Cheap flights from Illinois to Aspen from $161

The month of September is, on average, the cheapest month to fly to Aspen from Illinois, with most prices found around $382. If you aren’t able to travel to Aspen during the month of September, then flying in August is also cheap. Prices for this month can be found on momondo for an average of $421.

The cheapest day to depart from Illinois to Aspen is on a Tuesday when prices can be found for as low as $359. The most expensive day to fly to Aspen is Thursday, with ticket prices averaging around $620.

At noon is the cheapest time of day to fly from Illinois to Aspen when you can find flight prices for as low as $439. Flying to Aspen at noon is an ideal time because this is during off-peak travel hours. Try not to purchase tickets in the afternoon because they tend to be around $540. Of course, these prices can vary depending on the time of year and what airport you fly to.

Fly from Chicago O'Hare Intl to Aspen Pitkin County for the best Illinois - Aspen Pitkin County flight prices

You are more likely to see cheaper flights to Aspen from Illinois when booking weeks ahead of your departure date. In general, you can expect to find flights to Aspen for around $462 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Aspen from Illinois for as low as $354 on momondo.

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

As of February 2026, 7 flights take off from Illinois and land in Aspen each day. The most common flight departure time for this route is 3:00PM, with 50% of daily flights taking off at noon.

As of February 2026, 54 flights take off from Illinois and land in Aspen each week. The most common flight departure day for this route is Mon, with 15% of weekly flights taking off on this day.