New York City from Madison, Oct 23–25: $2,084 for two, all in
The verdict
Our verdict
Worth it, if
- $912 per person below the typical fare on this route
- Lowest in 30 days on this route
- The Cloud One New York-Downtown, part of the Motel One Group, rated 8.8 by 7,961 guests
The catch: Not nonstop: a stop on the way, 5h 59m in all.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
Round-trip flights on Delta from Madison to New York City cost $469 per person for Oct 23–25, 2026 when we checked, $912 below the typical fare on this route. Three places to stay start at $493 a night for the 2-night stay. The total, before you go: $1,948 for two, flights and The Cloud One New York-Downtown, part of the Motel One Group with taxes and fees. Prices move; every link below shows the live price.

The total, before you go
$2,084 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
| For two | |
|---|---|
| Flights for two, round trip | $938 |
| The Cloud One New York-Downtown, part of the Motel One Group, 2 nights, two guests, taxes in | $1,010 |
| Resort fee, collected at the desk | $136 |
| The total, before you go | $2,084 |
| A checked bag each, round trip (not in the total) | about $140 |
$912 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 Delta, $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
$469 per person, round trip
$938 for two, taxes and fees included · Delta · 1 stop · 5h 59m
Out Fri, Oct 23, 6:00 AM – Fri, Oct 23, 12:59 PM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Delta | $469 | 1 stop | 5h 59m |
| Delta. Operated by Republic Airways Delta Connection | $621 | nonstop | 2h 20m |
| United. Operated by SkyWest DBA United Express | $482 | 1 stop | 5h 22m |
Prices checked Oct 14, 2026, 9:08 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
Tweak this trip
Why New York City
Why we picked it: New York City is the best value we priced for the weekend: $469 round trip, 67% under the typical price.
New York City delivers Broadway, world-class museums, skyline views and a restaurant for every cuisine on earth, all reachable by subway.
Weather in New York City, Oct 23–25
Highs 67–69°F, little rain expected
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri, Oct 23 | 69 °F | 52 °F | 13% |
| Sat, Oct 24 | 69 °F | 58 °F | 11% |
| Sun, Oct 25 | 67 °F | 58 °F | 18% |
Where to stay in New York City
The Cloud One New York-Downtown, part of the Motel One Group
$1,010 for 2 nights, two guests · $505 a night
See roomsPark Terrace Hotel
$1,648 for 2 nights, two guests · $824 a night
See roomsYotel New York Times Square
$986 for 2 nights, two guests · $493 a night
See roomsAll hotels in New York City 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 New York City
- Midtown: Times Square, Broadway theatres and the most hotel choice.
- SoHo / NoLIta: Boutique hotels amid cast-iron streets, shops and restaurants.
- Upper West Side: Quieter residential blocks next to Central Park and museums.
- Williamsburg, Brooklyn: Rooftop bars and skyline views one subway stop from Manhattan.
- Lower Manhattan: Weekend rates near the 9/11 Memorial, ferries and the Brooklyn Bridge.
What to do in New York City
Signature experiences
- See a Broadway show after a walk through Times Square
- Walk the High Line to Chelsea Market
- Take the Staten Island Ferry past the Statue of Liberty
- Spend a morning at the Met or MoMA
- Cross the Brooklyn Bridge on foot at sunset
- Watch the sunset from Top of the Rock
Tours and tickets in New York City
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 Madison | Dane County Regional (MSN) |
|---|---|
| Airports in New York City | John F. Kennedy International (JFK), Newark Liberty International (EWR), LaGuardia (LGA) |
| Flight time | 5h 59m (1 stop) |
| Distance | 807 miles each way |
| Time difference | +1 hour |
What 2 nights in New York City costs
| Estimate | |
|---|---|
| Flights for two | $938 |
| Hotel, 2 nights (The Cloud One New York-Downtown, part of the Motel One Group) | $1,010 |
| Food, getting around and tickets, 2 days for two | $760 |
| Total for two | $2,708 |
Flights and hotel are the prices we found; spending is a planning estimate for a luxury destination, per person per day times two.
Price history: Madison to New York City
| Per person | |
|---|---|
| This trip | $469 per person |
| Lowest in the last 30 days | $469 (Oct 15, 2026) |
| Typical price, last 60 days | $1,381 |
| Price checks | 10 |
Good to know
- Passport: no passport needed for travelers from the United States: a government photo ID is enough for New York City.
- Currency: US dollar (USD).
Questions readers ask
How much does 2 nights in New York City from Madison cost?
About $2,708 for two: $938 in flights, $1,010 for the hotel and $760 for food, getting around and tickets.
What is the weather like in New York City Oct 23–25?
Highs 67–69°F, little rain expected
Do I need a passport for New York City?
No. No passport needed for travelers from the United States: a government photo ID is enough for New York City.
How long is the flight from Madison to New York City?
5h 59m with 1 stop on Delta, on the fare we found.
Is $469 a good price for Madison to New York City?
It is 66% below the typical $1,381 per person we see on this route, which is why it made the list.
Also found for you
The newest finds from Madison.
Just found · from MadisonLowest in 30 days
Orlando
Nov 5–10, 2026 · 5 nights
- Breeze nonstop from Madison, 3 hours, leaving 6:00 PM Thursday
- $328 per person, $331 below the typical fare on this route
- Highs of 78–81°F for Nov 5–10, lows near 64°F
$1,344 for two · 5 nights · flights, hotel, taxes & fees
Flights $656 + hotel $688, taxes in · a checked bag each adds about $160
Breeze · nonstop · 3h
The catch: Resort fees and a checked bag aren't in the total, Rosen Inn at Pointe Orlando has no free cancellation, and three of the days lean toward drizzle.
