Cheap flights from Michigan to Chicago from $59

The month of September is, on average, the cheapest month to fly to Chicago from Michigan, with most prices found around $151. If you’re not able to fly to Chicago in September, then August is your next best option. Flight prices from Michigan to Chicago during August average around $163.

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $524. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Michigan to Chicago for around $720.

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Michigan to Chicago during this time can be as low as $512. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $881.

Fly from Detroit Metropolitan Wayne County to Chicago Midway for the best Michigan - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Michigan when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $279 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Michigan for as low as $111 on momondo.

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

Delta, United Airlines, and Denver Air Connection are the most popular carriers operating from Michigan to Chicago

United Airlines, American Airlines and Delta are the top three most popular airlines that fly to Chicago from Michigan according to our data. United Airlines is the first choice among our users, with 45% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 4 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

As of April 2026, there are 153 flights per day flying from Michigan to Chicago. The most common time of day flights depart is 5:00PM, with 43% of flights taking off in the afternoon.

As of April 2026, 1,074 flights take off from Michigan and land in Chicago each week. The most common flight departure day for this route is Wed, with 20% of weekly flights taking off on this day.