Madrid to Chicago: buy now or wait?
Wait FareScore 21/100
€335 Today's best fare
Cheaper than 21% of what we have seen
19 Nov TAP Portugal With a stop
Usually €332 Cheapest in November (~€332)
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All fares Madrid → Chicago
Cheapest first. Every price is live and goes straight to booking.
19 Nov
17:00
TAP Portugal · 28h 30m
With a stop
€335
6 Nov
06:40
TAP Portugal · 14h 50m
Direct
€341
10 Nov
17:00
TAP Portugal · 28h 30m
With a stop
€342
16 Dec
05:30
Air Europa · 16h 00m
With a stop
€372
16 Dec
06:40
TAP Portugal · 14h 50m
Direct
€383
1 Dec
09:20
TAP Portugal · 36h 10m
With a stop
€393
What the history says
Prices recorded 42
Typical price €332
Lowest we saw €309
Based on 42 prices we recorded on this exact route, compared against the same departure month.
Best booking window
0–13 days — is when this route has been cheapest to book: €277 typical, on 7 observations.
Cheapest months to fly to Chicago
November €332 32 observations
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 (92,167 flights on 19,004 routes, 2026-06-14 to 2026-11-03), that window had the smallest average premium over each flight's lowest fare: +16.8%, 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 +3.3% and Tuesday +4.1%, 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 September 2026 was the dearest at +6.2%. Covers September 2026, October 2026, November 2026, December 2026; fares observed 2026-06-14 to 2026-11-03.
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