Cheap flights from Colorado Springs to Chicago from $128

The month of October is, on average, the cheapest month to fly to Chicago from Colorado Springs, with most prices found around $149. If you’re not able to fly to Chicago in October, then May is your next best option. Flight prices from Colorado Springs to Chicago during May average around $179.

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $418. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Colorado Springs to Chicago for around $545.

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Colorado Springs to Chicago during this time can be as low as $443. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $498.

Fly from Colorado Springs to Chicago Midway for the best Colorado Springs - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Colorado Springs when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $369 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Colorado Springs for as low as $225 on momondo.

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

No. A direct flight is the cheapest option for a flight between Colorado Springs to Chicago.

As of June 2026, prices for Colorado Springs to Chicago flights are approximately 36% more expensive when compared to flights at the same time last year.

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

United Airlines, American Airlines and Frontier are the top three most popular airlines that fly to Chicago from Colorado Springs according to our data. United Airlines is the first choice among our users, with 35% 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 June 2026, 5 flights take off from Colorado Springs and land in Chicago each day. The most common flight departure time for this route is 12:00PM, with 56% of daily flights taking off in the afternoon.

As of June 2026, there are 41 flights per week flying from Colorado Springs to Chicago. The most common day of the week flights depart is Thu, with 17% of flights taking off on this day.