Cheap flights from Chicago O'Hare Intl Airport to Madison from $106

The month of December is, on average, the cheapest month to fly to Madison from Chicago O'Hare Intl Airport, with most prices found around $0. If you’re not able to fly to Madison in December, then September is your next best option. Flight prices from Chicago O'Hare Intl Airport to Madison during September average around $239.

The cheapest day to depart from Chicago O'Hare Intl Airport to Madison is on a Friday when prices can be found for as low as $239. 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 $542.

According to our data, the cheapest time of day to fly to Madison is in the evening. momondo users have found flights departing from Chicago O'Hare Intl Airport to Madison in the evening for as low as $460. 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 afternoon when prices are around $470.

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

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

As of August 2026, prices for Chicago O'Hare Intl Airport to Madison flights are approximately 112% more expensive when compared to flights at the same time last year.

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, United 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.

The number of flights available between Chicago O'Hare Intl Airport and Madison is 32 per day as of August 2026. The most frequent departure time is 5:00PM, with 49% of daily flights leaving in the afternoon.

As of August 2026, 229 flights take off from Chicago O'Hare Intl Airport and land in Madison each week. The most common flight departure day for this route is Fri, with 20% of weekly flights taking off on this day.