Cheap flights from Detroit to Chicago from C$ 132

The month of November is another great option to travel to Chicago, with average flight prices from Detroit averaging around C$ 378.

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as C$ 935. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Friday because tickets tend to average around C$ 1,203. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

In the evening is the cheapest time of day to fly from Detroit to Chicago when you can find flight prices for as low as C$ 630. Flying to Chicago in the evening is an ideal time because this is during off-peak travel hours. In the afternoon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 1,453 per ticket.

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 C$ 485 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 C$ 260 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.

You could potentially save up to 45% on your flight if you consider stops on a Detroit to Chicago flight.

As of September 2026, prices for Detroit to Chicago flights are approximately 370% more expensive when compared to flights at the same time last year.

77 flights are operational daily from Detroit to Chicago as of September 2026. The most popular departure time for this route is 12:00p.m., with 48% of flights per day taking off in the afternoon.

As of September 2026, 541 flights take off from Detroit and land in Chicago each week. The most common flight departure day for this route is Thu, with 17% of weekly flights taking off on this day.