Worth it from Madison this week, from £361
Madison, WI flies out of Dane County Regional (MSN). This week's picks start at £361 per person, return, taxes and fees included. Over the last 30 days the cheapest routes we priced from Madison were Orlando (from £247), Los Angeles (from £283), Nashville (from £323).
11 new picks from Madison this week · last one 6 hours ago · next check in 03:34 · New picks from Madison land here as we find them.
Our picks from Madison right now
Each with the reasons, the catch and the total before you go.
Next weekend · from Madison22% below typical
Nashville
16 – 18 Oct 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
£1,094 for two · 2 nights · flights, hotel, taxes & fees
Flights £722 + hotel £372, taxes in · a checked bag each adds about £121
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.
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The weekend after · from MadisonLowest in 30 days
Palm Springs
23 – 25 Oct 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
£1,151 for two · 2 nights · flights, hotel, taxes & fees
Flights £811 + hotel £340, taxes in · a checked bag each adds about £121
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.
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Nine nights away · from MadisonNot worth it this week
Kyoto & Osaka
14 – 23 Nov 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
£4,386 for two · 9 nights · flights, hotel, taxes & fees
Flights £3,112 + hotel £1,274, taxes in · a checked bag each adds about £121
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.
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Most loved from Madison
What readers clicked, hearted and shared in the last 7 days.
Just found · from MadisonLowest in 30 daysWorth it, if
New York City
23 – 25 Oct 2026 · 2 nights
- £687 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
£1,571 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights £707 + hotel £761 + resort fee £103, taxes in · a checked bag each adds about £106
Delta · with a stop · 5h 59m
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.
Just found · from MadisonLowest in 30 days
Orlando
5 – 10 Nov 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
£1,013 for two · 5 nights · flights, hotel, taxes & fees
Flights £494 + hotel £519, taxes in · a checked bag each adds about £121
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
23 – 25 Oct 2026 · 2 nights
- £580 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
£891 for two · 2 nights · flights, hotel, taxes & fees
Flights £677 + hotel £214, taxes in · a checked bag each adds about £106
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.
Also priced this week from Madison
The other finalists of the last refresh, cheapest fare we found per person.
| Destination | Dates | From | Nonstop |
|---|---|---|---|
| Orlando | 23 – 25 Oct 2026 | £247 | yes |
| Los Angeles | 5 – 10 Nov 2026 | £283 | no |
| Great Smoky Mountains | 23 – 25 Oct 2026 | £338 | no |
| New York City | 23 – 25 Oct 2026 | £354 | no |
| Las Vegas | 23 – 25 Oct 2026 | £376 | no |
| Phoenix & Scottsdale | 5 – 10 Nov 2026 | £426 | no |
| Sedona | 14 – 21 Nov 2026 | £426 | no |
| Aruba | 5 – 10 Nov 2026 | £482 | no |
| Mexico City | 5 – 10 Nov 2026 | £494 | no |
| Cancún | 5 – 10 Nov 2026 | £536 | no |
| Honolulu & Oahu | 14 – 21 Nov 2026 | £558 | no |
| Banff and Lake Louise | 3 – 8 Dec 2026 | £565 | no |
Cheapest routes from Madison, last 30 days
| Destination | Lowest | Typical | Checks |
|---|---|---|---|
| Orlando | £247 | £565 | 15 · nonstop seen |
| Los Angeles | £283 | £430 | 5 |
| Nashville | £323 | £467 | 5 |
| Great Smoky Mountains | £338 | £918 | 7 |
| New York City | £354 | £1,041 | 10 |
| Las Vegas | £376 | £528 | 10 |
| Palm Springs | £406 | £552 | 6 |
| Phoenix & Scottsdale | £426 | £450 | 4 |
| Sedona | £426 | £426 | 1 |
| Aruba | £482 | £626 | 7 |
| Mexico City | £494 | £528 | 5 |
| Cancún | £536 | £571 | 5 |
| Honolulu & Oahu | £558 | £1,044 | 3 |
| Banff and Lake Louise | £565 | £565 | 1 |
| Cozumel | £642 | £642 | 1 |
More trips from Madison
Every other trip page from Madison still ahead of its date.
- New York City, 23 – 25 Oct 2026 from £354 Just found
- Orlando, 5 – 10 Nov 2026 from £247 Just found
- Great Smoky Mountains, 23 – 25 Oct 2026 from £338 Just found
- Orlando, 13 – 18 Nov 2026 from £250 Just found
- Las Vegas, 23 – 25 Oct 2026 from £391 Just found
- Orlando, 16 – 18 Oct 2026 from £429 Just found
- Los Angeles, 14 – 21 Nov 2026 from £283 Just found
- Kyoto & Osaka, 3 – 8 Dec 2026 from £1,309 Just found
Questions about flying from Madison
Which airports do the trips from Madison use?
Dane County Regional (MSN). Fares are the cheapest return we found across them for the exact dates, per person, taxes and fees included.
How often do the Madison picks change?
Around the clock: we check live prices every few minutes across the cities and new picks from Madison land on this page as they are published. A pick stays until its departure date, then moves to the archive with the price it had.
What are the cheapest places to fly from Madison right now?
In the last 30 days: Orlando from £247, Los Angeles from £283, Nashville from £323, Great Smoky Mountains from £338, New York City from £354, per person return.
Can I ask for a specific trip?
Yes. Use the Ask box: say the destination or the kind of trip and the dates, and a page with live prices appears under Madison within a few minutes.
Planning something from Madison?
Tell us what the trip is for and we pick the one that’s worth it.
Prices converted from US dollars at the rate of 15 Oct 2026.