How often are flights from Chicago to Madison delayed?

Historically, on average around 17% of flights between Chicago and Madison have experienced a delay on any given week. The average delay length over the past 12 months has been 114 minutes.

How many flights depart from Chicago to Madison on average per day?

As of December 2025, there are 33 flights per day flying from Chicago to Madison. The most common time of day flights depart is 6:00PM, with 48% of flights taking off in the evening.

Which airline has the best punctuality record on Chicago to Madison flights?

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 16% of their flights experiencing any sort of delay.

What is the most punctual flight time for Chicago to Madison flights?

Generally, flights departing in the morning tend to experience fewer delays. Flights at night have, in the past, seen delays more frequently in comparison.

How many flights depart from Chicago to Madison on average per week?

As of December 2025, there are 237 flights per week flying from Chicago to Madison. The most common day of the week flights depart is Thu, with 19% of flights taking off on this day.

What is the cheapest airline that flies from Chicago to Madison Truax Field?

American Airlines and Frontier are the most popular carriers operating from Chicago to Madison Truax Field

What day of the week experiences the fewest flight delays on this route?

Tuesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

What airlines fly to Madison?

United Airlines, Denver Air Connection and American Airlines are the top three most popular airlines that fly to Madison from Chicago according to our data. United Airlines is the first choice among our users, with 52% of people opting to fly with this airline when traveling to Madison. Keep in mind that there are 3 different airlines that fly to Madison on a routine basis, so you have a few additional options to choose from.

When did momondo last update prices for flights from Chicago to Madison Truax Field Airport?

Prices for flights from Chicago to Madison Truax Field Airport are refreshed on a daily basis.

How many operators does momondo search for flights from Chicago to Madison Truax Field Airport?

As of December 2025, there is 1 operator available to choose from for flights from Chicago to Madison Truax Field Airport.

How old do you have to be to fly from Chicago to Madison Truax Field Airport?

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Madison Truax Field Airport.

What documentation or ID do you need to fly to Madison Truax Field Airport?

The required travel and health documents for your Madison Truax Field Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Madison Truax Field Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$121 Cheap Flights from Chicago to Madison in 2025/26

Q: What is the typical price of a round-trip flight between Chicago and Madison?

Prices are currently low for flights on this route. Typical prices usually range from $189 to $209. The lowest price recently found on this route was $179.

