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

256 flights are operational weekly from Madison to Chicago as of January 2026. The most popular departure day for this route is Wed, with 18% of flights per week taking off on this day.

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

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

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

The number of flights available between Madison and Chicago is 36 per day as of January 2026. The most frequent departure time is 5:00PM, with 50% of daily flights leaving at noon.

What airlines fly to Chicago?

American Airlines, United Airlines and Denver Air Connection are the top three most popular airlines that fly to Chicago from Madison according to our data. American Airlines is the first choice among our users, with 51% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 3 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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

Prices for flights from Madison Truax Field Airport to Chicago were last updated today.

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

There are 2 operators available for flights from Madison Truax Field Airport to Chicago as of January 2026.

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

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 Madison Truax Field Airport to Chicago.

What documentation or ID do you need to fly to Chicago?

The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

$137 Cheap Flights from Madison to Chicago in 2026

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6:30 am - 7:47 am

MSN

ORD

1h 17mnonstop

1:55 pm - 2:57 pm

ORD

MSN

1h 02mnonstop

$179United Airlines

Wed, Feb 11 - Sun, Feb 15

6:30 am - 7:42 am

MSN

ORD

1h 12mnonstop

8:10 pm - 9:16 pm

ORD

MSN

1h 06mnonstop

$190United Airlines

Sat, Mar 28 - Thu, Apr 2

5:25 pm - 6:45 pm

MSN

ORD

1h 20mnonstop

1:00 pm - 2:10 pm

ORD

MSN

1h 10mnonstop

$209United Airlines

Wed, Jan 28 - Sun, Feb 1

11:29 am - 12:40 pm

MSN

ORD

1h 11mnonstop

9:45 am - 10:55 am

ORD

MSN

1h 10mnonstop

$214American Airlines

Tue, Jan 27 - Sat, Feb 7

7:20 am - 8:39 am

MSN

ORD

1h 19mnonstop

5:40 pm - 6:44 pm

ORD

MSN

1h 04mnonstop

$229American Airlines

Wed, Jan 28 - Sun, Feb 1

10:05 am - 11:15 am

MSN

ORD

1h 10mnonstop

4:55 pm - 6:00 pm

ORD

MSN

1h 05mnonstop

$234American Airlines

Sat, May 2 - Sun, May 24

8:15 am - 9:32 am

MSN

ORD

1h 17mnonstop

1:55 pm - 2:57 pm

ORD

MSN

1h 02mnonstop

$239United Airlines

Wed, Feb 11 - Sun, Feb 15

8:25 pm - 9:40 pm

MSN

ORD

1h 15mnonstop

8:17 am - 9:23 am

ORD

MSN

1h 06mnonstop

$244American Airlines

Fri, May 15 - Fri, May 22

5:00 am - 6:08 am

MSN

ORD

1h 08mnonstop

8:05 am - 9:11 am

ORD

MSN

1h 06mnonstop

$267American Airlines

Sun, Mar 8 - Fri, Mar 13

2:48 pm - 11:41 pm

MSN

MDW

8h 53m

1 stop

6:00 am - 7:11 pm

MDW

MSN

13h 11m

2 stops

$455Multiple Airlines

Thu, Feb 12 - Fri, Mar 13

American Airlines flights from Madison to Chicago

Our best American Airlines deals on Madison to Chicago flight tickets

American Airlines

Jan 27

MSN11:29 amMadison Truax Field

1h 11m

ORD12:40 pmChicago O'Hare Intl

Feb 7

ORD9:45 amChicago O'Hare Intl

1h 10m

MSN10:55 amMadison Truax Field

$214

American Airlines

Jan 23

MSN11:29 amMadison Truax Field

1h 11m

ORD12:40 pmChicago O'Hare Intl

Jan 27

ORD5:40 pmChicago O'Hare Intl

1h 04m

MSN6:44 pmMadison Truax Field

$224

American Airlines

Jan 28

MSN7:20 amMadison Truax Field

1h 19m

ORD8:39 amChicago O'Hare Intl

Feb 1

ORD5:40 pmChicago O'Hare Intl

1h 04m

MSN6:44 pmMadison Truax Field

$229

United Airlines flights from Madison to Chicago

Our best United Airlines deals on Madison to Chicago flight tickets

United Airlines

Feb 11

MSN6:30 amMadison Truax Field

1h 17m

ORD7:47 amChicago O'Hare Intl

Feb 15

ORD1:55 pmChicago O'Hare Intl

1h 02m

MSN2:57 pmMadison Truax Field

$179

United Airlines

Mar 28

MSN6:30 amMadison Truax Field

1h 12m

ORD7:42 amChicago O'Hare Intl

Apr 2

ORD8:10 pmChicago O'Hare Intl

1h 06m

MSN9:16 pmMadison Truax Field

$190

United Airlines

Jan 28

MSN5:25 pmMadison Truax Field

1h 20m

ORD6:45 pmChicago O'Hare Intl

Feb 1

ORD1:00 pmChicago O'Hare Intl

1h 10m

MSN2:10 pmMadison Truax Field

$209

Fly from

Fly to

Route

Depart

Return

Price

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Wed 2/11

6:30 am-7:47 am

Nonstop1h 17m

Chicago O'Hare Intl

Sun 2/15

1:55 pm-2:57 pm

Nonstop1h 02m

$179

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sat 3/28

6:30 am-7:42 am

Nonstop1h 12m

Chicago O'Hare Intl

Thu 4/2

8:10 pm-9:16 pm

Nonstop1h 06m

$190

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Wed 1/28

5:25 pm-6:45 pm

Nonstop1h 20m

Chicago O'Hare Intl

Sun 2/1

1:00 pm-2:10 pm

Nonstop1h 10m

$209

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Tue 1/27

11:29 am-12:40 pm

Nonstop1h 11m

Chicago O'Hare Intl

Sat 2/7

9:45 am-10:55 am

Nonstop1h 10m

$214

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Wed 1/28

7:20 am-8:39 am

Nonstop1h 19m

Chicago O'Hare Intl

Sun 2/1

5:40 pm-6:44 pm

Nonstop1h 04m

$229

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sat 5/2

10:05 am-11:15 am

Nonstop1h 10m

Chicago O'Hare Intl

Sun 5/24

4:55 pm-6:00 pm

Nonstop1h 05m

$234

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Wed 2/11

8:15 am-9:32 am

Nonstop1h 17m

Chicago O'Hare Intl

Sun 2/15

1:55 pm-2:57 pm

Nonstop1h 02m

$239

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Fri 5/15

8:25 pm-9:40 pm

Nonstop1h 15m

Chicago O'Hare Intl

Fri 5/22

8:17 am-9:23 am

Nonstop1h 06m

$244

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sun 3/8

5:00 am-6:08 am

Nonstop1h 08m

Chicago O'Hare Intl

Fri 3/13

8:05 am-9:11 am

Nonstop1h 06m

$267

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Thu 2/12

2:48 pm-11:41 pm

1 stop8h 53m

Chicago Midway

Fri 3/13

6:00 am-7:11 pm

2 stops13h 11m

$455

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Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Madison to Chicago

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

Other information

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

The cheapest day to depart on your flight to Chicago is on a Saturday when prices can be found for as low as $407. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Madison to Chicago for around $626.

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

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Madison to Chicago during this time can be as low as $434. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $530.

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

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

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

