Direct from New YorkChicago
1.9 hrs of uninterrupted productivity or relaxation. Charter your flight today.
New York to Chicago
by private jet
Departing New York
The financial capital of the world, New York City is home to Wall Street, Fortune 500 headquarters, world-class dining, and iconic cultural institutions. From high-stakes boardroom meetings in Midtown to Broadway shows and gallery openings, New York attracts executives, entrepreneurs, and tastemakers year-round.
Arriving in Chicago
Chicago is the commercial heart of the Midwest—a city of broad shoulders, bold architecture, and serious business. From commodities trading in the Loop to manufacturing deals in the suburbs, Chicago connects America's coasts with its agricultural and industrial heartland.
Why fly private on
this route
The commercial experience
New York
Commercial flights from NYC airports mean navigating some of the busiest airspace in the world. TSA lines at JFK regularly exceed 45 minutes, and delays cascade through the system daily.
Chicago
O'Hare's weather delays are legendary—winter snowstorms and summer thunderstorms ripple cancellations nationwide. Midway is closer to downtown but cramped and chaotic.
The private advantage
From New York
Skip the chaos of JFK and Newark commercial terminals. Private aviation in New York means departing from dedicated FBOs where you can arrive 15 minutes before takeoff, not 2 hours. For time-sensitive business travelers, this translates to an extra half-day of productivity.
To Chicago
O'Hare is the nation's most delay-prone airport. Private aviation means departing from Chicago Executive (PWK) in Wheeling, where your biggest delay is waiting for your coffee. Perfect for day trips to coasts or quick hops to Detroit, Minneapolis, or Indianapolis.
Save hours, not just minutes
When you factor in airport arrival, security, boarding, deplaning, and ground transportation, private aviation saves 3-5 hours on each trip compared to commercial.
Popular for
this route
Airports we serve
New York, NY/NJ
Teterboro (TEB) is the premier choice for Manhattan-bound travelers—just 12 miles from Midtown with no commercial traffic. Westchester County (HPN) offers a quieter alternative for those north of the city.
Chicago, IL
Chicago Executive Airport (PWK) offers the best combination of proximity to downtown (45 min) and efficient operations. DuPage Airport (DPA) serves the western suburbs.
Insider tips
Morning departure, evening return - maximize your day
Also from New York
Explore other popular routes departing from New York
Common questions
A private jet flight from New York to Chicago takes approximately 1.9 hrs depending on aircraft type. Light jets average 2.1 hours, while long-range jets can complete the journey in 1.8 hours.
Charter costs for New York to Chicago vary based on aircraft type and availability. Light jets start around $4,500/hour, midsize jets around $6,500/hour, and heavy jets around $8,500/hour. For a 1.9 hrs flight, total costs typically range from $15,000 to $50,000+.
For New York, popular private jet airports include TEB, HPN, LGA. In Chicago, private jets commonly use PWK, MDW, ORD. These airports offer FBO services with private terminals, expedited security, and premium amenities.
Yes, same-day charter is often available on this route. ReserveJets offers 24/7 booking with as little as 4 hours notice for our fleet aircraft. Availability depends on aircraft positioning, but this is a popular route with frequent options.
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