New York City from Milwaukee, 5 – 9 Nov: £1,648 for two, all in
This page’s text is in English for now; a translation is on its way.
The verdict
Our verdict
Worth it, if
- $329 per person, $564 below the typical fare on this route
- Westgate New York Grand Central: 8.4 from 1,751 reviews, free cancellation
- Typical highs of 57–64°F for Nov 5–9, good walking weather
The catch: The Southwest fare leaves at 5:30 AM with one stop, 6h 10m in all, and a checked bag is about $140 for two, not in the total.
Worth it if you'll take an early one-stop flight for this fare; skip it if you'd rather fly the United nonstop at $678 for two.
Worth it if you can handle a 5:30 AM start and one stop: $2,187 for two, all in, covers the Southwest flights at $658 and 4 nights at Westgate New York Grand Central at $1,344 plus its $185 property fee, with taxes and fees included. You leave Thursday, Nov 5 and fly home Monday, Nov 9, 2026, so you get 4 nights. The Southwest flight has one stop and takes 6h 10m, and a checked bag and spending money aren't in the total.
The total, before you go
£1,648 for two · 4 nights · flights, hotel, taxes, fees & the resort fee
| For two | |
|---|---|
| Flights for two, return | £496 |
| Westgate New York Grand Central, 4 nights, two guests, taxes in | £1,013 |
| Resort fee, collected at the desk | £139 |
| The total, before you go | £1,648 |
| Hold luggage each, return (not in the total) | about £106 |
£425 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 Southwest, £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
£248 per person, return
£496 for two, taxes and fees included · Southwest · 1 stop · 6h 10m
Out Thu, Nov 5, 5:30 AM – Thu, Nov 5, 12:40 PM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Southwest | £248 | 1 stop | 6h 10m |
| United. Operated by Republic Airways DBA United Express | £256 | nonstop | 2h 23m |
| American. Operated by SkyWest Airlines as American Eagle | £292 | 1 stop | 4h 15m |
Prices checked 14 Oct 2026, 18:32 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 $329 per person round trip on Southwest, $564 below the typical fare on this route. That's 63% under the $893 median of our earlier checks, and it's the lowest fare we've seen in 30 days across 13 checks. With the hotel, the whole trip comes to $2,187 for two, all in, before you go. In early November, New York City usually has highs of 57–64°F and lows near 44°F. That's jacket weather, good for long walks between museums and neighborhoods, and the normals show Friday, Nov 6 as clear. November is also the month of the NYC Marathon and the Macy's Thanksgiving Day Parade, and it comes before December's holiday windows and peak hotel prices. These prices are what we found on Oct 14, and they can change.
The kind of trip this is
This is a city getaway built on Broadway, big museums, skyline views and a restaurant for every cuisine, all reachable by subway. It suits a couple or two friends who like to walk all day and eat well, and four nights give you time to fill. The cool fall air keeps the walking easy. If you want a beach or a slow, quiet trip, skip this one.
Weather in New York City, 5 – 9 Nov
Typical highs 57–64°F, lows near 44°F this time of year
| Day | Typical high | Typical low | Typical weather |
|---|---|---|---|
| Thu 5 Nov | 63 °F | 44 °F | Overcast |
| Fri 6 Nov | 62 °F | 47 °F | Clear |
| Sat 7 Nov | 64 °F | 46 °F | Overcast |
| Sun 8 Nov | 59 °F | 44 °F | Partly cloudy |
| Mon 9 Nov | 57 °F | 40 °F | Overcast |
Weather data by Open-Meteo.com · averages, not a forecast
Where to stay in New York City
We checked three hotels in Manhattan. All three are 4-star, room-only rooms with free cancellation. Westgate New York Grand Central is the best-value pick and the one in our total: $1,344 for the stay ($336 a night) in a Luxe Queen, rated 8.4 from 1,751 reviews, plus $185 in fees paid at the property. Hyatt Regency Times Square is the top-rated pick at 8.6 from 2,230 reviews, for $1,823 ($456 a night) in a Superior King Room plus $247 at the property. Yotel New York Times Square is the budget pick at $1,343 ($336 a night) for a Premium Queen Room with City View. It's rated 7.4 from 7,609 reviews, with $185 at the property. Midtown, home to Times Square and the Broadway theaters, has the most hotel choice.
