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$93+ Cheap flights from Madison (MSN) to Chicago (CHI)

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 10/17. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — CHI
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap flight deals from Madison to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Madison (MSN) to Chicago (CHI). 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 16, 2025.

Round-trip from

$179
(American Airlines)

One-way from

$93
(Kiwi.com)

Popular in

November

Cheapest in

June

Average price

$209

Good round-trip deal

$309 or less

Good one-way deal

$201 or less
From Madison Truax Field to Chicago (CHI)
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One-way flight from Madison Truax Field to Chicago (CHI)
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Highest demand for flights based on searches. 31% potential increase in price ($137 potential increase over avg. RT price).
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Cheapest flight prices on average. 14% potential price decrease ($38 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 Madison Truax Field to Chicago (CHI).
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Price to beat on a one-way flight from Madison Truax Field to Chicago (CHI).
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Find flight deals from Madison to Chicago

Cheapest flights from Madison to Chicago
Explore the most affordable flight options available from Madison to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2025.

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.
Fri 10/108:25 pmMSN - ORD
Nonstop1h 05mAmerican Airlines
Sun 10/128:59 amORD - MSN
Nonstop1h 16mAmerican Airlines
Deal found 9/14$179
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.
Wed 12/105:00 amMSN - ORD
Nonstop1h 09mAmerican Airlines
Sat 12/133:02 pmORD - MSN
Nonstop1h 07mAmerican Airlines
Deal found 9/15$182
This United Airlines deal was found by Cheapflights users on 9/16. 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 10/26:30 amMSN - ORD
Nonstop1h 07mUnited Airlines
Wed 10/88:52 amORD - MSN
Nonstop1h 03mUnited Airlines
Deal found 9/16$184
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/43:48 pmMSN - ORD
Nonstop1h 12mUnited Airlines
Sun 10/58:52 amORD - MSN
Nonstop1h 03mUnited Airlines
Deal found 9/15$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.
Thu 9/256:30 amMSN - ORD
Nonstop1h 07mUnited Airlines
Tue 10/72:02 pmORD - MSN
Nonstop1h 04mUnited Airlines
Deal found 9/14$194
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 9/236:41 pmMSN - ORD
Nonstop1h 11mAmerican Airlines
Thu 10/28:47 amORD - MSN
Nonstop1h 12mAmerican Airlines
Deal found 9/14$199
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.
Thu 10/98:25 pmMSN - ORD
Nonstop1h 05mAmerican Airlines
Thu 10/168:59 amORD - MSN
Nonstop1h 16mAmerican Airlines
Deal found 9/15$224
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.
Sat 9/205:00 amMSN - ORD
Nonstop1h 00mAmerican Airlines
Mon 10/208:59 amORD - MSN
Nonstop1h 16mAmerican Airlines
Deal found 9/14$225
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.
Wed 9/1712:19 pmMSN - ORD
Nonstop1h 11mUnited Airlines
Sun 9/212:02 pmORD - MSN
Nonstop1h 00mUnited Airlines
Deal found 9/14$240
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.
Fri 9/1910:16 amMSN - ORD
Nonstop1h 08mAmerican Airlines
Mon 10/2012:40 pmORD - MSN
Nonstop1h 04mAmerican Airlines
Deal found 9/14$244
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 9/266:30 amMSN - ORD
Nonstop1h 07mUnited Airlines
Sun 9/2812:50 pmORD - MSN
Nonstop1h 00mUnited Airlines
Deal found 9/14$249
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 10/128:25 pmMSN - ORD
Nonstop1h 05mAmerican Airlines
Sun 10/198:59 amORD - MSN
Nonstop1h 16mAmerican Airlines
Deal found 9/14$257

Cheapflights Fare Finder

 
Customize your flight search to find flights from Madison to Chicago 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 16, 2025.
Use the filters below to find and compare flights from Madison to Chicago that are best for you.

