The routes from Chicago we cover so far, with a one-way estimate for the jet size most groups choose. Each guide explains what moves the price and which airports to use.
| Route | Usual jet | Time in the air | One way, estimate |
|---|---|---|---|
| Chicago to Miami | Light jet | about 2 hr 55 min | $16,000–$21,500 |
| Chicago to New York | Light jet | about 1 hr 55 min | $10,500–$14,000 |
| Chicago to Aspen | Midsize jet | about 2 hr 35 min | $16,500–$22,000 |
| Chicago to Las Vegas | Light jet | about 3 hr 55 min | $21,500–$29,000 |
| Chicago to Naples | Light jet | about 2 hr 50 min | $15,500–$20,500 |
| Chicago to Scottsdale | Light jet | about 3 hr 45 min | $20,500–$27,500 |
2026 estimates, typical fees included. See how we estimate prices.
Airports in Chicago
- Chicago Midway International Airport (MDW). On the southwest side, closer to the Loop than O'Hare.
- Chicago Executive Airport (PWK). In Wheeling, convenient for the North Shore suburbs.