Cheap flights from Madison (MSN) to Chicago (CHI) from $89

This is the cheapest one-way flight price, found on 9/25. Prices may vary by date and flight preferences.
MSN — CHI
Oct 1 — Oct 81

The best prices from Madison Truax Field to Chicago are usually found in February or December, booked 46 days in advance, depart on a Tuesday or Thursday and return on a Tuesday

How to find the cheapest flight from Madison (MSN) to Chicago (CHI)

All the information you need to plan the best MSN to CHI flight in 2023: compare Madison to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.

Popular in

July

Cheapest in

February

Average price

$240

Round-trip from

$207
High demand for flights, 32% potential price rise
Best time to find cheap flights, 32% potential price drop
Average for round-trip flights in September 2023
From Madison Truax Field to Chicago (CHI)

MSN - CHI

Price

$207 - $364

CHI

Temperature

23 - 73.4 °F

CHI

Rainfall

1.7 - 4.9 inches

What is the cheapest day to fly round-trip from Madison to Chicago?

Flights from Madison to Chicago are found to be more expensive on Friday. This shouldn't discourage you from searching as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to Chicago.

How far in advance should I book a flight from Madison to Chicago?

To save on the cost of your flight from Madison to Chicago, book at least 47 days before your planned departure. Booking around this time can save you about 99% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $326 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $430.

What is the cheapest month to fly from Madison to Chicago?

The best pricing can be found in the month of February. Prices to Chicago from Madison average $245. You can even find prices in February for less than $245, as users have found deals to Chicago from as low as $167. The month of July appears to be one of the more expensive times to travel to Chicago from Madison. Flying in the targeted month can save you up to 47%.

When is the cheapest time to fly from Madison to Chicago (MSN - CHI)?

A simple way to save on the total cost of your ticket is to fly from Madison to Chicago in the morning. If you’re flexible enough to do this you can expect to save up to 17% on your trip compared to booking a flight at noon.

Cheap American Airlines flights from Madison to Chicago

Consider these cheap American Airlines flights we've found departing from Madison to Chicago. Make sure to check back often as deals are often changing.

Cheap United Airlines flights from Madison to Chicago

Have a look at some of the cheapest available United Airlines flights departing from Madison and landing in Chicago. If these deals don't fit your criteria, make sure to check back soon as new deals are always added.

Cheap Madison to Chicago flights in September & October 2023

The best prices found for MSN to CHI flights for September, October
Listed are some of the best fares we've found on flights departing from Madison to Chicago in 2023. For more flight deals, be sure to check back very soon.

Madison to Chicago 2023 flight deals

Cheap flights to Chicago from Madison found for this year
Listed are some of the best fares we've found on flights departing from Madison to Chicago in 2023. For more flight deals, be sure to check back very soon.

Non-stop flights to Chicago from Madison

Save time with Madison to Chicago direct flight deals
For a quicker trip, book one of these direct flights from Madison to Chicago. Select from other flights from Madison to Chicago by using the search form above.

Madison to Chicago flights leaving soon

Late deals on return flights to Chicago from Madison, departing today and this week
Book one of these great deals on flights from Madison to Chicago. To prevent any unwanted surprises, users should verify their flight info before booking.

One-way flights to Chicago from Madison

The cheapest one-way flights from Madison to Chicago
Some of the best available deals we've found on one-way flights from Madison to Chicago. Those needing a return flight from Madison to Chicago can use the search form above.

Find flights from Madison to Chicago within your budget

Use the slider to find flights from Madison to Chicago that fit your budget.