Westgate New York Grand Central
£1,013 for 4 nights, two guests · £253 a night
See roomsHyatt Regency Times Square
£1,374 for 4 nights, two guests · £344 a night
See roomsYotel New York Times Square
£1,012 for 4 nights, two guests · £253 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
- 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 Milwaukee | Milwaukee Mitchell International (MKE) |
|---|---|
| Airports in New York City | John F. Kennedy International (JFK), Newark Liberty International (EWR), LaGuardia (LGA) |
| Flight time | 6h 10m (1 stop) |
| Distance | 732 miles each way |
| Time difference | +1 hour |
What 4 nights in New York City costs
| Estimate | |
|---|---|
| Flights for two | £496 |
| Hotel, 4 nights (Westgate New York Grand Central) | £1,013 |
| Food, getting around and tickets, 4 days for two | £1,146 |
| Total for two | £2,655 |
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: Milwaukee to New York City
| Per person | |
|---|---|
| This trip | £248 per person |
| Lowest in the last 30 days | £248 (14 Oct 2026) |
| Typical price, last 60 days | £673 |
| Price checks | 13 |
Good to know
- Passport: no passport needed for travellers from the United States: a government photo ID is enough for New York City.
- Currency: US dollar (USD).
- Macy's Thanksgiving Day Parade and the NYC Marathon
- No passport needed, and you pay in US dollars
- New York is 1 hour ahead of Milwaukee
- The Southwest flight leaves MKE at 5:30 AM and lands at 12:40 PM with one stop, 6h 10m in all
- All three hotels offer free cancellation and are room only, with no breakfast included
- We suggest budgeting $1,520 for spending, which works out to $190 per person a day
Questions readers ask
Is it worth it?
For most readers, yes. The fare is $329 per person, $564 below the typical fare on this route and the lowest we've seen in 30 days. The catch is the Southwest flight itself: it leaves at 5:30 AM and has one stop, 6h 10m in all.
How much is the whole trip for two?
$2,187 for two, all in. That's $658 for the flights plus $1,344 for 4 nights at Westgate New York Grand Central, its $185 property fee, and taxes and fees. A checked bag (about $140 for two) and spending money are extra.
Is there a nonstop?
Yes. We found a United Express nonstop at $339 per person ($678 for two). It leaves at 6:00 AM and lands at 9:23 AM, 2h 23m in the air. Our total uses the Southwest fare at $658 for two.
What is the weather like?
Highs for Nov 5–9 are usually 57–64°F, with lows near 44°F. The normals show mostly overcast days, with Friday, Nov 6 clear. Bring a jacket for the evenings.
Is 4 nights enough?
It's enough for a Broadway show, a morning at the Met or MoMA, the High Line, the Staten Island Ferry and a sunset walk across the Brooklyn Bridge, at a steady pace.
Do I need a passport?
No. It's a domestic trip from Milwaukee Mitchell International (MKE), you pay in US dollars, and New York is 1 hour ahead.
Also found for you
The newest finds from Milwaukee.
Just found · from MilwaukeeLowest in 30 daysWorth it, if
Asheville
23 – 25 Oct 2026 · 2 nights
- $664 per person, $604 below the typical fare on this route
- Peak fall foliage on the Blue Ridge Parkway for your dates
- Overcast, highs of 67–77°F, rain chance 8% to 16%
£501 per person · round trip · taxes & fees
Delta · with a stop · 4h 4m
The catch: The lowest fare has one stop and lands at 11:55 PM Friday, and peak foliage brings the busiest weekends of the year.
Worth it if a late Friday arrival is fine for a foliage weekend; skip it if you want a nonstop or quiet trails.
