There are 8 ways to get from Chicago to Oak Bluffs by plane, train, bus, car ferry, ferry, or car
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Fly Chicago O'Hare International Airport to Martha'S Vineyard Airport
best- Fly from Chicago O'Hare International Airport (ORD) to Martha'S Vineyard Airport (MVY)plane ORD - MVY
5h 14m$104–558Train, bus, car ferry
- Take the train from Chicago Union Station to Bostontrain
- Take the bus from Boston to Woods Holebus
- Take the carferry from Woods Hole to Oak Bluffscarferry
26h 35m$580–1,051Bus, ferry
- Take the bus from Chicago Bus Station to New York Midtownbus
- Take the bus from New York Midtown to Providencebus
- Take the ferry from Quonset Point Pier, Quonset Point, RI to Oak Bluffs, Martha's Vineyard, MAferry
28h$318–440Drive, car ferry
- Drive from Chicago to Woods Holecar
- Take the carferry from Woods Hole to Oak Bluffscarferry Woods Hole
18h 37m$183–423Fly Chicago Midway International Airport to Theodore Francis Green State Airport, ferry
- Fly from Chicago Midway International Airport (MDW) to Theodore Francis Green State Airport (PVD)plane MDW - PVD
- Take the ferry from Quonset Point Pier, Quonset Point, RI to Oak Bluffs, Martha's Vineyard, MAferry
6h 47m$182–530Fly Chicago O'Hare International Airport to Theodore Francis Green State Airport, ferry
- Fly from Chicago O'Hare International Airport (ORD) to Theodore Francis Green State Airport (PVD)plane ORD - PVD
- Take the ferry from Quonset Point Pier, Quonset Point, RI to Oak Bluffs, Martha's Vineyard, MAferry
7h 14m$152–370Fly Chicago Midway International Airport to Boston Logan Airport, bus, car ferry
- Fly from Chicago Midway International Airport (MDW) to Boston Logan Airport (BOS)plane MDW - BOS
- Take the bus from Logan International Airport to Woods Hole Terminalbus
- Take the carferry from Woods Hole to Oak Bluffscarferry
8h 28m$160–865Fly Chicago O'Hare International Airport to Boston Logan Airport, bus, car ferry
- Fly from Chicago O'Hare International Airport (ORD) to Boston Logan Airport (BOS)plane ORD - BOS
- Take the bus from Logan International Airport to Woods Hole Terminalbus
- Take the carferry from Woods Hole to Oak Bluffscarferry
8h 48m$114–605
Chicago O'Hare International Airport (ORD) to Martha'S Vineyard Airport (MVY) flights
Comparing Your Travel Options
The cheapest way to get from Chicago to Oak Bluffs is to fly and ferry which costs $150 - $370 and takes 7h 14m.
The fastest way to get from Chicago to Oak Bluffs is to fly which takes 5h 14m and costs $100 - $600.
The distance between Chicago and Oak Bluffs is 922 miles.
The best way to get from Chicago to Oak Bluffs without a car is to train and bus and car ferry which takes 26h 35m and costs $550 - $1,100.
It takes approximately 5h 14m to get from Chicago to Oak Bluffs, including transfers.
Oak Bluffs is 1h ahead of Chicago. It is currently 11:42 AM in Chicago and 12:42 PM in Oak Bluffs.
There are 273+ hotels available in Oak Bluffs.
What companies run services between Chicago, IL, USA and Oak Bluffs, MA, USA?
American Airlines and Delta fly from Chicago O'Hare International Airport (ORD) to Martha'S Vineyard Airport (MVY) 3 times a day.
- Website
- aa.com
Flights from Chicago O'Hare International Airport to Martha'S Vineyard Airport
- Ave. Duration
- 2h 33m
- When
- Saturday
- Estimated price
- $100–550
Flights from Chicago O'Hare International Airport to Martha'S Vineyard Airport via Philadelphia
- Ave. Duration
- 4h 35m
- When
- Every day
- Estimated price
- $110–600
Flights from Chicago O'Hare International Airport to Martha'S Vineyard Airport via New York La Guardia
- Ave. Duration
- 5h 22m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $110–600
Flights from Chicago O'Hare International Airport to Theodore Francis Green State Airport
- Ave. Duration
- 2h 25m
- When
- Every day
- Estimated price
- $40–230
Flights from Chicago O'Hare International Airport to Theodore Francis Green State Airport via Philadelphia
- Ave. Duration
- 4h 51m
- When
- Every day
- Estimated price
- $45–240
Flights from Chicago O'Hare International Airport to Theodore Francis Green State Airport via Reagan Washington
- Ave. Duration
- 5h 8m
- When
- Every day
- Estimated price
- $45–240
Flights from Chicago O'Hare International Airport to Boston Logan Airport
- Ave. Duration
- 2h 30m
- When
- Every day
- Estimated price
- $75–390
- Website
- united.com
Flights from Chicago O'Hare International Airport to Theodore Francis Green State Airport
- Ave. Duration
- 2h 32m
- When
- Every day
- Estimated price
- $40–230
Flights from Chicago O'Hare International Airport to Theodore Francis Green State Airport via Washington Dulles
- Ave. Duration
- 4h 38m
- When
- Monday
- Estimated price
- $45–240
Flights from Chicago O'Hare International Airport to Boston Logan Airport
