Price observed over the last 3 months for a round trip.
Compare all flight tickets and find cheap flights from Chicago to Madison
The cheapest flights right now
Chicago – Madison
Outbound – Nov 5, 2026
direct
1h 16m Return – Nov 9, 2026
direct
1h 14m $309
yesterday
Chicago – Madison
Outbound – Nov 6, 2026
direct
1h 2m Return – Nov 8, 2026
direct
1h 16m $415
yesterday
* Prices are in USD per passenger, including taxes, for a round trip. Prices are based on searches carried out within the last 72 hours. Please note that availability and ticket prices are subject to change and should not be considered as the final price quoted.
Cheapest flight tickets
$244
Average price of a round trip
$273
Average flight ticket price recorded over the last 3 months for a round trip.
Flight duration
1h9
A flight from Chicago to Madison takes on average 1h9.
Best time
August
According to user searches, the ideal month to go to Madison is August.
The best flight deals for a weekend
Chicago – Madison
Outbound – Nov 5, 2026
direct
1h 16m Return – Nov 9, 2026
direct
1h 14m $309
yesterday
Chicago – Madison
Outbound – Nov 6, 2026
direct
1h 2m Return – Nov 8, 2026
direct
1h 16m $415
yesterday
* Prices are in USD per passenger, including taxes, for a round trip. Prices are based on searches carried out within the last 72 hours. Please note that availability and ticket prices are subject to change and should not be considered as the final price quoted.
Tips for finding a cheap flight from Chicago to Madison
Check out our tips for booking your flight to Madison (USA) from Chicago (USA) at the cheapest possible price.
Usually, the cheapest month to pick up a ticket on this route is September, with an average flight ticket price of $273 (calculation over the last two years). The most touristic season corresponds to the months of September, October and November.
For the cheapest flights, it is advisable to buy your ticket at least 24 days before the departure date.
The airline offering the cheapest flight tickets is American Airlines. A ticket from the airline American Airlines to Madison costs on average $265.
The airlines that offer the most flights are American Airlines, United Airlines and American Airlines.
Price of flight tickets from Chicago to Madison
Here is some information and tips to know before booking your flight:
- Flight ticket prices range from $244 to $313
- The average price of a flight ticket is about $273
- Prices are lowest for stays in the month of September
- The month in which booking a ticket is cheaper is: September
info departure city :
Chicago, USA
airports :
Chicago-Merrill C. Meigs Field Airport (CGX)
Chicago FSS (CHI)
Chicago-Midway International Airport (MDW)
Chicago-O'Hare International Airport (ORD)
local time :
Chicago is a city in the country USA, the time zone is [[timezone]]. In Chicago, it is currently {fromLocalTime}, the temperature is on average 16°C, with a minimum of 15°C and a maximum of 18°C.
The city of Chicago (CHI) has 4 airport(s): Chicago-Merrill C. Meigs Field, Chicago FSS, Chicago-Midway and Chicago-O'Hare
destination info :
Madison, USA
airport :
Dane County-Truax Field Regional Airport (MSN)
local time :
Madison is in the country USA, the time zone is [[timezone]]. In Madison, it is currently {toLocalTime}, the temperature is on average 12°C, with a minimum of 10°C and a maximum of 13°C.
The city of Madison has 1 airport(s): Dane County-Truax Field
Useful info about Madison
What is the least touristic period to go to Madison?
If you want to visit Madison during the least touristic period, choose the month of August.
What is the most popular time to travel to Madison?
In Madison, the most popular month is September. It is during this period that the prices offered by airlines are also the highest.
When should I book my flight from Chicago to Madison?
According to our data, it is recommended to book your flight 24 days before your departure. If you book your flight ticket 4 weeks before your departure, you may find a price below average. The cheapest day to book a flight from Chicago to Madison is Thursday.
What are the arrival and destination airports when traveling between Chicago and Madison?
When you leave, you can leave from Chicago-O'Hare, and you will arrive at Dane County-Truax Field.
How to reach Chicago airport from the city centre?
The airport Chicago-Merrill C. Meigs Field is located 4 km, Chicago FSS is located 29 km, Chicago-Midway is located 12 km or Chicago-O'Hare is located 29 km from the city centre. You can access it by using public transportation, taking a taxi, or renting a car.
Are there other means of transportation to go from Chicago to Madison?
Airplane is the only means of transportation listed on Liligo for this journey.
Are there big differences in weather between Chicago and Madison?
In summer, the average temperature is 21°C in Madison and 22°C in Chicago. The average rainfall in summer is 118 mm in Madison and 145 mm in Chicago. In summer, it is warmer in Chicago and it rains less in Madison. In winter, it is colder in Chicago and it rains more in Chicago.
