Bluebird
Boston, Massachusetts

Private charter · MDW → BOS

Chicago to Boston

858 miles. One price for the whole airplane.

Photo: King of Hearts · CC BY-SA 4.0

Price your flight from Chicago to Boston

Trip type
1

Times are local to each departure airport.

The trip

Chicago to Boston, door to door faster.

Trade about 18½ hours on the road for about a short flight in the air. Bluebird flies you direct from Chicago Midway International Airport in Chicago to Boston Logan International Airport in Boston, 858 miles in a private jet with two pilots up front. Need a different size of aircraft? We'll source one sized for the trip. The price is for the whole aircraft, with every fee and tax shown before you book.

Distance
858 mi
Flight
—
Driving
18½ hours
Passengers
Up to 1
MDWChicagoBOSBoston
MDW → BOS858 miles direct

Departing Chicago

Airports in Chicago

  • MDW

    Major airport

    Chicago Midway International Airport

    Chicago · KMDW

    From downtown
    9 mi
    Longest runway
    6,522 ft

  • ORD

    Major airport

    Chicago O'Hare International Airport

    Chicago · KORD

    From downtown
    16 mi
    Longest runway
    13,000 ft

  • PWK

    Commercial airport

    Chicago Executive Airport

    Chicago/Prospect Heights/Wheeling · KPWK

    From downtown
    21 mi
    Longest runway
    5,001 ft

  • GYY

    Commercial airport

    Gary/Chicago International Airport

    Gary · KGYY

    From downtown
    21 mi
    Longest runway
    8,859 ft

Arriving Boston

Airports in Boston

  • BOS

    Major airport

    Boston Logan International Airport

    Boston · KBOS

    From downtown
    3 mi
    Longest runway
    10,083 ft

  • BED

    Commercial airport

    Laurence G Hanscom Field

    Bedford · KBED

    From downtown
    14 mi
    Longest runway
    7,011 ft

  • BVY

    Commercial airport

    Beverly Regional Airport

    Beverly / Danvers · KBVY

    From downtown
    17 mi
    Longest runway
    5,001 ft

  • LWM

    Commercial airport

    Lawrence Municipal Airport

    Lawrence · KLWM

    From downtown
    25 mi
    Longest runway
    5,001 ft

When you land

Things to do in Boston

Boston is New England’s capital in every practical sense: home to state government, a large financial and asset-management industry, world-renowned hospitals such as Massachusetts General and a life sciences cluster that spills across the river into Cambridge’s Kendall Square, near MIT and Harvard. Dozens of colleges and universities give the region a constant flow of researchers, founders, investors, parents and prospective students, and the Seaport, the Back Bay and the Longwood Medical Area each function almost as a downtown of their own.

  1. 01

    Freedom Trail

    A red-brick line leads 2.5 miles past 16 Revolutionary-era sites, from Boston Common and the Old State House to Paul Revere’s House and the USS Constitution in Charlestown.

  2. 02

    Fenway Park

    The oldest ballpark in Major League Baseball has hosted the Red Sox since 1912, and guided tours take visitors up to the seats atop the towering left-field wall known as the Green Monster.

  3. 03

    Museum of Fine Arts, Boston

    One of the largest art museums in the country, the MFA spans ancient Egypt to contemporary work, with standout collections of American paintings, Japanese art and French Impressionism.

  4. 04

    Isabella Stewart Gardner Museum

    A Venetian-style palazzo built around a flowering courtyard holds Gardner’s personal collection of European art, displayed just as she arranged it, including the empty frames left by a famous 1990 theft.

  5. 05

    North End

    Boston’s oldest residential neighborhood is known for narrow streets, Italian restaurants and cannoli from bakeries along Hanover Street, as well as the Old North Church of “one if by land” fame.

  6. 06

    Boston Harbor Islands

    Seasonal ferries from Long Wharf reach a national and state park of harbor islands, including Georges Island, crowned by Civil War–era Fort Warren, and Spectacle Island’s hilltop skyline views.

Explore Boston charter

Questions

Chicago to Boston flights

How long is a private flight from Chicago to Boston?

About a short flight in a private jet, for 858 miles direct. Driving the same trip takes about 18½ hours.

Which airports do flights from Chicago to Boston use?

You can depart from Chicago Midway International Airport (MDW), Chicago O'Hare International Airport (ORD), or Chicago Executive Airport (PWK) and arrive at Boston Logan International Airport (BOS), Laurence G Hanscom Field (BED), or Beverly Regional Airport (BVY). Pick whichever is closest to where you're starting and where you're headed.

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

The price depends on the date, departure time, aircraft and where the airplane is positioned. Enter your trip above to see an instant price for the whole airplane, with every tax and fee included.

Can I book a round trip between Chicago and Boston?

Yes. Choose round trip when you search, and pick your return date and time. Flights from Boston back to Chicago are priced the same way.

Return flight

Boston to Chicago

More flights from Chicago

More flights to Boston

Explore Chicago private charter and Boston private charter, airports and things to do. Arriving at Boston Logan International Airport (BOS).

Chicago to Boston, on your schedule

Choose your departure time and see a price for the whole aircraft. Bring up to 1 passengers for the same price.

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