Cheap flights from Denver to Chicago from $99

The month of December is, on average, the cheapest month to fly to Chicago Midway Airport from Denver, with most prices found around $240. If you are unable to visit Chicago Midway Airport during the month of December, then departing from Denver during the month April is also very affordable. Most momondo users find prices during this month for around $275.

According to our data, Friday is the cheapest day to fly to Chicago Midway Airport from Denver. The lowest ticket price found for a Friday departure recently was $347. 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 Denver because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $458.

Flying to Chicago Midway Airport from Denver in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $344 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $466. Of course, these prices can vary depending on the time of year and what airport you fly to.

Fly from Denver Intl to Chicago Midway for the best Denver Intl - Chicago Midway flight prices

You are more likely to see cheaper flights to Chicago Midway Airport from Denver when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $331 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Denver for as low as $217 on momondo.

There is only 1 cabin class available to choose from on Denver 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.

You could potentially save up to 13% on your flight if you consider stops on a Denver to Chicago Midway Airport flight.

As of November 2026, prices for Denver to Chicago Midway Airport flights are approximately 106% more expensive when compared to flights at the same time last year.

The number of flights available between Denver and Chicago Midway Airport is 3 per day as of November 2026. The most frequent departure time is 10:00AM, with 54% of daily flights leaving at noon.

As of November 2026, 22 flights take off from Denver and land in Chicago Midway Airport each week. The most common flight departure day for this route is Mon, with 27% of weekly flights taking off on this day.