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4:50 pm - 5:55 pm

ORD

MSN

1h 05mnonstop

8:10 pm - 9:30 pm

MSN

ORD

1h 20mnonstop

$179American Airlines

Wed, Dec 31 - Sat, Jan 3

8:12 am - 9:30 am

ORD

MSN

1h 18mnonstop

8:10 pm - 9:30 pm

MSN

ORD

1h 20mnonstop

$180American Airlines

Thu, Dec 25 - Sun, Dec 28

12:28 pm - 1:32 pm

ORD

MSN

1h 04mnonstop

6:00 am - 7:14 am

MSN

ORD

1h 14mnonstop

$194American Airlines

Wed, Dec 17 - Thu, Dec 25

8:00 am - 9:18 am

ORD

MSN

1h 18mnonstop

8:10 pm - 9:30 pm

MSN

ORD

1h 20mnonstop

$209American Airlines

Fri, Dec 19 - Tue, Dec 23

5:00 am - 10:08 am

ORD

MSN

5h 08m1 stop

8:10 pm - 9:30 pm

MSN

ORD

1h 20mnonstop

$219American Airlines

Thu, Dec 25 - Sun, Dec 28

10:50 am - 12:03 pm

ORD

MSN

1h 13mnonstop

6:30 am - 7:47 am

MSN

ORD

1h 17mnonstop

$239United Airlines

Wed, Jan 28 - Sat, Jan 31

12:55 pm - 2:01 pm

ORD

MSN

1h 06mnonstop

5:00 am - 6:21 am

MSN

ORD

1h 21mnonstop

$269United Airlines

Wed, Dec 17 - Sun, Dec 21

1:49 pm - 10:19 am

MDW

MSN

20h 30m1 stop

6:30 am - 6:32 pm

MSN

MDW

12h 02m1 stop

$355Delta

Wed, Jan 14 - Sun, Jan 18

9:32 am - 10:50 pm

MDW

MSN

13h 18m2 stops

6:30 am - 6:32 pm

MSN

MDW

12h 02m1 stop

$383Delta

Wed, Jan 14 - Sun, Jan 18

9:29 am - 8:45 pm

MDW

MSN

11h 16m1 stop

7:00 am - 5:26 pm

MSN

MDW

10h 26m1 stop

$576Delta

Thu, Dec 25 - Sun, Dec 28

American Airlines flights from Chicago to Madison

Our best American Airlines deals on Chicago to Madison flight tickets

American Airlines

Dec 31

ORD4:50 pmChicago O'Hare Intl

1h 05m

MSN5:55 pmMadison Truax Field

Jan 3

MSN8:10 pmMadison Truax Field

1h 20m

ORD9:30 pmChicago O'Hare Intl

$179

Find similar

American Airlines

Dec 25

ORD8:12 amChicago O'Hare Intl

1h 18m

MSN9:30 amMadison Truax Field

Dec 28

MSN8:10 pmMadison Truax Field

1h 20m

ORD9:30 pmChicago O'Hare Intl

$180

Find similar

American Airlines

Dec 17

ORD12:28 pmChicago O'Hare Intl

1h 04m

MSN1:32 pmMadison Truax Field

Dec 25

MSN6:00 amMadison Truax Field

1h 14m

ORD7:14 amChicago O'Hare Intl

$194

Find similar

United Airlines flights from Chicago to Madison

Our best United Airlines deals on Chicago to Madison flight tickets

United Airlines

Jan 28

ORD10:50 amChicago O'Hare Intl

1h 13m

MSN12:03 pmMadison Truax Field

Jan 31

MSN6:30 amMadison Truax Field

1h 17m

ORD7:47 amChicago O'Hare Intl

$239

Find similar

United Airlines

Dec 17

ORD12:55 pmChicago O'Hare Intl

1h 06m

MSN2:01 pmMadison Truax Field

Dec 21

MSN5:00 amMadison Truax Field

1h 21m

ORD6:21 amChicago O'Hare Intl

$269

Find similar

United Airlines

Jan 28

ORD7:00 amChicago O'Hare Intl

14h 20m

1 stop

MSN9:20 pmMadison Truax Field

Jan 31

MSN5:26 pmMadison Truax Field

1h 21m

ORD6:47 pmChicago O'Hare Intl

$335

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Wed 12/31

4:50 pm-5:55 pm

Nonstop1h 05m

Madison Truax Field

Sat 1/3

8:10 pm-9:30 pm

Nonstop1h 20m

$179

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Thu 12/25

8:12 am-9:30 am

Nonstop1h 18m

Madison Truax Field

Sun 12/28

8:10 pm-9:30 pm

Nonstop1h 20m

$180

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Wed 12/17

12:28 pm-1:32 pm

Nonstop1h 04m

Madison Truax Field

Thu 12/25

6:00 am-7:14 am

Nonstop1h 14m

$194

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Fri 12/19

8:00 am-9:18 am

Nonstop1h 18m

Madison Truax Field

Tue 12/23

8:10 pm-9:30 pm

Nonstop1h 20m

$209

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Thu 12/25

5:00 am-10:08 am

1 stop5h 08m

Madison Truax Field

Sun 12/28

8:10 pm-9:30 pm

Nonstop1h 20m

$219

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Wed 1/28

10:50 am-12:03 pm

Nonstop1h 13m

Madison Truax Field

Sat 1/31

6:30 am-7:47 am

Nonstop1h 17m

$239

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Wed 12/17

12:55 pm-2:01 pm

Nonstop1h 06m

Madison Truax Field

Sun 12/21

5:00 am-6:21 am

Nonstop1h 21m

$269

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Wed 1/14

1:49 pm-10:19 am

1 stop20h 30m

Madison Truax Field

Sun 1/18

6:30 am-6:32 pm

1 stop12h 02m

$355

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Wed 1/14

9:32 am-10:50 pm

2 stops13h 18m

