Cheap flights from Milwaukee to Chicago from $72

The month of October is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Milwaukee averaging around $179.

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Friday when prices can be found for as low as $434. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday 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 $531.

Flying to Chicago O'Hare Intl Airport from Milwaukee in the morning is the least expensive time of day to depart. momondo users have found prices as low as $435 when looking at flights departing in the morning. Try not to purchase tickets in the evening because they tend to be around $674. Of course, these prices can vary depending on the time of year and what airport you fly to.

Fly from Milwaukee-Mitchell to Chicago O'Hare Intl for the best Milwaukee-Mitchell - Chicago O'Hare Intl flight prices

There are 4 cabin classes available to choose from on Milwaukee-Mitchell to Chicago O'Hare Intl 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 12% 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 122 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, SkyWest 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 March 2026, there are 31 flights per day flying from Milwaukee to Chicago O'Hare Intl Airport. The most common time of day flights depart is 2:00PM, with 44% of flights taking off at noon.

As of March 2026, there are 217 flights per week flying from Milwaukee to Chicago O'Hare Intl Airport. The most common day of the week flights depart is Thu, with 25% of flights taking off on this day.