$156+ Cheap flights from Chicago (CHI) to Madison (MSN)
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 1/6. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MSN
Nov 8 — Nov 151
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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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 Chicago to Madison
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Best
Last-minute
One-way
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 October 9, 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 October 9, 2026.
This deal was found by Cheapflights users on 10/5. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/212:00 pm -
Nonstop1h 04m
Wed 10/283:00 pm -
Nonstop1h 19m
Deal found 10/5![United Airlines logo]()
$288
This United Airlines deal was found by Cheapflights users on 10/7. 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.
Thu 10/2910:05 pm -
Nonstop1h 02m
Sun 11/16:25 am -
Nonstop1h 19m
Deal found 10/7![United Airlines logo]()
$289
This American Airlines deal was found by Cheapflights users on 10/8. 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.
Sun 11/229:05 am -
Nonstop1h 19m
Sun 11/295:01 am -
Nonstop1h 29m
Deal found 10/8![American Airlines logo]()
$290
This United Airlines deal was found by Cheapflights users on 10/6. 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.
Sat 10/247:52 pm -
Nonstop1h 08m
Sat 10/313:49 pm -
Nonstop1h 16m
Deal found 10/6![United Airlines logo]()
$304
This American Airlines deal was found by Cheapflights users on 10/8. 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.
Fri 10/166:59 am -
Nonstop1h 12m
Sun 11/17:19 am -
Nonstop1h 31m
Deal found 10/8![American Airlines logo]()
$319
This United Airlines deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” 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 10/172:00 pm -
Nonstop1h 04m
Sun 10/186:35 pm -
Nonstop1h 20m
Deal found 10/4![United Airlines logo]()
$334
This Kiwi.com deal was found by Cheapflights users on 10/6. 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 11/36:30 am -
2 stops27h 28m
Tue 11/1010:30 am -
1 stop30h 37m
Deal found 10/6![Multiple Airlines logo]()
$371
This United Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/115:54 pm -
Nonstop1h 13m
Sat 11/148:15 am -
Nonstop1h 16m
Deal found 10/8![United Airlines logo]()
$379
This American Airlines deal was found by Cheapflights users on 10/6. 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.
Tue 10/610:00 pm -
Nonstop1h 12m
Tue 10/137:04 pm -
Nonstop1h 25m
Deal found 10/6![American Airlines logo]()
$380
This American Airlines deal was found by Cheapflights users on 10/6. 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.
Tue 10/135:00 am -
1 stop5h 37m
Tue 10/207:04 pm -
Nonstop1h 25m
Deal found 10/6![American Airlines logo]()
$404
This American Airlines deal was found by Cheapflights users on 10/5. 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.
Wed 10/216:59 am -
Nonstop1h 12m
Sun 10/257:05 pm -
Nonstop1h 25m
Deal found 10/5![American Airlines logo]()
$426
This American Airlines deal was found by Cheapflights users on 10/5. 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.
Wed 10/711:00 pm -
Nonstop1h 12m
Sun 10/116:10 am -
Nonstop1h 14m
Deal found 10/5![American Airlines logo]()
$430
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 October 9, 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 October 9, 2026.
This United Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/181:55 pm -
Nonstop1h 09m
Sun 12/205:00 am -
Nonstop1h 23m
Deal found 10/8![United Airlines logo]()
$289
This American Airlines deal was found by Cheapflights users on 10/5. 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 10/166:59 am -
Nonstop1h 12m
Sun 11/17:19 am -
Nonstop1h 31m
Deal found 10/5![American Airlines logo]()
$319
This United Airlines deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” 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 10/172:00 pm -
Nonstop1h 04m
Sun 10/186:35 pm -
Nonstop1h 20m
Deal found 10/4![United Airlines logo]()
$334
This American Airlines deal was found by Cheapflights users on 10/6. 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.
