You’re standing in General Mitchell International, clutching a coffee from Valentine Coffee Roasters, and looking at the departure board. New York City is calling. It’s only about 740 miles away. That's a drop in the bucket compared to a cross-country haul, yet planning Milwaukee to NYC flights feels surprisingly complicated once you start looking at the three-airport circus that is the New York metro area.
Most people just click "cheapest" on a search engine and hope for the best. Big mistake.
If you land at JFK but your hotel is in Jersey City, you've just signed up for a two-hour commute that might cost more than your actual plane ticket. Honestly, the "deal" you found on that budget carrier might vanish the moment you realize you're landing 20 miles further from your actual destination than you intended.
The Direct Flight Reality Check
Let's talk brass tacks. If you want to get there without a layover in O'Hare (which, let’s be real, is a gamble given Chicago's weather track record), your options are actually pretty streamlined.
Delta and United own this route.
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Delta is the heavy hitter for non-stop service into LaGuardia (LGA) and John F. Kennedy (JFK). They run these routes like clockwork, often using regional jets like the Embraer 170 or CRJ-900. It’s a quick trip—usually about 2 hours and 20 minutes in the air. You go up, they hand you a Biscoff cookie, you look at some clouds over Lake Erie, and you’re descending over the Hudson.
United, on the other hand, is your go-to if you're heading to Newark Liberty (EWR). They run several non-stops daily. Newark gets a bad rap, but if you’re heading to the West Side of Manhattan or anywhere in New Jersey, it is objectively the better choice.
Which Airport Should You Actually Pick?
This is where travelers trip up. New York isn't just one place. Choosing between LGA, JFK, and EWR is a strategic move.
LaGuardia (LGA)
It used to be a dump. Now, after a multi-billion dollar facelift, it’s arguably the nicest airport in the country. Terminal B and C are stunning. It’s also the closest to Manhattan. If you’re staying in Midtown or the Upper East Side, book this. No question. Just remember: there’s no subway here. You’re taking a bus (the M60 or Q70) or an Uber.
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Newark (EWR)
Don't let the "New Jersey" label scare you. EWR is actually faster to reach from Penn Station than JFK is. You hop on the NJ Transit train, and you’re at 34th Street in about 25 minutes. If you’re a United loyalist, this is your home base.
John F. Kennedy (JFK)
For domestic flights from MKE, JFK is often the "long way 'round." It’s out in southern Queens. The AirTrain to the subway works, but it’s a hike. Use JFK if you’re catching an international connection or if Delta has a price so low you can’t ignore it.
Playing the Pricing Game
Money talks.
Right now, in 2026, we’re seeing round-trip prices for Milwaukee to NYC flights hovering around the $200 to $300 mark for direct routes. If you’re seeing $450, you’re booking too late or trying to fly during a holiday weekend.
January and February are historically the "dead zones" where airlines practically beg you to fly. You can often snag tickets for under $150 if you’re willing to brave a New York winter. Conversely, October is incredibly popular because everyone wants to see the leaves change in Central Park, so prices spike.
A weird quirk of this route? Saturday is often the cheapest day to fly. Business travelers have gone home, and the weekenders are already there. If you can swing a Saturday-to-Tuesday trip, your wallet will thank you.
The Connection Trap
Is it worth stopping in Detroit or Charlotte to save $40?
Probably not.
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When you factor in the "misery tax"—the risk of a delayed first leg, the cost of airport food during a three-hour layover, and the general exhaustion of a 6-hour travel day for a 700-mile trip—the direct flight wins every time. Frontier and American often offer connecting flights that look cheap on paper, but once you add a carry-on bag fee, you’re usually within $20 of the Delta non-stop price anyway.
Actionable Strategy for Your Trip
Stop overthinking and follow this checklist for your next booking:
- Check the map first: If your hotel is in Brooklyn, look at JFK or LGA. If it’s in Chelsea or Hell’s Kitchen, EWR is your best friend.
- Book 45 days out: This is the sweet spot for domestic Milwaukee routes. Prices tend to bottom out here before the "business traveler surge" kicks in at the 14-day mark.
- The "Tuesday at 2 PM" myth is dead: Don't wait for a specific time of day to book. Use a price tracker like Google Flights or Hopper and pounce when the notification hits your phone.
- Check Southwest too: They don't show up on many comparison sites. They fly from MKE to LGA with a stop, and if you’re hauling two heavy suitcases, their "bags fly free" policy might actually make them the cheapest option despite the connection.
Once you land, skip the "shuttle vans" and use the apps or the trains. New York moves fast, and now you know how to get there without getting fleeced.
Next Steps
- Determine exactly where you are staying in NYC to narrow down your airport choice (LGA, EWR, or JFK).
- Set a price alert on Google Flights for your specific dates to catch the 45-day price dip.
- Verify baggage fees if you are considering a budget carrier like Frontier, as these can easily double the base fare.