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Chicago is the financial hub of the Midwest, and TriStar flies into Chicago Midway — closer to the Loop than O'Hare, with fast FBO access. TriStar keeps aircraft positioned nearby year-round for same-day and next-morning departures. Every quote is fixed all-in before you commit.
Routes & pricing
Typical one-way charter pricing on the lanes we fly most for Chicago. Tap a route for the full breakdown.
| Route | Distance | Flight time | One-way from |
|---|---|---|---|
| Chicago → AtlantaMDW → PDK | 502 nm | ~2 h 25 min | $8,300Piston |
| Chicago → New YorkMDW → TEB | 619 nm | ~2 h 55 min | $9,800Piston |
| Chicago → DallasMDW → DAL | 690 nm | ~3 h 15 min | $10,800Piston |
| Chicago → BostonMDW → BOS | 746 nm | ~2 h 30 min | $14,100Turboprop |
| Chicago → HoustonMDW → HOU | 815 nm | ~2 h 45 min | $15,100Turboprop |
| Chicago → MiamiMDW → OPF | 1,023 nm | ~3 h 25 min | $18,100Turboprop |
Airport intelligence
Chicago Midway handles 4 runways, the longest 6,522 ft. Closer to the loop than o'hare, with fast fbo access.
Runways
4longest 6,522 ft of concreteMax aircraft
Heavy6,522 ft handles midsize and heavy jetsElevation
620 ftChicago Midway International AirportFBOs
2Signature Aviation, Atlantic AviationChoosing your airport
Distances are measured from the Chicago city centre. Runway length determines the largest cabin that can operate — the shortest fields are light-jet only.
| Airport | From centre | Longest runway | Largest jet |
|---|---|---|---|
| Chicago Midway International Airport KMDW / MDW | 8 nm | 6,522 ft 4 runways · concrete | Midsize Midsize jets; heavy jets with payload limits |
| Chicago O'Hare International Airport KORD / ORD | 14 nm | 13,000 ft 8 runways · concrete | Heavy Heavy jets (Gulfstream, Falcon) at full range |
| Gary Chicago International Airport KGYY / GYY | 18 nm | 8,859 ft 2 runways · asphalt | Heavy Heavy jets (Gulfstream, Falcon) at full range |
| Lewis University Airport KLOT / LOT | 26 nm | 6,500 ft 2 runways · concrete | Midsize Midsize jets; heavy jets with payload limits |
| Dupage Airport KDPA / DPA | 28 nm | 7,571 ft 4 runways · concrete | Heavy Heavy jets (Gulfstream, Falcon) at full range |
| Waukegan Regional Airport KUGN / UGN | 34 nm | 6,001 ft 2 runways · asphalt | Midsize Midsize jets; heavy jets with payload limits |
Chicago Midway International Airport is closest to the centre at 8 nm; Chicago O'Hare International Airport has the longest runway at 13,000 ft, so it is the safe choice for heavy jets or full payload.
| Runway | Length | Width | Surface | Lighting |
|---|---|---|---|---|
| 13L/31R | 6,522 ft | 150 ft wide | Concrete | Lit |
| 04R/22L | 6,445 ft | 150 ft wide | Paved | Lit |
| 04L/22R | 5,507 ft | 150 ft wide | Asphalt | Lit |
| 13R/31L | 3,859 ft | 60 ft wide | Concrete | Lit |
Get exact prices
Leave your route and a contact — a live dispatcher hand-picks Chicago options with fixed all-in prices.
Fly for less
Repositioning flights sell at up to 75% off the standard charter price. Inventory updates daily.
Why TriStar
Every flight is operated by a certificated FAR Part 135 air carrier, vetted for safety before you are booked. Our safety standard →
We prioritise operators audited to the industry's independent safety ratings, plus background and FAA-compliance checks.
One quoted price, no hidden positioning or handling fees, no account or card needed to see prices.
Our team has worked dispatch, flight ops, crew scheduling and charter sales. About TriStar →
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, transfers 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.