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

MSN — CHI
Oct 11 — Oct 181

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

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 2022: compare Madison to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.

MSN - CHI

Price

$79 - $483

CHI

Temperature

23 - 73.4 °F

CHI

Rainfall

1.7 - 4.9 inches

Popular inNovemberHigh demand for flights, 38% potential price rise
Cheapest inFebruaryBest time to find cheap flights, 74% potential price drop
Average price$327Average for round-trip flights in October 2022
Round-trip from$79From Madison Truax Field to Chicago (CHI)

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 Sunday. 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 46 days before your planned departure. Booking around this time can save you about 81% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $294 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $439.

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 $300. You can even find prices in February for less than $300, as users have found deals to Chicago from as low as $60. The month of November 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 61%.

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 34% on your trip compared to booking a flight at noon.

Cheap flights from Madison to Chicago in October, November 2022

The best prices found for MSN to CHI flights for October, November
Nov 11 - Nov 13
MSN

Madison Truax Field

ORD

Chicago O'Hare Intl

Nonstop

0h 57m
ORD

Chicago O'Hare Intl

MSN

Madison Truax Field

Nonstop

0h 55m
$168

United Airlines

Pick Dates

Deal found 10/4/22

Nov 30 - Jan 31
MSN

Madison Truax Field

ORD

Chicago O'Hare Intl

1 stop

7h 18m
ORD

Chicago O'Hare Intl

MSN

Madison Truax Field

Nonstop

1h 07m
$175

American Airlines

Pick Dates

Deal found 10/3/22

Oct 21 - Oct 26
MSN

Madison Truax Field

ORD

Chicago O'Hare Intl

Nonstop

0h 59m
ORD

Chicago O'Hare Intl

MSN

Madison Truax Field

Nonstop

1h 01m
$193

United Airlines

Pick Dates

Deal found 10/5/22

Madison to Chicago 2022 flight deals

Cheap flights to Chicago from Madison found for this year
Nov 11 - Nov 13
MSN

Madison Truax Field

ORD

Chicago O'Hare Intl

Nonstop

0h 57m
ORD

Chicago O'Hare Intl

MSN

Madison Truax Field

Nonstop

0h 55m
$168

United Airlines

Pick Dates

Deal found 10/4/22

Nov 30 - Jan 31
MSN

Madison Truax Field

ORD

Chicago O'Hare Intl

1 stop

7h 18m
ORD

Chicago O'Hare Intl

MSN

Madison Truax Field

Nonstop

1h 07m
$175

American Airlines

Pick Dates

Deal found 10/3/22

Oct 21 - Oct 26
MSN

Madison Truax Field

ORD

Chicago O'Hare Intl

Nonstop

0h 59m
ORD

Chicago O'Hare Intl

MSN

Madison Truax Field

Nonstop

1h 01m
$193

United Airlines

Pick Dates

Deal found 10/5/22

Cheap American Airlines flights from Madison to Chicago

Nov 30 - Jan 31
MSN

Madison Truax Field

ORD

Chicago O'Hare Intl

1 stop

7h 18m
ORD

Chicago O'Hare Intl

MSN

Madison Truax Field

Nonstop

1h 07m
$175

American Airlines

Pick Dates

Deal found 10/3/22

Jan 25 - Feb 1
MSN

Madison Truax Field

ORD

Chicago O'Hare Intl

1 stop

4h 50m
ORD

Chicago O'Hare Intl

MSN

Madison Truax Field

1 stop

6h 39m
$183

American Airlines

Pick Dates

Deal found 10/5/22

Nov 30 - Jan 31
MSN

Madison Truax Field

ORD

Chicago O'Hare Intl

1 stop

7h 18m
ORD

Chicago O'Hare Intl

MSN

Madison Truax Field

1 stop

6h 39m
$199

American Airlines

Pick Dates

Deal found 10/3/22

Cheap United Airlines flights from Madison to Chicago

Nov 11 - Nov 13
MSN

Madison Truax Field

ORD

Chicago O'Hare Intl

Nonstop

0h 57m
ORD

Chicago O'Hare Intl

MSN

Madison Truax Field

Nonstop

0h 55m
$168

United Airlines

Pick Dates

Deal found 10/4/22

Oct 21 - Oct 26
MSN

Madison Truax Field

ORD

Chicago O'Hare Intl

Nonstop

0h 59m
ORD

Chicago O'Hare Intl

MSN

Madison Truax Field

Nonstop

1h 01m
$193

United Airlines

Pick Dates

Deal found 10/5/22

Oct 21 - Oct 23
MSN

Madison Truax Field

ORD

Chicago O'Hare Intl

Nonstop

0h 59m
ORD

Chicago O'Hare Intl

MSN

Madison Truax Field

Nonstop

1h 00m
$218

United Airlines

Pick Dates

Deal found 10/4/22

Non-stop flights to Chicago from Madison

Save time with Madison to Chicago direct flight deals
Nov 11 - Nov 13
MSN

Madison Truax Field

ORD

Chicago O'Hare Intl

Nonstop

0h 57m
ORD

Chicago O'Hare Intl

MSN

Madison Truax Field

Nonstop

0h 55m
$168

United Airlines

Pick Dates

Deal found 10/4/22

Oct 21 - Oct 26
MSN

Madison Truax Field

ORD

Chicago O'Hare Intl

Nonstop

0h 59m
ORD

Chicago O'Hare Intl

MSN

Madison Truax Field

Nonstop

1h 01m
$193

United Airlines

Pick Dates

Deal found 10/5/22

Oct 21 - Oct 23
MSN

Madison Truax Field

ORD

Chicago O'Hare Intl

Nonstop

0h 59m
ORD

Chicago O'Hare Intl

MSN

Madison Truax Field

Nonstop

1h 00m
$218

United Airlines

Pick Dates

Deal found 10/4/22

Last minute flights from Madison to Chicago

Late deals on return flights to Chicago from Madison, departing today and this week
Oct 11 - Nov 3
MSN

Madison Truax Field

ORD

Chicago O'Hare Intl

Nonstop

1h 04m
ORD

Chicago O'Hare Intl

MSN

Madison Truax Field

Nonstop

0h 55m
$252

United Airlines

Pick Dates

Deal found 10/4/22

Oct 15 - Oct 22
MSN

Madison Truax Field

ORD

Chicago O'Hare Intl

Nonstop

1h 01m
ORD

Chicago O'Hare Intl

MSN

Madison Truax Field

Nonstop

1h 01m
$258

United Airlines

Pick Dates

Deal found 10/6/22

Oct 15 - Oct 22
MSN

Madison Truax Field

ORD

Chicago O'Hare Intl

Nonstop

0h 59m
ORD

Chicago O'Hare Intl

MSN

Madison Truax Field

1 stop

6h 22m
$267

American Airlines

Pick Dates

Deal found 10/6/22

One-way flights to Chicago from Madison

The cheapest one-way flights from Madison to Chicago
Oct 24
MSN

Madison Truax Field

ORD

Chicago O'Hare Intl

2 stops

19h 29m
$131

Multiple Airlines

Pick Dates

Deal found 10/4/22

Jan 11
MSN

Madison Truax Field

ORD

Chicago O'Hare Intl

1 stop

7h 27m
$132

Multiple Airlines

Pick Dates

Deal found 10/5/22

Oct 24
MSN

Madison Truax Field

ORD

Chicago O'Hare Intl

2 stops

19h 29m
$161

Multiple Airlines

Pick Dates

Deal found 10/5/22

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 25 outbound flights to Chicago per day. 4 airlines have flights to Chicago from Madison Truax Field on a regular basis.

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

Some of our airline partners flying from Madison Truax Field to Chicago 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 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 United Airlines for just $168, but on average you can expect to pay $246.

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

Cheapflights has at least 14 direct flights from Madison to Chicago under $200. A good price for a nonstop flight from Madison to Chicago is less than $345.

Are there last-minute flights available from Madison to Chicago for under $300?

There are currently 15+ open flights from Madison to Chicago within the next 7 days for less than $300.

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

According to our current data, United Airlines ($168), and American Airlines ($175) offers the cheapest pricing from Madison to Chicago. United Airlines is priced at 43% lower than the current average price of a flight leaving 3 months from now.

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

Train, Bus and American Airlines are the most popular airlines when flying from Madison to Chicago.

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 Japan Airlines (95%), Republic Airways (93%) or Qatar Airways (92%) 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 $216, our data indicates the cheapest price to be $184. The most popular route (Madison Truax Field - Chicago O'Hare Intl), is priced around $168.

Alternative routes for Madison to Chicago

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

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-timeCOVID-19 safety
United AirlinesCheapest$137Average$222FlexibilityNo cancel feeOn-time69%COVID-19 safety
Search United Airlines flights
American AirlinesCheapest$187Average$355FlexibilityNo cancel feeOn-time71%COVID-19 safety
Search American Airlines flights

Hourly flight availability from Madison to Chicago

See what time of day planes typically take off from Madison to Chicago
19%of flight departuresEarly morningMidnight to 6 am
56%of flight departuresMorning6 am to noon
25%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
Sunday22daily flights
Monday28daily flights
Tuesday27daily flights
Wednesday29daily flights
Thursday27daily flights
Friday26daily flights
Saturday22daily flights