Tue 10/1311:00 pm -
Nonstop1h 12m
Tue 10/203:28 pm -
Nonstop1h 16m
Deal found 10/6![American Airlines logo]()
$334
This United Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/115:54 pm -
Nonstop1h 13m
Sat 11/148:15 am -
Nonstop1h 16m
Deal found 10/8![United Airlines logo]()
$379
This United Airlines deal was found by Cheapflights users on 10/6. 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 11/48:45 am -
Nonstop1h 16m
Wed 11/412:30 pm -
Nonstop1h 19m
Deal found 10/6![United Airlines logo]()
$512
This United Airlines deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2612:29 pm -
Nonstop1h 12m
Mon 10/263:49 pm -
Nonstop1h 16m
Deal found 10/4![United Airlines logo]()
$512
This United Airlines deal was found by Cheapflights users on 10/7. 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.
Thu 10/299:47 pm -
1 stop15h 38m
Sun 11/15:00 am -
Nonstop1h 20m
Deal found 10/7![United Airlines logo]()
$538
Last-minute flights from Chicago to MadisonDiscover last-minute flight deals from Chicago to Madison. Data last updated October 9, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Madison. Data last updated October 9, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 10/5. 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 10/102:00 pm -
Nonstop1h 04m
Sun 10/116:49 am -
Nonstop1h 11m
Deal found 10/5![United Airlines logo]()
$430
This American Airlines deal was found by Cheapflights users on 10/6. 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.
Tue 10/135:00 am -
1 stop5h 37m
Tue 10/207:04 pm -
Nonstop1h 25m
Deal found 10/6![American Airlines logo]()
$404
This American Airlines deal was found by Cheapflights users on 10/8. 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.
Fri 10/166:59 am -
Nonstop1h 12m
Sun 11/17:19 am -
Nonstop1h 31m
Deal found 10/8![American Airlines logo]()
$319
This United Airlines deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” 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 10/172:00 pm -
Nonstop1h 04m
Sun 10/186:35 pm -
Nonstop1h 20m
Deal found 10/4![United Airlines logo]()
$334
This deal was found by Cheapflights users on 10/5. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/212:00 pm -
Nonstop1h 04m
Wed 10/283:00 pm -
Nonstop1h 19m
Deal found 10/5![United Airlines logo]()
$288
This American Airlines deal was found by Cheapflights users on 10/5. 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.
Wed 10/216:59 am -
Nonstop1h 12m
Sun 10/257:05 pm -
Nonstop1h 25m
Deal found 10/5![American Airlines logo]()
$426
This United Airlines deal was found by Cheapflights users on 10/6. 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.
Sat 10/247:52 pm -
Nonstop1h 08m
Sat 10/313:49 pm -
Nonstop1h 16m
Deal found 10/6![United Airlines logo]()
$304
This American Airlines deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2610:00 pm -
Nonstop1h 12m
Sat 10/317:14 am -
1 stop7h 06m
Deal found 10/4![American Airlines logo]()
$478
This United Airlines deal was found by Cheapflights users on 10/7. 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.
Thu 10/2910:05 pm -
Nonstop1h 02m
Sun 11/16:25 am -
Nonstop1h 19m
Deal found 10/7![United Airlines logo]()
$289
This Kiwi.com deal was found by Cheapflights users on 10/6. 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 11/36:30 am -
2 stops27h 28m
Tue 11/1010:30 am -
1 stop30h 37m
Deal found 10/6![Multiple Airlines logo]()
$371
This United Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/115:54 pm -
Nonstop1h 13m
Sat 11/148:15 am -
Nonstop1h 16m
Deal found 10/8![United Airlines logo]()
$379
This American Airlines deal was found by Cheapflights users on 10/8. 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.
Sun 11/229:05 am -
Nonstop1h 19m
Sun 11/295:01 am -
Nonstop1h 29m
Deal found 10/8![American Airlines logo]()
$290
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 October 9, 2026.
Search for one-way flight options from Chicago to Madison. Find affordable one-way fares based on user searches. Data last updated October 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/65:16 pm -
1 stop24h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Multiple Airlines logo]()
$156
This Kiwi.com deal was found by Cheapflights users on 10/7. 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.
Mon 12/710:37 pm -
2 stops35h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Multiple Airlines logo]()
$159
This Kiwi.com deal was found by Cheapflights users on 10/7. 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.
