Charter New Haven to Chicago privately from US$28,000, about 1h 57m gate to gate. Request your price in minutes.
This route runs both ways — New Haven (HVN) to Chicago (MDW) and Chicago to New Haven — timed and priced alike.
The straight-line distance between New Haven and Chicago is about 1,237 km (769 miles), or 668 nautical miles.
From US$28,000 · Reply within the hour · No obligation
Chartering a private jet from New Haven to Chicago (and Chicago to New Haven) ranges from US$28,000 for a midsize jet like the Cessna Citation XLS+, up to US$54,000 for a super midsize jet such as the Challenger 350. Charters on this route are dog- and pet-friendly, with in-cabin access for your companion.
A stand-up cabin and more baggage room for medium-haul comfort. 7-9 seats and 3,900 km of range make it a dependable fit here.
Intercontinental comfort with a full stand-up cabin and separate sleeping area. It seats 9-12 and is a frequent choice on sectors of this length.
| Category | Outbound | Return (±10% wind) | From (USD) | Seats |
|---|---|---|---|---|
| Midsize Jet · rec. | 1h 57m | 1h 45m – 2h 09m | US$28,000 | 7-9 |
| Super Midsize Jet | 1h 49m | 1h 38m – 2h 00m | US$38,500 | 9-12 |
| Aircraft | Flight time | Cost range (USD) | Passengers |
|---|---|---|---|
| Cessna Citation XLS+ | 1h 57m | US$28,000 – US$39,000 | 7-9 |
| Hawker 900XP | 1h 56m | US$31,000 – US$43,000 | 7-9 |
| Embraer Praetor 500 | 1h 51m | US$33,500 – US$47,000 | 8-10 |
| Aircraft | Flight time | Cost range (USD) | Passengers |
|---|---|---|---|
| Challenger 350 | 1h 49m | US$38,500 – US$54,000 | 9-12 |
| Cessna Citation Longitude | 1h 49m | US$42,500 – US$59,500 | 9-12 |
| Embraer Praetor 600 | 1h 51m | US$46,000 – US$65,000 | 9-12 |
The return leg uses the same aircraft and guide pricing; timings may shift up to ±10% depending on winds.
Guide prices are one-way estimates incl. positioning; taxes/handling extra. Round-trip and one-way both available.
On New Haven–Chicago, pricing is a function of the route distance and headwinds, fuel costs at both ends, and handling charges at origin and destination. We verify against current aircraft availability before quoting a firm price.
Both cities are served by several airports, giving flexibility on slots and routing:
New Haven, United States: Tweed New Haven Airport, Calverton Executive Airpark, Waterbury Oxford Airport, Francis S Gabreski Airport and Long Island MacArthur Airport.
Chicago, United States: Chicago O'Hare International Airport, Dupage Airport, Chicago Executive Airport, Chicago Midway International Airport, Gary/Chicago International Airport and Lewis University Airport.
Observed traffic points to a weekday route with afternoon departures, on the departures logged so far.
New Haven→Chicago runs about 21 minutes longer, which is the prevailing wind rather than the distance.
| Direction | Departures observed | Typical block | Fastest seen | Aircraft observed |
|---|---|---|---|---|
| New Haven → Chicago | 10 | 124 min | 108 min | Cessna Citation Latitude (3), Cessna Citation XLS (2) |
| Chicago → New Haven | 12 | 103 min | 97 min | Cessna Citation Latitude (3) |
22 movements observed, 2025-08-17 to 2026-08-16.
22 business-aviation flights were tracked between New Haven and Chicago from 17 August 2025 to 16 August 2026 – about 0.4 a week, on 22 separate days.
91% were jets and 9% turboprops. 10 flights set out from the New Haven side and 12 from the Chicago side.
Busiest full month: November 2025 (5 flights). The first and last bars (lighter) are part-months.
Tuesday is the busiest day for this route. Days are by departure date (UTC).
| City | Airfields used (tracked flights) |
|---|---|
| New Haven | Tweed New Haven Airport (HVN) – 10 flights; Igor I Sikorsky Memorial Airport (BDR) – 9 flights; Long Island MacArthur Airport (ISP) – 2 flights; Francis S Gabreski Airport (FOK) – 1 flights |
| Chicago | Chicago Midway International Airport (MDW) – 14 flights; Dupage Airport (DPA) – 8 flights |
Source: open ADS-B network (adsb.lol), 17 August 2025 to 16 August 2026. These are tracked business-aviation movements – a floor, not a census: flights without an active transponder are not seen, and not every flight is a charter.
