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

CHI — MSN
Feb 7 — Feb 141

The best prices from Chicago to Madison Truax Field are usually found in March or November, booked 53 days in advance, depart on a Friday or Saturday and return on a Thursday

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

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

CHI - MSN

Price

$60 - $678

MSN

Temperature

19.4 - 71.6 °F

MSN

Rainfall

1.2 - 4.5 inches

Popular inMayHigh demand for flights, 60% potential price rise
Cheapest inMarchBest time to find cheap flights, 78% potential price drop
Average price$312Average for round-trip flights in February 2023
Round-trip from$60From Chicago (CHI) to Madison Truax Field

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

Flying to your destination on a Sunday can be more expensive, but this shouldn’t discourage you from finding affordable options to get to Madison. Check prices with Cheapflights to find a great deal for your trip.

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

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 50 days in advance, which can save you up to 57% on flights from Chicago to Madison compared to booking the week you need them. Waiting 50 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $268. For sooner than that we have options available in the next 3 days from $268.

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

March can be a great time to fly to Madison from Chicago with a flight ticket averaging about $270. Cheapflights users have found deals in the month of March for as cheap as $60. The most expensive prices can be found in the month of May.

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

A simple way to save on the total cost of your ticket is to fly from Chicago to Madison in the evening. If you’re flexible enough to do this you can expect to save up to 33% on your trip compared to booking a flight in the afternoon.

Cheap flights from Chicago to Madison in February, March 2023

The best prices found for CHI to MSN flights for February, March
Feb 23 - Feb 26
ORD

