Cheap flights from Denver to Chicago from $106

The month of January is, on average, the cheapest month to fly to Chicago from Denver, with most prices found around $231. If you’re not able to fly to Chicago in January, then November is your next best option. Flight prices from Denver to Chicago during November average around $247.

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $330. 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 Denver to Chicago for around $547.

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Denver to Chicago during this time can be as low as $261. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $550.

Fly from Denver Intl to Chicago O'Hare Intl for the best Denver Intl - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Denver when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $299 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Denver for as low as $225 on momondo.

There are 4 cabin classes available to choose from on Denver 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 8% on your flight if you consider stops on a Denver to Chicago flight.

As of September 2026, prices for Denver to Chicago flights are approximately 77% more expensive when compared to flights at the same time last year.

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

United Airlines, American Airlines and Frontier are the top three most popular airlines that fly to Chicago from Denver according to our data. United Airlines is the first choice among our users, with 41% 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.

As of September 2026, there are 57 flights per day flying from Denver to Chicago. The most common time of day flights depart is 9:00AM, with 45% of flights taking off in the afternoon.

The number of flights available between Denver and Chicago is 403 per week as of September 2026. The most frequent departure day is Fri, with 21% of weekly flights leaving on this day.