There are 9 ways to get from Dorchester to Chicago by plane, train (Amtrak), bus (Flixbus), car, train, or bus
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Fly Boston Logan Airport to Chicago Midway International Airport
best- Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane BOS - MDW
5h 1m$90–462Train to Theodore Francis Green State Airport, fly to Chicago O'Hare International Airport
cheapest- Take the train from Ruggles to TF Green Airporttrain
- Fly from Theodore Francis Green State Airport (PVD) to Chicago O'Hare International Airport (ORD)plane PVD - ORD
5h 43m$71–360Train (Amtrak)
- Take the train from Boston to Chicago Union Stationtrain Lake Shore Limited
23h 36m$252–602Bus (Flixbus)
- Take the bus from Boston to New York Midtownbus FlixBus 2610 / ...
- Take the bus from New York Midtown to Chicago Bus Stationbus FlixBus N2640 / ...
26h 57m$172–272Drive 981.1 mi
- Drive from Dorchester to Chicagocar 981.1 mi
16h 55m$180–259Fly Boston Logan Airport to Chicago O'Hare International Airport
- Fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD)plane BOS - ORD
5h 18m$605–912Train to Theodore Francis Green State Airport, fly to Chicago Midway International Airport
- Take the train from Ruggles to TF Green Airporttrain
- Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)plane PVD - MDW
5h 36m$91–440Bus to Manchester Airport, fly to Chicago Midway International Airport
- Take the bus from Boston to Boston Manchester Airportbus
- Fly from Manchester Airport (MHT) to Chicago Midway International Airport (MDW)plane MHT - MDW
6h 23m$132–670Bus to Manchester Airport, fly to Chicago O'Hare International Airport
- Take the bus from Boston to Boston Manchester Airportbus
- Fly from Manchester Airport (MHT) to Chicago O'Hare International Airport (ORD)plane MHT - ORD
6h 51m$107–520
Dorchester to Chicago by subway and train (Amtrak)
Comparing Your Travel Options
The cheapest way to get from Dorchester to Chicago is to train and fly which costs $70 - $360 and takes 5h 43m.
The fastest way to get from Dorchester to Chicago is to fly which takes 5h 1m and costs $90 - $470.
No, there is no direct bus from Dorchester to Chicago station. However, there are services departing from Boston and arriving at Chicago Bus Station via New York Midtown. The journey, including transfers, takes approximately 26h 57m.
No, there is no direct train from Dorchester to Chicago station. However, there are services departing from Shawmut and arriving at Chicago Union Station via Boston. The journey, including transfers, takes approximately 23h 36m.
The distance between Dorchester and Chicago is 883 miles. The road distance is 986.9 miles.
The best way to get from Dorchester to Chicago without a car is to train which takes 23h 36m and costs $250 - $600.
It takes approximately 5h 1m to get from Dorchester to Chicago, including transfers.
Dorchester to Chicago bus services, operated by Flixbus USA, depart from Boston station.
Dorchester to Chicago train services, operated by Amtrak, depart from Boston station.
The best way to get from Dorchester to Chicago is to fly which takes 5h 1m and costs $90 - $470. Alternatively, you can train, which costs $250 - $600 and takes 23h 36m, you could also bus, which costs $170 - $280 and takes 26h 57m.
What companies run services between Dorchester, MA, USA and Chicago, IL, USA?
Southwest Airlines and Delta fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW) every 4 hours. Alternatively, Amtrak operates a train from Boston to Chicago Union Station once daily. Tickets cost $250–600 and the journey takes 22h 22m.
- Website
- aa.com
Flights from Boston Logan Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h 2m
- When
- Every day
- Estimated price
- $65–360
Flights from Theodore Francis Green State Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 44m
- When
- Every day
- Estimated price
- $60–340
Flights from Theodore Francis Green State Airport to Chicago O'Hare International Airport via Philadelphia
- Ave. Duration
- 5h 14m
- When
- Every day
- Estimated price
- $65–350
Flights from Manchester Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 48m
- When
- Every day
- Estimated price
- $95–500
Flights from Manchester Airport to Chicago O'Hare International Airport via Philadelphia
- Ave. Duration
- 5h 20m
- When
- Every day
- Estimated price
- $100–550
Flights from Manchester Airport to Chicago O'Hare International Airport via Reagan Washington
- Ave. Duration
- 5h 43m
- When
- Every day
- Estimated price
- $100–550
Flights from Manchester Airport to Chicago O'Hare International Airport via Charlotte
- Ave. Duration
- 6h 4m
- When
- Every day
- Estimated price
- $130–650
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Boston to Chicago Union Station
- Ave. Duration
- 22h 22m
- Frequency
- Once daily
- Estimated price
- $250–600
- Website
- Amtrak
- Phone
- +1 (855) 626-8585
- Website
- Flixbus USA
Bus from Boston to New York Midtown
- Ave. Duration
- 4h 20m
- Frequency
- Every 4 hours
- Estimated price
- $30–50
- Schedules at
- Flixbus USA
Bus from New York Midtown to Chicago Bus Station
- Ave. Duration
- 20h 25m
- Frequency
- Twice daily
- Estimated price
- $140–220
- Schedules at
- Flixbus USA
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
Dorchester to Chicago bus services, operated by Flixbus USA, arrive at New York Midtown station.
Chicago is 1h behind Dorchester. It is currently 3:23 AM in Dorchester and 2:23 AM in Chicago.
Dorchester to Chicago train services, operated by Amtrak, arrive at Chicago Union Station.
Yes, the driving distance between Dorchester to Chicago is 987 miles. It takes approximately 16h 55m to drive from Dorchester to Chicago.
There are 1301+ hotels available in Chicago.