There are 9 ways to get from Chicago to Hyannis by plane, bus, train, bus (Flixbus, Greyhound), 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 Boston Logan Airport, bus
best- Fly from Chicago O'Hare International Airport (ORD) to Boston Logan Airport (BOS)plane ORD - BOS
- Take the bus from Logan International Airport to Hyannis Transportation Centerbus
6h 53m$150–425Fly 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)plane ORD - PVD
- Take the train from TF Green Airport to South Stationtrain
- Take the bus from Boston South Station to Hyannis Transportation Centerbus
9h 16m$68–341Train, bus
- Take the train from Chicago Union Station to Bostontrain Lake Shore Limited
- Take the bus from Boston South Buses to Hyannis Transportation Centerbus Hyannis - South Shore to Logan Airport
24h 34m$117–420Bus
- Take the bus from Chicago Bus Station to Newark Penn Stationbus
- Take the bus from Newark Penn Station to Bostonbus
- Take the bus from Boston South Station to Hyannis Transportation Centerbus
28h 5m$148–262Drive 1,026 mi
- Drive from Chicago to Hyanniscar 1,026 mi
17h 51m$188–271Fly Chicago Midway International Airport to Boston Logan Airport, bus
- Fly from Chicago Midway International Airport (MDW) to Boston Logan Airport (BOS)plane MDW - BOS
- Take the bus from Logan International Airport to Hyannis Transportation Centerbus
6h 32m$140–645Fly Chicago Midway International Airport to Manchester Airport, bus
- Fly from Chicago Midway International Airport (MDW) to Manchester Airport (MHT)plane MDW - MHT
- Take the bus from Boston Manchester Airport to Bostonbus
- Take the bus from Boston South Station to Hyannis Transportation Centerbus
8h 41m$146–764Fly 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)plane MDW - PVD
- Take the train from TF Green Airport to South Stationtrain
- Take the bus from Boston South Station to Hyannis Transportation Centerbus
8h 56m$94–461Fly Chicago Midway International Airport to Barnstable Municipal Airport
- Fly from Chicago Midway International Airport (MDW) to Barnstable Municipal Airport (HYA)plane MDW - HYA
5h 48m$122–655
Chicago to Hyannis by train and bus
Questions & Answers
The cheapest way to get from Chicago to Hyannis is to fly and train and bus which costs $65 - $350 and takes 9h 16m.
The fastest way to get from Chicago to Hyannis is to fly which takes 5h 48m and costs $120 - $700.
No, there is no direct bus from Chicago station to Hyannis. However, there are services departing from Chicago Bus Station and arriving at Hyannis Transportation Center via Newark Penn Station and Boston South Station. The journey, including transfers, takes approximately 28h 5m.
The distance between Chicago and Hyannis is 965 miles. The road distance is 1032 miles.
The best way to get from Chicago to Hyannis without a car is to train and bus which takes 24h 34m and costs $110 - $420.
It takes approximately 6h 53m to get from Chicago to Hyannis, including transfers.
Chicago to Hyannis bus services, operated by Flixbus USA, depart from Chicago Bus Station.
The best way to get from Chicago to Hyannis is to bus which takes 28h 5m and costs $140 - $270. Alternatively, you can fly, which costs $120 - $700 and takes 5h 48m.
Chicago to Hyannis bus services, operated by Flixbus USA, arrive at Newark Penn Station.
Hyannis is 1h ahead of Chicago. It is currently 4:23 AM in Chicago and 5:23 AM in Hyannis.
What companies run services between Chicago, IL, USA and Hyannis, MA, USA?
You can take a bus from Chicago Bus Station to Hyannis Transportation Center via Newark Penn Station, Boston, and Boston South Station in around 28h 5m. Alternatively, Southwest Airlines and American Airlines fly from Chicago Midway International Airport (MDW) to Barnstable Municipal Airport (HYA) twice daily.