Fly from

Any airport

Fly to

Any airport

Budget

$178 - $374

Route

Depart

Return

Price

Madison Truax FieldChicago O'Hare Intl

MSN - ORD

MSNORD

Madison Truax Field

Mon 10/16

Nonstop1h 04m

Chicago O'Hare Intl

Mon 11/13

Nonstop1h 06m

Madison Truax FieldChicago O'Hare Intl

MSN - ORD

MSNORD

Madison Truax Field

Mon 10/23

Nonstop1h 04m

Chicago O'Hare Intl

Sun 11/5

Nonstop1h 06m

Madison Truax FieldChicago O'Hare Intl

MSN - ORD

MSNORD

Madison Truax Field

Sat 3/23

Nonstop0h 56m

Chicago O'Hare Intl

Wed 3/27

Nonstop0h 58m

Madison Truax FieldChicago O'Hare Intl

MSN - ORD

MSNORD

Madison Truax Field

Thu 11/2

Nonstop1h 08m

Chicago O'Hare Intl

Sun 11/5

Nonstop1h 04m

Madison Truax FieldChicago O'Hare Intl

MSN - ORD

MSNORD

Madison Truax Field

Thu 10/12

Nonstop1h 03m

Chicago O'Hare Intl

Sun 10/15

Nonstop1h 00m

Madison Truax FieldChicago O'Hare Intl

MSN - ORD

MSNORD

Madison Truax Field

Tue 10/24

1 stop10h 19m

Chicago O'Hare Intl

Wed 11/1

Nonstop1h 02m

Madison Truax FieldChicago O'Hare Intl

MSN - ORD

MSNORD

Madison Truax Field

Fri 12/22

Nonstop1h 14m

Chicago O'Hare Intl

Wed 12/27

Nonstop1h 03m

Madison Truax FieldChicago O'Hare Intl

MSN - ORD

MSNORD

Madison Truax Field

Fri 10/13

Nonstop0h 59m

Chicago O'Hare Intl

Sun 10/15

Nonstop1h 03m

Madison Truax FieldChicago O'Hare Intl

MSN - ORD

MSNORD

Madison Truax Field

Tue 10/24

1 stop7h 09m

Chicago O'Hare Intl

Wed 11/1

1 stop7h 32m

Flights are sorted by cheapest first

Deals found on 9/25

Reviews of airlines servicing Chicago

To help decide which airline to fly from Madison to Chicago, see what other customers have to say about American Airlines and United Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
1,890 reviews

Crew

8.1

Comfort

7.3

Boarding

7.7

Overall

7.4

Entertainment

7.0

Food

6.7

Reviews

1 / 10

It's a 40 min flight leaving on time and arriving on time is really all there is to it. Flight crew is always exceptional!

United Airlines
7.4
Good
1,890 reviews
United Airlines
7.4
Good
1,890 reviews

Crew

8.1

Comfort

7.3

Boarding

7.7

Overall

7.4

Entertainment

7.0

Food

6.7

Reviews

1 / 10

It's a 40 min flight leaving on time and arriving on time is really all there is to it. Flight crew is always exceptional!

American Airlines
7.2
Good
2,635 reviews
United Airlines
7.4
Good
1,890 reviews

Crew

8.1

Comfort

7.3

Boarding

7.7

Overall

7.4

Entertainment

7.0

Food

6.7

Reviews

1 / 10

It's a 40 min flight leaving on time and arriving on time is really all there is to it. Flight crew is always exceptional!

Frontier
5.8
Fair
762 reviews
United Airlines
7.4
Good
1,890 reviews

Crew

8.1

Comfort

7.3

Boarding

7.7

Overall

7.4

Entertainment

7.0

Food

6.7

Reviews

1 / 10

It's a 40 min flight leaving on time and arriving on time is really all there is to it. Flight crew is always exceptional!

Related info for your journey

Useful info, stats and facts about Madison to Chicago flights.

What airport do you fly from for flights from Madison to Chicago?

For a flight from Madison to Chicago, you will be flying from Truax Field. Madison Truax Field (MSN) is just 5.4 mi from the center of the city. Truax Field is the only Madison airport and it handles 28 outbound flights to Chicago per day. 2 airlines have flights to Chicago from Madison Truax Field on a regular basis.

Can I find flights from Madison to Chicago for under $200 on Cheapflights?

Yes, there are multiple flights from Madison to Chicago for under $200. The cheapest flight booked recently is on American Airlines for just $178, but on average you can expect to pay $345.

