Cheap flights from Illinois to Aspen from $207

The month of May is, on average, the cheapest month to fly to Aspen from Illinois, with most prices found around $299. If you aren’t able to travel to Aspen during the month of May, then flying in April is also cheap. Prices for this month can be found on momondo for an average of $443.

The cheapest day to depart from Illinois to Aspen is on a Tuesday when prices can be found for as low as $421. The most expensive day to fly to Aspen is Wednesday, with ticket prices averaging around $635.

In the afternoon is the cheapest time of day to fly from Illinois to Aspen when you can find flight prices for as low as $440. Flying to Aspen in the afternoon is an ideal time because this is during off-peak travel hours. Try not to purchase tickets in the evening because they tend to be around $631. 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 $522 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 $421 on momondo.

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

As of October 2026, 4 flights take off from Illinois and land in Aspen each day. The most common flight departure time for this route is 7:00PM, with 50% of daily flights taking off at noon.

As of October 2026, 28 flights take off from Illinois and land in Aspen each week. The most common flight departure day for this route is Mon, with 14% of weekly flights taking off on this day.