Fly from

Madison

Fly to

Chicago

Route

Depart

Return

Price

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sun 10/12

5:45 pm-6:55 pm

Nonstop1h 10m

Chicago O'Hare Intl

Sun 10/19

8:52 am-9:55 am

Nonstop1h 03m

$179

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Fri 10/10

8:25 pm-9:30 pm

Nonstop1h 05m

Chicago O'Hare Intl

Sun 10/12

8:59 am-10:15 am

Nonstop1h 16m

$179

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Wed 12/24

6:40 am-8:01 am

Nonstop1h 21m

Chicago O'Hare Intl

Thu 1/8

8:57 am-10:10 am

Nonstop1h 13m

$179

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sat 2/14

6:30 am-7:42 am

Nonstop1h 12m

Chicago O'Hare Intl

Sun 2/15

6:10 pm-7:08 pm

Nonstop0h 58m

$179

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Thu 10/2

6:30 am-7:37 am

Nonstop1h 07m

Chicago O'Hare Intl

Wed 10/8

8:52 am-9:55 am

Nonstop1h 03m

$184

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sat 10/4

3:48 pm-5:00 pm

Nonstop1h 12m

Chicago O'Hare Intl

Sun 10/5

8:52 am-9:55 am

Nonstop1h 03m

$189

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sat 12/27

8:15 am-9:36 am

Nonstop1h 21m

Chicago O'Hare Intl

Sat 1/3

5:55 pm-7:05 pm

Nonstop1h 10m

$189

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sun 3/15

2:25 pm-3:41 pm

Nonstop1h 16m

Chicago O'Hare Intl

Sun 3/29

7:50 pm-8:54 pm

Nonstop1h 04m

$190

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Mon 10/20

6:30 am-7:37 am

Nonstop1h 07m

Chicago O'Hare Intl

Sun 10/26

8:51 am-10:00 am

Nonstop1h 09m

$194

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Thu 10/9

8:25 pm-9:30 pm

Nonstop1h 05m

Chicago O'Hare Intl

Thu 10/16

8:59 am-10:15 am

Nonstop1h 16m

$224

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 27 results
1
2
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Best time to book a flight from Madison to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Madison 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 Madison to Chicago

What is the cheapest month to book a flight from Madison to Chicago?

Currently, August is the cheapest month in which you can book a flight from Madison to Chicago (average of $245). Flying from Madison to Chicago in March is currently the most expensive (average of $321). 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 MSN to CHI?

Find hourly flight availability from Madison to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 16, 2025.

A simple way to save on the total cost of your ticket is to fly from Madison to Chicago in the morning. If you’re flexible enough to do this you can expect to save up to 10% on your trip compared to booking a flight in the afternoon.

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

Use this chart to determine the cheapest time to fly round-trip from Madison to Chicago. Price data was last updated on October 20, 2024.

Travelers seeking maximum savings on their Madison to Chicago flight should consider departing on Thursday evenings when fares are most often at their lowest. Saturday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Madison to Chicago

Explore weekly flight availability from Madison to Chicago. 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 16, 2025.

The most flights from MSN to CHI are scheduled on a Monday (49 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (13 on average).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated September 16, 2025.
See what other customers who have flown with United Airlines and American Airlines from Madison to Chicago have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,924 reviews

Food

6.6

Comfort

7.3

Entertainment

7.1

Overall

7.4

Boarding

7.7

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
8,924 reviews
United Airlines
7.4
Good
8,924 reviews

Food

6.6

Comfort

7.3

Entertainment

7.1

Overall

7.4

Boarding

7.7

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,924 reviews

Food

6.6

Comfort

7.3

Entertainment

7.1

Overall

7.4

Boarding

7.7

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

Related info for your journey

Find useful and relevant information for your journey from Madison to Chicago. 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 from for flights from Madison to Chicago?

    For a flight from Madison to Chicago, you will be flying from Truax Field. Madison Truax Field (MSN) is just 5.4 mi from the center of the city. Truax Field is the only Madison airport and it handles 35 outbound flights to Chicago per day. 2 airlines have flights to Chicago from Madison Truax Field on a regular basis.

  • How long is the flight from Madison to Chicago?

    There are many flights that can get you from Madison to Chicago in 1h 05m. Fly via United Airlines, American Airlines, or Delta to get the fastest option. Airlines will cover a distance of 108 mi. This flight may include one or multiple stops.

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

    According to our current data, American Airlines ($184), and United Airlines ($219) offers the cheapest pricing from Madison to Chicago. American Airlines is priced at 39% lower than the current average price of a flight leaving 3 months from now.

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

    No one likes to see their flight delayed. When booking a flight from Madison to Chicago consider choosing Avianca (85%), Copa Airlines (84%) or Japan Airlines (77%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Madison to Chicago?

    Looking for the cheapest flight from Madison to Chicago? While on average our users pay $776, our data indicates the cheapest price to be $130. The most popular route (Madison Truax Field - Chicago O'Hare Intl), is priced around $179.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Madison to Chicago 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 Madison to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Madison to Chicago (average of $245). Flying from Madison to Chicago in March is currently the most expensive (average of $321). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Madison to Chicago

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Top 2 airlines flying from Madison to Chicago

Discover the top 2 airlines that operate flights from Madison to Chicago. 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 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$184Average$280FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$219Average$290FlexibilityNo cancel feeOn-time69%

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