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 50% 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.

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

The number of flights available between Madison and Chicago is 29 per day as of November 2025. The most frequent departure time is 6:00PM, with 45% of daily flights leaving in the afternoon.

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

205 flights are operational weekly from Madison to Chicago as of November 2025. The most popular departure day for this route is Wed, with 22% of flights per week taking off on this day.

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 November 2025.

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.

$113 Cheap Flights from Madison to Chicago in 2025/26

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

Prices are currently low for flights on this route. Typical prices usually range from $194 to $224. The lowest price recently found on this route was $179.

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Madison to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

8:10 pm - 9:30 pmMSN-ORD

1h 20mnonstop

6:25 pm - 7:40 pmORD-MSN

1h 15mnonstop

$179American Airlines

Find Deal

Sat, Dec 20 - Sat, Dec 27

2:03 pm - 3:18 pmMSN-ORD

1h 15mnonstop

8:35 am - 9:37 amORD-MSN

1h 02mnonstop

$209American Airlines

Find Deal

Tue, Dec 9 - Sat, Dec 13

1:40 pm - 2:55 pmMSN-ORD

1h 15mnonstop

12:04 pm - 1:09 pmORD-MSN

1h 05mnonstop

$224American Airlines

Find Deal

Thu, Dec 4 - Thu, Dec 11

3:59 pm - 5:10 pmMSN-ORD

1h 11mnonstop

7:47 pm - 8:47 pmORD-MSN

1h 00mnonstop

$239United Airlines

Find Deal

Fri, Dec 5 - Sun, Dec 7

1:56 pm - 3:11 pmMSN-ORD

1h 15mnonstop

12:28 pm - 1:32 pmORD-MSN

1h 04mnonstop

$254American Airlines

Find Deal

Sat, Dec 13 - Wed, Dec 17

3:58 pm - 5:09 pmMSN-ORD

1h 11mnonstop

8:51 am - 10:00 amORD-MSN

1h 09mnonstop

$320United Airlines

Find Deal

Sat, Nov 29 - Mon, Dec 1

6:20 am - 6:37 pmMSN-MDW

12h 17m1 stop

5:00 pm - 10:19 amMDW-MSN

17h 19m1 stop

$390Delta

Find Deal

Tue, Feb 17 - Sat, Feb 21

4:34 pm - 8:45 pmMSN-MDW

28h 11m2 stops

3:10 pm - 5:28 pmMDW-MSN

26h 18m1 stop

$444Multiple Airlines

Find Deal

Tue, Dec 23 - Tue, Dec 30

4:34 pm - 8:45 pmMSN-MDW

28h 11m2 stops

3:10 pm - 5:28 pmMDW-MSN

26h 18m1 stop

$445Multiple Airlines

Find Deal

Tue, Dec 23 - Tue, Dec 30

6:20 am - 6:37 pmMSN-MDW

12h 17m1 stop

9:34 am - 10:38 pmMDW-MSN

13h 04m2 stops

$465Delta

Find Deal

Tue, Feb 17 - Sat, Feb 21

United Airlines flights from Madison to Chicago

Our best United Airlines deals on Madison to Chicago flight tickets

United Airlines

Dec 5

MSN3:59 pmMadison Truax Field

1h 11m

ORD5:10 pmChicago O'Hare Intl

Dec 7

ORD7:47 pmChicago O'Hare Intl

1h 00m

MSN8:47 pmMadison Truax Field

$239

Find similar

United Airlines

Nov 29

MSN3:58 pmMadison Truax Field

1h 11m

ORD5:09 pmChicago O'Hare Intl

Dec 1

ORD8:51 amChicago O'Hare Intl

1h 09m

MSN10:00 amMadison Truax Field

$320

Find similar

United Airlines

Dec 13

MSN3:09 pmMadison Truax Field

18h 31m

1 stop

ORD9:40 amChicago O'Hare Intl

Dec 14

ORD12:55 pmChicago O'Hare Intl

1h 06m

MSN2:01 pmMadison Truax Field

$329

Find similar

American Airlines flights from Madison to Chicago

Our best American Airlines deals on Madison to Chicago flight tickets

American Airlines

Dec 23

MSN8:10 pmMadison Truax Field

1h 20m

ORD9:30 pmChicago O'Hare Intl

Dec 30

ORD8:12 amChicago O'Hare Intl

1h 18m

MSN9:30 amMadison Truax Field

$179

Find similar

American Airlines

Mar 10

MSN8:16 pmMadison Truax Field

1h 16m

ORD9:32 pmChicago O'Hare Intl

Mar 17

ORD1:15 pmChicago O'Hare Intl

1h 04m

MSN2:19 pmMadison Truax Field

$180

Find similar

American Airlines

Dec 9

MSN2:03 pmMadison Truax Field

1h 15m

ORD3:18 pmChicago O'Hare Intl

Dec 13

ORD8:35 amChicago O'Hare Intl

1h 02m

MSN9:37 amMadison Truax Field

$209

Find similar

Fly from

Fly to

Route

Depart

Return

Price

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sat 12/20

8:10 pm-9:30 pm

Nonstop1h 20m

Chicago O'Hare Intl

Sat 12/27

6:25 pm-7:40 pm

Nonstop1h 15m

$179

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Tue 12/9

2:03 pm-3:18 pm

Nonstop1h 15m

Chicago O'Hare Intl

Sat 12/13

8:35 am-9:37 am

Nonstop1h 02m

$209

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Thu 12/4

1:40 pm-2:55 pm

Nonstop1h 15m

Chicago O'Hare Intl

Thu 12/11

12:04 pm-1:09 pm

Nonstop1h 05m

$224

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Fri 12/5

3:59 pm-5:10 pm

Nonstop1h 11m

Chicago O'Hare Intl

Sun 12/7

7:47 pm-8:47 pm

Nonstop1h 00m

$239

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sat 12/13

1:56 pm-3:11 pm

Nonstop1h 15m

Chicago O'Hare Intl

Wed 12/17

12:28 pm-1:32 pm

Nonstop1h 04m

$254

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Sat 11/29

