Cheap flights from Colorado to Chicago from $99

The month of April is, on average, the cheapest month to fly to Chicago Midway Airport from Colorado, with most prices found around $275. If you are unable to visit Chicago Midway Airport during the month of April, then departing from Colorado during the month January is also very affordable. Most momondo users find prices during this month for around $288.

According to our data, Friday is the cheapest day to fly to Chicago Midway Airport from Colorado. 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 Colorado 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 Colorado 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 Colorado - Chicago Midway flight prices

You are more likely to see cheaper flights to Chicago Midway Airport from Colorado 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 Colorado for as low as $217 on momondo.

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

As of November 2026, there are 3 flights per day flying from Colorado to Chicago Midway Airport. The most common time of day flights depart is 10:00AM, with 50% of flights taking off at noon.

As of November 2026, 22 flights take off from Colorado 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.