There are 4 cabin classes available to choose from on Madison Truax Field to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Madison to Chicago flight prices changed over time?

When to book flights from Madison to Chicago

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

Estimated round-trip price

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

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

Best Price Found	$264
Fastest flight time	1h 05m
Direct flights	Tue, Wed, Thu, Fri, Sat and Sun
Airports in Chicago	3 airports

The best one-way flight to Chicago from Madison in the past 72 hours is $264. The best round-trip flight deal from Madison to Chicago found on momondo in the last 72 hours is $323.

The fastest flight from Madison to Chicago takes 1h 05m

Direct flights go from Madison to Chicago on Tuesday, Wednesday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.

There are 3 airports in Chicago. From Madison there are direct flights to Chicago O'Hare Intl (ORD).

Search flight deals

How far is Madison Truax Field to Chicago by plane?
Madison Truax Field and Chicago are 122.4 mi apart from one another. In terms of flight time, this usually takes a little over 1h 05m.
When did momondo last update prices for flights from Madison Truax Field Airport to Chicago?
Prices for flights from Madison Truax Field Airport to Chicago were last updated today.
How many operators does momondo search for flights from Madison Truax Field Airport to Chicago?
There are 2 operators available for flights from Madison Truax Field Airport to Chicago as of January 2026.
How old do you have to be to fly from Madison Truax Field Airport to Chicago?
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 Madison Truax Field Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Madison to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Madison to Chicago is Boeing 787-9 Dreamliner (11.07% of total bookings). The next most popular plane models are Airbus A220-300 (10.73%), Boeing 737-800 (9.88%), and Embraer 175 (7.84%).
What is the most popular airline from Madison to Chicago?
momondo data reveals that the most frequently booked airline on the route from Madison to Chicago is United Airlines, representing 100% of all bookings.

Best airlines flying from Madison to Chicago

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

Airline	Rating	Free Cancellation	Price
American Airlines	PriceFrom $179	Free Cancellation	Rating 7.2 11,129 reviews		Search American Airlines flights
United Airlines	PriceFrom $179	Free Cancellation	Rating 7.4 9,163 reviews		Search United Airlines flights

United Airlines Flights From Madison to Chicago
Across 47 United Airlines flights from Madison to Chicago this week, the average price was $279, with the best United Airlines deals starting from $179 round-trip. 9,163 users have rated United Airlines on momondo, with an average score of 7.4/10.
American Airlines Flights From Madison to Chicago
Another popular option for Madison to Chicago flights is American Airlines (7.2/10, 11,129 ratings). American Airlines flies from Madison to Chicago around 26 times per week, with deals starting from $179 round-trip and rising to an average price of around $249.

Merrillville

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Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Munster

Crown Point

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

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

Finding the right flight to Chicago from Madison is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

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

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

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

Once all potential Madison to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

Of course. momondo tracks the price of Madison to Chicago 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 Madison to Chicago from $137

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Madison to Chicago departing on 1/28. 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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Big names and deals

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American Airlines flights from Madison to Chicago

Our best American Airlines deals on Madison to Chicago flight tickets

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How to get the cheapest flight ticket from Madison to Chicago

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

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

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Madison to Chicago during this time can be as low as $434. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $530.

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

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

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

There are 4 cabin classes available to choose from on Madison Truax Field to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Madison to Chicago flight prices changed over time?

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

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

What airlines fly to Chicago?

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

The number of flights available between Madison and Chicago is 36 per day as of January 2026. The most frequent departure time is 5:00PM, with 50% of daily flights leaving at noon.

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

256 flights are operational weekly from Madison to Chicago as of January 2026. The most popular departure day for this route is Wed, with 18% of flights per week taking off on this day.

When to book flights from Madison to Chicago

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

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

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

How far is Madison Truax Field to Chicago by plane?

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

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

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

What documentation or ID do you need to fly to Chicago?

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

What is the most popular airline from Madison to Chicago?

Best airlines flying from Madison to Chicago

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

United Airlines Flights From Madison to Chicago

American Airlines Flights From Madison to Chicago

Traveling to a place near Chicago?

Why use momondo?

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

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

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

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

An easier way to manage your Chicago 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

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago