Cheap flights from Madison to Chicago (MSN - CHI)

Know your dates, get live prices in seconds:

From
To
Depart
Return
Any month
Compare vs. Cheapflights |
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime

We work with more than 300 partners to bring you better travel deals

The best prices from Madison Truax Field to Chicago are usually found in August or July, booked 29 days in advance, depart on a Saturday or Tuesday and return on a Wednesday

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
$73 - $377
CHI
Temperature
23 - 73.4 °F
CHI
Precipitation
1.7 - 4.9 inches

Popular in

April

High demand for flights, 42% potential price rise

Cheapest in

August

Best time to find cheap flights, 67% potential price drop

Average price

$229

Average for round-trip flights in January 2022

Round-trip from

$73

From Madison Truax Field to Chicago (CHI)

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
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 Saturday. 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.

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 evening. If you’re flexible enough to do this you can expect to save up to 26% on your trip compared to booking a flight in the afternoon.

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

The best pricing can be found in the month of August. Prices to Chicago from Madison average $218. You can even find prices in August for less than $218, as users have found deals to Chicago from as low as $31. The month of April 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 72%.

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 29 days before your planned departure. Booking around this time can save you about 34% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $283 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $308.

Cheap flights from Madison to Chicago in January, February 2022

The best prices found for MSN to CHI flights for January, February
17 Feb - 21 Feb
$78pp
MSN
Madison Truax Field
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
MSN
Madison Truax Field
13 Feb - 15 Feb
$88pp
MSN
Madison Truax Field
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
MSN
Madison Truax Field
17 Feb - 21 Feb
$161pp
MSN
Madison Truax Field
United Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
MSN
Madison Truax Field

Madison Truax Field to Chicago 2022 flight deals

Cheap flights to Chicago from Madison found for this year
17 Feb - 21 Feb
$78pp
MSN
Madison Truax Field
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
MSN
Madison Truax Field
13 Feb - 15 Feb
$88pp
MSN
Madison Truax Field
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
MSN
Madison Truax Field
17 Feb - 21 Feb
$161pp
MSN
Madison Truax Field
United Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
MSN
Madison Truax Field

Non-stop flights to Chicago from Madison

Save time with Madison to Chicago direct flight deals
17 Feb - 21 Feb
$78pp
MSN
Madison Truax Field
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
MSN
Madison Truax Field
13 Feb - 15 Feb
$88pp
MSN
Madison Truax Field
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
MSN
Madison Truax Field
19 Feb - 19 Feb
$174pp
MSN
Madison Truax Field
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
MSN
Madison Truax Field

Last minute flights from Madison to Chicago

Late deals on round-trip flights to Chicago from Madison, departing today and this week
4 Feb - 7 Feb
$219pp
MSN
Madison Truax Field
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
   
2 STOPS
MSN
Madison Truax Field
4 Feb - 7 Feb
$220pp
MSN
Madison Truax Field
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
   
2 STOPS
MSN
Madison Truax Field
4 Feb - 7 Feb
$232pp
MSN
Madison Truax Field
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
MSN
Madison Truax Field

One-way flights to Chicago from Madison

The cheapest one-way flights from Madison to Chicago
12:20 pm - 5:36 am
United Airlines
1 Stop
17h 16m
MSN - ORD
United Airlines
$218
United
9:05 am - 6:00 pm
Frontier
2 Stops
32h 55m
MSN - ORD
Frontier
$275
Kiwi.com
5:45 am - 6:46 am
American Airlines
Nonstop
1h 01m
MSN - ORD
American Airlines

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Madison</span> to <span class="emphasized">Chicago</span> flights.

Flight FAQs

From Madison to Chicago

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 13 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. American Airlines, United 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 American Airlines with this kind of flexibility.

Can I find flights from Madison to Chicago for under $100 on Cheapflights?

Yes, there are multiple flights from Madison to Chicago for under $100. The cheapest flight booked recently is on United Airlines for just $78, but on average you can expect to pay $196.

Are there nonstop flights from Madison to Chicago for under $100 on Cheapflights?

Cheapflights has at least 13 direct flights from Madison to Chicago under $100. A good price for a nonstop flight from Madison to Chicago is less than $260.

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

There are currently 17+ open flights from Madison to Chicago within the next 7 days for less than $300.

What days are nonstop flights available from Madison to Chicago?

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

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

On average, you can expect to see 33 flights from Madison to Chicago a day.
Early Morning (Midnight to 6am) - 30% of flight departures
Morning (6am - Noon) - 36% of flight departures
Afternoon (Noon - 6pm) - 33% 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. Fly via United Airlines or American 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, United Airlines ($78), and American Airlines ($218) offers the cheapest pricing from Madison to Chicago. United Airlines is priced at 64% 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 $39 on United Airlines. Other airlines that offer cheap prices include American Airlines from $49 and Frontier from $275 one-way.

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 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 $24. The most popular route (Madison Truax Field - Chicago O'Hare Intl), is priced around $180.

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 (100%), Iberia (94%) or GoJet (92%) as they are the most reliable in getting you off to your destination on time.

COVID Restrictions

View COVID Travel Restrictions for Chicago, IL

Do I need a COVID test to fly to Chicago from Madison?

Information is based on travel restrictions for travel to Chicago within the United States

Most visitors from Madison Truax Field need to provide a negative COVID-19 test result and/or quarantine to enter Chicago.

COVID-19 testing requirements
Visitors from Madison Truax Field must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 24 hours before departing to Chicago.

Quarantine requirements
Visitors from Madison Truax Field are not required to quarantine after entering Chicago.

Do I need a test to fly back to Madison from Chicago?

Returning to Madison Truax Field from Chicago

COVID-19 testing requirements
Visitors from Chicago must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 24 hours before departing to Madison Truax Field.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering Madison Truax Field.

Hide COVID Travel Restrictions for Chicago, IL

Alternative routes for Madison to Chicago

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

Destination information for Chicago

Things to know before you go - useful duration and weather info for your trip from Madison to Chicago.
Flight duration from MSN to Chicago
1h 02m
Average temperature for January in Chicago
33.8 °F
Avg rainfall for January in Chicago
0.7 ″

Airports servicing Madison

Airports servicing Chicago

Midway (MDW)
Rockford (RFD)

Hourly flight availability from Madison to Chicago

See what time of day planes typically take off from Madison towards Chicago.
Morning 6 AM to noon 51% of MSN to CHI departures
Afternoon Noon to 6 PM 36% of MSN to CHI departures
Early morning Midnight to 6 AM 13% of MSN to CHI departures
Evening 6 PM to midnight 0% of MSN to CHI departures
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.
Sunday
6 daily flights
Monday
17 daily flights
Tuesday
21 daily flights
Wednesday
18 daily flights
Thursday
14 daily flights
Friday
14 daily flights
Saturday
6 daily flights
Home North America USA Illinois Chicago Cheap flights from Madison to Chicago