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 44% 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.

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

As of August 2025, there are 173 flights per week flying from Chicago to Madison. The most common day of the week flights depart is Fri, with 23% of flights taking off on this day.

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

As of August 2025, there are 24 flights per day flying from Chicago to Madison. The most common time of day flights depart is 5:00PM, with 43% of flights taking off in the afternoon.

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

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

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 August 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.

$144 Cheap Flights from Chicago to Madison in 2025

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 $248 to $267. The lowest price recently found on this route was $179.

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Find the cheapest flights from Chicago to Madison

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

6:04 pm - 7:09 pmORD-MSN

1h 05mnonstop

5:43 pm - 6:50 pmMSN-ORD

1h 07mnonstop

$179United Airlines

Find Deal

Wed, Sep 10 - Wed, Sep 17

12:00 pm - 12:59 pmORD-MSN

0h 59mnonstop

8:14 pm - 9:19 pmMSN-ORD

1h 05mnonstop

$184American Airlines

Find Deal

Thu, Aug 21 - Fri, Aug 29

9:05 pm - 10:15 pmORD-MSN

1h 10mnonstop

6:11 pm - 7:13 pmMSN-ORD

1h 02mnonstop

$189United Airlines

Find Deal

Fri, Aug 15 - Sun, Aug 17

2:20 pm - 3:24 pmORD-MSN

1h 04mnonstop

8:14 pm - 9:19 pmMSN-ORD

1h 05mnonstop

$199American Airlines

Find Deal

Wed, Aug 13 - Sat, Aug 16

6:42 pm - 7:54 pmORD-MSN

1h 12mnonstop

6:41 pm - 7:52 pmMSN-ORD

1h 11mnonstop

$224American Airlines

Find Deal

Fri, Sep 19 - Tue, Sep 23

12:00 pm - 12:59 pmORD-MSN

0h 59mnonstop

8:14 pm - 9:19 pmMSN-ORD

1h 05mnonstop

$229American Airlines

Find Deal

Fri, Aug 15 - Mon, Aug 18

12:45 pm - 1:49 pmORD-MSN

1h 04mnonstop

8:15 am - 9:27 amMSN-ORD

1h 12mnonstop

$235United Airlines

Find Deal

Fri, Aug 29 - Mon, Sep 1

6:10 am - 10:50 pmORD-MSN

16h 40m1 stop

6:05 am - 9:35 pmMSN-ORD

15h 30m1 stop

$385Delta

Find Deal

Sat, Aug 23 - Sat, Aug 30

8:20 pm - 10:19 amORD-MSN

13h 59m1 stop

6:05 am - 9:35 pmMSN-ORD

15h 30m1 stop

$412Delta

Find Deal

Fri, Aug 22 - Sat, Aug 30

6:10 am - 10:50 pmORD-MSN

16h 40m1 stop

6:05 am - 3:00 pmMSN-ORD

8h 55m1 stop

$435Delta

Find Deal

Sat, Aug 23 - Sun, Aug 31

United Airlines flights from Chicago to Madison

Our best United Airlines deals on Chicago to Madison flight tickets

United Airlines

Sep 10

ORD6:04 pmChicago O'Hare Intl

1h 05m

MSN7:09 pmMadison Truax Field

Sep 17

MSN5:43 pmMadison Truax Field

1h 07m

ORD6:50 pmChicago O'Hare Intl

$179

Find similar

United Airlines

Aug 15

ORD9:05 pmChicago O'Hare Intl

1h 10m

MSN10:15 pmMadison Truax Field

Aug 17

MSN6:11 pmMadison Truax Field

1h 02m

ORD7:13 pmChicago O'Hare Intl

$189

Find similar

United Airlines

Aug 29

ORD12:45 pmChicago O'Hare Intl

1h 04m

MSN1:49 pmMadison Truax Field

Sep 1

MSN8:15 amMadison Truax Field

1h 12m

ORD9:27 amChicago O'Hare Intl

$235

Find similar

American Airlines flights from Chicago to Madison

Our best American Airlines deals on Chicago to Madison flight tickets

American Airlines

Aug 21

ORD12:00 pmChicago O'Hare Intl

0h 59m

MSN12:59 pmMadison Truax Field

Aug 29

MSN8:14 pmMadison Truax Field

1h 05m

ORD9:19 pmChicago O'Hare Intl

$184

Find similar

American Airlines

Aug 13

ORD2:20 pmChicago O'Hare Intl

1h 04m

MSN3:24 pmMadison Truax Field

Aug 16

MSN8:14 pmMadison Truax Field

1h 05m

ORD9:19 pmChicago O'Hare Intl

$199

Find similar

American Airlines

Sep 19

ORD6:42 pmChicago O'Hare Intl

1h 12m

MSN7:54 pmMadison Truax Field

Sep 23

MSN6:41 pmMadison Truax Field

1h 11m

ORD7:52 pmChicago O'Hare Intl

$224

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Wed 9/10

6:04 pm-7:09 pm

Nonstop1h 05m

Madison Truax Field

Wed 9/17

5:43 pm-6:50 pm

Nonstop1h 07m

$179

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Thu 8/21

