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Madison

$124+ 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 1/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MSN
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Cheap 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 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$179
(American Airlines)

One-way from

$124
(American Airlines)

Popular in

April

Cheapest in

December

Average price

$315

Good one-way deal

$279 or less
Provider with most accurate pricing for Chicago (CHI)-Madison Truax Field flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Madison Truax Field flights.
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From Chicago (CHI) to Madison Truax Field
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One-way flight from Chicago (CHI) to Madison Truax Field
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Highest demand for flights based on searches. 36% potential increase in price ($217 potential increase over avg. RT price).
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Cheapest flight prices on average. 11% potential price decrease ($40 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Price to beat on a one-way flight from Chicago (CHI) to Madison Truax Field.
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Find flight deals from Chicago to Madison

Cheapest flights from Chicago to Madison
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 30, 2025.

This American Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2011:40 amORD - MSN
Nonstop1h 00mAmerican Airlines
Sun 11/238:12 pmMSN - ORD
Nonstop1h 18mAmerican Airlines
Deal found 10/29$179
This American Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/138:35 amORD - MSN
Nonstop1h 02mAmerican Airlines
Sat 12/208:10 pmMSN - ORD
Nonstop1h 20mAmerican Airlines
Deal found 10/29$180
This American Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/169:43 pmORD - MSN
Nonstop1h 06mAmerican Airlines
Mon 11/245:00 amMSN - ORD
Nonstop1h 15mAmerican Airlines
Deal found 10/28$194
This United Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/223:35 pmORD - MSN
Nonstop1h 10mUnited Airlines
Sun 12/2810:45 amMSN - ORD
Nonstop1h 20mUnited Airlines
Deal found 10/28$203
This United Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/44:50 pmORD - MSN
Nonstop1h 00mUnited Airlines
Sat 11/156:20 amMSN - ORD
Nonstop1h 11mUnited Airlines
Deal found 10/27$204
This American Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/128:15 amORD - MSN
Nonstop1h 04mAmerican Airlines
Fri 12/198:10 pmMSN - ORD
Nonstop1h 20mAmerican Airlines
Deal found 10/27$232
This American Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/38:15 amORD - MSN
Nonstop1h 03mAmerican Airlines
Fri 12/198:10 pmMSN - ORD
Nonstop1h 20mAmerican Airlines
Deal found 10/27$251
This United Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1312:57 pmORD - MSN
Nonstop1h 06mUnited Airlines
Mon 11/176:30 amMSN - ORD
Nonstop1h 11mUnited Airlines
Deal found 10/29$269
This American Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/298:50 amORD - MSN
Nonstop1h 16mAmerican Airlines
Wed 11/51:53 pmMSN - ORD
Nonstop1h 13mAmerican Airlines
Deal found 10/28$270
This American Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/311:17 pmORD - MSN
Nonstop1h 02mAmerican Airlines
Sun 11/29:48 amMSN - ORD
Nonstop1h 14mAmerican Airlines
Deal found 10/27$278
This American Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/286:35 pmORD - MSN
Nonstop1h 20mAmerican Airlines
Sat 11/111:16 amMSN - ORD
Nonstop1h 09mAmerican Airlines
Deal found 10/28$283
This Kiwi.com deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/612:30 pmMDW - MSN
1 stop6h 45mFrontier
Sun 11/98:00 pmMSN - MDW
2 stops26h 11mFrontier
Deal found 10/27$463

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 October 30, 2025.
Use the filters below to find and compare flights from Chicago to Madison that are best for you.