Worth it if you want theme parks and warm days after a short nonstop; skip it if you're after a quiet beach trip.
Tweak this trip
Just found · from MadisonLowest in 30 daysWorth it, if
Great Smoky Mountains
Oct 23–25, 2026 · 2 nights
- $769 per person below the typical fare on this route
- Lowest in 30 days on this route
- Zoders Inn and Suites, rated 8.2 by 1,812 guests
$1,182 for two · 2 nights · flights, hotel, taxes & fees
Flights $898 + hotel $284, taxes in · a checked bag each adds about $140
Delta · with a stop · 4h 3m
The catch: Not nonstop: a stop on the way, 4h 3m in all.
Worth it if you want to be outside all day; skip it if you want to lie by a pool.
Tweak this trip
Just found · from MadisonLowest in 30 daysWorth it, if
Orlando
Nov 13–18, 2026 · 5 nights
- $425 per person below the typical fare on this route
- Lowest in 30 days on this route
- Free cancellation at Avanti International Resort
$1,216 for two · 5 nights · flights, hotel, taxes & fees
Flights $664 + hotel $552, taxes in · a checked bag each adds about $160
American · with a stop · 4h 43m
The catch: Not nonstop: a stop on the way, 4h 43m in all.
Worth it with kids who are up for long days; skip it if you want quiet.
Tweak this trip
More trips
Next weekend · from Madison22% below typical
Nashville
Oct 16–18, 2026 · 2 nights
- $479 per person, $140 below the typical fare on this route
- Highs of 63–74°F, with a 1% to 3% chance of rain each day
- La Quinta scores 8.1 from 2,792 reviews, with breakfast and free cancellation
$1,452 for two · 2 nights · flights, hotel, taxes & fees
Flights $958 + hotel $494, taxes in · a checked bag each adds about $160
United. Operated by SkyWest DBA United Express · with a stop · 3h 40m
The catch: It's one stop and 3h 40m on the 5:00 AM flight, and checked bags run about $160 for two, which isn't in the total.
Worth it if you want live music, hot chicken and a quick weekend; skip it if a 5:00 AM start or a connection is a dealbreaker.
The weekend after · from MadisonLowest in 30 days
Palm Springs
Oct 23–25, 2026 · 2 nights
- Fare at $538 per person, $194 below the typical fare
- Clear forecast, highs of 80–86°F, rain chance at 1% or less
- L3 Oasis Hotel scores 8 from 2,157 reviews, free cancellation
$1,527 for two · 2 nights · flights, hotel, taxes & fees
Flights $1,076 + hotel $451, taxes in · a checked bag each adds about $160
American · with a stop · 5h 42m
The catch: It's one stop and 5h 42m out on American, a checked bag is about $160 for two, and any resort fee isn't in the total.
Worth it if you want a warm, slow pool weekend in the desert; skip it if a one-stop flight feels too long for 2 nights.
Nine nights away · from MadisonNot worth it this week
Kyoto & Osaka
Nov 14–23, 2026 · 9 nights
- Autumn leaves peak mid-to-late November at Tofuku-ji, Eikan-do and Arashiyama
- APA Hotel Kyoto Ekimae scores 7.9 from 3,276 reviews, free cancellation
- Highs of 57–64°F, easy walking weather for temples and Nara
$5,819 for two · 9 nights · flights, hotel, taxes & fees
Flights $4,129 + hotel $1,690, taxes in · a checked bag each adds about $160
MX + B6 + NH · with a stop · 64h 49m
The catch: The fare is $2,065 per person against a $1,814 median on earlier checks, and the flight out has three stops and lands two days later.
Worth it if fall leaves in Kyoto are the whole point and the dates are fixed; skip it if you can wait for the fare to come down.
Just found · from MadisonLowest in 30 days
Orlando
Nov 5–10, 2026 · 5 nights
- Breeze nonstop from Madison, 3 hours, leaving 6:00 PM Thursday
- $328 per person, $331 below the typical fare on this route
- Highs of 78–81°F for Nov 5–10, lows near 64°F
$1,344 for two · 5 nights · flights, hotel, taxes & fees
Flights $656 + hotel $688, taxes in · a checked bag each adds about $160
Breeze · nonstop · 3h
The catch: Resort fees and a checked bag aren't in the total, Rosen Inn at Pointe Orlando has no free cancellation, and three of the days lean toward drizzle.
Worth it if you want theme parks and warm days after a short nonstop; skip it if you're after a quiet beach trip.
Just found · from MadisonLowest in 30 daysWorth it, if
Great Smoky Mountains
Oct 23–25, 2026 · 2 nights
- $769 per person below the typical fare on this route
- Lowest in 30 days on this route
- Zoders Inn and Suites, rated 8.2 by 1,812 guests
$1,182 for two · 2 nights · flights, hotel, taxes & fees
Flights $898 + hotel $284, taxes in · a checked bag each adds about $140
Delta · with a stop · 4h 3m
The catch: Not nonstop: a stop on the way, 4h 3m in all.
Worth it if you want to be outside all day; skip it if you want to lie by a pool.
All trips from Madison · New York City from every city · Prices on this route · Trips in October 2026 · Home
New York City 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.
Image credits
- Photo: Pixabay / Pexels, Pexels License
- Photo: Denil Dominic / Pexels, Pexels License
- Photo: Vlad Alexandru Popa / Pexels, Pexels License