Are there nonstop flights from Madison to Chicago for under $200 on Cheapflights?

Cheapflights has at least 12 direct flights from Madison to Chicago under $200. A good price for a nonstop flight from Madison to Chicago is less than $324.

Are there last-minute flights available from Madison to Chicago for under $400?

There are currently 7+ open flights from Madison to Chicago within the next 7 days for less than $400.

What days are nonstop flights available from Madison to Chicago?

Days when nonstop flights are available for this flight are: Sunday, Tuesday, Wednesday, Thursday, Friday, Saturday.

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

On average, you can expect to see 45 flights from Madison to Chicago a day.
Early Morning (Midnight to 6am) - 9% of flight departures
Morning (6am - Noon) - 53% of flight departures
Afternoon (Noon - 6pm) - 38% of flight departures

How long is the flight from Madison to Chicago?

There are many flights that can get you from Madison to Chicago in 1h 04m. Fly via American Airlines or United Airlines to get the fastest option. Airlines will cover a distance of 109 mi. All flights are typically nonstop.

What are the cheapest airlines flying from Madison to Chicago round-trip?

According to our current data, American Airlines ($178), and United Airlines ($258) offers the cheapest pricing from Madison to Chicago. American Airlines is priced at 27% lower than the current average price of a flight leaving 3 months from now.

What are the cheapest airlines to fly from Madison to Chicago one-way?

One-way options have recently been found by users for as low as $89 on American Airlines. Other airlines that offer cheap prices include Frontier from $100 and United Airlines from $109 one-way.

What are the most reliable airlines from Madison to Chicago?

No one likes to see their flight delayed. When booking a flight from Madison to Chicago consider choosing Republic Airways (90%), GoJet (87%) or Air Canada (85%) as they are the most reliable in getting you off to your destination on time.

What are the cheapest flights from Madison to Chicago?

Looking for the cheapest flight from Madison to Chicago? While on average our users pay $969, our data indicates the cheapest price to be $129. The most popular route (Madison Truax Field - Chicago O'Hare Intl), is priced around $228.

What does MSN to ORD mean?

Great question - MSN to ORD just means Madison Truax Field Airport to Chicago O'Hare Intl Airport. Now you’ll know what these unique codes when you look for flights! Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD) are other airports near this flight route and their unique identifiers/IATA codes.

Top 2 airlines flying from Madison to Chicago

The chart below displays the airlines Cheapflights users traveling from Madison to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$113Average$198FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
American AirlinesCheapest$138Average$254FlexibilityNo cancel feeOn-time71%
Search American Airlines flights

Hourly flight availability from Madison to Chicago

See what time of day planes typically take off from Madison to Chicago
11%of flight departuresEarly morningMidnight to 6 am
36%of flight departuresMorning6 am to noon
53%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Weekly flight availability from Madison to Chicago

See how many times per day planes take to the skies headed from Madison to Chicago
Sunday31daily flights
Monday33daily flights
Tuesday26daily flights
Wednesday27daily flights
Thursday31daily flights
Friday33daily flights
Saturday17daily flights

Fly with Cheapflights

What makes Cheapflights the go-to destination for all your flight needs

How does Cheapflights help users find flights from Madison to Chicago?

Cheapflights helps you search for flights from Madison to Chicago via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.

Why should you use Cheapflights to find cheap flight tickets from Madison to Chicago?

Cheapflights helps you find that perfect flight to Chicago from Madison by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Can Cheapflights find flights from Madison to Chicago with no change fees?

Cheapflights does show flights with no change fees to all users. To see these options for flights from Madison to Chicago, users can toggle the no change fees filter when performing a flight search.

Can Cheapflights notify me if prices for flights from Madison to Chicago become cheaper?

Yes! Start tracking prices for Madison to Chicago flights today and get alerted whenever prices for these flights change. To access this feature, navigate to the search form above to perform a search, which will then prompt you for a valid email address to use the tool.

100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.