Kyoto & Osaka from Milwaukee, 14 – 23 Nov: £3,898 for two, all in
The verdict
Our verdict
Worth it, if
- Autumn leaves peak mid-to-late November at Tofuku-ji, Eikan-do and Arashiyama
- Fare is $1,308 per person, $203 below the typical fare
- hotel anddoggy Kyoto Nijo scores 9.5 from 385 reviews
The catch: Two stops on the way out add up to 20h 45m from a 5:00 AM Milwaukee departure, and hold luggage is about $160 for two.
Worth it if 20h 45m with two stops is fine for nine nights of temples and food; skip it if you want a direct flight.
Worth it if the long flight doesn't bother you: $5,164 for two, all in. That's the flights at $2,616, hotel anddoggy Kyoto Nijo at $2,336 and $212 paid at the hotel, with taxes and fees included, for Nov 14–23, 2026, nine nights. You'd fly United (operated by SkyWest DBA United Express) with two stops, so it isn't direct, and hold luggage and spending money are extra.
The total, before you go
£3,898 for two · 9 nights · flights, hotel, taxes, fees & the resort fee
| For two | |
|---|---|
| Flights for two, return | £1,975 |
| hotel anddoggy Kyoto Nijo, 9 nights, two guests, taxes in | £1,763 |
| Resort fee, collected at the desk | £160 |
| The total, before you go | £3,898 |
| Hold luggage each, return (not in the total) | about £121 |
£153 per person below the typical fare on this route.
Not in it: seat selection on basic fares and hold luggage (about £30 each way per bag on United, £121 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
£987 per person, return
£1,975 for two, taxes and fees included · United. Operated by SkyWest DBA United Express · 2 stops · 20h 45m
Out Sat, Nov 14, 5:00 AM – Sun, Nov 15, 4:45 PM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| United. Operated by SkyWest DBA United Express | £987 | 2 stops | 20h 45m |
| United + ANA. Operated by Republic Airways DBA United Express | £993 | 2 stops | 22h |
| Alaska + EVA Air | £1,049 | 2 stops | 26h 15m |
Prices checked 15 Oct 2026, 19:42 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
Tweak this trip
Why now
The fare is $1,308 per person, $203 below the typical fare on this route, a 13% gap, and the lowest we've seen in 30 days. For two, that's $2,616 for the flights and $5,164 for the whole trip with the hotel, taxes and fees included, as found when we checked; prices move. The timing matters too: the autumn leaves at Tofuku-ji, Eikan-do and Arashiyama peak in mid-to-late November, with evening illuminations, and these dates sit right in that window. Expect typical highs of 57–64°F and lows near 43°F, good walking weather for temple days with a jacket. Nine nights gives you room for Kyoto, Osaka and Nara without rushing, so the long journey over earns its keep.
The kind of trip this is
This is a culture-and-food trip at a walking pace: early mornings at shrines and temples, afternoons in gardens and markets, evenings eating your way through Osaka. It suits a couple or two friends who like to wander, don't mind an early alarm for the quiet hours, and want a city break with nature close by. With nine nights, you can mix busy days with slow ones.
Weather in Kyoto & Osaka, 14 – 23 Nov
Typical highs 57–64°F, lows near 43°F this time of year
| Day | Typical high | Typical low | Typical weather |
|---|---|---|---|
| Sat 14 Nov | 62 °F | 44 °F | Overcast |
| Sun 15 Nov | 64 °F | 44 °F | Overcast |
| Mon 16 Nov | 63 °F | 43 °F | Drizzle |
| Tue 17 Nov | 64 °F | 45 °F | Overcast |
| Wed 18 Nov | 57 °F | 42 °F | Drizzle |
| Thu 19 Nov | 58 °F | 41 °F | Overcast |
| Fri 20 Nov | 60 °F | 42 °F | Overcast |
| Sat 21 Nov | 62 °F | 41 °F | Overcast |
| Sun 22 Nov | 62 °F | 44 °F | Overcast |
| Mon 23 Nov | 58 °F | 43 °F | Overcast |
Weather data by Open-Meteo.com · averages, not a forecast
Where to stay in Kyoto & Osaka
Our best-value pick is hotel anddoggy Kyoto Nijo: $2,336 for the stay ($260 a night), a 9.5 score from 385 reviews, in Nakagyo Ward near Kawaramachi. It has no free cancellation, and $212 is paid at the property. KABIN Kyoto is the top-rated pick on a big sample, 9.1 from 2,894 reviews, at $2,500 for the stay ($278 a night) in the Gion area, plus $227 at the property. La'gent Hotel Kyoto Nijo costs $2,523 ($280 a night), scores 8.7 from 3,915 reviews and is the only one of the three with free cancellation, plus $229 at the property. Downtown Kyoto (Kawaramachi and Shijo) puts Nishiki Market and Pontocho alley close by. Gion and Higashiyama is the area for teahouse streets and the temple walk from Kiyomizu-dera to Nanzen-ji.
hotel anddoggy Kyoto Nijo
£1,763 for 9 nights, two guests · £196 a night
See roomsKABIN Kyoto
£1,887 for 9 nights, two guests · £210 a night
See roomsLa'gent Hotel Kyoto Nijo
£1,905 for 9 nights, two guests · £211 a night
See roomsAll hotels in Kyoto & Osaka 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 Kyoto & Osaka
- Gion and Higashiyama: Wooden teahouses, geisha streets and the temple walk from Kiyomizu-dera to Nanzen-ji.
