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Private Jet Charter Chicago to Boston

At 746 nautical miles, Chicago to Boston is an easy 2 h 30 min flight for almost any jet in the fleet. It is one of the corridors where empty legs appear most often, so flexible dates can cut the price dramatically. Chicago is the financial and industrial hub of the Midwest; Boston is the financial and academic hub of New England. TriStar keeps aircraft positioned around both and quotes a fixed all-in price before you commit.

Call dispatch — 24/7
746 nmgreat-circle distance
~2 h 30 minnonstop flight time
$14,100one-way from
−75%on empty legs

Routes & pricing

Chicago to Boston — price by aircraft class

Indicative one-way pricing for the 746 nm leg, cheapest cabin first. Every quote is fixed all-in before you commit — the calculator above prices your exact date in seconds.

Aircraft classSeatsFlight timeOne-way from
TurbopropKing Air / PC-12 class8~2 h 30 min$14,100
Light JetCitation CJ / Phenom 300 class7~1 h 40 min$21,000
Midsize JetLearjet 60 / Citation XLS class8~1 h 30 min$28,400
Heavy JetGulfstream / Falcon class14~1 h 25 min$48,400
Boston → ChicagoChicago → New YorkChicago → Los AngelesChicago → MiamiChicago → Las Vegas

Aircraft & airports

Which jets can fly Chicago → Boston

This leg is 746 nm. Two things decide what we can dispatch: the aircraft's range, and the runway available at each end.

Cabin classRunway neededRangeChicagoBostonFlies this route
Turboprop
King Air / PC-12		3,500 ft✓ 1,300 nm✓✓Yes
Light Jet
Citation CJ / Phenom 300		4,500 ft✓ 2,000 nm✓✓Yes
Midsize Jet
Learjet 60 / Citation XLS		5,500 ft✓ 2,900 nm✓✓Yes
Heavy Jet
Gulfstream / Falcon		6,500 ft✓ 7,000 nm✓✓Yes

The shorter of the two fields is General Edward Lawrence Logan International Airport at 10,083 ft, so it sets the ceiling for this route. Boston has 6 jet-capable airports in total — if your preferred aircraft does not fit, dispatch can reposition you via Laurence G Hanscom Field (BED).

Chicago airports

  • Chicago Midway International Airport (MDW) — 8 nm from centre, 6,522 ft, midsize-jet capable
  • Chicago O'Hare International Airport (ORD) — 14 nm from centre, 13,000 ft, heavy-jet capable
  • Gary Chicago International Airport (GYY) — 18 nm from centre, 8,859 ft, heavy-jet capable
  • Lewis University Airport (LOT) — 26 nm from centre, 6,500 ft, midsize-jet capable

Boston airports

  • General Edward Lawrence Logan International Airport (BOS) — 2 nm from centre, 10,083 ft, heavy-jet capable
  • Laurence G Hanscom Field (BED) — 12 nm from centre, 7,011 ft, midsize-jet capable
  • Beverly Regional Airport (BVY) — 15 nm from centre, 5,001 ft, light-jet capable
  • Lawrence Municipal Airport (LWM) — 22 nm from centre, 5,001 ft, light-jet capable

Runway figures are typical balanced-field requirements; actual limits depend on temperature, field elevation and payload, which dispatch confirms for your date.

Get exact prices

Get your Chicago → Boston price

Leave a contact and a live dispatcher sends 5+ real aircraft for Chicago–Boston with fixed all-in prices.

  • 5+ real aircraft with photos and fixed all-in prices
  • Reply from a live dispatcher, usually within 30 minutes
  • No account, no card, no spam

One reply with your options and exact price.

Fly for less

Live empty legs around Chicago

Repositioning flights on and around the Chicago–Boston corridor sell at up to 75% off. Inventory updates daily — if the timing fits, it is the smartest way to fly private.

Airport intelligence

Where you fly from and to

Real runway and handling data for both ends — plus live weather at Boston.

Chicago MidwayMDW · 6,522 ft

Departure — closer to the Loop than O'Hare, with fast FBO access. 4 runways, longest 6,522 ft concrete, elevation 620 ft.

Logan InternationalBOS · 10,083 ft

Arrival — minutes across the harbor from downtown Boston. 6 runways, longest 10,083 ft asphalt, elevation 20 ft.

Why TriStar

Certified operators. Real prices. Human dispatch.

FAA Part 135 only

Every flight is operated by a certificated FAR Part 135 air carrier, vetted for safety before you are booked. Our safety standard →

ARGUS & WYVERN

We prioritise operators audited to the industry's independent safety ratings, plus background and FAA-compliance checks.

Fixed all-in pricing

One quoted price, no hidden positioning or handling fees, no account or card needed to see prices.

10+ years, every side

Our team has worked dispatch, flight ops, crew scheduling and charter sales. About TriStar →

The process

How booking works

Tell us the route

Calculator, WhatsApp, Telegram or a call — a live dispatcher picks it up 24/7.

Get 2–3 real options

Exact aircraft with photos, total fixed price, and empty-leg alternatives if your dates flex.

Approve — wheels up

Contract and payment are handled digitally. Catering, cars and customs are arranged by your concierge.

Good to know

Flying private from Chicago to Boston

How much is a private jet from Chicago to Boston?
Chicago to Boston is 746 nm, so the cheapest suitable cabin is a turboprop at about $14,100 one-way. A heavy jet on the same leg runs about $48,400. Charter is priced by block hour, so the gap between cabins widens with distance rather than being a fixed percentage. Every quote we send is all-in — crew, fuel, handling, landing and segment fees, taxes and concierge.
How long is the flight from Chicago to Boston?
Airborne time is about 1h 25m in a jet and up to 2h 30m in the slowest cabin we would offer for 746 nm. Your quote is based on block time — taxi, climb and descent add roughly 20–40 minutes on top of the airborne figure, which is why the billed hours are higher than the flight time. Door-to-door you still save the security queue, the boarding process and the bag wait.
Which aircraft can fly Chicago to Boston?
The longest runway available is 13,000 ft at Chicago O'Hare International Airport (ORD) and 10,083 ft at General Edward Lawrence Logan International Airport (BOS), so General Edward Lawrence Logan International Airport at 10,083 ft sets the ceiling for this route. That clears turboprop, light jet, midsize jet, heavy jet on the 746 nm leg. Real limits also move with temperature, field elevation and payload, which dispatch checks against the actual date before quoting.
Which airport should I use for Boston?
Boston has 6 jet-capable civil airports. General Edward Lawrence Logan International Airport (BOS) is nearest the centre at 2 nm. Tell dispatch which matters more — ground time or cabin size — and we price both.
Are there empty leg flights between Chicago and Boston?
Yes — aircraft reposition through the Chicago–Boston corridor regularly, and when one matches your dates the price can fall by up to 75% against a standard charter. On a leg this length repositioning flights are less frequent but worth far more when they appear. Live inventory for this corridor is listed further up the page and refreshes daily.
Can I fly Chicago to Boston at short notice?
Usually yes. We regularly move aircraft on the Chicago–Boston corridor same-day when a suitable tail is free and the crew is legal on duty time. Short notice is also when repositioning flights surface, so a late request sometimes prices better than a planned one — call dispatch rather than assuming it is too late.

Your Chicago–Boston jet is closer than you think

One message to dispatch — two or three real aircraft options with fixed prices, usually within half an hour.

+1 833 800 0230