Fly from

Chicago

Fly to

Madison

Route

Depart

Return

Price

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Fri 12/5

1:55 pm-2:54 pm

Nonstop0h 59m

Madison Truax Field

Sun 12/7

6:30 am-7:41 am

Nonstop1h 11m

$179

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Thu 12/11

10:15 pm-11:21 pm

Nonstop1h 06m

Madison Truax Field

Mon 12/15

5:00 am-6:09 am

Nonstop1h 09m

$179

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Thu 11/20

11:40 am-12:40 pm

Nonstop1h 00m

Madison Truax Field

Sun 11/23

8:12 pm-9:30 pm

Nonstop1h 18m

$179

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Sat 11/29

6:35 pm-7:41 pm

Nonstop1h 06m

Madison Truax Field

Sat 12/6

3:55 pm-5:10 pm

Nonstop1h 15m

$179

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Tue 12/9

3:02 pm-4:09 pm

Nonstop1h 07m

Madison Truax Field

Sat 12/13

7:00 am-8:21 am

Nonstop1h 21m

$179

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Sat 12/13

8:35 am-9:37 am

Nonstop1h 02m

Madison Truax Field

Sat 12/20

8:10 pm-9:30 pm

Nonstop1h 20m

$180

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Fri 4/24

7:50 pm-8:54 pm

Nonstop1h 04m

Madison Truax Field

Sun 4/26

7:00 am-8:05 am

Nonstop1h 05m

$203

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Fri 12/12

8:15 am-9:19 am

Nonstop1h 04m

Madison Truax Field

Fri 12/19

8:10 pm-9:30 pm

Nonstop1h 20m

$232

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Sat 3/14

9:35 pm-10:38 pm

Nonstop1h 03m

Madison Truax Field

Tue 3/17

3:58 pm-5:10 pm

Nonstop1h 12m

$239

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Thu 11/13

12:57 pm-2:03 pm

Nonstop1h 06m

Madison Truax Field

Mon 11/17

6:30 am-7:41 am

Nonstop1h 11m

$269

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 31 results
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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.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Madison flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Madison flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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.
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

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 $178). Flying from Chicago to Madison in March is currently the most expensive (average of $384). 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 30, 2025.

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 33% on your trip compared to booking a flight in the morning.

What is the cheapest day to fly from Chicago to Madison?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Madison. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Madison flight should consider departing on Thursday at noon 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 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 30, 2025.
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.
United Airlines
7.4
Good
8,998 reviews

Overall

7.4

Boarding

7.7

Entertainment

7.1

Crew

8.1

Comfort

7.3

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
United Airlines
7.4
Good
8,998 reviews
United Airlines
7.4
Good
8,998 reviews

Overall

7.4

Boarding

7.7

Entertainment

7.1

Crew

8.1

Comfort

7.3

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000

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.

  • What airport do you fly into for flights to Madison from Chicago?

    Most people fly into Madison Truax Field (MSN) if they book a flight to Madison from Chicago. On average, Truax Field has 13 inbound flights from Chicago per day from 1 airline. Madison Truax Field is conveniently located just 5.4 mi from Madison’s city center.

  • How long is the flight from Chicago to Madison?

    There are many flights that can get you from Chicago to Madison in 59m. Fly via United Airlines or American Airlines to get the fastest option. The distance between Chicago and Madison is about 108 mi. All flights are typically nonstop.

  • What is the cheapest airline to fly from Chicago to Madison round-trip?

    Cheapflights users have booked flights from Chicago to Madison round-trip from $199. You may be able to fly from Chicago to Madison for 47% less than the average price by searching for this airline.

  • What are the most reliable airlines from Chicago to Madison?

    No one likes to see their flight delayed. When booking a flight from Chicago to Madison consider choosing GoJet (85%), ANA (81%) or Envoy Air (81%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Chicago to Madison?

    On average you can expect to pay $308 for a flight from Chicago to Madison. The cheapest flight overall is $279 while the most popular route, (Chicago O'Hare Intl - Madison Truax Field) is currently priced at $179.

  • Can I find deals for flights from Chicago to Madison that include hotel bookings?

    Yes. In addition to deals on Chicago to Madison flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Madison?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Madison.

  • Can I find deals for business class flights from Chicago to Madison?

    Yes. Cheapflights offers flight deals from Chicago to Madison by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • 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 $178). Flying from Chicago to Madison in March is currently the most expensive (average of $384). 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.

See more FAQs

Traveling to a place near Madison?

Book flights to Madison if you plan to visit one of these locations
Portage
Middleton
Baraboo
Fitchburg

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Alternative routes for Chicago to Madison

See prices for flight routes from nearby airports that may be better suited for you.
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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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$199Average$283FlexibilityNo cancel feeOn-time69%

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