Cheap flights from Chicago to Colorado Springs from $108

The month of November is another great option to travel to Colorado Springs, with average flight prices from Chicago averaging around $139.

The cheapest day to depart from Chicago to Colorado Springs is on a Wednesday when prices can be found for as low as $328. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Chicago to Colorado Springs for around $421.

Flying to Colorado Springs from Chicago in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $274 when looking at flights departing in the afternoon. Flights to Colorado Springs are more costly in the evening, with an average ticket price of $394. Departure times in the evening fall within the peak daily travel times, which is why tickets can be more expensive.

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

You are more likely to see cheaper flights to Colorado Springs from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Colorado Springs for around $356 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Colorado Springs from Chicago for as low as $244 on momondo.

There are 4 cabin classes available to choose from on Chicago to Colorado Springs 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 26% on your flight if you consider stops on a Chicago to Colorado Springs flight.

As of July 2026, prices for Chicago to Colorado Springs flights are approximately 39% more expensive when compared to flights at the same time last year.

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

United Airlines, American Airlines and Frontier are the top three most popular airlines that fly to Colorado Springs from Chicago according to our data. United Airlines is the first choice among our users, with 36% of people opting to fly with this airline when traveling to Colorado Springs. Keep in mind that there are 6 different airlines that fly to Colorado Springs on a routine basis, so you have a few additional options to choose from.

As of July 2026, 5 flights take off from Chicago and land in Colorado Springs each day. The most common flight departure time for this route is 7:00PM, with 58% of daily flights taking off in the evening.

As of July 2026, there are 39 flights per week flying from Chicago to Colorado Springs. The most common day of the week flights depart is Mon, with 15% of flights taking off on this day.