Cheap flights from Chicago to Madison from $155

The month of December is, on average, the cheapest month to fly to Madison from Chicago, with most prices found around $288. If you’re not able to fly to Madison in December, then November is your next best option. Flight prices from Chicago to Madison during November average around $368.

The cheapest day to depart from Chicago to Madison is on a Friday when prices can be found for as low as $309. Be sure to avoid booking your departure on a Tuesday as prices are generally higher than usual. According to our data, the average ticket price to Madison on Tuesday is $552.

According to our data, the cheapest time of day to fly to Madison is in the afternoon. momondo users have found flights departing from Chicago to Madison in the afternoon for as low as $476. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In contrast, the most expensive time of day to depart to Madison is in the morning when prices are around $516.

Fly from Chicago O'Hare Intl to Madison Truax Field for the best Chicago - Madison Truax Field flight prices

There are 4 cabin classes available to choose from on Chicago to Madison flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Historically, on average around 19% of flights between Chicago and Madison have experienced a delay on any given week. The average delay length over the past 12 months has been 116 minutes.

Generally, flights departing in the morning tend to experience fewer delays. Flights at night have, in the past, seen delays more frequently in comparison.

Saturday is statistically the day of the week which experiences the fewest number of delays on this flight route. Friday has historically seen more delays on average compared to the rest of the week.

According to our data, American Airlines have had the least number of delays on this route over the last 12 months; with about 19% of their flights experiencing any sort of delay.

As of November 2026, there are 40 flights per day flying from Chicago to Madison. The most common time of day flights depart is 10:00PM, with 41% of flights taking off in the afternoon.

As of November 2026, there are 281 flights per week flying from Chicago to Madison. The most common day of the week flights depart is Mon, with 20% of flights taking off on this day.