RareNonstop · 5h
CHI to SJUPuerto Rico
San Juan
$162
usually $340
−52%
Most monthly lows $287–$340. Cheaper than every other month on record (3).
Flights · CHI → HNL
Chicago to Honolulu
Best fare, round trip
$567
−15%
below its usual $665
you keep $98
Found
- Depart
- Sun 15 Nov
- Return
- Sun 22 Nov
- Stay
- 7 nights
- Flight
- 1 stop · 10.5h
- Airline
Southwest
Most of this route’s monthly lows fall between $632 and $699. The drop beats 40% of measured fares on the board, over 6 observed months.
Cached fare — the booking search re-prices live before you pay.
United StatesHonoluluWaikīkī sunsets and volcanic ridgelines — mainland fare wars put Hawai‘i under $300 more often than you’d think.Best windowApr–Jun · Sep–NovAirportsDaniel K. Inouye (HNL)Every route into HonoluluFare seasonality
When this route gets cheap.
Fares bottom out in November around $567 and peak in March near $772, 36% dearer, across the 6 months we track. The cheapest itinerary we are tracking makes one stop and takes about 10.5 hours outbound, on a 7-night trip — ticketed under Southwest, which on a connecting fare need not operate every leg. At $567 for 6,838 km each way, that works out to about $41 per 1,000 km flown. That is below the $44 per 1,000 km typical of long-haul fares here. Across the 14 departure cities we track at a similar distance from Honolulu, this fare ranks 6th — 46% above the $388 from Dallas. That puts it in the cheaper half of the 30 routes of similar length we watch out of Chicago, where the middle fare is $729. The best time to be in Honolulu: Apr–Jun · Sep–Nov.
The 7 days we hold a cached fare for
Press a date to compare its fares
The median cached fare across this calendar is 7% higher than when tracking began on 8 Aug — $617 then versus $662 now, across 22 recorded snapshots. This is a calendar-level trend, so an individual deal above can be lower. The lowest single day we have seen here is $230, on 8 Nov.
- Sat 31 Oct$632
- Sun 15 Nov$567lowest
- Mon 30 Nov$709
- Mon 7 Dec$699
- Tue 8 Dec$734
- Sat 16 Jan$662
- Sun 17 Jan$645
These are the only days we have a cached price for on this route so far — not the only days it flies. The search above covers any date.
Cached fares · checked 17 Oct 2026
Cheapest in Nov, around $567
15% below the $665 typical fare
$632Oct, around the usual price. Compare October fares.$567Nov, the cheapest month. Compare November fares.$699Dec, above the usual price. Compare December fares.$645Jan ’27, around the usual price. Compare January fares.$666Feb, around the usual price. Compare February fares.$772Mar, above the usual price. Compare March fares.
CheapestBelow usualUsualAbove usualPress a month to compare its fares
Cheapest round-trip fare found each month, Chicago to Honolulu, from cached prices.
Route facts
- Airports
- O’Hare (ORD) · Midway (MDW) ↔ Daniel K. Inouye (HNL)
- Flight time
- ≈10.5 hours outbound
- Distance
- ≈6,838 km each way
- Typical price
- $665 round-trip (seasonal median)
- Airlines on the board
- Southwest
- Itineraries
- Connections on current fares
- Best months to visit
- Apr–Jun · Sep–Nov
Good to know
CHI → HNL, answered.
Is $567 a good price for Chicago to Honolulu?
Only slightly. The seasonal median is around $665 round-trip and this fare is 15% under it. We do not call a drop notable until 20%, so this is an ordinary price for the route rather than a reason to hurry.
What is the cheapest month to fly from Chicago to Honolulu?
Across 6 months of cached-fare history, Nov comes out cheapest on this route. The best months to actually be in Honolulu are Apr–Jun · Sep–Nov — when those overlap, that's your window.
How far in advance should I book CHI → Honolulu?
We do not publish a number for this, because we cannot measure it yet. Answering it honestly means watching the same departure date on this route over many weeks as it approaches, and that archive is still filling up — so any "book N days ahead" figure here would be borrowed from somewhere else rather than measured. What we can measure is which month is cheap: across 6 months of cached fares, Nov comes out lowest on this route. Our guide Why flight prices change covers what does move a fare.
Are there nonstop flights from Chicago to Honolulu?
The current cheapest fares involve a connection, ticketed under Southwest. We hold no nonstop fare on this route right now, which does not mean none flies — search your exact dates to see what does.
Are these prices guaranteed?
No — these are cached fares found on real searches (this one on 17 October). Airlines reprice constantly, so the booking search re-checks the live price before you pay. Fresher finds are far more likely to still be available.
Next step
Sleeping in Honolulu?
Lock the flight first — then compare stays for 15–22 Nov · 7 nights.
Browse hotelsMissed it?
Cached fares expire. This route has a feed of its own — follow it and the next CHI → HNL drop reaches you as soon as we find it.
Follow this route’s feedKeep browsing
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