HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Madison

$114+ 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 1/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MSN
dic. 20 — dic. 271
sáb. 12/20
sáb. 12/27
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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

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 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 noviembre 20, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$179
(American Airlines)

One-way from

$114
(Kiwi.com)

Popular in

April

Cheapest in

December

Average price

$413

Good round-trip deal

$319 or less

Good one-way deal

$284 or less
Provider with most accurate pricing for Chicago (CHI)-Madison Truax Field flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Madison Truax Field flights.
Search Deals
From Chicago (CHI) to Madison Truax Field
Search Deals
One-way flight from Chicago (CHI) to Madison Truax Field
Search Deals
Highest demand for flights based on searches. 35% potential increase in price ($213 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 12% potential price decrease ($43 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Madison Truax Field.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Madison Truax Field.
Search Deals

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 noviembre 20, 2025.

This United Airlines deal was found by Cheapflights users on 11/18. 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.
jue. 12/1110:35 amORD - MSN
Nonstop1h 09mUnited Airlines
dom. 12/142:48 pmMSN - ORD
Nonstop1h 15mUnited Airlines
Deal found 11/18$179
This United Airlines deal was found by Cheapflights users on 11/18. 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.
mié. 12/1712:55 pmORD - MSN
Nonstop1h 06mUnited Airlines
mié. 12/245:00 amMSN - ORD
Nonstop1h 21mUnited Airlines
Deal found 11/18$190
This American Airlines deal was found by Cheapflights users on 11/18. 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.
mié. 12/33:02 pmORD - MSN
Nonstop1h 07mAmerican Airlines
dom. 12/75:00 amMSN - ORD
Nonstop1h 11mAmerican Airlines
Deal found 11/18$209
This American Airlines deal was found by Cheapflights users on 11/18. 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.
mié. 12/105:15 pmORD - MSN
Nonstop1h 02mAmerican Airlines
sáb. 12/134:39 pmMSN - ORD
Nonstop1h 18mAmerican Airlines
Deal found 11/18$239
This United Airlines deal was found by Cheapflights users on 11/19. 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.
jue. 12/412:55 pmORD - MSN
Nonstop0h 56mUnited Airlines
lun. 12/86:30 amMSN - ORD
Nonstop1h 11mUnited Airlines
Deal found 11/19$269
This United Airlines deal was found by Cheapflights users on 11/19. 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.
lun. 12/2910:35 amORD - MSN
Nonstop1h 13mUnited Airlines
lun. 12/295:26 pmMSN - ORD
Nonstop1h 21mUnited Airlines
Deal found 11/19$294
This American Airlines deal was found by Cheapflights users on 11/18. 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.
mié. 12/1712:28 pmORD - MSN
Nonstop1h 04mAmerican Airlines
mié. 12/246:00 amMSN - ORD
Nonstop1h 14mAmerican Airlines
Deal found 11/18$305
This United Airlines deal was found by Cheapflights users on 11/18. 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.
sáb. 11/226:35 pmORD - MSN
Nonstop1h 06mUnited Airlines
lun. 11/243:58 pmMSN - ORD
Nonstop1h 11mUnited Airlines
Deal found 11/18$320
This Kiwi.com deal was found by Cheapflights users on 11/18. 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.
mié. 12/312:29 pmORD - MSN
1 stop22h 42mMultiple Airlines
dom. 12/72:40 pmMSN - ORD
1 stop24h 43mMultiple Airlines
Deal found 11/18$389
This Delta deal was found by Cheapflights users on 11/19. 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.
mié. 12/101:50 pmMDW - MSN
1 stop9h 07mDelta
sáb. 12/136:00 amMSN - MDW
1 stop7h 10mDelta
Deal found 11/19$494
This KAYAK deal was found by Cheapflights users on 11/18. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/29:34 amMDW - MSN
1 stop10h 56mDelta
jue. 12/49:40 amMSN - MDW
1 stop8h 20mDelta
Deal found 11/18$995