Tweak this trip
Just found · from Milwaukee53% below typicalWorth it, if
New Orleans
13 – 17 Nov 2026 · 4 nights
- £287 per person below the typical fare on this route
- Free cancellation at Wyndham Garden New Orleans Downtown
- Typical highs 67–70°F, lows near 57°F this time of year
£1,113 for two · 4 nights · flights, hotel, taxes & fees
Flights £490 + hotel £623, taxes in · a checked bag each adds about £106
Southwest · with a stop · 4h 10m
The catch: Not nonstop: a stop on the way, 4h 10m in all.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
Tweak this trip
Just found · from MilwaukeeLowest in 30 daysWorth it, if
Nashville
23 – 25 Oct 2026 · 2 nights
- £231 per person below the typical fare on this route
- Lowest in 30 days on this route
- Best Western Plus Nashville Airport Hotel - BNA, rated 8.1 by 1,350 guests
£1,495 for two · 2 nights · flights, hotel, taxes & fees
Flights £1,189 + hotel £305, taxes in · a checked bag each adds about £121
United · with a stop · 7h 53m
The catch: Not nonstop: a stop on the way, 7h 53m in all.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
Tweak this trip
More trips
Just found · from Milwaukee
Las Vegas
16 – 18 Oct 2026 · 2 nights
- Nonstop on Southwest, 3h 50m
- Free cancellation at Excalibur
- Highs 79–82°F, little rain expected
£1,973 for two · 2 nights · flights, hotel, taxes & fees
Flights £1,633 + hotel £340, taxes in · a checked bag each adds about £106
Southwest · nonstop · 3h 50m
The catch: £23 per person above the typical fare on this route.
Worth it if you want late nights and a crowd; skip it if you want to sleep.
The weekend after · from Milwaukee21% below typicalWorth it, if
Orlando
23 – 25 Oct 2026 · 2 nights
- Fare is $206 per person below the typical on this route
- Westgate Town Center Resort: 8.5 from 1,755 reviews, free cancellation
- October brings the EPCOT Food & Wine Festival and Halloween events
£1,309 for two · 2 nights · flights, hotel, taxes & fees
Flights £1,104 + hotel £205, taxes in · a checked bag each adds about £121
American. Operated by SkyWest Airlines as American Eagle · with a stop · 19h 42m
The catch: The $732 fare has 1 stop and 19h 42m of travel, landing Saturday at 4:01 PM, and a checked bag is about $160 for two.
Worth it if a Saturday evening and a full Sunday in the parks is enough; skip it if you'd rather pay $740 per person for the Southwest nonstop.
A week away · from MilwaukeeWorth it, if
Honolulu & Oahu
14 – 21 Nov 2026 · 7 nights
- $588 per person, $243 below the highest fare we saw
- Ramada Plaza by Wyndham Waikiki scores 8 from 1,298 reviews
- Highs of 81–82°F, plus humpback whales offshore in November
£1,688 for two · 7 nights · flights, hotel, taxes & fees
Flights £886 + hotel £802, taxes in · a checked bag each adds about £121
American. Operated by SkyWest Airlines as American Eagle · with a stop · 11h 38m
The catch: With one stop, the flight out takes 11h 38m, none of the three hotels offers free cancellation, and a checked bag runs about $160 for two.
Worth it if a long travel day is fine for a week of warm water and Waikiki; skip it if you need a nonstop or a refundable room.
Just found · from MilwaukeeLowest in 30 daysWorth it, if
Asheville
23 – 25 Oct 2026 · 2 nights
- $664 per person, $604 below the typical fare on this route
- Peak fall foliage on the Blue Ridge Parkway for your dates
- Overcast, highs of 67–77°F, rain chance 8% to 16%
£501 per person · round trip · taxes & fees
Delta · with a stop · 4h 4m
The catch: The lowest fare has one stop and lands at 11:55 PM Friday, and peak foliage brings the busiest weekends of the year.
Worth it if a late Friday arrival is fine for a foliage weekend; skip it if you want a nonstop or quiet trails.
Just found · from Milwaukee53% below typicalWorth it, if
New Orleans
13 – 17 Nov 2026 · 4 nights
- £287 per person below the typical fare on this route
- Free cancellation at Wyndham Garden New Orleans Downtown
- Typical highs 67–70°F, lows near 57°F this time of year
£1,113 for two · 4 nights · flights, hotel, taxes & fees
Flights £490 + hotel £623, taxes in · a checked bag each adds about £106
Southwest · with a stop · 4h 10m
The catch: Not nonstop: a stop on the way, 4h 10m in all.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
All trips from Milwaukee · New York City from every city · Prices on this route · Trips in November 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.
Prices converted from US dollars at the rate of 15 Oct 2026.
Image credits
- Photo: Vlad Alexandru Popa / Pexels, Pexels License
- Photo: Pixabay / Pexels, Pexels License
- Photo: Denil Dominic / Pexels, Pexels License