There are 9 ways to get from Brockton to Chicago by train, plane, train (Amtrak), bus (Flixbus), car, 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.
Train to Boston Logan Airport, fly to Chicago Midway International Airport
best- Take the train from Brockton to South Stationtrain
- Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane BOS - MDW
5h 23m$87–439Train to Theodore Francis Green State Airport, fly to Chicago O'Hare International Airport
cheapest- Take the train from South Station to TF Green Airporttrain
- Fly from Theodore Francis Green State Airport (PVD) to Chicago O'Hare International Airport (ORD)plane PVD - ORD
7h 53m$80–380Train (Amtrak)
- Take the train from Boston to Chicago Union Stationtrain Lake Shore Limited
24h 3m$274–609Bus (Flixbus)
- Take the bus from Boston to New York Midtownbus FlixBus 2610 / ...
- Take the bus from New York Midtown to Chicago Bus Stationbus FlixBus N2641 / ...
24h 18m$153–255Drive 989.4 mi
- Drive from Brockton to Chicagocar 989.4 mi
17h 10m$181–261Fly 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 43m$607–1,019Bus 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 47m$113–578Train to Theodore Francis Green State Airport, fly to Chicago Midway International Airport
- Take the train from South Station to TF Green Airporttrain
- Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)plane PVD - MDW
7h 30m$90–430Fly Boston Logan Airport to General Mitchell International Airport, train
- Fly from Boston Logan Airport (BOS) to General Mitchell International Airport (MKE)plane BOS - MKE
- Take the train from Milwaukee to Chicago Union Stationtrain
7h 53m$679–1,978
Brockton to Chicago by train (Amtrak)
Questions & Answers
The cheapest way to get from Brockton to Chicago is to bus which costs $150 - $260 and takes 24h 18m.
The fastest way to get from Brockton to Chicago is to train and fly which takes 5h 23m and costs $85 - $440.
No, there is no direct bus from Brockton to Chicago station. However, there are services departing from Main St and Church St and arriving at Chicago Bus Station via Boston and New York Midtown. The journey, including transfers, takes approximately 24h 18m.
No, there is no direct train from Brockton to Chicago station. However, there are services departing from Brockton and arriving at Chicago Union Station via Boston. The journey, including transfers, takes approximately 24h 3m.
The distance between Brockton and Chicago is 899 miles. The road distance is 995.2 miles.
The best way to get from Brockton to Chicago without a car is to train which takes 24h 3m and costs $270 - $650.
It takes approximately 5h 23m to get from Brockton to Chicago, including transfers.
Brockton to Chicago bus services, operated by Flixbus USA, depart from Boston station.
Brockton to Chicago train services, operated by Amtrak, depart from Boston station.
The best way to get from Brockton to Chicago is to train which takes 24h 3m and costs $270 - $650. Alternatively, you can bus, which costs $150 - $260 and takes 24h 18m, you could also fly, which costs $600 - $1,100 and takes 5h 43m.
What companies run services between Brockton, MA, USA and Chicago, IL, USA?
Amtrak operates a train from Boston to Chicago Union Station once daily. Tickets cost $270–600 and the journey takes 22h 22m. Alternatively, you can take a bus from Main St and Church St to Chicago Bus Station via Ashmont Station OB, Ashmont, South Station, Boston, and New York Midtown in around 24h 18m.
- Website
- southwest.com
Flights from Boston Logan Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 35m
- When
- Every day
- Estimated price
- $80–420
Flights from Manchester Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 21m
- When
- Every day
- Estimated price
- $100–550
Flights from Manchester Airport to Chicago Midway International Airport via Baltimore
- Ave. Duration
- 4h 38m
- When
- Tuesday, Wednesday, Monday, Thursday, Friday, and Sunday
- Estimated price
- $110–600
Flights from Manchester Airport to Chicago Midway International Airport via Nashville
- Ave. Duration
- 5h
- When
- Monday, Thursday, and Friday
- Estimated price
- $140–650
Flights from Theodore Francis Green State Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 25m
- When
- Every day
- Estimated price
- $75–400
Flights from Theodore Francis Green State Airport to Chicago Midway International Airport via Baltimore
- Ave. Duration
- 5h 4m
- When
- Tuesday, Wednesday, Monday, Thursday, Friday, and Sunday
- Estimated price
- $85–420
Flights from Boston Logan Airport to General Mitchell International Airport via Chicago Midway International Airport
- Ave. Duration
- 4h 45m
- When
- Saturday, Monday, Thursday, and Friday
- Estimated price
- $130–650
Flights from Boston Logan Airport to General Mitchell International Airport via Baltimore
- Ave. Duration
- 4h 55m
- When
- Tuesday, Wednesday, and Sunday
- Estimated price
- $130–700
Train from Brockton to South Station
- Ave. Duration
- 41 min
- Frequency
- Hourly
- Estimated price
- $3–10
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Adult
- $3–10
Train from South Station to TF Green Airport
- Ave. Duration
- 1h 30m
- Frequency
- Every 4 hours
- Estimated price
- $9–16
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Adult
- $9–16
Train from South Station to TF Green Airport
- Ave. Duration
- 1h 30m
- Frequency
- Every 4 hours
- Estimated price
- $9–16
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Adult
- $9–16
- Phone
- +1 (855) 626-8585
- Website
- Flixbus USA
Bus from Boston to New York Midtown
- Ave. Duration
- 4h 20m
- Frequency
- Hourly
- Estimated price
- $29–50
- Schedules at
- Flixbus USA
Bus from New York Midtown to Chicago Bus Station
- Ave. Duration
- 16h 55m
- Frequency
- Twice daily
- Estimated price
- $120–200
- 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
More Questions & Answers
Brockton to Chicago bus services, operated by Flixbus USA, arrive at New York Midtown station.
Chicago is 1h behind Brockton. It is currently 9:03 AM in Brockton and 8:03 AM in Chicago.
Brockton to Chicago train services, operated by Amtrak, arrive at Chicago Union Station.
Yes, the driving distance between Brockton to Chicago is 995 miles. It takes approximately 17h 10m to drive from Brockton to Chicago.
There are 1305+ hotels available in Chicago.