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 noviembre 20, 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

jue. 2/12

8:06 am-9:10 am

Nonstop1h 04m

Madison Truax Field

sáb. 2/21

7:42 pm-9:15 pm

Nonstop1h 33m

$179

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

jue. 12/11

10:35 am-11:44 am

Nonstop1h 09m

Madison Truax Field

dom. 12/14

2:48 pm-4:03 pm

Nonstop1h 15m

$179

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

jue. 12/11

8:15 am-9:19 am

Nonstop1h 04m

Madison Truax Field

dom. 12/14

10:21 am-11:32 am

Nonstop1h 11m

$179

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

sáb. 1/3

6:25 pm-7:40 pm

Nonstop1h 15m

Madison Truax Field

sáb. 1/10

11:29 am-12:40 pm

Nonstop1h 11m

$180

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

mié. 12/17

12:55 pm-2:01 pm

Nonstop1h 06m

Madison Truax Field

mié. 12/24

5:00 am-6:21 am

Nonstop1h 21m

$190

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

jue. 12/4

12:04 pm-1:09 pm

Nonstop1h 05m

Madison Truax Field

dom. 12/7

5:00 am-6:11 am

Nonstop1h 11m

$209

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

mié. 12/3

3:02 pm-4:09 pm

Nonstop1h 07m

Madison Truax Field

dom. 12/7

5:00 am-6:11 am

Nonstop1h 11m

$209

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

mié. 11/26

8:22 am-9:24 am

Nonstop1h 02m

Madison Truax Field

dom. 11/30

8:12 pm-9:30 pm

Nonstop1h 18m

$239

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

mié. 12/10

12:28 pm-1:32 pm

Nonstop1h 04m

Madison Truax Field

sáb. 12/13

1:56 pm-3:11 pm

Nonstop1h 15m

$239

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

jue. 12/4

12:55 pm-1:51 pm

Nonstop0h 56m

Madison Truax Field

lun. 12/8

6:30 am-7:41 am

Nonstop1h 11m

$269

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/17

Showing 1-10 of 22 results
1
2
3

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 November.
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 noviembre 20, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago to Madison in the afternoon. If you’re flexible enough to do this you can expect to save up to 23% on your trip compared to booking a flight in the 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.

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 noviembre 20, 2025.

The most flights from CHI to MSN are scheduled on a Thursday (44 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (25 on average).

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 noviembre 20, 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
9,029 reviews

Food

6.6

Comfort

7.3

Entertainment

7.1

Boarding

7.7

Overall

7.4

Crew

8.1

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
9,029 reviews
United Airlines
7.4
Good
9,029 reviews

Food

6.6

Comfort

7.3

Entertainment

7.1

Boarding

7.7

Overall

7.4

Crew

8.1

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 35 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 1h 04m. Fly via American Airlines or United 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 Republic Airways (93%), ANA (82%) or Envoy Air (78%) 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 $360 for a flight from Chicago to Madison. The cheapest flight overall is $249 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Madison

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Minneapolis flights
Midway to Minneapolis flights
St. Louis to O'Hare Intl flights
St. Louis to Minneapolis flights
O'Hare Intl to Duluth flights
St. Louis to Madison flights
Moline to O'Hare Intl flights
O'Hare Intl to Madison flights
Decatur to O'Hare Intl flights
O'Hare Intl to Appleton flights
O'Hare Intl to Green Bay flights
St. Louis to Milwaukee flights
St. Louis to Green Bay flights
Moline to Minneapolis flights
O'Hare Intl to Milwaukee flights
Evansville to O'Hare Intl flights
Midway to Duluth flights
Peoria to O'Hare Intl flights
Springfield to O'Hare Intl flights
St. Louis to Wausau flights
Bloomington to Minneapolis flights
Peoria to Minneapolis flights
O'Hare Intl to Eau Claire flights
Midway to Milwaukee flights
St. Louis to Duluth flights
Midway to Green Bay flights
Quincy to O'Hare Intl flights
Burlington to O'Hare Intl flights
Dubuque to O'Hare Intl flights
O'Hare Intl to Wausau flights
Midway to Madison flights
Evansville to Minneapolis flights
Midway to Wausau flights
Bloomington to O'Hare Intl flights
Champaign to O'Hare Intl flights
Dubuque to Minneapolis flights
O'Hare Intl to La Crosse flights
O'Hare Intl to Escanaba flights
Paducah to O'Hare Intl flights
Springfield to Minneapolis flights
Champaign to Minneapolis flights
Bloomington to Madison flights
St. Louis to Escanaba flights
Moline to Madison flights
Springfield to Madison flights
O'Hare Intl to Rhinelander flights
O'Hare Intl to Ironwood flights
St. Louis to Rhinelander flights
Midway to Rhinelander flights
Midway to La Crosse flights

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 noviembre 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$199Average$288FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.