Big Island (Kona & Hilo) from Chicago, Nov 14–23: $3,070 for two, all in
The verdict
Our verdict
Worth it, if
- $206 per person below the typical fare on this route
- Kalani Kai#104, rated 9 by 6 guests
- Typical highs 80–81°F, lows near 70°F this time of year
The catch: Not nonstop: 2 stops on the way, 13h 57m in all.
Worth it if you want sun, sand and a pool; skip it if you want a city to walk.
Round-trip flights on Alaska. Operated by Alaska as Hawaiian Airlines from Chicago to Big Island (Kona & Hilo) cost $666 per person for Nov 14–23, 2026 when we checked, $206 below the typical fare on this route. Three places to stay start at $167 a night for the 9-night stay. The total, before you go: $2,833 for two, flights and Kalani Kai#104 with taxes and fees. Prices move; every link below shows the live price.
The total, before you go
$3,070 for two · 9 nights · flights, hotel, taxes, fees & the resort fee
| For two | |
|---|---|
| Flights for two, round trip | $1,332 |
| Kalani Kai#104, 9 nights, two guests, taxes in | $1,501 |
| Resort fee, collected at the desk | $237 |
| The total, before you go | $3,070 |
| A checked bag each, round trip (not in the total) | about $140 |
$206 per person below the typical fare on this route.
Not in it: seat picks on basic fares and a checked bag (about $35 each way per bag on Alaska, $140 for two round trip); the resort fee is counted above. Prices are what we found at the time shown; the booking site’s checkout is the binding one.
The flight
$666 per person, round trip
$1,332 for two, taxes and fees included · Alaska. Operated by Alaska as Hawaiian Airlines · 2 stops · 13h 57m
Out Sat, Nov 14, 7:20 AM – Sat, Nov 14, 5:17 PM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Alaska. Operated by Alaska as Hawaiian Airlines | $666 | 2 stops | 13h 57m |
| American | $690 | 1 stop | 12h 12m |
| Delta | $690 | 1 stop | 11h 36m |
Prices checked Oct 15, 2026, 7:51 PM CDT. Prices change; the binding price is the one on the booking site.
Paid links: when you book through a link on this page, the booking site pays us a referral fee. Your price does not change. How we earn
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Why Big Island (Kona & Hilo)
Why we picked it: Big Island (Kona & Hilo) is the best value we priced for a week away: $666 round trip, 24% under the typical price.
The Big Island packs active volcanoes, snow-capped Mauna Kea, black and green sand beaches and Kona coffee farms into one road-trip island.
Weather in Big Island (Kona & Hilo), Nov 14–23
Typical highs 80–81°F, lows near 70°F this time of year
| Day | Typical high | Typical low | Typical weather |
|---|---|---|---|
| Sat, Nov 14 | 80 °F | 70 °F | Drizzle |
| Sun, Nov 15 | 80 °F | 71 °F | Partly cloudy |
| Mon, Nov 16 | 80 °F | 69 °F | Partly cloudy |
| Tue, Nov 17 | 80 °F | 70 °F | Overcast |
| Wed, Nov 18 | 81 °F | 70 °F | Overcast |
| Thu, Nov 19 | 81 °F | 70 °F | Overcast |
| Fri, Nov 20 | 80 °F | 69 °F | Overcast |
| Sat, Nov 21 | 80 °F | 69 °F | Partly cloudy |
| Sun, Nov 22 | 81 °F | 70 °F | Overcast |
| Mon, Nov 23 | 80 °F | 70 °F | Overcast |
Weather data by Open-Meteo.com · averages, not a forecast
Where to stay in Big Island (Kona & Hilo)
Kalani Kai#104
$1,501 for 9 nights, two guests · $167 a night
See roomsAston Kona By The Sea
$3,990 for 9 nights, two guests · $443 a night
See roomsKona Bali Kai Couples Studio Near Beach- AC, Pool, Hot Tub, Laundry, Lanai, WIFI
$1,739 for 9 nights, two guests · $193 a night
See roomsAll hotels in Big Island (Kona & Hilo) for these dates
Paid links: when you book through a link on this page, the booking site pays us a referral fee. Your price does not change. How we earn
Where in Big Island (Kona & Hilo)
- Kohala Coast (Waikoloa, Mauna Lani, Mauna Kea): The island's sunniest resort strip with golden beaches and golf.
- Kailua-Kona: Walkable seaside town with coffee shops, snorkel tours and mid-range hotels.
- Volcano Village: Rainforest B&Bs at the gate of Hawaii Volcanoes National Park.
- Hilo: Rainy east-side town near waterfalls and the volcano, at budget rates.
- Captain Cook / Kealakekua: Coffee-farm country above the best snorkelling bay.
What to do in Big Island (Kona & Hilo)
Signature experiences
- See the Kilauea caldera at Hawaii Volcanoes National Park
- Snorkel with manta rays at night off Kona
- Stargaze from the Mauna Kea visitor station
- Kayak and snorkel Kealakekua Bay at the Captain Cook monument
- Walk the black sand of Punaluu Beach
- Tour a Kona coffee farm
Tours and tickets in Big Island (Kona & Hilo)
Paid links: when you book through a link on this page, the booking site pays us a referral fee. Your price does not change. How we earn
Getting there and around
| Airports in Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
|---|---|
| Airports in Big Island (Kona & Hilo) | Kona International (KOA), Hilo International (ITO) |
| Flight time | 13h 57m (2 stops) |
| Distance | 4,223 miles each way |
| Time difference | -4 hours |
Paid links: when you book through a link on this page, the booking site pays us a referral fee. Your price does not change. How we earn
What 9 nights in Big Island (Kona & Hilo) costs
| Estimate | |
|---|---|
| Flights for two | $1,332 |
| Hotel, 9 nights (Kalani Kai#104) | $1,501 |
| Food, getting around and tickets, 9 days for two | $2,340 |
| Total for two | $5,173 |
Flights and hotel are the prices we found; spending is a planning estimate for an upscale destination, per person per day times two.
Price history: Chicago to Big Island (Kona & Hilo)
| Per person | |
|---|---|
| This trip | $666 per person |
| Lowest in the last 30 days | $643 (Oct 13, 2026) |
| Typical price, last 60 days | $872 |
| Price checks | 13 |
Good to know
- Passport: no passport needed for travelers from the United States: a government photo ID is enough for Big Island (Kona & Hilo).
- Currency: US dollar (USD).
Questions readers ask
How much does 9 nights in Big Island (Kona & Hilo) from Chicago cost?
About $5,173 for two: $1,332 in flights, $1,501 for the hotel and $2,340 for food, getting around and tickets.
What is the weather like in Big Island (Kona & Hilo) Nov 14–23?
Typical highs 80–81°F, lows near 70°F this time of year
Do I need a passport for Big Island (Kona & Hilo)?
No. No passport needed for travelers from the United States: a government photo ID is enough for Big Island (Kona & Hilo).
How long is the flight from Chicago to Big Island (Kona & Hilo)?
13h 57m with 2 stops on Alaska. Operated by Alaska as Hawaiian Airlines, on the fare we found.
Is $666 a good price for Chicago to Big Island (Kona & Hilo)?
It is 24% below the typical $872 per person we see on this route, which is why it made the list.
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All trips from Chicago · Big Island (Kona & Hilo) from every city · Prices on this route · Trips in November 2026 · Home
Big Island (Kona & Hilo) in pictures
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- Photo: Ham Chitnupong / Pexels, Pexels License
- Photo: Josh Withers / Pexels, Pexels License