Madison Truax Field

Sun 1/18

6:30 am-6:32 pm

1 stop12h 02m

$383

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Thu 12/25

9:29 am-8:45 pm

1 stop11h 16m

Madison Truax Field

Sun 12/28

7:00 am-5:26 pm

1 stop10h 26m

$576

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How to get the cheapest flight ticket from Chicago to Madison

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Delays

Other information

What is the typical price of a round-trip flight between Chicago and Madison?

What is the cheapest day to depart on your flight to Madison?

The cheapest day to depart from Chicago to Madison is on a Friday when prices can be found for as low as $239. Be sure to avoid booking your departure on a Monday as prices are generally higher than usual. According to our data, the average ticket price to Madison on Monday is $413.

What is the cheapest time of day to depart on your flight to Madison?

According to our data, the cheapest time of day to fly to Madison is in the afternoon. momondo users have found flights departing from Chicago to Madison in the afternoon for as low as $283. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In contrast, the most expensive time of day to depart to Madison is in the evening when prices are around $315.

What is the cheapest Chicago to Madison Truax Field flight route?

Fly from Chicago O'Hare Intl to Madison Truax Field for the best Chicago - Madison Truax Field flight prices

What cabin class options are available on Chicago to Madison Truax Field flights?

There are 3 cabin classes available to choose from on Chicago to Madison Truax Field flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Chicago to Madison flight prices changed over time?

As of December 2025, prices for Chicago to Madison flights are approximately 132% more expensive when compared to flights at the same time last year.

When to book flights from Chicago to Madison

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Madison according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Chicago to Madison (CHI to MSN) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Madison

Best Price Found	$203
Fastest flight time	1h 02m
Direct flights	Every day
Airports in Madison	1 airport

The best one-way flight to Madison from Chicago in the past 72 hours is $203. The best round-trip flight deal from Chicago to Madison found on momondo in the last 72 hours is $254.

The fastest flight from Chicago to Madison takes 1h 02m

Direct flights go from Chicago to Madison every day.

There is 1 airport near Madison: Madison Truax Field (MSN)

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How far is Chicago to Madison Truax Field by plane?
Chicago and Madison Truax Field are 122.4 mi apart from one another. Typically, this will take 1h 02m by plane in normal conditions.
When did momondo last update prices for flights from Chicago to Madison Truax Field Airport?
Prices for flights from Chicago to Madison Truax Field Airport are refreshed on a daily basis.
How many operators does momondo search for flights from Chicago to Madison Truax Field Airport?
As of December 2025, there is 1 operator available to choose from for flights from Chicago to Madison Truax Field Airport.
How old do you have to be to fly from Chicago to Madison Truax Field Airport?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Madison Truax Field Airport.
What documentation or ID do you need to fly to Madison Truax Field Airport?
The required travel and health documents for your Madison Truax Field Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Madison Truax Field Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Chicago to Madison?
Based on momondo bookings for flights between Chicago and Madison, the leading plane model is Canadair (Bombardier) Regional Jet 700, making up 19.28% of the total bookings. Other popular models include Embraer 175 (Enhanced Winglets) with 14.46%, Canadair (Bombardier) Regional Jet CRJ-550 with 13.25%, and Airbus A319 with 12.05%.
What is the most popular airline from Chicago to Madison?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Chicago to Madison is United Airlines (100% of total bookings).

