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$584–1,057Bus, 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$311–433Drive, car ferry
- Drive from Chicago to Woods Holecar
- Take the carferry from Woods Hole to Oak Bluffscarferry Woods Hole
18h 37m$195–440Fly 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 52m$188–540Fly 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 19m$162–420Fly 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 Boston to Woods Holebus
- Take the carferry from Woods Hole to Oak Bluffscarferry
9h 8m$626–1,203Fly 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 Boston to Woods Holebus
- Take the carferry from Woods Hole to Oak Bluffscarferry
8h 56m$126–753
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 $160 - $420 and takes 7h 19m.
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 2:55 AM in Chicago and 3:55 AM in Oak Bluffs.
There are 285+ hotels available in Oak Bluffs.
What companies run services between Chicago, IL, USA and Oak Bluffs, MA, USA?
American Airlines flies from Chicago O'Hare International Airport (ORD) to Martha'S Vineyard Airport (MVY) twice daily.
- Website
- southwest.com
Flights from Chicago Midway International Airport to Theodore Francis Green State Airport
- Ave. Duration
- 2h 12m
- When
- Every day
- Estimated price
- $75–400
Flights from Chicago Midway International Airport to Theodore Francis Green State Airport via Baltimore
- Ave. Duration
- 4h 36m
- When
- Every day
- Estimated price
- $80–420
Flights from Chicago Midway International Airport to Theodore Francis Green State Airport via Reagan Washington
- Ave. Duration
- 4h 31m
- When
- Tuesday, Wednesday, Monday, Thursday, Friday, and Sunday
- Estimated price
- $85–420
Flights from Chicago Midway International Airport to Boston Logan Airport
- Ave. Duration
- 2h 21m
- When
- Every day
- Estimated price
- $100–550
- Website
- united.com
Flights from Chicago O'Hare International Airport to Theodore Francis Green State Airport
- Ave. Duration
- 2h 37m
- When
- Every day
- Estimated price
- $50–280
Flights from Chicago O'Hare International Airport to Theodore Francis Green State Airport via Washington Dulles
- Ave. Duration
- 4h 50m
- When
- Monday, Tuesday, Wednesday, Thursday, and Sunday
- Estimated price
- $55–290
Flights from Chicago O'Hare International Airport to Boston Logan Airport
- Ave. Duration
- 2h 31m
- When
- Every day
- Estimated price
- $70–380
- 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
- $100–550
Flights from Chicago O'Hare International Airport to Martha'S Vineyard Airport via New York La Guardia
- Ave. Duration
- 5h 31m
- When
- Every day
- Estimated price
- $100–550
Flights from Chicago O'Hare International Airport to Theodore Francis Green State Airport
- Ave. Duration
- 2h 31m
- When
- Every day
- Estimated price
- $50–280
Flights from Chicago O'Hare International Airport to Theodore Francis Green State Airport via Reagan Washington
- Ave. Duration
- 4h 59m
- When
- Every day
- Estimated price
- $55–290
Flights from Chicago O'Hare International Airport to Boston Logan Airport
- Ave. Duration
- 2h 39m
- When
- Every day
- Estimated price
- $70–380
Flights from Chicago O'Hare International Airport to Boston Logan Airport via Syracuse
- Ave. Duration
- 4h 15m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $75–380
- Website
- delta.com
Flights from Chicago O'Hare International Airport to Theodore Francis Green State Airport via Detroit
- Ave. Duration
- 4h 45m
- When
- Every day
- Estimated price
- $50–280
Flights from Chicago O'Hare International Airport to Boston Logan Airport
- Ave. Duration
- 2h 36m
- When
- Every day
- Estimated price
- $70–380
Flights from Chicago Midway International Airport to Boston Logan Airport via Detroit
- Ave. Duration
- 4h 50m
- When
- Every day
- Estimated price
- $100–550
- Website
- jetblue.com
Flights from Chicago O'Hare International Airport to Boston Logan Airport
- Ave. Duration
- 2h 43m
- When
- Every day
- Estimated price
- $70–380
Rome2Rio's guide to Amtrak
Contact DetailsContact 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
- $15–26
- Website
- Peter Pan
Bus from Boston to Woods Hole
- Ave. Duration
- 2h 15m
- Frequency
- Every 3 hours
- Estimated price
- $15–28
- Website
- Peter Pan
Bus from Boston to Woods Hole
- Ave. Duration
- 2h 15m
- Frequency
- Every 3 hours
- Estimated price
- $15–28
- 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
- $150–230
- Schedules at
- Flixbus USA
Bus from New York Midtown to Providence
- Ave. Duration
- 3h 35m
- Frequency
- Once daily
- Estimated price
- $27–45
- Schedules at
- Flixbus USA
- 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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