Big Island (Kona & Hilo) from Chicago, 14 – 23 Nov: £2,318 for two, all in
The verdict
Our verdict
Worth it, if
- £156 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.
Big Island (Kona & Hilo) is 9 nights from Chicago, 14 – 23 Nov 2026. The cheapest round trip we found is £503 per person (Alaska. Operated by Alaska as Hawaiian Airlines, 2 stops, 13h 57m), 24% below the typical £658 on this route. Hotels start at £126 a night; Typical highs 80–81°F, lows near 70°F this time of year.
The total, before you go
£2,318 for two · 9 nights · flights, hotel, taxes, fees & the resort fee
| For two | |
|---|---|
| Flights for two, return | £1,006 |
| Kalani Kai#104, 9 nights, two guests, taxes in | £1,133 |
| Resort fee, collected at the desk | £179 |
| The total, before you go | £2,318 |
| Hold luggage each, return (not in the total) | about £106 |
£156 per person below the typical fare on this route.
Not in it: seat selection on basic fares and hold luggage (about £26 each way per bag on Alaska, £106 for two return); 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
£503 per person, return
£1,006 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 | £503 | 2 stops | 13h 57m |
| American | £521 | 1 stop | 12h 12m |
| Delta | £521 | 1 stop | 11h 36m |
Prices checked 15 Oct 2026, 19:51 GMT-5. 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), 14 – 23 Nov
Typical highs 80–81°F, lows near 70°F this time of year
| Day | Typical high | Typical low | Typical weather |
|---|---|---|---|
| Sat 14 Nov | 80 °F | 70 °F | Drizzle |
| Sun 15 Nov | 80 °F | 71 °F | Partly cloudy |
| Mon 16 Nov | 80 °F | 69 °F | Partly cloudy |
| Tue 17 Nov | 80 °F | 70 °F | Overcast |
| Wed 18 Nov | 81 °F | 70 °F | Overcast |
| Thu 19 Nov | 81 °F | 70 °F | Overcast |
| Fri 20 Nov | 80 °F | 69 °F | Overcast |
| Sat 21 Nov | 80 °F | 69 °F | Partly cloudy |
| Sun 22 Nov | 81 °F | 70 °F | Overcast |
| Mon 23 Nov | 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
£1,133 for 9 nights, two guests · £126 a night
See roomsAston Kona By The Sea
£3,012 for 9 nights, two guests · £334 a night
See roomsKona Bali Kai Couples Studio Near Beach- AC, Pool, Hot Tub, Laundry, Lanai, WIFI
£1,313 for 9 nights, two guests · £146 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 | £1,006 |
| Hotel, 9 nights (Kalani Kai#104) | £1,133 |
| Food, getting around and tickets, 9 days for two | £1,766 |
| Total for two | £3,905 |
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 | £503 per person |
| Lowest in the last 30 days | £485 (13 Oct 2026) |
| Typical price, last 60 days | £658 |
| Price checks | 13 |
Good to know
- Passport: no passport needed for travellers 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 £3,905 for two: £1,006 in flights, £1,133 for the hotel and £1,766 for food, getting around and tickets.
What is the weather like in Big Island (Kona & Hilo) 14 – 23 Nov?
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 travellers 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 £503 a good price for Chicago to Big Island (Kona & Hilo)?
It is 24% below the typical £658 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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Prices converted from US dollars at the rate of 16 Oct 2026.
Image credits
- Photo: Brian Wolf / Pexels, Pexels License
- Photo: Ham Chitnupong / Pexels, Pexels License
- Photo: Josh Withers / Pexels, Pexels License