Best airlines flying from Chicago to Madison

Compare and see reviews for airlines that fly from Chicago to Madison with momondo

Airline	Rating	Free Cancellation	Price
United Airlines	PriceFrom $199	Free Cancellation	Rating 7.4 9,062 reviews		Search United Airlines flights

United Airlines Flights From Chicago to Madison
Across 34 United Airlines flights from Chicago to Madison this week, the average price was $288, with the best United Airlines deals starting from $199 round-trip. 9,062 users have rated United Airlines on momondo, with an average score of 7.4/10.

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Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Madison?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Madison. momondo saves you time and could save you money on your trip.

Can I find flights from Chicago to Madison with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Chicago to Madison flights to just show those with flexible booking policies.

How can momondo help me find flights from Chicago to Madison?

momondo helps you find the best flight between Chicago and Madison by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Chicago to Madison right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago to Madison flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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Cheap flights from Chicago to Madison from $121

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Madison departing on 2/3. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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How to get the cheapest flight ticket from Chicago to Madison

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Chicago and Madison?

What is the cheapest day to depart on your flight to Madison?

The cheapest day to depart from Chicago to Madison is on a Friday when prices can be found for as low as $239. Be sure to avoid booking your departure on a Monday as prices are generally higher than usual. According to our data, the average ticket price to Madison on Monday is $413.

What is the cheapest time of day to depart on your flight to Madison?

What is the cheapest Chicago to Madison Truax Field flight route?

Fly from Chicago O'Hare Intl to Madison Truax Field for the best Chicago - Madison Truax Field flight prices

What cabin class options are available on Chicago to Madison Truax Field flights?

There are 3 cabin classes available to choose from on Chicago to Madison Truax Field flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Chicago to Madison flight prices changed over time?

As of December 2025, prices for Chicago to Madison flights are approximately 132% more expensive when compared to flights at the same time last year.

What is the cheapest airline that flies from Chicago to Madison Truax Field?

American Airlines and Frontier are the most popular carriers operating from Chicago to Madison Truax Field

What airlines fly to Madison?

How often are flights from Chicago to Madison delayed?

Historically, on average around 17% of flights between Chicago and Madison have experienced a delay on any given week. The average delay length over the past 12 months has been 114 minutes.

What is the most punctual flight time for Chicago to Madison flights?

Generally, flights departing in the morning tend to experience fewer delays. Flights at night have, in the past, seen delays more frequently in comparison.

What day of the week experiences the fewest flight delays on this route?

Tuesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

Which airline has the best punctuality record on Chicago to Madison flights?

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 16% of their flights experiencing any sort of delay.

How many flights depart from Chicago to Madison on average per day?

As of December 2025, there are 33 flights per day flying from Chicago to Madison. The most common time of day flights depart is 6:00PM, with 48% of flights taking off in the evening.

How many flights depart from Chicago to Madison on average per week?

As of December 2025, there are 237 flights per week flying from Chicago to Madison. The most common day of the week flights depart is Thu, with 19% of flights taking off on this day.

When to book flights from Chicago to Madison

Cheap Chicago to Madison (CHI to MSN) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Madison

Best Price Found

Fastest flight time

Direct flights

Airports in Madison

How far is Chicago to Madison Truax Field by plane?

When did momondo last update prices for flights from Chicago to Madison Truax Field Airport?

How many operators does momondo search for flights from Chicago to Madison Truax Field Airport?

How old do you have to be to fly from Chicago to Madison Truax Field Airport?

What documentation or ID do you need to fly to Madison Truax Field Airport?

What is the most popular plane model from Chicago to Madison?

What is the most popular airline from Chicago to Madison?

Best airlines flying from Chicago to Madison

Compare and see reviews for airlines that fly from Chicago to Madison with momondo

United Airlines Flights From Chicago to Madison

Traveling to a place near Madison?

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Madison?

Can I find flights from Chicago to Madison with flexible booking policies on momondo?

How can momondo help me find flights from Chicago to Madison?

I’m not ready to book a flight from Chicago to Madison right now. Can momondo alert me if prices change?

An easier way to manage your Madison trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

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