There are 9 ways to get from Chicago to Eastham by plane, bus, train, bus (Flixbus), 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 Midway International Airport to Boston Logan Airport, bus
best- Fly from Chicago Midway International Airport (MDW) to Boston Logan Airport (BOS)MDW - BOS
- Take the bus from Logan International Airport to Hyannis Transportation Center
8h 13m$124–534Fly Chicago O'Hare International Airport to Theodore Francis Green State Airport, train, bus
cheapest- Fly from Chicago O'Hare International Airport (ORD) to Theodore Francis Green State Airport (PVD)ORD - PVD
- Take the train from Providence to South Station
- Take the bus from Boston South Station to Hyannis Transportation Center
10h 49m$72–956Train, bus
- Take the train from Chicago Union Station to BostonLake Shore Limited
- Take the bus from Boston South Buses to Hyannis Transportation CenterHyannis - South Shore to Logan Airport
26h 14m$162–720Bus
- Take the bus from Chicago Bus Station to New York Midtown
- Take the bus from New York Midtown to Boston
- Take the bus from Boston South Station to Hyannis Transportation Center
29h 45m$149–373Drive 1,047.1 mi
- Drive from Chicago to Eastham1,047.1 mi
18h 7m$192–276Fly Chicago O'Hare International Airport to Boston Logan Airport, bus
- Fly from Chicago O'Hare International Airport (ORD) to Boston Logan Airport (BOS)ORD - BOS
- Take the bus from Logan International Airport to Hyannis Transportation Center
8h 32m$134–384Fly Chicago Midway International Airport to Theodore Francis Green State Airport, train, bus
- Fly from Chicago Midway International Airport (MDW) to Theodore Francis Green State Airport (PVD)MDW - PVD
- Take the train from Providence to South Station
- Take the bus from Boston South Station to Hyannis Transportation Center
10h 25m$82–1,006Fly Chicago Midway International Airport to Manchester Airport, bus
- Fly from Chicago Midway International Airport (MDW) to Manchester Airport (MHT)MDW - MHT
- Take the bus from Boston Manchester Airport to Boston
- Take the bus from Boston South Station to Hyannis Transportation Center
10h 22m$130–654Fly Chicago Midway International Airport to Barnstable Municipal Airport
- Fly from Chicago Midway International Airport (MDW) to Barnstable Municipal Airport (HYA)MDW - HYA
8h 6m$118–637
Chicago to Eastham by train and bus
Questions & Answers
The cheapest way to get from Chicago to Eastham is to drive which costs $190 - $280 and takes 18h 7m.
The fastest way to get from Chicago to Eastham is to fly which takes 8h 6m and costs $110 - $650.
No, there is no direct bus from Chicago station to Eastham. However, there are services departing from Chicago Bus Station and arriving at Eastham via New York Midtown, Boston South Station and Hyannis Transportation Center. The journey, including transfers, takes approximately 29h 45m.
The distance between Chicago and Eastham is 975 miles. The road distance is 1053.2 miles.
The best way to get from Chicago to Eastham without a car is to train and bus which takes 26h 14m and costs $160 - $750.
It takes approximately 8h 13m to get from Chicago to Eastham, including transfers.
Chicago to Eastham bus services, operated by Flixbus USA, depart from Chicago Bus Station.
The best way to get from Chicago to Eastham is to bus which takes 29h 45m and costs $140 - $380. Alternatively, you can fly, which costs $110 - $650 and takes 8h 6m.
Chicago to Eastham bus services, operated by Flixbus USA, arrive at New York Midtown station.
Eastham is 1h ahead of Chicago. It is currently 2:24 PM in Chicago and 3:24 PM in Eastham.
What companies run services between Chicago, IL, USA and Eastham, MA, USA?
You can take a bus from Chicago Bus Station to Eastham via New York Midtown, Boston, Boston South Station, and Hyannis Transportation Center in around 29h 45m. Alternatively, Southwest Airlines, Cape Air, and American Airlines fly from Chicago Midway International Airport (MDW) to Barnstable Municipal Airport (HYA) twice daily.