Chicago O'Hare Intl

MSN

Madison Truax Field

Nonstop

0h 58m
MSN

Madison Truax Field

ORD

Chicago O'Hare Intl

Nonstop

1h 02m
$108

United Airlines

Pick Dates

Deal found 2/1

Mar 4 - Mar 8
ORD

Chicago O'Hare Intl

MSN

Madison Truax Field

Nonstop

0h 58m
MSN

Madison Truax Field

ORD

Chicago O'Hare Intl

Nonstop

0h 58m
$113

United Airlines

Pick Dates

Deal found 2/1

Mar 1 - Mar 8
ORD

Chicago O'Hare Intl

MSN

Madison Truax Field

Nonstop

0h 56m
MSN

Madison Truax Field

ORD

Chicago O'Hare Intl

Nonstop

0h 58m
$128

United Airlines

Pick Dates

Deal found 1/30

Chicago to Madison 2023 flight deals

Cheap flights to Madison from Chicago found for this year
Feb 23 - Feb 26
ORD

Chicago O'Hare Intl

MSN

Madison Truax Field

Nonstop

0h 58m
MSN

Madison Truax Field

ORD

Chicago O'Hare Intl

Nonstop

1h 02m
$108

United Airlines

Pick Dates

Deal found 2/1

Mar 4 - Mar 8
ORD

Chicago O'Hare Intl

MSN

Madison Truax Field

Nonstop

0h 58m
MSN

Madison Truax Field

ORD

Chicago O'Hare Intl

Nonstop

0h 58m
$113

United Airlines

Pick Dates

Deal found 2/1

Mar 1 - Mar 8
ORD

Chicago O'Hare Intl

MSN

Madison Truax Field

Nonstop

0h 56m
MSN

Madison Truax Field

ORD

Chicago O'Hare Intl

Nonstop

0h 58m
$128

United Airlines

Pick Dates

Deal found 1/30

Cheap United Airlines flights from Chicago to Madison

Feb 23 - Feb 26
ORD

Chicago O'Hare Intl

MSN

Madison Truax Field

Nonstop

0h 58m
MSN

Madison Truax Field

ORD

Chicago O'Hare Intl

Nonstop

1h 02m
$108

United Airlines

Pick Dates

Deal found 2/1

Mar 4 - Mar 8
ORD

Chicago O'Hare Intl

MSN

Madison Truax Field

Nonstop

0h 58m
MSN

Madison Truax Field

ORD

Chicago O'Hare Intl

Nonstop

0h 58m
$113

United Airlines

Pick Dates

Deal found 2/1

Mar 1 - Mar 8
ORD

Chicago O'Hare Intl

MSN

Madison Truax Field

Nonstop

0h 56m
MSN

Madison Truax Field

ORD

Chicago O'Hare Intl

Nonstop

0h 58m
$128

United Airlines

Pick Dates

Deal found 1/30

Cheap American Airlines flights from Chicago to Madison

Mar 4 - Mar 8
ORD

Chicago O'Hare Intl

MSN

Madison Truax Field

Nonstop

1h 26m
MSN

Madison Truax Field

ORD

Chicago O'Hare Intl

1 stop

7h 36m
$186

American Airlines

Pick Dates

Deal found 2/1

Feb 25 - Mar 4
ORD

Chicago O'Hare Intl

MSN

Madison Truax Field

Nonstop

1h 14m
MSN

Madison Truax Field

ORD

Chicago O'Hare Intl

1 stop

5h 18m
$196

American Airlines

Pick Dates

Deal found 1/30

Feb 9 - Feb 12
ORD

Chicago O'Hare Intl

MSN

Madison Truax Field

1 stop

4h 46m
MSN

Madison Truax Field

ORD

Chicago O'Hare Intl

Nonstop

1h 06m
$221

American Airlines

Pick Dates

Deal found 1/31

Non-stop flights to Madison from Chicago

Save time with Chicago to Madison direct flight deals
Feb 23 - Feb 26
ORD

Chicago O'Hare Intl

MSN

Madison Truax Field

Nonstop

0h 58m
MSN

Madison Truax Field

ORD

Chicago O'Hare Intl

Nonstop

1h 02m
$108

United Airlines

Pick Dates

Deal found 2/1

Mar 4 - Mar 8
ORD

Chicago O'Hare Intl

MSN

Madison Truax Field

Nonstop

0h 58m
MSN

Madison Truax Field

ORD

Chicago O'Hare Intl

Nonstop

0h 58m
$113

United Airlines

Pick Dates

Deal found 2/1

Mar 1 - Mar 8
ORD

Chicago O'Hare Intl

MSN

Madison Truax Field

Nonstop

0h 56m
MSN

Madison Truax Field

ORD

Chicago O'Hare Intl

Nonstop

0h 58m
$128

United Airlines

Pick Dates

Deal found 1/30

Last minute flights from Chicago to Madison

Late deals on return flights to Madison from Chicago, departing today and this week
Feb 9 - Feb 12
ORD

Chicago O'Hare Intl

MSN

Madison Truax Field

Nonstop

1h 04m
MSN

Madison Truax Field

ORD

Chicago O'Hare Intl

Nonstop

1h 02m
$138

United Airlines

Pick Dates

Deal found 1/31

Feb 9 - Feb 12
ORD

Chicago O'Hare Intl

MSN

Madison Truax Field

1 stop

4h 46m
MSN

Madison Truax Field

ORD

Chicago O'Hare Intl

Nonstop

1h 06m
$221

American Airlines

Pick Dates

Deal found 1/31

Feb 9 - Feb 12
ORD

Chicago O'Hare Intl

MSN

Madison Truax Field

1 stop

4h 46m
MSN

Madison Truax Field

ORD

Chicago O'Hare Intl

1 stop

7h 36m
$229

American Airlines

Pick Dates

Deal found 1/31

One-way flights to Madison from Chicago

The cheapest one-way flights from Chicago to Madison
Mar 8
MDW

Chicago Midway

MSN

Madison Truax Field

1 stop

13h 58m
$78

Frontier

Pick Dates

Deal found 2/1

Mar 14
ORD

Chicago O'Hare Intl

MSN

Madison Truax Field

2 stops

15h 23m
$143

Multiple Airlines

Pick Dates

Deal found 1/30

Apr 5
MDW

Chicago Midway

MSN

Madison Truax Field

1 stop

14h 14m
$144

Frontier

Pick Dates

Deal found 2/1

Reviews of Airlines Servicing Madison

Delta
7.9
Good
2,045 reviews

Comfort

7.9

Food

7.2

Entertainment

7.8

Boarding

8.0

Overall

7.9

Crew

8.5

Reviews

1 / 10

The flight was delayed leaving ORD by 10 minutes which wasn't a problem. But the plane took a long time to push back from the gate and because of the weather, the plane had to be de-iced. That took 30 minutes or more which caused a problem for many passengers making connections in Atlanta. I appreciate the need for safety and that takes priority over all other considerations, but it would have been nice if flights in Atlanta could have been notified about the delay and those that had tight connections could have made their flights.

Delta
7.9
Good
2,045 reviews
Delta
7.9
Good
2,045 reviews

Comfort

7.9

Food

7.2

Entertainment

7.8

Boarding

8.0

Overall

7.9

Crew

8.5

Reviews

1 / 10

The flight was delayed leaving ORD by 10 minutes which wasn't a problem. But the plane took a long time to push back from the gate and because of the weather, the plane had to be de-iced. That took 30 minutes or more which caused a problem for many passengers making connections in Atlanta. I appreciate the need for safety and that takes priority over all other considerations, but it would have been nice if flights in Atlanta could have been notified about the delay and those that had tight connections could have made their flights.

United Airlines
7.6
Good
1,189 reviews
Delta
7.9
Good
2,045 reviews

Comfort

7.9

Food

7.2

Entertainment

7.8

Boarding

8.0

Overall

7.9

Crew

8.5

Reviews

1 / 10

The flight was delayed leaving ORD by 10 minutes which wasn't a problem. But the plane took a long time to push back from the gate and because of the weather, the plane had to be de-iced. That took 30 minutes or more which caused a problem for many passengers making connections in Atlanta. I appreciate the need for safety and that takes priority over all other considerations, but it would have been nice if flights in Atlanta could have been notified about the delay and those that had tight connections could have made their flights.

