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Chicago's charter traffic splits between Midway — ten miles from the Loop with full-service FBOs — and Chicago Executive up north for Lake County and the northern suburbs. TriStar positions midsize and super-midsize aircraft through both fields weekly, which keeps one-way pricing sharp.
Routes & pricing
Typical one-way charter pricing on the lanes we fly most. Every quote is fixed all-in before you commit — the calculator above prices your exact route in seconds.
| Route | Distance | Flight time | One-way from |
|---|---|---|---|
| Chicago → New YorkMDW → TEB | 619 nm | ~1.4 h | from $8,000Piston |
| Chicago → MiamiMDW → MIA | 1,029 nm | ~2.3 h | from $14,800Turboprop |
| Chicago → DallasMDW → DAL | 690 nm | ~1.6 h | from $8,900Piston |
| Chicago → AspenMDW → ASE | 884 nm | ~2 h | from $12,700Turboprop |
| Chicago → Las VegasMDW → LAS | 1,319 nm | ~3 h | from $23,400Light Jet |
Fly for less
Repositioning flights sell at up to 75% off the standard charter price. Inventory updates daily — if the timing fits, it is the smartest way to fly private.
Airports
We quote every departure against the airport that actually saves you time — not just the biggest one.
Closest jet field to the Loop; premium FBO row.
North-side alternative for Evanston, Northbrook, Lake Forest.
Western suburbs with long runways for heavy jets.
The process
Calculator, WhatsApp, Telegram or a call — a live dispatcher picks it up 24/7.
Exact aircraft with photos, total fixed price, and empty-leg alternatives if your dates flex.
Contract and payment are handled digitally. Catering, cars and customs are arranged by your concierge.
Good to know
One message to dispatch — two or three real aircraft options with fixed prices, usually within half an hour.