- Ave. Duration
- 2h 26m
- When
- Every day
- Estimated price
- $75–390
- Website
- southwest.com
Flights from Chicago Midway International Airport to Theodore Francis Green State Airport
- Ave. Duration
- 2h 12m
- When
- Every day
- Estimated price
- $70–390
Flights from Chicago Midway International Airport to Theodore Francis Green State Airport via Baltimore
- Ave. Duration
- 5h
- When
- Tuesday and Wednesday
- Estimated price
- $75–400
Flights from Chicago Midway International Airport to Theodore Francis Green State Airport via Reagan Washington
- Ave. Duration
- 5h
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $80–410
Flights from Chicago Midway International Airport to Boston Logan Airport
- Ave. Duration
- 2h 15m
- When
- Every day
- Estimated price
- $120–650
- Website
- delta.com
Flights from Chicago O'Hare International Airport to Martha'S Vineyard Airport via New York La Guardia
- Ave. Duration
- 4h 20m
- When
- Monday to Saturday
- Estimated price
- $110–600
Flights from Chicago O'Hare International Airport to Theodore Francis Green State Airport via Detroit
- Ave. Duration
- 4h 10m
- When
- Every day
- Estimated price
- $40–230
Flights from Chicago Midway International Airport to Boston Logan Airport via Detroit
- Ave. Duration
- 4h 44m
- When
- Every day
- Estimated price
- $120–650
Flights from Chicago O'Hare International Airport to Boston Logan Airport
- Ave. Duration
- 2h 24m
- When
- Every day
- Estimated price
- $75–390
- Website
- jetblue.com
Flights from Chicago O'Hare International Airport to Boston Logan Airport
- Ave. Duration
- 2h 46m
- When
- Every day
- Estimated price
- $75–390
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Chicago Union Station to Boston
- Ave. Duration
- 22h 2m
- Frequency
- Once daily
- Estimated price
- $550–900
- Website
- Amtrak
- Phone
- 1-800-343-9999
- Website
- Peter Pan
Bus from Boston to Woods Hole
- Ave. Duration
- 1h 45m
- Frequency
- Every 3 hours
- Estimated price
- $14–26
- Website
- Peter Pan
- Phone
- +1 (855) 626-8585
- Website
- Flixbus USA
Bus from Chicago Bus Station to New York Midtown
- Ave. Duration
- 20h 10m
- Frequency
- Twice daily
- Estimated price
- $160–240
- Schedules at
- Flixbus USA
Bus from New York Midtown to Providence
- Ave. Duration
- 3h 35m
- Frequency
- Once daily
- Estimated price
- $28–45
- Schedules at
- Flixbus USA
- Phone
- +1 (508) 746-0378
- [email protected]
- Website
- Plymouth & Brockton
Bus from Logan International Airport to Woods Hole Terminal
- Ave. Duration
- 2h
- Frequency
- 3 times a day
- Estimated price
- $29–40
- Website
- Plymouth & Brockton
- One Way - Adult
- $29–40
Bus from Logan International Airport to Woods Hole Terminal
- Ave. Duration
- 2h
- Frequency
- 3 times a day
- Estimated price
- $29–40
- Website
- Plymouth & Brockton
- One Way - Adult
- $29–40
- Phone
- +1 (508) 477-8600
- Website
- Steamship Authority
Car ferry from Woods Hole to Oak Bluffs
- Ave. Duration
- 44 min
- Frequency
- 3 times a day
- Estimated price
- $8–170
- Schedules at
- Steamship Authority
- Passenger
- $11
- Passenger Automobiles
- $70–170
Car ferry from Woods Hole to Oak Bluffs
- Ave. Duration
- 44 min
- Frequency
- 3 times a day
- Estimated price
- $8–170
- Schedules at
- Steamship Authority
- Passenger
- $11
- Passenger Automobiles
- $70–170
Car ferry from Woods Hole to Oak Bluffs
- Ave. Duration
- 44 min
- Frequency
- 3 times a day
- Estimated price
- $8–170
- Schedules at
- Steamship Authority
- Passenger
- $11
- Passenger Automobiles
- $70–170
Car ferry from Woods Hole to Oak Bluffs
- Ave. Duration
- 44 min
- Frequency
- 3 times a day
- Estimated price
- $8–170
- Schedules at
- Steamship Authority
- Passenger
- $11
- Passenger Automobiles
- $70–170
- Phone
- +1 401-295-4040
- [email protected]
- Website
- Vineyard Fast Ferry
Ferry from Quonset Point Pier, Quonset Point, RI to Oak Bluffs, Martha's Vineyard, MA
- Ave. Duration
- 1h 45m
- Frequency
- 3 times a day
- Estimated price
- $75–90
- Schedules at
- Vineyard Fast Ferry
- Infants 0-2
- $30–45
- Children 3-11
- $60–75
- Seniors 60+
- $65–85
- Adult 12-59
- $75–90
Ferry from Quonset Point Pier, Quonset Point, RI to Oak Bluffs, Martha's Vineyard, MA
- Ave. Duration
- 1h 45m
- Frequency
- 3 times a day
- Estimated price
- $75–90
- Schedules at
- Vineyard Fast Ferry
- Infants 0-2
- $30–45
- Children 3-11
- $60–75
- Seniors 60+
- $65–85
- Adult 12-59
- $75–90
Ferry from Quonset Point Pier, Quonset Point, RI to Oak Bluffs, Martha's Vineyard, MA
- Ave. Duration
- 1h 45m
- Frequency
- 3 times a day
- Estimated price
- $75–90
- Schedules at
- Vineyard Fast Ferry
- Infants 0-2
- $30–45
- Children 3-11
- $60–75
- Seniors 60+
- $65–85
- Adult 12-59
- $75–90
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