Route brief · CHI → HNL
Chicago → Honolulu
$271
−60% vs typical
seasonal median $675 · difference $404
Feb 15 '27 – Feb 18 '27 · 3 nights
Southwest2 stops
- Usual monthly lows
- $365–$678
- Board rank
- Stronger than 98%
- Route sample
- 8 observed months
Cached fare — the booking search re-prices live before you pay.
Destination briefHNLHonoluluWaikīkī 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)All routes into HonoluluWhen this route gets cheap.
Cached-fare history: across 8 months, Feb is the cheapest for CHI → HNL. Best time to be there: Apr–Jun · Sep–Nov.
Fares bottom out in February around $271 and peak in June near $814 — a $543 spread across the 8 months we track. The cheapest itinerary we are tracking makes 2 stops and takes about 11.5 hours outbound, on a 3-night trip — ticketed under Southwest, which on a connecting fare need not operate every leg. At $271 for 6,838 km each way, that works out to about $20 per 1,000 km flown. That is well under the $44 that long-haul fares on this board typically run. Across the 14 departure cities we track at a similar distance from Honolulu, this fare ranks 2nd — 3% above the $263 from Houston. It is also the 2nd cheapest of the 30 routes of similar length we watch out of Chicago.
Day-level prices for the next 3 months
Tap any day → live search
The median cached fare across this calendar is 8% lower than when tracking began on Aug 8 — $617 then versus $568 now, across 7 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 $268, on Oct 30.
Cached day-level data for this route is sparse — 10 of 93 days priced, from 49 tracked fares. The days below are shown as found, with no cheapest-day or below-median call.
Cheapest in Feb · around $271
60% below the $675 typical fare
Cheapest round-trip fare found per month · Chicago → Honolulu · cached-price history
Route facts
- Airports
- O’Hare (ORD) · Midway (MDW) ↔ Daniel K. Inouye (HNL)
- Flight time
- ~11.5 hours outbound
- Distance
- ~6,838 km each way
- Typical price
- $675 round-trip (seasonal median)
- Airlines on the board
- Southwest
- Itineraries
- Connections on current fares
- Best months to visit
- Apr–Jun · Sep–Nov
CHI → HNL, answered.
Is $271 a good price for Chicago to Honolulu?
Yes — the seasonal median for this route is around $675 round-trip. At $271 you're 60% below that, saving about $404, which we rate exceptional for this route.
What is the cheapest month to fly from Chicago to Honolulu?
Across 8 months of cached-fare history, Feb 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 8 months of cached fares, Feb comes out lowest on this route. See /guides/what-moves-a-flight-price/ for what does move a fare.
Are there nonstop flights from Chicago to Honolulu?
The current cheapest fares involve a connection, ticketed under Southwest. Nonstop options exist on many dates at higher prices — check the live search for your exact dates.
Are these prices guaranteed?
No — these are cached fares found on real searches (this one on September 1). 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 Feb 15 '27 – Feb 18 '27 · 3 nights.
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Missed 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.
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