Cheap flights from Detroit to Chicago from $99

The month of December is, on average, the cheapest month to fly to Chicago from Detroit, with most prices found around $262. If you’re not able to fly to Chicago in December, then April is your next best option. Flight prices from Detroit to Chicago during April average around $308.

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $532. 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 Detroit to Chicago for around $790.

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Detroit to Chicago during this time can be as low as $547. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $1,019.

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

You are more likely to see cheaper flights to Chicago from Detroit when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $365 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Detroit for as low as $199 on momondo.

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

Southwest, Delta, and United Airlines are the most popular carriers operating from Detroit to Chicago

Delta, United Airlines and American Airlines are the top three most popular airlines that fly to Chicago from Detroit according to our data. Delta is the first choice among our users, with 53% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

The number of flights available between Detroit and Chicago is 52 per day as of October 2026. The most frequent departure time is 4:00PM, with 50% of daily flights leaving in the afternoon.

The number of flights available between Detroit and Chicago is 370 per week as of October 2026. The most frequent departure day is Wed, with 26% of weekly flights leaving on this day.