New York to Chicago: buy now or wait?
Typical one-way fare New York→Chicago: €91 (median of 51 daily lowest fares we tracked); under €77 is a good price; cheapest month: November; book 28–41 days ahead.
Cheaper than 33% of what we have seen
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All fares New York → Chicago
Cheapest first. Every price is live and goes straight to booking.
What the history says
Based on 1,617 prices we recorded on this exact route, compared against the same departure month.
Best booking window
28–41 days — is when this route has been cheapest to book: €96 typical, on 220 observations. That is about €26 less than booking in the last two weeks.
Cheapest months to fly to Chicago
Booking tips from our fare data
- How far in advance should you book a flight?
- Book 1.5–2 months before departure. Tracking the same flights at every lead time (110,945 flights on 21,717 routes, 2026-06-14 to 2026-11-10), that window had the smallest average premium over each flight's lowest fare: +16.3%, against +48.8% in the last 3 days.
- Are domestic flights cheaper than international flights?
- Yes. The median one-way fare on a domestic route was €121.25, against €160 for international flights within the same continent and €269 for intercontinental ones (79,553 routes, fares observed 2026-06-14 to 2026-11-10).
- How much does a flight in Europe cost?
- €114 one way at the median, across 28,636 routes within Europe (fares observed 2026-06-14 to 2026-11-10). The cheapest countries to fly to were Albania (€58), Malta (€64), Italy (€76); the dearest Belarus (€299) and Russia (€291).
Price drops on Telegram
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