Find Private Flights from boston (bos) to chicago (ord)

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Boston to Chicago Charter Flights & Private Jets

Large Air Taxi

Speedy, powerful twin-engine aircraft for families and groups.

Piper Navajo, Cessna 402 or similar


6h 0m

7

4


$ 16,606USD
total for up to 7 travelers
Customize & Book

Light Jet

Medium-range flights with turbojet speed. Cruise above the weather with high-altitude comfort.

Hawker 400, Citation CJ, Phenom 300 or similar


2h 19m

7

4


$ 19,711USD
total for up to 7 travelers
Customize & Book

Executive Air Taxi

Your turbo-powered hauler. Fits moderate groups with luggage, including car seats, strollers, bikes, skis, and golf clubs.

Pilatus PC-12, Beechcraft King Air, Piper Meridian, Cessna Conquest, Socata TBM or similar


3h 20m

5-8

6


$ 21,068USD
total for up to 5-8 travelers
Customize & Book

Personal Jet

A nice efficient jet option for a small group with a short to medium-range mission.

Cirrus Visionjet, Embraer Phenom, Citation Mustang, Eclipse 500 or similar


2h 43m

4

2


$ 21,137USD
total for up to 4 travelers
Customize & Book

Midsize Jet

Many midsize and most "super midsize" jets have transcontinental range for your group of as many as 8 passengers.

Hawker 800, Citation Excel, Learjet 60 or similar


2h 22m

8

5


$ 22,348USD
total for up to 8 travelers
Customize & Book

Large Jet

Long range capability with all the comforts for groups as large as a dozen or more.

Gulfstream IV, Challenger 604, Falcon 900 or similar


2h 12m

10-12

10


$ 33,732USD
total for up to 10-12 travelers
Customize & Book

Book private charter flights from Boston, MA to Chicago, IL. Choose the most convenient airport serving the Chicago area, including Chicago O'hare International Airport (ORD), and Chicago O'hare International Airport (ORD). Pick the private plane best suited for your itinerary: from small piston engine planes, to turboprops, to light jets, midsize, large cabin, and ultra-long range business jets.

Linear Air offers air charter flights to destinations around the world, with a wide range of private planes and business jets available for flights when you want them.

How much does a private flight from Boston to Chicago cost?

The total private charter cost between Boston to Chicago ranges from $16606 to $33732 for the specified travel dates. The total fare price for the entire charter plane (price per person is based on the number of passengers entered above).

What are Chicago's surrounding cities and towns?

Bensenville
Schiller Park
Franklin Park
Wood Dale
Elk Grove Village
Norridge
Des Plaines
Park Ridge
River Grove
Harwood Heights

How long does a flight from Boston to Chicago take?

Flight time depends on the aircraft class and model you choose from among single-engine or twin-engine propeller planes, turboprops, and private jets.

The flight distance from Boston to Chicago is 751 miles and flight time ranges from 2h 12m to 6h 0m, based on plane type. If you were to drive from Boston to Chicago, it would take 20 hours 44 minutes to drive 1037 miles.

Popular Charter Flights for Airports Near Chicago

Easy Booking with Linear Air

1. FIND YOUR AIRPORTS

Simply enter your flight search above for destinations in the U.S., Canada, Mexico, Bermuda, the Caribbean and Europe. For more help on flight searches, please see How It Works. Air taxis fly to 10x more airports than airlines. Your search will help you find the closest one to you!

2. SELECT YOUR PLANE

Once you've searched above, select your flight. Choose your aircraft type: luxury jet, business-class turbo-prop, or affordable air taxi: based on number of seats, speed, and non-stop range. And the entire plane is yours!

3. SHARE SEATS & SAVE

Share extra seats and receive credit for future plane or jet rental. Simply enter your flight search above, select your flight, continue your purchase, and, as you enter your Billing Address, simply check "I would like to share my extra seat!"

Frequently Asked Questions: Private Flights from Boston to Chicago

The total private charter flight cost from Boston to Chicago ranges from $16,606 to $33,732 for the entire aircraft.
Large Air Taxi: $16,606
Light Jet: $19,711
Executive Air Taxi: $21,068
Personal Jet: $21,137
Midsize Jet: $22,348
Large Jet: $33,732
Flight time depends on the aircraft class you choose from among single-engine or twin-engine propeller planes, turboprops and business jets. The flight distance from Boston to Chicago is 1037 miles and flight time ranges from 2h 12m to 6h 0m, based on type of plane. If you were to drive from Boston to Chicago it would take 20 hours 44 minutes to drive 1037 miles.
Large Air Taxi: 6h 0m
Light Jet: 2h 19m
Executive Air Taxi: 3h 20m
Personal Jet: 2h 43m
Midsize Jet: 2h 22m
Large Jet: 2h 12m
Fly to Chicago to visit the following cities or towns:
Harwood Heights
Itasca
Addison
Elmhurst
Melrose Park
Berkeley
Niles
Elmwood Park
Mount Prospect
Bellwood
Panera Bread
Angelo's Ristorante and Banquets
Rosalia's Deli
Buffalo Wild Wings
Chipotle
100 South
Cafe Amano
Cupcakes for Courage
Lou Malnati's
Pazzi Di Pizza
Evergreen Aqua Park
Six Flags Great America
The University of Chicago
Parks College (historical)
Boston to Chicago Private Flights