- Downtown Kyoto (Kawaramachi and Shijo): Central shopping and dining with Nishiki Market and Pontocho alley at hand.
- Kyoto Station area: Convenient for the shinkansen and day trips, with large hotels.
- Arashiyama: Quiet riverside ryokan stays by the bamboo grove in the western hills.
- Osaka Namba and Dotonbori: Street-food neon and nightlife, 15 minutes from Kyoto by express train.
What to do in Kyoto & Osaka
- Walk Fushimi Inari's torii-gate tunnels before 8am
- Arashiyama bamboo grove and the gardens of Tenryu-ji, with autumn colour on these dates
- Kaiseki dinner at a Gion ryotei for one slow evening
- Nishiki Market food crawl in central Kyoto
- Takoyaki and okonomiyaki on Dotonbori, 15 minutes from Kyoto by express train
- Day trip to Nara's deer park and the Great Buddha of Todai-ji
Tours and tickets in Kyoto & Osaka
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 Milwaukee | Milwaukee Mitchell International (MKE) |
|---|---|
| Airports in Kyoto & Osaka | Kansai International (KIX), Osaka Itami (ITM) |
| Flight time | 20h 45m (2 stops) |
| Distance | 6,382 miles each way |
| Time difference | +15 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 Kyoto & Osaka costs
| Estimate | |
|---|---|
| Flights for two | £1,975 |
| Hotel, 9 nights (hotel anddoggy Kyoto Nijo) | £1,763 |
| Food, getting around and tickets, 9 days for two | £1,766 |
| Total for two | £5,505 |
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: Milwaukee to Kyoto & Osaka
| Per person | |
|---|---|
| This trip | £987 per person |
| Lowest in the last 30 days | £987 (16 Oct 2026) |
| Typical price, last 60 days | £1,141 |
| Price checks | 6 |
Good to know
- Passport: passport needed: travellers from the United States need a valid passport for Kyoto & Osaka; check the expiry rule of the country before you book.
- Currency: Japanese yen (JPY).
- Autumn leaves at Tofuku-ji, Eikan-do and Arashiyama peak in mid-to-late November, with evening illuminations.
- You need a passport for Japan, and the currency is the Japanese yen.
- Kyoto is 15 hours ahead of Milwaukee.
- The outbound flight leaves MKE Saturday, Nov 14 at 5:00 AM and lands at Kansai International (KIX) Sunday, Nov 15 at 4:45 PM.
- The total includes the $212 paid at hotel anddoggy Kyoto Nijo; hold luggage (about $160 for two) is not included.
- Only La'gent Hotel Kyoto Nijo offers free cancellation; the other two hotels don't.
Questions readers ask
Is it worth it?
Worth it if the long flight works for you. The fare is $1,308 per person, $203 below the typical fare on this route and the lowest in 30 days, and the dates line up with the autumn-leaf peak. The trade-off is two stops and 20h 45m on the way out.
How much is the whole trip for two?
$5,164 for two, all in: flights at $2,616, hotel anddoggy Kyoto Nijo at $2,336 for nine nights, and $212 paid at the hotel, with taxes and fees. Hold luggage (about $160 for two) and spending money are extra.
Do I need a passport?
Yes, Japan requires a passport. Bring a card that works abroad or some Japanese yen.
What is the weather like?
Typical highs run 57–64°F, with lows near 43°F. Most days are usually overcast, and the normals show drizzle on Nov 16 and Nov 18, so pack layers and a light rain jacket.
Is 9 nights enough?
Yes, for a full first look. Nine nights covers Kyoto's temples and gardens, an Osaka evening on Dotonbori and a day trip to Nara, with room for slow days. Osaka Namba is 15 minutes from Kyoto by express train.
Which airport do I fly into?
This fare lands at Kansai International (KIX). Osaka Itami (ITM) also serves the area.
Also found for you
The newest finds from Milwaukee.
Just found · from MilwaukeeLowest in 30 days
Orlando
27 Nov – 2 Dec 2026 · 5 nights
- Nonstop on Frontier, 2h 51m
- £349 per person below the typical fare on this route
- Lowest in 30 days on this route
£805 for two · 5 nights · flights, hotel, taxes, fees & the resort fee
Flights £460 + hotel £310 + resort fee £35, taxes in · a checked bag each adds about £181
Frontier · nonstop · 2h 51m
The catch: The best-value hotel is rated 7.8; a better one costs more.
Worth it with kids who are up for long days; skip it if you want quiet.
