Chicago to Denver: buy now or wait?
Typical one-way fare Chicago→Denver: €46 (median of 29 daily lowest fares we tracked); under €39 is a good price; cheapest month: December; book 42–55 days ahead.
Cheaper than 38% of what we have seen
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Fare Desk notes
Today's data shows a clear advantage for early booking on the Chicago to Denver route. Frontier Airlines currently leads the market with one-way fares starting at €28, while Southwest Airlines offers options from €76 and American Airlines sells from €89. With the median fare for this route sitting at €34, our verdict today is Buy now. Today's €28 fare on Frontier Airlines for departure on 16 December 2026 is non-stop and matches the lowest fare we logged across 271 total observations.
This €28 price is cheaper than 65% of the fares we logged for this route. Looking at historical trends, December stands out as the cheapest month overall with a typical fare of €64 based on a sample of 118 fares, followed by October at €78 and September at €84. The optimal booking window falls between 42 and 55 days before departure, where the typical fare is €58, providing a saving of €103 compared to last-minute bookings. For the return path from Denver to Chicago, today's fare is €48 against a typical price of €68.
Piratefly Fare Desk · prices checked on
All fares Chicago → Denver
Cheapest first. Every price is live and goes straight to booking.
What the history says
Based on 281 prices we recorded on this exact route, compared against the same departure month.
Best booking window
42–55 days — is when this route has been cheapest to book: €64 typical, on 82 observations. That is about €97 less than booking in the last two weeks.
Cheapest months to fly to Denver
Booking tips from our fare data
- How far in advance should you book a flight?
- Book 1–1.5 months before departure. Tracking the same flights at every lead time (97,668 flights on 19,841 routes, 2026-06-14 to 2026-11-05), that window had the smallest average premium over each flight's lowest fare: +16.7%, against +49.3% in the last 3 days.
- What is the cheapest day of the week to fly?
- Wednesday. Comparing each fare with the median of its own route, Wednesday departures were +3.5% and Tuesday +4.3%, while Friday was the dearest at +10.5%. Weekend departures cost more than midweek ones.
- What is the cheapest month to fly?
- November 2026. Comparing each route's fares month by month (booked 8–60 days ahead), November 2026 departures were -1.1% against the route's own median, while January 2027 was the dearest at +22.7%. Covers September 2026, October 2026, November 2026, December 2026, January 2027; fares observed 2026-06-14 to 2026-11-05.
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