- Website
- aa.com
Flights from Chicago O'Hare International Airport to Boston Logan Airport
- Ave. Duration
- 2h 22m
- When
- Every day
- Estimated price
- $75–420
Flights from Chicago O'Hare International Airport to Theodore Francis Green State Airport
- Ave. Duration
- 2h 19m
- When
- Every day
- Estimated price
- $50–280
Flights from Chicago O'Hare International Airport to Theodore Francis Green State Airport via Philadelphia
- Ave. Duration
- 4h 27m
- When
- Monday, Tuesday, Wednesday, Friday, Saturday, and Sunday
- Estimated price
- $55–290
Flights from Chicago O'Hare International Airport to Theodore Francis Green State Airport via Reagan Washington
- Ave. Duration
- 4h 35m
- When
- Every day
- Estimated price
- $55–300
Flights from Chicago Midway International Airport to Barnstable Municipal Airport via Reagan Washington
- Ave. Duration
- 5h 2m
- When
- Every day
- Estimated price
- $130–700
Flights from Chicago Midway International Airport to Barnstable Municipal Airport via New York La Guardia
- Ave. Duration
- 5h 59m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $120–650
- Website
- southwest.com
Flights from Chicago Midway International Airport to Boston Logan Airport
- Ave. Duration
- 2h 15m
- When
- Every day
- Estimated price
- $110–600
Flights from Chicago Midway International Airport to Manchester Airport
- Ave. Duration
- 2h 5m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $120–700
Flights from Chicago Midway International Airport to Manchester Airport via Baltimore
- Ave. Duration
- 4h 25m
- When
- Monday, Thursday, Saturday, and Sunday
- Estimated price
- $130–750
Flights from Chicago Midway International Airport to Theodore Francis Green State Airport
- Ave. Duration
- 2h 10m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $75–400
Flights from Chicago Midway International Airport to Theodore Francis Green State Airport via Baltimore
- Ave. Duration
- 4h 21m
- When
- Monday, Tuesday, Wednesday, Saturday, and Sunday
- Estimated price
- $80–420
Flights from Chicago Midway International Airport to Theodore Francis Green State Airport via Reagan Washington
- Ave. Duration
- 4h 10m
- When
- Monday, Tuesday, Wednesday, and Sunday
- Estimated price
- $80–420
- Website
- united.com
Flights from Chicago O'Hare International Airport to Boston Logan Airport
- Ave. Duration
- 2h 26m
- When
- Every day
- Estimated price
- $75–420
Flights from Chicago O'Hare International Airport to Theodore Francis Green State Airport
- Ave. Duration
- 2h 23m
- 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 18m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $55–300
- Website
- delta.com
Flights from Chicago O'Hare International Airport to Boston Logan Airport
- Ave. Duration
- 2h 28m
- When
- Every day
- Estimated price
- $75–420
Flights from Chicago Midway International Airport to Boston Logan Airport via Detroit
- Ave. Duration
- 5h 20m
- When
- Every day
- Estimated price
- $110–600
Flights from Chicago O'Hare International Airport to Theodore Francis Green State Airport via Detroit
- Ave. Duration
- 4h 32m
- When
- Monday, Thursday, and Friday
- Estimated price
- $50–280
Flights from Chicago Midway International Airport to Theodore Francis Green State Airport via Detroit
- Ave. Duration
- 4h 10m
- When
- Monday to Friday
- Estimated price
- $75–400
- Website
- jetblue.com
Flights from Chicago O'Hare International Airport to Boston Logan Airport
- Ave. Duration
- 2h 27m
- When
- Every day
- Estimated price
- $75–420
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
- $85–390
- Website
- https://www.amtrak.com/home.html
- Phone
- +1-617-222-3200
- Website
- mbta.com
Train from TF Green Airport to South Station
- Ave. Duration
- 1h 29m
- Frequency
- Every 4 hours
- Estimated price
- $6–16
- Website
- https://www.mbta.com
- Adult
- $6–16
- 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 Newark Penn Station
- Ave. Duration
- 19h 25m
- Frequency
- Once daily
- Estimated price
- $100–160
- Schedules at
- flixbus.com
Bus from Newark Penn Station to Boston
- Ave. Duration
- 4h 30m
- Frequency
- Twice daily
- Estimated price
- $35–65
- Schedules at
- flixbus.com
Rome2Rio's guide to Greyhound USA
Contact Details
- Phone
- +1 214-849-8100
- ifsr@greyhound.com
- Website
- greyhound.com
Bus from Newark Penn Station to Boston
- Ave. Duration
- 5h 5m
- Frequency
- 4 times a day
- Estimated price
- $35–65
- Website
- https://www.greyhound.com/
Bus from Boston Manchester Airport to Boston
- Ave. Duration
- 1h 30m
- Frequency
- Twice daily
- Estimated price
- $13–19
- Website
- https://www.greyhound.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
Want to know more about travelling around United States
Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.
Related travel guides
Travelling to the US: What do I need to know?
Read the travel guide
Why you should take the train in the US
Read the travel guide
Need to know: Greyhound
Read the travel guide
More Questions & Answers
Yes, the driving distance between Chicago to Hyannis is 1032 miles. It takes approximately 17h 51m to drive from Chicago to Hyannis.
There are 679+ hotels available in Hyannis.
