Tweak this trip
Just found · from MilwaukeeLowest in 30 daysWorth it, if
Great Smoky Mountains
23 – 25 Oct 2026 · 2 nights
- $467 per person round trip, $949 below the typical fare
- Clear forecast for all three days, highs 72–73°F, rain chance 5% or less
- Gatlinburg lodge rated 8.1 from 3,296 reviews, with a balcony room
£1,085 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights £705 + hotel £341 + resort fee £39, taxes in · a checked bag each adds about £121
American. Operated by PSA Airlines as American Eagle · with a stop · 4h 28m
The catch: The outbound has one stop, takes 268 minutes and lands near midnight on a peak-foliage weekend, and a checked bag is about $160 for two.
Worth it if you want fall color and easy trails on a short weekend; skip it if crowds or a late one-stop flight wear you out.
Tweak this trip
Just found · from MilwaukeeLowest in 30 days
Miami
27 Nov – 1 Dec 2026 · 4 nights
- Nonstop on American, 7:00 AM out of Milwaukee, 3h 20m to Miami
- $319 per person, $153 below the typical fare on this route
- Normal highs of 78–80°F across all 4 nights
£1,061 for two · 4 nights · flights, hotel, taxes, fees & the resort fee
Flights £482 + hotel £516 + resort fee £63, taxes in · a checked bag each adds about £121
American. Operated by Envoy Air as American Eagle · nonstop · 3h 20m
The catch: A checked bag is about $160 for two and not in the total, and Casablanca Residences Miami Beach has no free cancellation.
Worth it if you want warm beach days, Art Deco streets and Cuban food; skip it if you need clear blue skies every day.
Tweak this trip
More trips
Just found · from Milwaukee32% below typicalWorth it, if
Nashville
23 – 25 Oct 2026 · 2 nights
- $532 per person, $259 below the typical fare on this route
- Highs of 77–78°F and a 1–6% rain chance all weekend
- Breakfast included at the Best Western, rated 8.1 from 1,348 reviews
£1,156 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights £803 + hotel £306 + resort fee £47, taxes in · a checked bag each adds about £121
American. Operated by SkyWest Airlines as American Eagle · with a stop · 5h 7m
The catch: One stop makes the flight 5h 7m and you land at 12:26 AM Saturday, and a checked bag is about $160 for two.
Worth it if you want a music-and-hot-chicken weekend at a lower fare; skip it if a nonstop or a downtown bed matters more.
The weekend after · from MilwaukeeLowest in 30 daysWorth it, if
Asheville
30 Oct – 1 Nov 2026 · 2 nights
- Delta fare $369 per person, $876 below the typical fare
- Peak fall foliage on the Blue Ridge Parkway that weekend
- Best Western with breakfast, 8.3 from 1,417 reviews, $355 for two nights
£856 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights £557 + hotel £268 + resort fee £31, taxes in · a checked bag each adds about £106
Delta · with a stop · 4h 38m
The catch: The Delta flight has one stop and takes 4h 38m, leaving Milwaukee at 5:30 AM, and a checked bag runs about $140 for two.
Worth it if you can handle a 5:30 AM start and crowds on a foliage weekend; skip it if you need a nonstop.
Just found · from MilwaukeeLowest in 30 days
Orlando
27 Nov – 2 Dec 2026 · 5 nights
- Nonstop on Frontier, 2h 51m
- £349 per person below the typical fare on this route
- Lowest in 30 days on this route
£805 for two · 5 nights · flights, hotel, taxes, fees & the resort fee
Flights £460 + hotel £310 + resort fee £35, taxes in · a checked bag each adds about £181
Frontier · nonstop · 2h 51m
The catch: The best-value hotel is rated 7.8; a better one costs more.
Worth it with kids who are up for long days; skip it if you want quiet.
Just found · from MilwaukeeLowest in 30 daysWorth it, if
Great Smoky Mountains
23 – 25 Oct 2026 · 2 nights
- $467 per person round trip, $949 below the typical fare
- Clear forecast for all three days, highs 72–73°F, rain chance 5% or less
- Gatlinburg lodge rated 8.1 from 3,296 reviews, with a balcony room
£1,085 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights £705 + hotel £341 + resort fee £39, taxes in · a checked bag each adds about £121
American. Operated by PSA Airlines as American Eagle · with a stop · 4h 28m
The catch: The outbound has one stop, takes 268 minutes and lands near midnight on a peak-foliage weekend, and a checked bag is about $160 for two.
Worth it if you want fall color and easy trails on a short weekend; skip it if crowds or a late one-stop flight wear you out.
All trips from Milwaukee · Kyoto & Osaka from every city · Prices on this route · Trips in November 2026 · Home
Kyoto & Osaka in pictures
Paid links: when you book through a link on this page, the booking site pays us a referral fee. Your price does not change. We use AI tools to draft the text of each page from the data on it; code checks every number in the draft against that data and rejects what does not match, and the team reviews pages and fixes or removes what readers report. How we pick · Report a mistake.
Prices converted from US dollars at the rate of 16 Oct 2026.
Image credits
- Photo: Mike The Fabrica / Pexels, Pexels License
- Photo: AXP Photography / Pexels, Pexels License
- Photo: Axel Garbet / Pexels, Pexels License