Private charter · MDW → PYM
Chicago to Plymouth
875 miles. One price for the whole airplane.
Price your flight from Chicago to Plymouth
The trip
Chicago to Plymouth, 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 Plymouth Municipal Airport in Plymouth, 875 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
- 875 mi
- Flight
- —
- Driving
- 18½ 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 Plymouth
Airports in Plymouth
PYM
Regional airportPlymouth Municipal Airport
Plymouth · KPYM
- From downtown
- 5 mi
- Longest runway
- 4,650 ft
EWB
Commercial airportNew Bedford Regional Airport
New Bedford · KEWB
- From downtown
- 25 mi
- Longest runway
- 5,400 ft
HYA
Commercial airportCape Cod Gateway Airport
Hyannis · KHYA
- From downtown
- 28 mi
- Longest runway
- 5,425 ft
When you land
Things to do in Plymouth
Plymouth was founded by the Pilgrims who arrived on the Mayflower in 1620, and the town still builds much of its identity around that history, from Plymouth Rock on the waterfront to the living history museum at Plimoth Patuxet. It is also one of the largest towns by area in Massachusetts, with ponds, cranberry bogs, pine barrens and coastline, and a growing community of new homes and planned neighborhoods such as The Pinehills. Healthcare, tourism, construction and retail form the backbone of the local economy.
- 01
Plimoth Patuxet Museums
This living history museum re-creates a 17th-century English village and a Wampanoag homesite, where costumed interpreters and Native staff explain daily life in the 1620s.
- 02
Mayflower II
A full-scale reproduction of the Pilgrims’ ship, built in England and sailed across the Atlantic in 1957, is berthed at State Pier and open for tours below deck.
- 03
Plymouth Rock
Under a granite portico on the waterfront, the boulder traditionally identified as the Pilgrims’ landing place remains one of the most visited historic sites in New England.
- 04
Pilgrim Hall Museum
Founded in 1824, the oldest continuously operating public museum in the country displays Pilgrim possessions, including furniture, a Bible and swords linked to the original settlers.
- 05
Myles Standish State Forest
Southeast of town, the forest’s pine barrens and kettle ponds offer miles of hiking, biking and horseback trails, plus swimming and camping in summer.
- 06
Plymouth Long Beach
A three-mile barrier beach on Plymouth Bay offers swimming, birding and views back toward the town and harbor, with off-road access for permitted vehicles at its far end.
Questions
Chicago to Plymouth flights
How long is a private flight from Chicago to Plymouth?
About a short flight in a private jet, for 875 miles direct. Driving the same trip takes about 18½ hours.
Which airports do flights from Chicago to Plymouth use?
You can depart from Chicago Midway International Airport (MDW), Chicago O'Hare International Airport (ORD), or Chicago Executive Airport (PWK) and arrive at Plymouth Municipal Airport (PYM), New Bedford Regional Airport (EWB), or Cape Cod Gateway Airport (HYA). Pick whichever is closest to where you're starting and where you're headed.
How much does a private charter from Chicago to Plymouth 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 Plymouth?
Yes. Choose round trip when you search, and pick your return date and time. Flights from Plymouth back to Chicago are priced the same way.
Return flight
Plymouth to Chicago
More flights from Chicago
More flights to Plymouth
Explore Chicago private charter and Plymouth private charter, airports and things to do. Arriving at Plymouth Municipal Airport (PYM).
Chicago to Plymouth, on your schedule
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