Home · Empty legs · Chicago

Empty leg flights Chicago

Repositioning jets in and out of Chicagoland sell for a fraction of the standard charter price — same aircraft, same crew, same safety standard. You trade schedule flexibility for the discount.

Live inventory

Empty legs around Chicago

Repositioning flights our dispatch is tracking right now. Inventory turns over daily.

The full live marketplace — every operator, every corridor — runs on EmptyLeg.Store, our empty-leg platform.

Browse all empty legs

Airports

6 jet airports serving Chicago

Where repositioning traffic actually lands. Distances are from the Chicago city centre; runway length decides which cabin can use the field.

Chicago Midway International AirportKMDW / MDW8 nm from the centre · longest runway 6,522 ft · 4 runwaysMidsize jets; heavy jets with payload limits
Chicago O'Hare International AirportKORD / ORD14 nm from the centre · longest runway 13,000 ft · 8 runwaysHeavy jets (Gulfstream, Falcon) at full range
Gary Chicago International AirportKGYY / GYY18 nm from the centre · longest runway 8,859 ft · 2 runwaysHeavy jets (Gulfstream, Falcon) at full range
Lewis University AirportKLOT / LOT26 nm from the centre · longest runway 6,500 ft · 2 runwaysMidsize jets; heavy jets with payload limits
Dupage AirportKDPA / DPA28 nm from the centre · longest runway 7,571 ft · 4 runwaysHeavy jets (Gulfstream, Falcon) at full range
Waukegan Regional AirportKUGN / UGN34 nm from the centre · longest runway 6,001 ft · 2 runwaysMidsize jets; heavy jets with payload limits

How it works

Getting an empty leg, in three steps

1. Tell us the corridor

Your airports, rough dates and a budget ceiling. Flexibility on timing is what unlocks the discount.

2. We watch the inventory

Dispatch monitors repositioning flights across the operators we work with, around the clock.

3. First refusal by email

You hear about a match before it goes public — with the operator, tail number and price already checked.

Get Chicago route alerts

Free with the TriStar Membership trial — two months, no credit card.

Good to know

Chicago empty leg questions

What is an empty leg flight from Chicago?

When an aircraft flies into or out of Chicago without passengers — repositioning after a drop-off or heading back to base — the operator sells that leg below the standard charter price. The aircraft, crew and safety standard are identical; only the pricing and the flexibility differ.

How much can I save on a Chicago empty leg?

Typically up to 75% against a standard charter on the same aircraft. The discount depends on how badly the operator needs the leg filled and how close the date is.

Which airports do Chicago empty legs use?

Any of the 6 jet-capable fields across Chicagoland. Most repositioning traffic runs through Chicago Midway International Airport (MDW), while Chicago O'Hare International Airport (ORD) has the longest runway at 13,000 ft for heavy aircraft, and Chicago Midway International Airport (MDW) is closest to the centre at 8 nm.

What's the catch with empty legs?

Flexibility. The date, time and sometimes the exact airport are set by the operator's other flight, and a leg can be withdrawn if their original booking changes. We tell you any conditions upfront rather than after you commit.

How do I get told about Chicago empty legs first?

Give dispatch your corridor and budget and we watch the inventory for you — route alerts go out by email the moment something matches, which usually beats the public listing.

Flying out of Chicago soon?

If your dates flex even by a day, say so — that is usually the difference between full charter price and an empty leg.

Request a charter