Private charter · MDW → HYA
Chicago to Hyannis
899 miles. One price for the whole airplane.
Price your flight from Chicago to Hyannis
The trip
Chicago to Hyannis, door to door faster.
Trade about 19 hours on the road for about a short flight in the air. Bluebird flies you direct from Chicago Midway International Airport in Chicago to Cape Cod Gateway Airport in Hyannis, 899 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
- 899 mi
- Flight
- —
- Driving
- 19 hours
- Passengers
- Up to 1
Departing Chicago
Airports in Chicago
MDW
Major airportChicago Midway International Airport
Chicago · KMDW
- From downtown
- 9 mi
- Longest runway
- 6,522 ft
ORD
Major airportChicago O'Hare International Airport
Chicago · KORD
- From downtown
- 16 mi
- Longest runway
- 13,000 ft
PWK
Commercial airportChicago Executive Airport
Chicago/Prospect Heights/Wheeling · KPWK
- From downtown
- 21 mi
- Longest runway
- 5,001 ft
GYY
Commercial airportGary/Chicago International Airport
Gary · KGYY
- From downtown
- 21 mi
- Longest runway
- 8,859 ft
Arriving Hyannis
Airports in Hyannis
HYA
Commercial airportCape Cod Gateway Airport
Hyannis · KHYA
- From downtown
- 1 mi
- Longest runway
- 5,425 ft
ACK
Commercial airportNantucket Memorial Airport
Nantucket · KACK
- From downtown
- 30 mi
- Longest runway
- 6,303 ft
MVY
Regional airportMartha's Vineyard Airport
Martha's Vineyard · KMVY
- From downtown
- 25 mi
- Longest runway
- 5,504 ft
When you land
Things to do in Hyannis
Hyannis is the largest village in the town of Barnstable and the main commercial hub of Cape Cod, with the Cape’s regional hospital, its largest shopping district, the ferry terminals for Nantucket and Martha’s Vineyard and the Cape Cod Gateway Airport. It is also known for its connection to the Kennedy family, whose compound stands in neighboring Hyannis Port. Beyond tourism, business here centers on healthcare, real estate, construction, marine trades and the services that support a population that swells every summer.
- 01
John F. Kennedy Hyannis Museum
On Main Street, this museum tells the story of President Kennedy’s summers on Cape Cod through photographs, films and exhibits on the family’s life in Hyannis Port.
- 02
Craigville Beach
A long, wide sandy beach on Nantucket Sound with warm, gentle water by Cape standards, Craigville is one of the most popular beaches on the south side of the Cape.
- 03
Hyannis Harbor and the HyArts District
Near the ferry docks, a collection of small artist shanties sells local work in season, steps from harbor cruises, fishing charters and waterfront restaurants.
- 04
Cape Cod Baseball League
Summer evenings bring free games featuring top college players at local fields, including the Hyannis Harbor Hawks at McKeon Park, where many future major leaguers have played.
- 05
Sandy Neck Beach
On the north side of Barnstable, a barrier beach stretches about six miles along Cape Cod Bay, with dunes, salt marsh trails and a historic colony of cottages near its tip.
- 06
Cape Cod National Seashore
About a half hour’s drive east, the national seashore protects 40 miles of Outer Cape beaches, dunes, lighthouses and trails, including Coast Guard and Nauset Light beaches in Eastham.
Questions
Chicago to Hyannis flights
How long is a private flight from Chicago to Hyannis?
About a short flight in a private jet, for 899 miles direct. Driving the same trip takes about 19 hours.
Which airports do flights from Chicago to Hyannis use?
You can depart from Chicago Midway International Airport (MDW), Chicago O'Hare International Airport (ORD), or Chicago Executive Airport (PWK) and arrive at Cape Cod Gateway Airport (HYA), Nantucket Memorial Airport (ACK), or Martha's Vineyard Airport (MVY). Pick whichever is closest to where you're starting and where you're headed.
How much does a private charter from Chicago to Hyannis 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 Hyannis?
Yes. Choose round trip when you search, and pick your return date and time. Flights from Hyannis back to Chicago are priced the same way.
Return flight
Hyannis to Chicago
More flights from Chicago
More flights to Hyannis
Explore Chicago private charter and Hyannis private charter, airports and things to do. Arriving at Cape Cod Gateway Airport (HYA).
Chicago to Hyannis, on your schedule
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