMSN
Chicago Midway
Sat 9/12
9:59 am-9:30 pm
1 stop11h 31m
Madison Truax Field
Tue 9/15
6:00 am-6:19 pm
1 stop12h 19m
$505
Showing 1-10 of 34 resultsSorted by cheapest first
Compare providers for flights from Chicago to Madison
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 Chicago to Madison 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 Chicago-Madison flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Madison flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Madison flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Madison 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 Chicago-Madison 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 Chicago to Madison
Have a flexible travel schedule? Discover the best time to fly to Madison from Chicago with our price prediction graph.
CHI-MSN
ORD-MSN
MDW-MSN
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 Chicago to Madison
CHI-MSN
ORD-MSN
MDW-MSN
What is the cheapest month to book a flight from Chicago to Madison?
Currently, September is the cheapest month in which you can book a flight from Chicago to Madison (average of $239). Flying from Chicago to Madison in April is currently the most expensive (average of $539). 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 CHI to MSN?
Find hourly flight availability from Chicago to Madison. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 10, 2026.
A simple way to save on the total cost of your ticket is to fly from Chicago to Madison at noon. If you’re flexible enough to do this you can expect to save up to 18% on your trip compared to booking a flight in the afternoon.
Weekly flight availability from Chicago to Madison
Explore weekly flight availability from Chicago to Madison. 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 10, 2026.
The most flights from CHI to MSN are scheduled on a Saturday (44 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (20 on average).
How much does it cost to fly round-trip from Chicago to Madison?
Airfare is below average for this route at the moment.
Chicago to Madison flights typically cost between $470 and $492 in October.The cheapest round-trip price found within the last 5 days was $249 on United Airlines (Oct 16-Nov 1).
How often are flights from Chicago to Madison delayed?
About 19% of weekly flights between Chicago and Madison have experienced delays in the past year, with the average delay time being 116 minutes.
What is the most punctual flight time for Chicago to Madison flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving at night tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Saturday tends to have the lowest number of delays on this route, whereas Friday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to Madison flights?
Over the last year, United Airlines have had the lowest number of delays on this route, with just 19% of flights being delayed.
Reviews of airlines servicing Madison
Get insights into the airlines that provide service to Madison. 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 Madison. Reviews last updated August 10, 2026.
See what other customers who have flown with United Airlines from Chicago to Madison have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
7.4
Boarding
7.7
Food
6.7
Entertainment
7.1
Comfort
7.3
Crew
8.1
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Overall
7.4
Boarding
7.7
Food
6.7
Entertainment
7.1
Comfort
7.3
Crew
8.1
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Related info for your journey
Find useful and relevant information for your journey from Chicago to Madison. 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 Madison?
Book flights to Madison if you plan to visit one of these locationsSun Prairie
Middleton
Fitchburg
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Top airline flying from Chicago to Madison
Discover the top airline that operate flights from Chicago to Madison. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$239 | Average$467 | FlexibilityNo cancel fee | On-time69% |