Chicago to New York Empty Leg Flights: 633 Private Jet Repositioning Legs Over the Past Year

633 empty-leg flights connected Chicago and New York over a rolling 12-month window of listings on SkyAccess, making this Midwest-to-Northeast corridor one of the most consistent private jet repositioning routes in the United States. That total counts both directions: 333 legs originating in Chicago (Midway area, KMDW) and 300 originating in Teterboro, New Jersey (KTEB), the primary private aviation gateway for the New York metro area.

Data source: SkyAccess live marketplace, pulled September 2026. All counts reflect a rolling 12-month window of listings, which includes future-dated inventory.

Why this corridor produces so many empty legs

An empty leg arises when a charter operator must reposition an aircraft after dropping off passengers at one city before picking up the next client elsewhere. The Chicago-New York pair generates repositioning traffic in both directions because both cities are major corporate hubs with dense private jet demand year-round. What makes this corridor especially valuable is the directional near-balance: 333 Chicago-bound legs versus 300 New York-bound legs means discounted repositioning inventory surfaces regularly going either way.

Seasonality and peak months

Activity on this corridor is not evenly spread across the calendar. Peak months in the rolling window were April 2026 (86 combined legs), March 2026 (78 legs), and June 2026 (75 legs). Late autumn also sees elevated volume: October 2025 recorded 69 legs and November 2025 recorded 60. The slowest stretch runs through midsummer (July through September 2026 totaled just 38 legs), reflecting compressed corporate travel during vacation season.

By quarter: Q4 2025 (October through December) produced 200 legs; Q1 2026 added 168; Q2 2026 was strongest at 212; and the partial Q3 2026 figure was 38. Spring and early autumn are the best times to find discounted empty-leg availability on this route.

Aircraft flying the corridor

Chicago to New York is roughly 720 nautical miles great-circle, well within the range of midsize and super-midsize jets. The most common aircraft type on this corridor was the Bombardier Challenger 300 (103 legs), a super-midsize typically seating 8 to 9 passengers. The Cessna Citation X followed with 87 legs. Midsize jets also feature heavily: the Beechcraft Hawker 800XP (41 legs) and Cessna Citation Excel (34 legs). Heavy jets including the Gulfstream G IV SP appeared on 37 legs, offering the largest cabins when operators need quick repositioning.

Browse available empty leg flights from Chicago (KMDW) and New York Teterboro (KTEB) on SkyAccess. Also explore Chicago to New York private jet routes for on-demand charter options when no empty leg fits your schedule.

What you typically pay versus a full charter

Empty-leg pricing on SkyAccess runs 25 to 75 percent below the comparable full-charter rate for the same aircraft on the same route. The discount reflects how urgently the operator needs to reposition: a same-day departure with flexible timing can fetch the deepest savings, while a leg with fixed timing a week out may price closer to the 25 percent end. SkyAccess lists 5,000-plus live empty-leg listings sourced from 900-plus FAA Part 135 certified charter operators. No membership is required to browse or book.

Frequently asked questions

How many empty leg flights fly between Chicago and New York?

Over a rolling 12-month window of listings, SkyAccess recorded 633 empty-leg repositioning flights connecting Chicago and New York in both directions: 333 originating in Chicago and 300 originating in Teterboro (the primary New York metro private aviation hub). Activity peaks in spring and early autumn.

Which aircraft types are most common on Chicago to New York empty legs?

Super-midsize jets dominate this corridor. The Bombardier Challenger 300 led with 103 legs over the rolling 12-month window, followed by the Cessna Citation X with 87 legs. Midsize jets such as the Beechcraft Hawker 800XP (41 legs) and Cessna Citation Excel (34 legs) also run the route regularly. Heavy jets appear occasionally, offering the largest cabins at the steepest discounts.

How much can you save on Chicago to New York empty leg flights?

Empty-leg pricing on SkyAccess runs 25 to 75 percent below the comparable full-charter rate for the same aircraft. The exact discount depends on timing, flexibility, and how urgently the operator needs to reposition the aircraft. No membership fee is required to book on SkyAccess.

This data is citable with attribution to SkyAccess. For same-day custom pulls, contact press@theskyaccess.com.