12:00 pm-12:59 pm

Nonstop0h 59m

Madison Truax Field

Fri 8/29

8:14 pm-9:19 pm

Nonstop1h 05m

$184

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Fri 8/15

9:05 pm-10:15 pm

Nonstop1h 10m

Madison Truax Field

Sun 8/17

6:11 pm-7:13 pm

Nonstop1h 02m

$189

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Wed 8/13

2:20 pm-3:24 pm

Nonstop1h 04m

Madison Truax Field

Sat 8/16

8:14 pm-9:19 pm

Nonstop1h 05m

$199

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Fri 9/19

6:42 pm-7:54 pm

Nonstop1h 12m

Madison Truax Field

Tue 9/23

6:41 pm-7:52 pm

Nonstop1h 11m

$224

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Fri 8/15

12:00 pm-12:59 pm

Nonstop0h 59m

Madison Truax Field

Mon 8/18

8:14 pm-9:19 pm

Nonstop1h 05m

$229

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Fri 8/29

12:45 pm-1:49 pm

Nonstop1h 04m

Madison Truax Field

Mon 9/1

8:15 am-9:27 am

Nonstop1h 12m

$235

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Sat 8/23

6:10 am-10:50 pm

1 stop16h 40m

Madison Truax Field

Sat 8/30

6:05 am-9:35 pm

1 stop15h 30m

$385

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Fri 8/22

8:20 pm-10:19 am

1 stop13h 59m

Madison Truax Field

Sat 8/30

6:05 am-9:35 pm

1 stop15h 30m

$412

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Sat 8/23

6:10 am-10:50 pm

1 stop16h 40m

Madison Truax Field

Sun 8/31

6:05 am-3:00 pm

1 stop8h 55m

$435

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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

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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 $219. 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 $334.

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 $239. 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 $329.

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 August 2025, prices for Chicago to Madison flights are approximately 76% 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	$188
Fastest flight time	0h 58m
Direct flights	Every day
Airports in Madison	1 airport

The best one-way flight to Madison from Chicago in the past 72 hours is $188. The best round-trip flight deal from Chicago to Madison found on momondo in the last 72 hours is $179.

The fastest flight from Chicago to Madison takes 0h 58m

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 0h 58m 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 August 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 19.40% of the total bookings. Other popular models include Embraer 170 with 17.91%, Canadair (Bombardier) Regional Jet CRJ-550 with 16.42%, and Embraer 175 (Enhanced Winglets) with 11.94%.
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 $179	Free Cancellation	Rating 7.4 8,904 reviews		Search United Airlines flights

United Airlines Flights From Chicago to Madison
Across 21 United Airlines flights from Chicago to Madison this week, the average price was $275, with the best United Airlines deals starting from $179 round-trip. 8,904 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.

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 $179

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Madison departing on 9/10. 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 $219. 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 $334.

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 August 2025, prices for Chicago to Madison flights are approximately 76% 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?

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

What airlines fly to Madison?

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

As of August 2025, there are 24 flights per day flying from Chicago to Madison. The most common time of day flights depart is 5:00PM, with 43% of flights taking off in the afternoon.

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

As of August 2025, there are 173 flights per week flying from Chicago to Madison. The most common day of the week flights depart is Fri, with 23% 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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