Bluebird
Rockland, Maine

Private charter · MDW → RKD

Chicago to Rockland

955 miles. One price for the whole airplane.

Photo: Quintin Soloviev · CC BY 4.0

Price your flight from Chicago to Rockland

Trip type
1

Times are local to each departure airport.

The trip

Chicago to Rockland, door to door faster.

Trade about 20½ hours on the road for about a short flight in the air. Bluebird flies you direct from Chicago Midway International Airport in Chicago to Knox County Regional Airport in Rockland, 955 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
955 mi
Flight
—
Driving
20½ hours
Passengers
Up to 1
MDWChicagoRKDRockland
MDW → RKD955 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 Rockland

Airports in Rockland

  • RKD

    Commercial airport

    Knox County Regional Airport

    Rockland · KRKD

    From downtown
    5 mi
    Longest runway
    5,412 ft

When you land

Things to do in Rockland

Rockland is a working harbor town on the western shore of Penobscot Bay, long known as a lobster and fishing port and now equally for art and food. The Farnsworth Art Museum, with its collection of works by three generations of the Wyeth family, and the Center for Maine Contemporary Art anchor a downtown full of galleries and restaurants. Just up the coast, Camden’s harbor, framed by the Camden Hills, is one of the most photographed in New England, and the region is home to a fleet of traditional schooners, or windjammers.

  1. 01

    Farnsworth Art Museum

    Known for its collection of works by N.C., Andrew and Jamie Wyeth, the museum also manages the Olson House in Cushing, the subject of Andrew Wyeth’s Christina’s World.

  2. 02

    Rockland Breakwater Lighthouse

    A walk of nearly a mile along a granite breakwater leads to a lighthouse at the harbor entrance, with views of the bay and passing boats.

  3. 03

    Camden Hills State Park

    A short drive north, a road and hiking trails climb Mount Battie, whose summit tower overlooks Camden Harbor and the islands of Penobscot Bay.

  4. 04

    Windjammer Cruises

    Traditional schooners based in Rockland and Camden offer day sails and multiday cruises through Penobscot Bay, with stops at islands and lobster bakes on the shore.

  5. 05

    Owls Head Transportation Museum

    Next to the airport, this museum displays antique automobiles, motorcycles and aircraft, many in working condition, with events through the season.

  6. 06

    Center for Maine Contemporary Art

    In a striking building designed by Toshiko Mori in downtown Rockland, the center presents exhibitions of contemporary work by artists connected to Maine.

Explore Rockland charter

Questions

Chicago to Rockland flights

How long is a private flight from Chicago to Rockland?

About a short flight in a private jet, for 955 miles direct. Driving the same trip takes about 20½ hours.

Which airports do flights from Chicago to Rockland use?

You can depart from Chicago Midway International Airport (MDW), Chicago O'Hare International Airport (ORD), or Chicago Executive Airport (PWK) and arrive at Knox County Regional Airport (RKD). Pick whichever is closest to where you're starting and where you're headed.

How much does a private charter from Chicago to Rockland 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 Rockland?

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

Return flight

Rockland to Chicago

More flights from Chicago

More flights to Rockland

Explore Chicago private charter and Rockland private charter, airports and things to do. Arriving at Knox County Regional Airport (RKD).

Chicago to Rockland, 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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