There are 9 ways to get from Brookline 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
4h 39m$96–464Train 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
22h 15m$250–600Bus (Flixbus)
- Take the bus from Brookline to New York Midtownbus FlixBus N2605 / ...
- Take the bus from New York Midtown to Chicago Bus Stationbus FlixBus N2640 / ...
25h 35m$171–266Drive 977.3 mi
- Drive from Brookline to Chicagocar 977.3 mi
16h 46m$179–258Fly 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
4h 56m$611–914Train 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 40m$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
7h 8m$107–520
Brookline to Chicago by train (Amtrak)
Comparing Your Travel Options
The cheapest way to get from Brookline to Chicago is to train and fly which costs $70 - $360 and takes 5h 43m.
The fastest way to get from Brookline to Chicago is to fly which takes 4h 39m and costs $95 - $470.
No, there is no direct bus from Brookline to Chicago station. However, there are services departing from Brookline and arriving at Chicago Bus Station via New York Midtown. The journey, including transfers, takes approximately 25h 35m.
Yes, there is a direct train departing from Boston and arriving at Chicago Union Station station. Services depart once daily, and operate every day. The journey takes approximately 22h 15m.
The distance between Brookline and Chicago is 879 miles. The road distance is 983 miles.
The best way to get from Brookline to Chicago without a car is to train which takes 22h 15m and costs $250 - $600.
It takes approximately 4h 39m to get from Brookline to Chicago, including transfers.
Brookline to Chicago bus services, operated by Flixbus USA, depart from Brookline station.
Brookline to Chicago train services, operated by Amtrak, depart from Boston station.
The best way to get from Brookline to Chicago is to fly which takes 4h 39m and costs $95 - $470. Alternatively, you can train, which costs $250 - $600 and takes 22h 15m, you could also bus, which costs $170 - $270 and takes 25h 35m.
What companies run services between Brookline, 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 15m.
- 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 15m
- Frequency
- Once daily
- Estimated price
- $250–600
- Website
- Amtrak
- Phone
- +1 (855) 626-8585
- Website
- Flixbus USA
Bus from Brookline to New York Midtown
- Ave. Duration
- 4h 10m
- Frequency
- Twice daily
- 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
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Booking & Getting There
Brookline to Chicago bus services, operated by Flixbus USA, arrive at New York Midtown station.
Chicago is 1h behind Brookline. It is currently 12:33 AM in Brookline and 11:33 PM in Chicago.
Brookline to Chicago train services, operated by Amtrak, arrive at Chicago Union Station.
Yes, the driving distance between Brookline to Chicago is 983 miles. It takes approximately 16h 46m to drive from Brookline to Chicago.
Book your Brookline to Chicago train tickets online with Omio.
Book your Brookline to Chicago bus tickets online with Omio and FlixBus.
There are 1301+ hotels available in Chicago.