Chicago to Honolulu: buy now or wait?
Buy now FareScore 82/100
usually $244 $198 ≈ €176 Today's best fare
Cheaper than 82% of what we have seen
10 Nov Hawaiian Airlines Direct
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All fares Chicago → Honolulu
Cheapest first. Every price is live and goes straight to booking.
10 Nov
13:00
Hawaiian Airlines · 14h 24m
Direct ↓9%
€193 €176
10 Nov
13:00
Alaska Airlines · 14h 24m
With a stop
€176
11 Nov
13:00
HA · 13h 30m
Direct
€180
11 Nov
13:00
AS · 13h 30m
With a stop
€180
5 Dec
23:46
Alaska Airlines · 21h 24m
With a stop
€231 €230
12 Nov
02:55
WN · 28h 37m
With a stop
€268
8 Jan
20:13
Alaska Airlines · 12h 21m
With a stop
€270
10 Nov
11:50
Southwest Airlines · 11h 35m
With a stop
€276
13 Dec
00:25
Southwest Airlines · 34h 29m
With a stop
€300 €299
9 Jan
01:50
Southwest Airlines · 42h 55m
With a stop
€303
2 Jan
12:15
Southwest Airlines · 11h 45m
With a stop
€342
9 Jan
20:13
Alaska Airlines · 12h 21m
Direct
€356
What the history says
Prices recorded 290
Typical price €217
Lowest we saw €109
You save today €41
Based on 290 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: €228 typical, on 32 observations. That is about €48 less than booking in the last two weeks.
Cheapest months to fly to Honolulu
September €190 14 observations
November €227 67 observations
October €257 152 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 (94,914 flights on 19,442 routes, 2026-06-14 to 2026-11-04), 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 +3.4% and Tuesday +4.2%, while Friday was the dearest at +10.6%. 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 +17.5%. Covers September 2026, October 2026, November 2026, December 2026, January 2027; fares observed 2026-06-14 to 2026-11-04.
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