Transport is disrupted due to the Russia-Ukraine war. Read more
- Website
- southwest.com
Flights from Chicago Midway International Airport to Boston Logan Airport
- Ave. Duration
- 2h 15m
- When
- Every day
- Estimated price
- $90–460
Flights from Chicago Midway International Airport to Theodore Francis Green State Airport
- Ave. Duration
- 2h 8m
- When
- Every day
- Estimated price
- $60–330
Flights from Chicago Midway International Airport to Theodore Francis Green State Airport via Baltimore
- Ave. Duration
- 4h 7m
- When
- Monday, Thursday, Friday, Saturday, and Sunday
- Estimated price
- $65–350
Flights from Chicago Midway International Airport to Theodore Francis Green State Airport via Reagan Washington
- Ave. Duration
- 4h 15m
- When
- Thursday and Sunday
- Estimated price
- $70–350
Flights from Chicago Midway International Airport to Manchester Airport
- Ave. Duration
- 2h 5m
- When
- Every day
- Estimated price
- $100–550
Flights from Chicago Midway International Airport to Manchester Airport via Baltimore
- Ave. Duration
- 4h 22m
- When
- Every day
- Estimated price
- $110–550
- Website
- aa.com
Flights from Chicago O'Hare International Airport to Boston Logan Airport
- Ave. Duration
- 2h 27m
- When
- Every day
- Estimated price
- $75–390
Flights from Chicago O'Hare International Airport to Theodore Francis Green State Airport
- Ave. Duration
- 2h 24m
- When
- Every day
- Estimated price
- $50–280
Flights from Chicago O'Hare International Airport to Theodore Francis Green State Airport via Philadelphia
- Ave. Duration
- 3h 56m
- When
- Sunday
- Estimated price
- $55–290
Flights from Chicago O'Hare International Airport to Theodore Francis Green State Airport via Reagan Washington
- Ave. Duration
- 4h 27m
- When
- Every day
- Estimated price
- $55–290
Flights from Chicago Midway International Airport to Barnstable Municipal Airport via Philadelphia
- Ave. Duration
- 4h 34m
- When
- Monday, Tuesday, Wednesday, and Saturday
- Estimated price
- $120–600
Flights from Chicago Midway International Airport to Barnstable Municipal Airport via Reagan Washington
- Ave. Duration
- 4h 55m
- When
- Saturday
- Estimated price
- $120–650
Flights from Chicago Midway International Airport to Barnstable Municipal Airport via New York La Guardia
- Ave. Duration
- 5h 56m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $110–600
- Website
- united.com
Flights from Chicago O'Hare International Airport to Boston Logan Airport
- Ave. Duration
- 2h 21m
- When
- Every day
- Estimated price
- $75–390
Flights from Chicago O'Hare International Airport to Theodore Francis Green State Airport
- Ave. Duration
- 2h 25m
- 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 25m
- When
- Every day
- Estimated price
- $55–290
- Website
- delta.com
Flights from Chicago Midway International Airport to Boston Logan Airport via Detroit
- Ave. Duration
- 4h 8m
- When
- Every day
- Estimated price
- $90–460
Flights from Chicago O'Hare International Airport to Boston Logan Airport
- Ave. Duration
- 2h 26m
- When
- Every day
- Estimated price
- $75–390
Flights from Chicago O'Hare International Airport to Theodore Francis Green State Airport via Detroit
- Ave. Duration
- 4h 19m
- When
- Every day
- Estimated price
- $50–280
- Website
- jetblue.com
Flights from Chicago O'Hare International Airport to Boston Logan Airport
- Ave. Duration
- 2h 28m
- When
- Every day
- Estimated price
- $75–390
Flights from Chicago Midway International Airport to Barnstable Municipal Airport via Boston Logan Airport
- Ave. Duration
- 3h 59m
- When
- Monday, Tuesday, Wednesday, Thursday, and Saturday
- Estimated price
- $110–600
- Website
- capeair.com
Flights from Chicago Midway International Airport to Barnstable Municipal Airport via Boston Logan Airport
- Ave. Duration
- 3h 59m
- When
- Monday, Tuesday, Wednesday, Thursday, and Saturday
- Estimated price
- $110–600
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Train from Chicago Union Station to Boston
- Ave. Duration
- 22h 2m
- Frequency
- Once daily
- Estimated price
- $130–700
- Website
- https://www.amtrak.com/home.html
- Phone
- +1-617-222-3200
- Website
- mbta.com
Train from Providence to South Station
- Ave. Duration
- 1h 15m
- Frequency
- Hourly
- Estimated price
- $5–14
- Website
- https://www.mbta.com
- Adult
- $5–14
Rome2Rio's guide to Amtrak Northeast Regional
Contact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Train from Providence to South Station
- Ave. Duration
- 48 min
- Frequency
- Every 3 hours
- Estimated price
- $6–210
- Website
- https://www.amtrak.com/home.html
- Schedules at
- https://www.amtrak.com/northeast-regional-train
- Coach
- $6–210
- Business Class
- $45–240
Rome2Rio's guide to Amtrak Acela
Contact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Train from Providence to South Station
- Ave. Duration
- 47 min
- Frequency
- Every 4 hours
- Estimated price
- $10–600
- Schedules at
- https://www.amtrak.com/acela-train
- Website
- https://www.amtrak.com/home.html
- Business Class
- $10–450
- First Class
- $110–600
- Phone
- +1 (508) 746-0378
- info@p-b.com
- Website
- p-b.com
Bus from Logan International Airport to Hyannis Transportation Center
- Ave. Duration
- 2h 15m
- Frequency
- Hourly
- Estimated price
- $28–40
- Website
- https://www.p-b.com
- One Way - Adult
- $28–40
Bus from Boston South Buses to Hyannis Transportation Center
- Ave. Duration
- 1h 50m
- Frequency
- Hourly
- Estimated price
- $27–35
- Website
- https://www.p-b.com
- One Way - Adult
- $27–35
- Phone
- +1 (855) 626-8585
- Website
- flixbus.com
Bus from Chicago Bus Station to New York Midtown
- Ave. Duration
- 20h 10m
- Frequency
- Once daily
- Estimated price
- $100–230
- Schedules at
- flixbus.com
Bus from New York Midtown to Boston
- Ave. Duration
- 4h 20m
- Frequency
- Every 3 hours
- Estimated price
- $30–75
- Schedules at
- flixbus.com
- Phone
- 1-800-343-9999
- Website
- peterpanbus.com
Bus from Boston South Station to Hyannis Transportation Center
- Ave. Duration
- 1h 35m
- Frequency
- Every 3 hours
- Estimated price
- $10–40
- Website
- https://peterpanbus.com
- Adult
- $10–40
Rome2Rio's guide to Greyhound USA
Contact Details
- Phone
- +1 214-849-8100
- ifsr@greyhound.com
- Website
- greyhound.com
Bus from Boston Manchester Airport to Boston
- Ave. Duration
- 1h 30m
- Frequency
- Twice daily
- Estimated price
- $14–30
- Website
- https://www.greyhound.com/
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More Questions & Answers
Yes, the driving distance between Chicago to Eastham is 1053 miles. It takes approximately 18h 7m to drive from Chicago to Eastham.
There are 711+ hotels available in Eastham.



