Tue 1/510:18 am -
1 stop23h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Multiple Airlines logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 10/8. 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.
Mon 11/97:50 pm -
2 stops38h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Multiple Airlines logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 10/8. 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.
Thu 11/51:04 pm -
3 stops44h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Multiple Airlines logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 10/6. 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 11/36:30 am -
2 stops27h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Multiple Airlines logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 10/7. 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 11/67:55 am -
2 stops26h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Multiple Airlines logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 10/7. 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 1/75:32 pm -
2 stops40h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Multiple Airlines logo]()
$177
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 October 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $288 |
One-way from | $156 (Kiwi.com) |
Popular in | June |
Cheapest in | December |
Average price | $289 |
Good round-trip deal | $429 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 7,457,451 searches. Data last updated October 9, 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
Wed 12/2
8:15 am-5:30 pm
2 stops33h 15m
Madison Truax Field
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$184
ChicagoMadison
ORD Chicago O'Hare Intl - MSN Madison Truax Field
ORDMSN
Chicago O'Hare Intl
Thu 12/3
10:37 pm-9:58 am
3 stops35h 21m
Madison Truax Field
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$202
ChicagoMadison
ORD Chicago O'Hare Intl - MSN Madison Truax Field
ORDMSN
Chicago O'Hare Intl
Tue 12/1
8:15 am-9:58 am
2 stops25h 43m
Madison Truax Field
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$204
ChicagoMadison
ORD Chicago O'Hare Intl - MSN Madison Truax Field
ORDMSN
Chicago O'Hare Intl
Fri 12/4
8:00 am-9:58 am
1 stop25h 58m
Madison Truax Field
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$217
ChicagoMadison
ORD Chicago O'Hare Intl - MSN Madison Truax Field
ORDMSN
Chicago O'Hare Intl
Tue 1/5
12:55 pm-2:11 pm
Nonstop1h 16m
Madison Truax Field
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$259
Quickest round-trip
ChicagoMadison
ORD Chicago O'Hare Intl - MSN Madison Truax Field
ORDMSN
Chicago O'Hare Intl
Thu 11/5
10:05 pm-11:07 pm
Nonstop1h 02m
Madison Truax Field
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$259
ChicagoMadison
ORD Chicago O'Hare Intl - MSN Madison Truax Field
ORDMSN
Chicago O'Hare Intl
Mon 11/9
10:05 pm-11:07 pm
Nonstop1h 02m
Madison Truax Field
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$259
ChicagoMadison
ORD Chicago O'Hare Intl - MSN Madison Truax Field
ORDMSN
Chicago O'Hare Intl
Fri 10/23
9:30 pm-10:35 pm
Nonstop1h 05m
Madison Truax Field
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$264
ChicagoMadison
ORD Chicago O'Hare Intl - MSN Madison Truax Field
ORDMSN
Chicago O'Hare Intl
Tue 12/8
9:59 am-7:16 pm
1 stop9h 17m
Madison Truax Field
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$277
ChicagoMadison
ORD Chicago O'Hare Intl - MSN Madison Truax Field
ORDMSN
Chicago O'Hare Intl
Fri 11/6
3:30 pm-10:13 am
1 stop18h 43m
Madison Truax Field
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$282
Showing 1-10 of 19 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 October.
| 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
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
What is the cheapest month to book a flight from Chicago to Madison?
Currently, December is the cheapest month in which you can book a flight from Chicago to Madison (average of $288). Flying from Chicago to Madison in September is currently the most expensive (average of $562). 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 October 9, 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 24% on your trip compared to booking a flight in the morning.
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 October 9, 2026.
The most flights from CHI to MSN are scheduled on a Wednesday (49 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (26 on average).
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, American 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 October 9, 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.
Entertainment
7.1
Food
6.7
Comfort
7.3
Boarding
7.7
Crew
8.1
Overall
7.4
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Entertainment
7.1
Food
6.7
Comfort
7.3
Boarding
7.7
Crew
8.1
Overall
7.4
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 7,457,451 searches. Data last updated October 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$292 | Average$478 | FlexibilityNo cancel fee | On-time69% |