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$149+ 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 5/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MSN
Apr 2 — Apr 91
Wed 4/2
Wed 4/9
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 March 28, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$179
(United Airlines)

One-way from

$149
(American Airlines)

Popular in

March

Cheapest in

August

Average price

$455

Good round-trip deal

$262 or less

Good one-way deal

$185 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. 19% potential increase in price ($69 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in March 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Madison Truax Field.
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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 March 28, 2025.

This United Airlines deal was found by Cheapflights users on 3/27. 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.
Sun 5/118:20 pmORD - MSN
Nonstop1h 08mUnited Airlines
Sun 5/186:30 amMSN - ORD
Nonstop1h 03mUnited Airlines
Deal found 3/27$179
This American Airlines deal was found by Cheapflights users on 3/27. 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.
Thu 6/198:16 amORD - MSN
Nonstop1h 04mAmerican Airlines
Sun 6/221:27 pmMSN - ORD
Nonstop1h 02mAmerican Airlines
Deal found 3/27$226
This Mytrip deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/211:53 amORD - MSN
1 stop22h 08mMultiple Airlines
Wed 5/75:05 pmMSN - ORD
1 stop26h 58mMultiple Airlines
Deal found 3/26$593
This KAYAK deal was found by Cheapflights users on 3/27. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/710:25 amORD - MSN
2 stops12h 35mDelta
Wed 4/96:20 pmMSN - ORD
1 stop14h 52mDelta
Deal found 3/27$1,070

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 March 28, 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

Sun 5/11

8:20 pm-9:28 pm

Nonstop1h 08m

Madison Truax Field

Sun 5/18

6:30 am-7:33 am

Nonstop1h 03m

$179

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Thu 6/19

8:16 am-9:20 am

Nonstop1h 04m

Madison Truax Field

Sun 6/22

1:27 pm-2:29 pm

Nonstop1h 02m

$226

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Fri 5/2

11:53 am-10:01 am

1 stop22h 08m

Madison Truax Field

Wed 5/7

5:05 pm-8:03 pm

1 stop26h 58m

$593

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Mon 4/7

10:25 am-11:00 pm

2 stops12h 35m

Madison Truax Field

Wed 4/9

6:20 pm-9:12 am

1 stop14h 52m

$1,070

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Sun 5/11

10:19 pm-11:26 pm

Nonstop1h 07m

$149

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Sun 5/11

7:10 am-9:06 pm

1 stop13h 56m

$272

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Tue 5/6

9:30 am-10:01 am

1 stop24h 31m

$291

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Mon 4/7

5:08 pm-11:00 pm

2 stops5h 52m

$561

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/27

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 March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice 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 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.
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, January is the cheapest month in which you can book a flight from Chicago to Madison (average of $338). Flying from Chicago to Madison in June is currently the most expensive (average of $423). 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 March 28, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago to Madison in the evening. If you’re flexible enough to do this you can expect to save up to 22% 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 June 16, 2024.

Travelers seeking maximum savings on their Chicago to Madison flight should consider departing on Tuesday at noon when fares are most often at their lowest. Tuesday mornings 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 March 28, 2025.

The most flights from CHI to MSN are scheduled on a Thursday (38 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 on average).

Rainfall in Madison by month

Plan your trip to Madison by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Madison ranges from 1.2 - 4.5 inches per month. June is typically the wettest month, when rainfall can reach 4.5 in. January is typically the driest time to visit Madison when rainfall is around 1.2 in.

Temperature in Madison by month

Plan your trip to Madison by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Madison, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 71.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 19.4 F).

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 March 28, 2025.
To help decide which airline to fly from Chicago to Madison, see what other customers have to say about Delta, United Airlines and American Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,896 reviews

Crew

8.5

Food

7.3

Entertainment

7.9

Overall

8.0

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,896 reviews
Delta
8.0
Very good
7,896 reviews

Crew

8.5

Food

7.3

Entertainment

7.9

Overall

8.0

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
United Airlines
7.4
Good
8,603 reviews
Delta
8.0
Very good
7,896 reviews

Crew

8.5

Food

7.3

Entertainment

7.9

Overall

8.0

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,896 reviews

Crew

8.5

Food

7.3

Entertainment

7.9

Overall

8.0

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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 16 inbound flights from Chicago per day from 2 airlines. Madison Truax Field is conveniently located just 5.4 mi from Madison’s city center.

  • What are the cheapest airlines flying from Chicago to Madison round-trip?

    Cheapflights users have booked flights from Chicago to Madison round-trip from $179. Other airlines that can offer you cheap pricing are American Airlines, from $226, and Delta, from $1,070. You may be able to fly from Chicago to Madison for 38% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Chicago to Madison one-way?

    $149 is the cheapest one-way deal found within the past few days, from American Airlines. You may also be able to find cheap deals on United Airlines and Delta, with prices starting from $272 and $561, respectively.

  • 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 Copa Airlines (85%), Emirates (85%) or Republic Airways (83%) 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 $284 for a flight from Chicago to Madison. The cheapest flight overall is $175 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, January is the cheapest month in which you can book a flight from Chicago to Madison (average of $338). Flying from Chicago to Madison in June is currently the most expensive (average of $423). 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Portage
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Top 2 airlines flying from Chicago to Madison

Discover the top 2 airlines 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 March 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$179Average$288FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$226Average$279FlexibilityNo cancel feeOn-time71%
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