There are 10 ways to get from Illinois to Massachusetts by plane, train (Amtrak), bus (Greyhound), car, train, bus, or bus (Flixbus)
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
best- Fly from Chicago O'Hare International Airport (ORD) to Boston Logan Airport (BOS)plane ORD - BOS
4h 34m$606–908Fly Chicago O'Hare International Airport to Bradley International Airport, train
cheapest- Fly from Chicago O'Hare International Airport (ORD) to Bradley International Airport (BDL)plane ORD - BDL
- Take the train from Windsor Locks to Springfieldtrain
5h 45m$86–447Train (Amtrak)
- Take the train from Chicago Union Station to Bostontrain Lake Shore Limited
22h 2m$260–600Bus via Brook Park (Greyhound)
- Take the bus from Chicago Bus Station to Cleveland Bus Stationbus Greyhound US0164
- Take the bus from Cleveland Bus Station to Bostonbus Greyhound US0171
22h 5m$154–254Drive 980.5 mi
- Drive from Chicago to Bostoncar 980.5 mi
16h 51m$179–259Fly Chicago Midway International Airport to Boston Logan Airport
- Fly from Chicago Midway International Airport (MDW) to Boston Logan Airport (BOS)plane MDW - BOS
4h 21m$106–558Fly Chicago Midway International Airport to Bradley International Airport
- Fly from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL)plane MDW - BDL
5h 31m$116–617Fly 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
6h 9m$110–568Fly Chicago Midway International Airport to Theodore Francis Green State Airport, train
- 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
6h 25m$86–421Bus (Flixbus)
- Take the bus from Chicago Bus Station to New York Midtownbus FlixBus N2640 / ...
- Take the bus from New York Midtown to Bostonbus FlixBus 2610 / ...
25h 30m$177–268
Illinois to Massachusetts by train (Amtrak)
Comparing Your Travel Options
The cheapest way to get from Illinois to Massachusetts is to bus via Brook Park which costs $150 - $260 and takes 22h 5m.
The fastest way to get from Illinois to Massachusetts is to fly which takes 4h 21m and costs $100 - $600.
No, there is no direct bus from Illinois station to Massachusetts. However, there are services departing from Chicago Bus Station and arriving at Boston via Cleveland Bus Station. The journey, including transfers, takes approximately 22h 5m.
Yes, there is a direct train departing from Chicago Union Station station and arriving at Boston. Services depart once daily, and operate every day. The journey takes approximately 22h 2m.
The distance between Illinois and Massachusetts is 890 miles. The road distance is 986.2 miles.
The best way to get from Illinois to Massachusetts without a car is to train which takes 22h 2m and costs $260 - $600.
It takes approximately 4h 34m to get from Illinois to Massachusetts, including transfers.
Illinois to Massachusetts bus services, operated by Greyhound USA, depart from Chicago Bus Station.
Illinois to Massachusetts train services, operated by Amtrak, depart from Chicago Union Station.
The best way to get from Illinois to Massachusetts is to fly which takes 4h 34m and costs $600 - $950. Alternatively, you can train, which costs $260 - $600 and takes 22h 2m, you could also bus via Brook Park, which costs $150 - $260 and takes 22h 5m.
What companies run services between Illinois, USA and Massachusetts, USA?
American Airlines, JetBlue Airways, and two other airlines fly from Chicago O'Hare International Airport (ORD) to Boston Logan Airport (BOS) hourly. Alternatively, Amtrak operates a train from Chicago Union Station to Boston once daily. Tickets cost $260–600 and the journey takes 22h 2m.
- Website
- southwest.com
Flights from Chicago Midway International Airport to Boston Logan Airport
- Ave. Duration
- 2h 22m
- When
- Every day
- Estimated price
- $100–550
Flights from Chicago Midway International Airport to Bradley International Airport
- Ave. Duration
- 2h 3m
- When
- Every day
- Estimated price
- $110–600
Flights from Chicago Midway International Airport to Bradley International Airport via Baltimore
- Ave. Duration
- 4h 36m
- When
- Monday to Saturday
- Estimated price
- $120–650
Flights from Chicago Midway International Airport to Manchester Airport
- Ave. Duration
- 2h 10m
- When
- Every day
- Estimated price
- $100–550
Flights from Chicago Midway International Airport to Manchester Airport via Baltimore
- Ave. Duration
- 4h 45m
- When
- Every day
- Estimated price
- $110–600
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 44m
- When
- Every day
- Estimated price
- $80–410
Flights from Chicago Midway International Airport to Theodore Francis Green State Airport via Reagan Washington
- Ave. Duration
- 4h 50m
- When
- Monday, Thursday, and Friday
- Estimated price
- $80–420
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
- $260–600
- Website
- Amtrak
Train from Windsor Locks to Springfield
- Ave. Duration
- 25 min
- Frequency
- Every 3 hours
- Estimated price
- $3–9
- Website
- Amtrak
Rome2Rio's guide to Greyhound USA
Contact DetailsContact Details
- Phone
- +1 214-849-8100
- [email protected]
- Website
- Greyhound
Bus from Chicago Bus Station to Cleveland Bus Station
- Ave. Duration
- 7h 10m
- Frequency
- Twice daily
- Estimated price
- $50–85
- Website
- Greyhound
Bus from Cleveland Bus Station to Boston
- Ave. Duration
- 13h 55m
- Frequency
- Once daily
- Estimated price
- $100–170
- Website
- Greyhound
Bus from Boston Manchester Airport to Boston
- Ave. Duration
- 1h 30m
- Frequency
- Twice daily
- Estimated price
- $8–13
- Website
- Greyhound
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
Booking & Getting There
Illinois to Massachusetts bus services, operated by Greyhound USA, arrive at Cleveland Bus Station.
Massachusetts is 1h ahead of Illinois. It is currently 5:13 PM in Illinois and 6:13 PM in Massachusetts.
Illinois to Massachusetts train services, operated by Amtrak, arrive at Boston station.
Yes, the driving distance between Illinois to Massachusetts is 986 miles. It takes approximately 16h 51m to drive from Illinois to Massachusetts.
Book your Illinois to Massachusetts train tickets online with Omio.
Book your Illinois to Massachusetts bus tickets online with Omio and FlixBus.
There are 1756+ hotels available in Massachusetts.