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

As of January 2026, there are 34 flights per day flying from Chicago to Madison. The most common time of day flights depart is 3:00PM, with 37% of flights taking off in the afternoon.

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 115 minutes.

What airlines fly to Madison?

United Airlines, American Airlines and Denver Air Connection 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 45% 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.

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

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

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 17% 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.

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.

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

As of January 2026, there are 239 flights per week flying from Chicago to Madison. The most common day of the week flights depart is Sun, with 18% of flights taking off on this day.

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 January 2026, 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.

$134 Cheap Flights from Chicago to Madison in 2026

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10:24 pm - 11:26 pm

ORD

MSN

1h 02mnonstop

8:24 pm - 9:31 pm

MSN

ORD

1h 07mnonstop

$179American Airlines

Wed, Feb 18 - Wed, Feb 25

8:02 am - 9:08 am

ORD

MSN

1h 06mnonstop

9:44 am - 10:55 am

MSN

ORD

1h 11mnonstop

$180American Airlines

Tue, Mar 10 - Tue, Mar 17

8:05 am - 9:11 am

ORD

MSN

1h 06mnonstop

8:24 pm - 9:31 pm

MSN

ORD

1h 07mnonstop

$194American Airlines

Fri, Feb 13 - Mon, Feb 16

1:55 pm - 2:57 pm

ORD

MSN

1h 02mnonstop

2:48 pm - 4:00 pm

MSN

ORD

1h 12mnonstop

$239United Airlines

Fri, Feb 20 - Tue, Feb 24

5:22 pm - 10:43 am

ORD

MSN

17h 21m

1 stop

7:25 pm - 8:13 am

MSN

ORD

12h 48m

1 stop

$324Multiple Airlines

Tue, Feb 24 - Mon, Mar 2

6:00 pm - 6:58 pm

ORD

MSN

0h 58mnonstop

4:23 pm - 9:38 am

MSN

ORD

17h 15m

1 stop

$378United Airlines

Fri, Feb 20 - Tue, Feb 24

7:10 am - 8:48 pm

ORD

MSN

13h 38m

1 stop

2:48 pm - 4:00 pm

MSN

ORD

1h 12mnonstop

$386United Airlines

Wed, Feb 18 - Wed, Feb 25

2:43 pm - 9:08 am

ORD

MSN

18h 25m

1 stop

6:01 pm - 4:55 pm

MSN

ORD

22h 54m

1 stop

$402Multiple Airlines

Tue, Mar 10 - Tue, Mar 17

10:07 am - 9:08 am

ORD

MSN

23h 01m

1 stop

6:36 pm - 10:11 pm

MSN

ORD

27h 35m

2 stops

$410Multiple Airlines

Tue, Feb 3 - Sat, Feb 7

10:19 am - 9:08 am

ORD

MSN

22h 49m

1 stop

6:01 pm - 11:21 am

MSN

ORD

17h 20m

2 stops

$411Multiple Airlines

Tue, Mar 10 - Tue, Mar 17

American Airlines flights from Chicago to Madison

Our best American Airlines deals on Chicago to Madison flight tickets

American Airlines

Feb 18

ORD10:24 pmChicago O'Hare Intl

1h 02m

MSN11:26 pmMadison Truax Field

Feb 25

MSN8:24 pmMadison Truax Field

1h 07m

ORD9:31 pmChicago O'Hare Intl

$179

American Airlines

Mar 10

ORD8:02 amChicago O'Hare Intl

1h 06m

MSN9:08 amMadison Truax Field

Mar 17

MSN9:44 amMadison Truax Field

1h 11m

ORD10:55 amChicago O'Hare Intl

$180

American Airlines

Feb 13

ORD8:05 amChicago O'Hare Intl

1h 06m

MSN9:11 amMadison Truax Field

Feb 16

MSN8:24 pmMadison Truax Field

1h 07m

ORD9:31 pmChicago O'Hare Intl

$194

United Airlines flights from Chicago to Madison

Our best United Airlines deals on Chicago to Madison flight tickets

United Airlines

Feb 20

ORD8:04 pmChicago O'Hare Intl

1h 03m

MSN9:07 pmMadison Truax Field

Feb 24

MSN6:30 amMadison Truax Field

1h 12m

ORD7:42 amChicago O'Hare Intl

$239

United Airlines

Jan 29

ORD8:00 pmChicago O'Hare Intl

1h 05m

MSN9:05 pmMadison Truax Field

Jan 31

MSN12:32 pmMadison Truax Field

1h 21m

ORD1:53 pmChicago O'Hare Intl

$330

United Airlines

Feb 20

ORD6:00 pmChicago O'Hare Intl

0h 58m

MSN6:58 pmMadison Truax Field

Feb 24

MSN4:23 pmMadison Truax Field

17h 15m

1 stop

ORD9:38 amChicago O'Hare Intl

$378

Fly from

Fly to

Route

Depart

Return

Price

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Wed 2/18

10:24 pm-11:26 pm

Nonstop1h 02m

Madison Truax Field

Wed 2/25

8:24 pm-9:31 pm

Nonstop1h 07m

$179

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Tue 3/10

8:02 am-9:08 am

Nonstop1h 06m

Madison Truax Field

Tue 3/17

9:44 am-10:55 am

Nonstop1h 11m

$180

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Fri 2/13

8:05 am-9:11 am

Nonstop1h 06m

Madison Truax Field

Mon 2/16