3:58 pm-5:09 pm

Nonstop1h 11m

Chicago O'Hare Intl

Mon 12/1

8:51 am-10:00 am

Nonstop1h 09m

$320

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Tue 2/17

6:20 am-6:37 pm

1 stop12h 17m

Chicago Midway

Sat 2/21

5:00 pm-10:19 am

1 stop17h 19m

$390

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Tue 12/23

4:34 pm-8:45 pm

2 stops28h 11m

Chicago Midway

Tue 12/30

3:10 pm-5:28 pm

1 stop26h 18m

$444

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Tue 12/23

4:34 pm-8:45 pm

2 stops28h 11m

Chicago Midway

Tue 12/30

3:10 pm-5:28 pm

1 stop26h 18m

$445

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Tue 2/17

6:20 am-6:37 pm

1 stop12h 17m

Chicago Midway

Sat 2/21

9:34 am-10:38 pm

2 stops13h 04m

$465

Flights are sorted by cheapest round-trip flights first.

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

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 Friday when prices can be found for as low as $427. 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 $628.

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 $450. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $528.

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	$238
Fastest flight time	1h 11m
Direct flights	Tue, Wed, Fri, Sat and Sun
Airports in Chicago	1 airport

The best one-way flight to Chicago from Madison in the past 72 hours is $238. The best round-trip flight deal from Madison to Chicago found on momondo in the last 72 hours is $305.

The fastest flight from Madison to Chicago takes 1h 11m

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

There is 1 airport near Chicago: 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 11m.
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 November 2025.
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 Airbus A319 (9.17% of total bookings). The next most popular plane models are Embraer 175 (8.79%), Boeing 737-800 (8.66%), and Boeing 787-9 Dreamliner (8.53%).
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
United Airlines	PriceFrom $179	Free Cancellation	Rating 7.4 9,050 reviews		Search United Airlines flights
American Airlines	PriceFrom $184	Free Cancellation	Rating 7.2 11,038 reviews		Search American Airlines flights

United Airlines Flights From Madison to Chicago
Across 35 United Airlines flights from Madison to Chicago this week, the average price was $290, with the best United Airlines deals starting from $179 round-trip. 9,050 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, 11,038 ratings). American Airlines flies from Madison to Chicago around 13 times per week, with deals starting from $184 round-trip and rising to an average price of around $256.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Crown Point

Munster

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.

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.

Start using Trips

Find my bookings

Get notified when prices go down

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

1 adult

Fri 12/26

Fri 1/2

Email me momondo's favorite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

Popular cities in the United States

Flights to New Yorkfrom $33

Flights to Los Angelesfrom $49

Flights to Miamifrom $48

Flights to Orlandofrom $48

Flights to Las Vegasfrom $49

Flights to San Franciscofrom $57

Flights to Washington, D.C.from $38

Flights to Bostonfrom $59

Flights to Atlantafrom $48

Flights to Dallasfrom $54

Flights to Seattlefrom $58

Flights to Denverfrom $57

Cheap flights from Madison to Chicago from $113

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 1/21. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Madison to Chicago

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

United Airlines flights from Madison to Chicago

Our best United Airlines deals on Madison to Chicago flight tickets

American Airlines flights from Madison to Chicago

Our best American Airlines deals on Madison to Chicago flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from Madison to Chicago that are best for you.

See travel insights to Chicago from

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

What is the typical price of a round-trip flight between Madison and 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 $450. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $528.

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 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 29 per day as of November 2025. The most frequent departure time is 6:00PM, with 45% of daily flights leaving in the afternoon.

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

205 flights are operational weekly from Madison to Chicago as of November 2025. The most popular departure day for this route is Wed, with 22% 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