Cheap flights from Milwaukee to Chicago from $97

The month of November is, on average, the cheapest month to fly to Chicago from Milwaukee, with most prices found around $0. If you’re not able to fly to Chicago in November, then July is your next best option. Flight prices from Milwaukee to Chicago during July average around $0.

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $431. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Milwaukee to Chicago for around $528.

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Milwaukee to Chicago during this time can be as low as $438. In contrast, the most expensive time of day to depart to Chicago is in the evening when prices are around $771.

Fly from Milwaukee-Mitchell to Chicago Midway for the best Milwaukee-Mitchell - Chicago flight prices

Historically, on average around 14% of flights between Milwaukee and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 123 minutes.

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

Tuesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday 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 11% of their flights experiencing any sort of delay.

As of September 2026, 38 flights take off from Milwaukee and land in Chicago each day. The most common flight departure time for this route is 1:00PM, with 49% of daily flights taking off at noon.

As of September 2026, 269 flights take off from Milwaukee and land in Chicago each week. The most common flight departure day for this route is Fri, with 22% of weekly flights taking off on this day.