Private Jet from Boston, US (BOS) to Chicago, US (MDW)
Charter private jets from Boston (BOS) to Chicago (MDW). Compare prices, view aircraft options and book your luxury flight instantly.
Mila Chase
Aviation Specialist
Charter private jets from Boston (BOS) to Chicago (MDW). Compare prices, view aircraft options and book your luxury flight instantly.
The route from Boston (BOS) to Chicago (MDW) covers approximately 1,382 km, with a median block time of 3h 12m on flights we actually tracked.
162 private flights from Boston to Chicago were tracked over the last 12 months — around 14 a month, a steady but not saturated sector.
Median block time on tracked flights is 3h 12m, about 94 minutes longer than a straight distance-and-cruise-speed estimate — taxi, routing and traffic flow account for the difference.
The Cessna Citation Latitude dominates the route, accounting for 34% of tracked movements, followed by the Embraer Phenom 300 and the Cessna Citation Longitude — a useful sanity check when a broker offers you something much larger or much older.
Traffic is strongly seasonal — October carried 22 flights against 7 in November, a 3.1× swing. Expect tighter availability and firmer quotes at the peak.
Browse available private jets for your charter flight from General Edward Lawrence Logan International Airport (BOS) - Boston to Chicago Midway International Airport (MDW) - Chicago. Compare aircraft options, prices, and specifications for 1 passenger.
$36,400 - $56,000
2.8h × $13,000-$20,000/hr
$33,600 - $50,400
2.8h × $12,000-$18,000/hr
$23,800 - $33,600
2.8h × $8,500-$12,000/hr
1,382 km transcontinental route
Observed private jet movements over the last 12 months
Demand peaks in October (22 flights) and bottoms out in November (7) — charter quotes on this route usually follow the same curve.
Half of the tracked flights were airborne for 3h 12m gate to gate, which is what operators bill against on this sector.
Charter rates applied to the 3h 12m median block time observed on this sector — one-way, before positioning, landing fees and taxes.
Source: ADS-B position reports for 12 months (July 2025 – June 2026), filtered to business jet and turboprop types. Movements are counted from aircraft actually on the ground at the airport, so the figures reflect observed traffic rather than published schedules or price estimates.
Boston, US
General Edward Lawrence Logan International Airport is a regional airport located in Boston, US. The airport provides excellent private aviation services with dedicated facilities.
Chicago, US
Chicago Midway International Airport is a regional airport located in Chicago, US. The airport provides excellent private aviation services with dedicated facilities.
Our recommended aircraft for this route, optimized for distance, passenger capacity, and cost efficiency.
Real-time cost calculation based on your selected aircraft type and passenger count.
Mid-Size Jet • 1 passenger
Includes fees & positioning
Premium onboard amenities including entertainment, catering, WiFi, and personalized cabin configuration for your flight.
Compare all available private jet options with detailed specifications, rental costs, and performance data.
| Aircraft | Flight Time | Passengers | Range | Price Range | Popularity | Suitability | Action |
|---|---|---|---|---|---|---|---|
Challenger 350 Bombardier Aerospace FASTEST | 2h 8m | Up to 8 | 5,926 km | $10,204 - $14,456 | ★★★★★ | 100% | |
Challenger 3500 Bombardier Aerospace | 2h 8m | Up to 8 | 6,296 km | $10,629 - $14,881 | ★★★★★ | 100% | |
Challenger 650 Bombardier Aerospace | 2h 8m | Up to 10 | 7,408 km | $11,692 - $15,944 | ★★★★★ | 100% | |
Global 5500 Bombardier Aerospace | 2h 8m | Up to 10 | 10,926 km | $13,818 - $19,133 | ★★★★★ | 100% | |
Global 6500 Bombardier Aerospace | 2h 8m | Up to 12 | 12,223 km | $15,306 - $21,259 | ★★★★★ | 100% | |
Global 7500 Bombardier Aerospace MOST POPULAR | 2h 8m | Up to 14 | 14,260 km | $21,259 - $29,762 | ★★★★★ | 100% |
Explore all aircraft classes suitable for this route. Compare by passenger capacity, range, and hourly rates to find the perfect jet.
Popular models:
Citation Mustang, Phenom 100, Eclipse 550
Ideal for:
Short business trips, regional flights
Popular models:
Citation CJ3+, Learjet 75, Phenom 300
Ideal for:
Medium-distance flights, small groups
Popular models:
Citation Latitude, Hawker 900XP, Learjet 60XR
Ideal for:
Continental flights, business groups
Popular models:
Citation X+, Challenger 350, G280
Ideal for:
Transcontinental flights, luxury travel
Popular models:
Falcon 900EX, Challenger 605, Legacy 650
Ideal for:
Long-range flights, large groups, luxury
Popular models:
G650ER, Global 7500, Falcon 8X
Ideal for:
Intercontinental flights, maximum luxury
Popular models:
King Air 350, TBM 960, Pilatus PC-12
Ideal for:
Short regional flights, cost-effective
Get personalized aircraft recommendations from our experts
View seasonal pricing patterns and demand fluctuations to find the best time to book your flight.
See which aircraft are most frequently chosen by travelers on this route.
Detailed breakdown of all fees including base flight cost, fuel surcharge, permits, crew, and positioning.
Monthly weather patterns and how they affect flight operations throughout the year.
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Find answers to common questions about charter costs, booking process, aircraft options, and travel requirements.
We tracked 162 private jet flights on this sector over the last 12 months from ADS-B data — an average of 14 per month. That is observed traffic, not an estimate.
Median block time on tracked flights is 3h 12m, measured from the last ground contact at Boston to the first ground contact at Chicago. Individual flights vary with routing, winds and traffic.
The types seen most often on this sector are Cessna Citation Latitude (34%), Embraer Phenom 300 (22%), Cessna Citation Longitude (17%). Booking one of these usually means shorter positioning and a better price than requesting a cabin class that rarely operates here.
October was the busiest month with 22 tracked flights, while November was the quietest at 7. Availability is tightest — and quotes firmest — around the peak.
Flight time varies by aircraft type, typically ranging from 1h to 1h for this 1,382km route.
Pricing depends on aircraft size and season, typically ranging from $13800 to $27600 for this route.
We recommend booking 24-48 hours in advance for best aircraft availability, though same-day flights are often possible.
Yes, pets are welcome on private jets. International flights require health certificates and may need quarantine arrangements.
Amenities vary by aircraft but may include Wi-Fi, entertainment systems, gourmet catering, bedroom suites, and shower facilities.
Basic refreshments are typically included, but gourmet catering can be arranged for an additional fee based on your preferences.
Detailed technical information including flight distance, navigation details, airspace regulations, and operational requirements.
Get personalized quotes from our network of verified operators. Compare prices, aircraft specifications, and book your perfect flight.
Aviation Specialist