American Airlines
7.4
Good
1,668 reviews
Delta
7.9
Good
2,045 reviews

Comfort

7.9

Food

7.2

Entertainment

7.8

Boarding

8.0

Overall

7.9

Crew

8.5

Reviews

1 / 10

The flight was delayed leaving ORD by 10 minutes which wasn't a problem. But the plane took a long time to push back from the gate and because of the weather, the plane had to be de-iced. That took 30 minutes or more which caused a problem for many passengers making connections in Atlanta. I appreciate the need for safety and that takes priority over all other considerations, but it would have been nice if flights in Atlanta could have been notified about the delay and those that had tight connections could have made their flights.

Frontier
6.1
Okay
537 reviews
Delta
7.9
Good
2,045 reviews

Comfort

7.9

Food

7.2

Entertainment

7.8

Boarding

8.0

Overall

7.9

Crew

8.5

Reviews

1 / 10

The flight was delayed leaving ORD by 10 minutes which wasn't a problem. But the plane took a long time to push back from the gate and because of the weather, the plane had to be de-iced. That took 30 minutes or more which caused a problem for many passengers making connections in Atlanta. I appreciate the need for safety and that takes priority over all other considerations, but it would have been nice if flights in Atlanta could have been notified about the delay and those that had tight connections could have made their flights.

Related info for your journey

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

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

Most people fly into Madison Truax Field (MSN) if they book a flight to Madison from Chicago. On average, Truax Field has 19 inbound flights from Chicago per day from 3 airlines. Madison Truax Field is conveniently located just 5.4 mi from Madison’s city center.

Which airlines flying from Chicago to Madison Truax Field have flexible cancellations due to COVID-19?

Some of our airline partners flying from Chicago to Madison Truax Field have new flexible policies in place due to COVID-19. United Airlines, American Airlines, and Bus are some of the carriers where you may find flexible cancellation policies. You can use our site to filter for airlines like United Airlines with this kind of flexibility.

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

Yes, there are multiple flights from Chicago to Madison for under $200. The cheapest flight booked recently is on United Airlines for just $108, but on average you can expect to pay $180.

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

Cheapflights has at least 20 direct flights from Chicago to Madison under $200. A good price for a nonstop flight from Chicago to Madison is less than $237.

Are there last-minute flights available from Chicago to Madison for under $200?

There are currently 19+ open flights from Chicago to Madison within the next 7 days for less than $200.

What days are nonstop flights available from Chicago to Madison?

You can find nonstop flights on the following days: Sunday, Monday, Tuesday, Thursday, Friday, Saturday.

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

On average, you can expect to see 26 flights from Chicago to Madison a day.
Morning (6am - Noon) - 38% of flight departures
Afternoon (Noon - 6pm) - 38% of flight departures
Evening (6pm - Midnight) - 23% of flight departures

How long is the flight from Chicago to Madison?

There are many flights that can get you from Chicago to Madison in 58m. Fly via United Airlines or American Airlines to get the fastest option. The distance between Chicago and Madison is about 109 mi. All flights are typically nonstop.

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

Cheapflights users have booked flights from Chicago to Madison round-trip from $108. Another airline that can offer you cheap pricing is American Airlines. You may be able to fly from Chicago to Madison for 59% less than the average price by searching for these airlines.

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

$78 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on United Airlines and American Airlines, with prices starting from $163 and $187, respectively.

What are the most popular airlines that fly from Chicago to Madison?

Before booking your flight from Chicago to Madison check out the most popular airlines for this route: Bus, American Airlines or United Airlines.

What are the most reliable airlines from Chicago to Madison?

No one likes to see their flight delayed. When booking a flight from Chicago to Madison consider choosing Piedmont Airlines (90%), GoJet (85%) or Lufthansa (83%) as they are the most reliable in getting you off to your destination on time.

What are the cheapest flights from Chicago to Madison?

On average you can expect to pay $426 for a flight from Chicago to Madison. The cheapest flight overall is $143 while the most popular route, (Chicago O'Hare Intl - Madison Truax Field) is currently priced at $113.

Alternative routes for Chicago to Madison

See prices for flight routes from nearby airports that may be better suited for you.

Top 2 airlines flying from Chicago to Madison

The chart below displays the airlines Cheapflights users traveling from Chicago to Madison choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
United AirlinesCheapest$136Average$266FlexibilityNo cancel feeOn-time69%COVID-19 safety
Search United Airlines flights
American AirlinesCheapest$175Average$246FlexibilityNo cancel feeOn-time71%COVID-19 safety
Search American Airlines flights

Hourly flight availability from Chicago to Madison

See what time of day planes typically take off from Chicago to Madison
1%of flight departuresEarly morningMidnight to 6 am
47%of flight departuresMorning6 am to noon
39%of flight departuresAfternoonNoon to 6 pm
13%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Weekly flight availability from Chicago to Madison

See how many times per day planes take to the skies headed from Chicago to Madison
Sunday12daily flights
Monday27daily flights
Tuesday24daily flights
Wednesday27daily flights
Thursday21daily flights
Friday18daily flights
Saturday10daily flights
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