New York City from Milwaukee, Nov 5–9: $2,187 for two, all in
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
$2,187 for two · 4 nights · flights, hotel, taxes, fees & the resort fee
| For two | |
|---|---|
| Flights for two, round trip | $658 |
| Westgate New York Grand Central, 4 nights, two guests, taxes in | $1,344 |
| Resort fee, collected at the desk | $185 |
| The total, before you go | $2,187 |
| A checked bag each, round trip (not in the total) | about $140 |
$564 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 Southwest, $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
$329 per person, round trip
$658 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 | $329 | 1 stop | 6h 10m |
| United. Operated by Republic Airways DBA United Express | $339 | nonstop | 2h 23m |
| American. Operated by SkyWest Airlines as American Eagle | $387 | 1 stop | 4h 15m |
Prices checked Oct 14, 2026, 6:32 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
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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, Nov 5–9
Typical highs 57–64°F, lows near 44°F this time of year
| Day | Typical high | Typical low | Typical weather |
|---|---|---|---|
| Thu, Nov 5 | 63 °F | 44 °F | Overcast |
| Fri, Nov 6 | 62 °F | 47 °F | Clear |
| Sat, Nov 7 | 64 °F | 46 °F | Overcast |
| Sun, Nov 8 | 59 °F | 44 °F | Partly cloudy |
| Mon, Nov 9 | 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
$1,344 for 4 nights, two guests · $336 a night
See roomsHyatt Regency Times Square
$1,823 for 4 nights, two guests · $456 a night
See roomsYotel New York Times Square
$1,343 for 4 nights, two guests · $336 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
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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 | $658 |
| Hotel, 4 nights (Westgate New York Grand Central) | $1,344 |
| Food, getting around and tickets, 4 days for two | $1,520 |
| Total for two | $3,522 |
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 | $329 per person |
| Lowest in the last 30 days | $329 (Oct 14, 2026) |
| Typical price, last 60 days | $893 |
| Price checks | 13 |
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).
- 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.
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