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Madison

$129+ 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 10/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MSN
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
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 September 17, 2025.

Round-trip from

$179
(American Airlines)

One-way from

$129
(Kiwi.com)

Popular in

April

Cheapest in

December

Average price

$285

Good round-trip deal

$298 or less

Good one-way deal

$218 or less
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. 37% potential increase in price ($224 potential increase over avg. RT price).
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Cheapest flight prices on average. 12% potential price decrease ($40 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 17, 2025.

This American Airlines deal was found by Cheapflights users on 9/15. 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 10/1112:40 pmORD - MSN
Nonstop1h 04mAmerican Airlines
Sun 10/128:25 pmMSN - ORD
Nonstop1h 05mAmerican Airlines
Deal found 9/15$179
This American Airlines deal was found by Cheapflights users on 9/14. 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 9/288:47 amORD - MSN
Nonstop1h 12mAmerican Airlines
Sun 10/58:18 pmMSN - ORD
Nonstop1h 09mAmerican Airlines
Deal found 9/14$184
This American Airlines deal was found by Cheapflights users on 9/14. 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 9/303:47 pmORD - MSN
Nonstop1h 10mAmerican Airlines
Sat 10/46:24 pmMSN - ORD
Nonstop1h 16mAmerican Airlines
Deal found 9/14$189
This United Airlines deal was found by Cheapflights users on 9/14. 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 9/2210:35 amORD - MSN
Nonstop1h 09mUnited Airlines
Mon 9/295:20 amMSN - ORD
Nonstop1h 10mUnited Airlines
Deal found 9/14$199
This United Airlines deal was found by Cheapflights users on 9/14. 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 11/74:50 pmORD - MSN
Nonstop1h 00mUnited Airlines
Sun 11/96:30 amMSN - ORD
Nonstop1h 11mUnited Airlines
Deal found 9/14$204
This United Airlines deal was found by Cheapflights users on 9/14. 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 9/268:52 amORD - MSN
Nonstop1h 03mUnited Airlines
Sat 9/275:45 pmMSN - ORD
Nonstop1h 10mUnited Airlines
Deal found 9/14$209
This United Airlines deal was found by Cheapflights users on 9/17. 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 12/265:55 pmORD - MSN
Nonstop1h 10mUnited Airlines
Fri 1/28:15 amMSN - ORD
Nonstop1h 21mUnited Airlines
Deal found 9/17$221
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/98:59 amORD - MSN
Nonstop1h 16mAmerican Airlines
Sun 10/128:25 pmMSN - ORD
Nonstop1h 05mAmerican Airlines
Deal found 9/14$224
This American Airlines deal was found by Cheapflights users on 9/17. 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 10/1710:31 pmORD - MSN
Nonstop1h 05mAmerican Airlines
Mon 10/278:25 pmMSN - ORD
Nonstop1h 05mAmerican Airlines
Deal found 9/17$231
This Expedia deal was found by Cheapflights users on 9/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/146:15 pmORD - MSN
Nonstop1h 06mUnited Airlines
Sat 11/228:25 amMSN - ORD
Nonstop1h 11mUnited Airlines
Deal found 9/15$241
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 9/302:32 pmMDW - MSN
2 stops18h 36mMultiple Airlines
Sat 10/49:48 amMSN - MDW
1 stop26h 56mMultiple Airlines
Deal found 9/14$291
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/281:56 pmMDW - MSN
2 stops19h 12mMultiple Airlines
Thu 10/308:00 pmMSN - MDW
1 stop15h 30mMultiple Airlines
Deal found 9/17$361

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 September 17, 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

Sat 10/18

10:23 am-11:25 am

Nonstop1h 02m

Madison Truax Field

Mon 10/20

8:25 pm-9:30 pm

Nonstop1h 05m

$179

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Tue 10/14

9:25 pm-10:28 pm

Nonstop1h 03m

Madison Truax Field

Tue 10/21

6:30 am-7:37 am

Nonstop1h 07m

$179

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Mon 10/13

8:59 am-10:15 am

Nonstop1h 16m

Madison Truax Field

Mon 10/20

8:25 pm-9:30 pm

Nonstop1h 05m

$179

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Mon 9/22

5:05 pm-6:08 pm

Nonstop1h 03m

Madison Truax Field

Mon 9/29

8:18 pm-9:27 pm

Nonstop1h 09m

$199

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Fri 9/26

8:52 am-9:55 am

Nonstop1h 03m

Madison Truax Field

Sat 9/27

5:45 pm-6:55 pm

Nonstop1h 10m

$209

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Sat 10/11

6:36 pm-11:51 pm

1 stop5h 15m

Madison Truax Field

Sun 10/12

8:25 pm-9:30 pm

Nonstop1h 05m

$235

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Fri 10/10

10:35 am-11:45 am

Nonstop1h 10m

Madison Truax Field

Sun 10/12

6:30 am-7:37 am

Nonstop1h 07m

$241

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Fri 10/17

12:48 pm-9:08 am

2 stops20h 20m

Madison Truax Field

Mon 10/27

7:59 pm-12:12 am

1 stop28h 13m

$276

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Tue 9/30

5:46 pm-9:08 am

1 stop15h 22m

Madison Truax Field

Sat 10/4

9:48 am-7:10 am

1 stop21h 22m

$279

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Sat 9/20

9:20 pm-10:23 pm

Nonstop1h 03m

Madison Truax Field

Mon 9/22

6:30 am-7:37 am

Nonstop1h 07m

$290

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 34 results
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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 March is currently the most expensive (average of $422). 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 September 17, 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 22% on your trip compared to booking a flight in the evening.

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 Friday mornings when fares are most often at their lowest. Sunday 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 September 17, 2025.

The most flights from CHI to MSN are scheduled on a Monday (47 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (23 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 September 17, 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
8,926 reviews

Crew

8.1

Food

6.6

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Julia,Sep 2025

BUF - DEN

The staff were amazing, from check in to boarding and on the flight. The range of entertainment options were really good as well.
United Airlines
7.4
Good
8,926 reviews
United Airlines
7.4
Good
8,926 reviews

Crew

8.1

Food

6.6

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Julia,Sep 2025

BUF - DEN

The staff were amazing, from check in to boarding and on the flight. The range of entertainment options were really good as well.

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 38 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 02m. 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 46% 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 (83%), Copa Airlines (81%) or Alaska Airlines (79%) 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 $312 for a flight from Chicago to Madison. The cheapest flight overall is $203 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 March is currently the most expensive (average of $422). 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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$199Average$283FlexibilityNo cancel feeOn-time69%

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