| Tweed New Haven Airport | Chicago Midway International Airport | |
|---|---|---|
| Code | KHVN / HVN | KMDW / MDW |
| Longest hard runway | 5,600 ft | 6,522 ft |
| Surface | Asphalt | Concrete |
| Field elevation | 12 ft | 620 ft |
| Aircraft | Runway | Range | On this route |
|---|---|---|---|
| Embraer Phenom 100EV Very Light Jet |
3,200 ft 2,400 ft spare |
2,180 km 633 km spare after reserves |
Non-stop |
| Cessna Citation M2 Very Light Jet |
2,900 ft 2,700 ft spare |
2,410 km 863 km spare after reserves |
Non-stop |
| Cessna Citation CJ3+ Light Jet |
3,500 ft 2,100 ft spare |
3,700 km 2,153 km spare after reserves |
Non-stop |
| Embraer Phenom 300E Light Jet |
3,278 ft 2,322 ft spare |
3,650 km 2,103 km spare after reserves |
Non-stop |
| Cessna Citation XLS+ Midsize Jet |
4,200 ft 1,400 ft spare |
3,900 km 2,353 km spare after reserves |
Non-stop |
| Hawker 900XP Midsize Jet |
5,576 ft 24 ft spare |
4,600 km 3,053 km spare after reserves |
Non-stop |
| Challenger 350 Super Midsize Jet |
4,930 ft 670 ft spare |
5,926 km 4,379 km spare after reserves |
Non-stop |
| Cessna Citation Longitude Super Midsize Jet |
4,900 ft 700 ft spare |
6,400 km 4,853 km spare after reserves |
Non-stop |
| Embraer Praetor 600 Super Midsize Jet |
4,692 ft 908 ft spare |
7,220 km 5,673 km spare after reserves |
Non-stop |
| Challenger 605 Heavy Jet |
5,440 ft 160 ft spare |
7,400 km 5,853 km spare after reserves |
Non-stop |
| Gulfstream G450 Heavy Jet |
5,300 ft 300 ft spare |
7,800 km 6,253 km spare after reserves |
Non-stop |
| Falcon 2000LXS Heavy Jet |
4,790 ft 810 ft spare |
7,400 km 5,853 km spare after reserves |
Non-stop |
| Bombardier Global 7500 Ultra Long Range Jet |
6,000 ft 400 ft short |
14,260 km 12,713 km spare after reserves |
Runway too short |
| Bombardier Global 6000 Long Range Jet |
5,800 ft 200 ft short |
11,112 km 9,565 km spare after reserves |
Runway too short |
| Gulfstream G650 Long Range Jet |
6,000 ft 400 ft short |
12,960 km 11,413 km spare after reserves |
Runway too short |
| Falcon 8X Long Range Jet |
4,800 ft 800 ft spare |
11,945 km 10,398 km spare after reserves |
Non-stop |
Alternates within range: Calverton Executive Airpark (10,001 ft, 39 km) · Waterbury Oxford Airport (5,800 ft, 32 km) · Francis S Gabreski Airport (9,002 ft, 51 km) · Long Island MacArthur Airport (7,006 ft, 55 km) · Dupage Airport (7,571 ft, 30 km) · Chicago Executive Airport (5,001 ft, 15 km) · Chicago Midway International Airport (6,522 ft, 25 km) · Gary/Chicago International Airport (8,859 ft, 57 km)
Fast responses matter when schedules shift. We turn around most New Haven–Chicago quote requests within 60 minutes.
Airline schedules are fixed; yours doesn't have to be. Depart New Haven–Chicago when the time is right.
Commercial adds hours in terminals. Private charter cuts the New Haven–Chicago trip to about 1h 57m gate to gate.
Private jets access far more airports than commercial flights — reducing transfers and getting you closer to where you need to be.
Demand on New Haven–Chicago comes from corporate trips and getaways in equal measure — a domestic route where private charter pays off in time and privacy.
Budget US$28,000 – US$54,000 one-way depending on aircraft; a midsize jet sits at the entry point. We confirm a firm figure against live availability.
Roughly 1h 57m gate to gate across the 1,237 km sector — timings shift a little with winds and aircraft.
Midsize Jet, Super Midsize Jet are the usual choices here; our pick is a midsize jet for value and comfort on this distance.
Yes — we handle last-minute New Haven–Chicago charters, often with as little as 4 hours' notice, subject to aircraft and crew availability.
Absolutely — pets travel in the cabin with you on this route; just tell us the details when you ask for a quote.
Of course: Chicago to New Haven runs on the same aircraft and pricing, so round trips are straightforward.
Between 17 August 2025 and 16 August 2026 we tracked 22 business-aviation flights between New Haven and Chicago – about 0.4 a week, flown on 22 different days. Tuesday was the busiest day of the week and November 2025 the busiest full month (5 flights). Tracking uses the open ADS-B network, so the true figure is somewhat higher.
Tracked flights used Tweed New Haven Airport (HVN) – 10 flights; Igor I Sikorsky Memorial Airport (BDR) – 9 flights; Long Island MacArthur Airport (ISP) – 2 flights; Francis S Gabreski Airport (FOK) – 1 flights on the New Haven side, and Chicago Midway International Airport (MDW) – 14 flights; Dupage Airport (DPA) – 8 flights on the Chicago side.
91% of the tracked flights were jets and 9% were turboprops. The most frequently seen aircraft was the Cessna Citation Latitude.
Other flights from New Haven | Chicago | United States | North America
