Cheap flights from Milwaukee to Chicago from $125

According to our data, Saturday is the cheapest day to fly to Chicago Midway Airport from Milwaukee. The lowest ticket price found for a Saturday departure recently was $402. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Milwaukee because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $436.

Flying to Chicago Midway Airport from Milwaukee at noon is the least expensive time of day to depart. momondo users have found prices as low as $385 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $421. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

There is only 1 cabin class available to choose from on Milwaukee to Chicago Midway Airport 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 23% 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 98 minutes.

Generally, flights departing at night tend to experience fewer delays. Flights in the evening 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. Thursday has historically seen more delays on average compared to the rest of the week.

According to our data, Southwest have had the least number of delays on this route over the last 12 months; with about 23% of their flights experiencing any sort of delay.

As of October 2026, 1 flights take off from Milwaukee and land in Chicago Midway Airport each day. The most common flight departure time for this route is 5:00AM, with 50% of daily flights taking off in the afternoon.

10 flights are operational weekly from Milwaukee to Chicago Midway Airport as of October 2026. The most popular departure day for this route is Mon, with 20% of flights per week taking off on this day.