Route Price Intelligence
Cheap Flights From Denver to Chicago
Live pricing benchmarks, monthly patterns, and historical lows for this route.
This Denver-Chicago fare usually runs about $255 round trip, right now it is down to $74 on Frontier, a 71% discount. Travel is open through the winter into early 2027, plenty of room for a deep-dish weekend or a visit to friends downtown. Chicago's museums, architecture tours and food scene make this one of the easiest short trips to book at a price this low.
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Best Time to Fly from Denver to Chicago
The cheapest time to fly from Denver to Chicago is typically October, when fares average around $146. The most expensive month tends to be July at around $331. For the best deals, consider flying in October, September, August.
Typical Price by Travel Month
Median round-trip fare for each month, with the typical price range, from our ongoing tracking of this route