8:24 pm-9:31 pm

Nonstop1h 07m

$194

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Fri 2/20

1:55 pm-2:57 pm

Nonstop1h 02m

Madison Truax Field

Tue 2/24

2:48 pm-4:00 pm

Nonstop1h 12m

$239

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Tue 2/24

5:22 pm-10:43 am

1 stop17h 21m

Madison Truax Field

Mon 3/2

7:25 pm-8:13 am

1 stop12h 48m

$324

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Fri 2/20

6:00 pm-6:58 pm

Nonstop0h 58m

Madison Truax Field

Tue 2/24

4:23 pm-9:38 am

1 stop17h 15m

$378

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Wed 2/18

7:10 am-8:48 pm

1 stop13h 38m

Madison Truax Field

Wed 2/25

2:48 pm-4:00 pm

Nonstop1h 12m

$386

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Tue 3/10

2:43 pm-9:08 am

1 stop18h 25m

Madison Truax Field

Tue 3/17

6:01 pm-4:55 pm

1 stop22h 54m

$402

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Tue 2/3

10:07 am-9:08 am

1 stop23h 01m

Madison Truax Field

Sat 2/7

6:36 pm-10:11 pm

2 stops27h 35m

$410

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Tue 3/10

10:19 am-9:08 am

1 stop22h 49m

Madison Truax Field

Tue 3/17

6:01 pm-11:21 am

2 stops17h 20m

$411

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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 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 Sunday as prices are generally higher than usual. According to our data, the average ticket price to Madison on Sunday is $450.

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 at noon. momondo users have found flights departing from Chicago to Madison at noon for as low as $285. 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 morning when prices are around $319.

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 4 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 January 2026, prices for Chicago to Madison flights are approximately 47% 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	0h 57m
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 $438.

The fastest flight from Chicago to Madison takes 0h 57m

Direct flights go from Chicago to Madison every day.

There is 1 airport in Madison. From Chicago there are direct flights to 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 0h 57m 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 January 2026, 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 15.69% of the total bookings. Other popular models include Embraer 175 (Enhanced Winglets) with 14.71%, Canadair (Bombardier) Regional Jet CRJ-550 with 13.73%, and Embraer 175 with 12.75%.
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 9,199 reviews		Search United Airlines flights

United Airlines Flights From Chicago to Madison
Across 33 United Airlines flights from Chicago to Madison this week, the average price was $438, with the best United Airlines deals starting from $199 round-trip. 9,199 users have rated United Airlines on momondo, with an average score of 7.4/10.

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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.

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Cheap flights from Chicago to Madison from $134

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 3/31. 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

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 Sunday as prices are generally higher than usual. According to our data, the average ticket price to Madison on Sunday is $450.

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 4 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 January 2026, prices for Chicago to Madison flights are approximately 47% 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, United 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 115 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 17% of their flights experiencing any sort of delay.

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

As of January 2026, there are 34 flights per day flying from Chicago to Madison. The most common time of day flights depart is 3:00PM, with 37% of flights taking off in the afternoon.

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

As of January 2026, there are 239 flights per week flying from Chicago to Madison. The most common day of the week flights depart is Sun, with 18% 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.

Find better results for your trip to the United States

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