There are 9 ways to get from Chicago to South Boston by plane, bus, train (Amtrak), bus (Flixbus, Greyhound), car, or train
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 Manchester Airport, bus
best- 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 O'Hare International Airport to Theodore Francis Green State Airport, train
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 Back Baytrain
6h 28m$66–311Train (Amtrak)
- Take the train from Chicago Union Station to Bostontrain Lake Shore Limited
22h 2m$250–600Bus
- Take the bus from Chicago Bus Station to Newark Penn Stationbus FlixBus N2640 / ...
- Take the bus from Newark Penn Station to Bostonbus Greyhound US0235 / ...
25h 30m$173–271Drive 981.6 mi
- Drive from Chicago to South Bostoncar 981.6 mi
16h 52m$180–259Fly Chicago O'Hare International Airport to Manchester Airport, bus
- Fly from Chicago O'Hare International Airport (ORD) to Manchester Airport (MHT)plane ORD - MHT
- Take the bus from Boston Manchester Airport to Bostonbus
6h 32m$80–408Fly 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 Back Baytrain
6h 19m$86–421Fly Chicago Midway International Airport to Bradley International Airport, bus
- Fly from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL)plane MDW - BDL
- Take the bus from Hartford Union Station to Bostonbus
7h 13m$128–684Fly Chicago Midway International Airport to Albany County Airport, bus
- Fly from Chicago Midway International Airport (MDW) to Albany County Airport (ALB)plane MDW - ALB
- Take the bus from Albany to Bostonbus
9h 20m$172–849
Chicago to South Boston by train (Amtrak)
Comparing Your Travel Options
The cheapest way to get from Chicago to South Boston is to fly and train which costs $65 - $320 and takes 6h 28m.
The fastest way to get from Chicago to South Boston is to fly and bus which takes 6h 9m and costs $110 - $600.
No, there is no direct bus from Chicago station to South Boston. However, there are services departing from Chicago Bus Station and arriving at Boston via Newark Penn Station. The journey, including transfers, takes approximately 25h 30m.
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 Chicago and South Boston is 903 miles. The road distance is 987.3 miles.
The best way to get from Chicago to South Boston without a car is to train which takes 22h 2m and costs $250 - $600.
It takes approximately 6h 9m to get from Chicago to South Boston, including transfers.
Chicago to South Boston bus services, operated by Flixbus USA, depart from Chicago Bus Station.
Chicago to South Boston train services, operated by Amtrak, depart from Chicago Union Station.
The best way to get from Chicago to South Boston is to train which takes 22h 2m and costs $250 - $600. Alternatively, you can bus, which costs $170 - $280 and takes 25h 30m.
What companies run services between Chicago, IL, USA and South Boston, MA, USA?
Amtrak operates a train from Chicago Union Station to Boston once daily. Tickets cost $250–600 and the journey takes 22h 2m. Alternatively, you can take a bus from Chicago Bus Station to Boston via Newark Penn Station in around 25h 30m.
- Website
- southwest.com
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
- $80–420
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
Flights from Chicago Midway International Airport to Bradley International Airport
- Ave. Duration
- 2h 3m
- When
- Every day
- Estimated price
- $110–650
Flights from Chicago Midway International Airport to Bradley International Airport via Baltimore
- Ave. Duration
- 4h 36m
- When
- Monday to Saturday
- Estimated price
- $130–700
Flights from Chicago Midway International Airport to Albany County Airport
- Ave. Duration
- 1h 53m
- When
- Every day
- Estimated price
- $140–800
Flights from Chicago Midway International Airport to Albany County Airport via Baltimore
- Ave. Duration
- 4h 20m
- When
- Every day
- Estimated price
- $160–850
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
- $250–600
- Website
- Amtrak
Rome2Rio's guide to Greyhound USA
Contact DetailsContact Details
- Phone
- +1 214-849-8100
- [email protected]
- Website
- Greyhound
Bus from Boston Manchester Airport to Boston
- Ave. Duration
- 1h 30m
- Frequency
- Twice daily
- Estimated price
- $8–13
- Website
- Greyhound
Bus from Newark Penn Station to Boston
- Ave. Duration
- 5h 5m
- Frequency
- 4 times a day
- Estimated price
- $40–65
- Website
- Greyhound
Bus from Boston Manchester Airport to Boston
- Ave. Duration
- 1h 30m
- Frequency
- Twice daily
- Estimated price
- $8–13
- Website
- Greyhound
Bus from Hartford Union Station to Boston
- Ave. Duration
- 1h 49m
- Frequency
- Every 2 hours
- Estimated price
- $15–25
- Website
- Greyhound
Want to know more about travelling around United States
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Booking & Getting There
Chicago to South Boston bus services, operated by Flixbus USA, arrive at Newark Penn Station.
South Boston is 1h ahead of Chicago. It is currently 9:42 AM in Chicago and 10:42 AM in South Boston.
Chicago to South Boston train services, operated by Amtrak, arrive at Boston station.
Yes, the driving distance between Chicago to South Boston is 987 miles. It takes approximately 16h 52m to drive from Chicago to South Boston.
Book your Chicago to South Boston train tickets online with Omio.
Book your Chicago to South Boston bus tickets online with Omio and FlixBus.
There are 1734+ hotels available in South Boston.