Bluebird
Annapolis, Maryland

Private charter · MDW → BWI

Chicago to Annapolis

609 miles. One price for the whole airplane.

Photo: Flickr user: high limitzz https://www.flickr.com/people/highlimitstudio/ · CC BY 2.0

Price your flight from Chicago to Annapolis

Trip type
1

Times are local to each departure airport.

The trip

Chicago to Annapolis, door to door faster.

Trade about 13 hours on the road for about a short flight in the air. Bluebird flies you direct from Chicago Midway International Airport in Chicago to Baltimore/Washington International Thurgood Marshall Airport in Annapolis, 609 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
609 mi
Flight
—
Driving
13 hours
Passengers
Up to 1
MDWChicagoBWIAnnapolis
MDW → BWI609 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 Annapolis

Airports in Annapolis

  • BWI

    Major airport

    Baltimore/Washington International Thurgood Marshall Airport

    Baltimore · KBWI

    From downtown
    17 mi
    Longest runway
    10,503 ft

  • MTN

    Commercial airport

    Martin State Airport

    Baltimore · KMTN

    From downtown
    25 mi
    Longest runway
    6,999 ft

  • ESN

    Regional airport

    Easton Airport / Newnam Field

    Easton · KESN

    From downtown
    26 mi
    Longest runway
    5,500 ft

When you land

Things to do in Annapolis

Annapolis is Maryland’s capital and one of the best-preserved colonial cities in the country, its brick streets winding between the domed State House and the waterfront at City Dock. The State House is the oldest in the nation still in continuous legislative use, and it briefly served as the U.S. capitol, where the Continental Congress ratified the Treaty of Paris. The United States Naval Academy fills the city with midshipmen, families and visiting officers, and government, lobbying, tourism and the marine industry drive the economy.

  1. 01

    United States Naval Academy

    Guided tours of the Academy’s waterfront campus visit the chapel, John Paul Jones’s crypt and Bancroft Hall, and visitors can watch the midshipmen’s noon formation.

  2. 02

    Maryland State House

    Visitors can tour the historic chambers, including the Old Senate Chamber where George Washington resigned his commission as commander in chief in 1783.

  3. 03

    City Dock and Ego Alley

    The narrow inlet at the heart of downtown draws a parade of yachts and sailboats, surrounded by restaurants, shops and the historic Market House.

  4. 04

    William Paca House and Garden

    The Georgian mansion of a signer of the Declaration of Independence has been restored with period furnishings and terraced gardens leading toward the water.

  5. 05

    Annapolis Maritime Museum

    In Eastport, the museum tells the story of the Chesapeake’s watermen and oyster industry, and runs boat trips to the Thomas Point Shoal Lighthouse.

  6. 06

    Sailing the Chesapeake

    Public sailing cruises, private charters and sailing schools leave from the harbor, and Wednesday evening races are a beloved local tradition.

Explore Annapolis charter

Questions

Chicago to Annapolis flights

How long is a private flight from Chicago to Annapolis?

About a short flight in a private jet, for 609 miles direct. Driving the same trip takes about 13 hours.

Which airports do flights from Chicago to Annapolis use?

You can depart from Chicago Midway International Airport (MDW), Chicago O'Hare International Airport (ORD), or Chicago Executive Airport (PWK) and arrive at Baltimore/Washington International Thurgood Marshall Airport (BWI), Martin State Airport (MTN), or Easton Airport / Newnam Field (ESN). Pick whichever is closest to where you're starting and where you're headed.

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

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

Return flight

Annapolis to Chicago

More flights from Chicago

More flights to Annapolis

Explore Chicago private charter and Annapolis private charter, airports and things to do. Arriving at Baltimore/Washington International Thurgood Marshall Airport (BWI).

Chicago to Annapolis, 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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