There are 10 ways to get from Westborough to Chicago by train, plane, train (Amtrak), bus (Greyhound, 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 Westborough to Back Baytrain
- Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane BOS - MDW
6h 14m$111–477Train, train to Theodore Francis Green State Airport, fly to Chicago O'Hare International Airport
cheapest- Take the train from Westborough to Back Baytrain
- Take the train from Back Bay to TF Green Airporttrain
- Fly from Theodore Francis Green State Airport (PVD) to Chicago O'Hare International Airport (ORD)plane PVD - ORD
8h 3m$91–384Train (Amtrak)
- Take the train from Worcester Union Station to Chicago Union Stationtrain Lake Shore Limited
22h 31m$260–619Bus
- Take the bus from Worcester Union Station to Newark Penn Stationbus Greyhound US0235 / ...
- Take the bus from Newark Penn Station to Chicago Bus Stationbus FlixBus N2640 / ...
24h 35m$202–302Drive 950.1 mi
- Drive from Westborough to Chicagocar 950.1 mi
16h 20m$174–251Train to Boston Logan Airport, fly to Chicago O'Hare International Airport
- Take the train from Westborough to Back Baytrain
- Fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD)plane BOS - ORD
6h 35m$626–937Train, bus to Manchester Airport, fly to Chicago Midway International Airport
- Take the train from Westborough to South Stationtrain
- Take the bus from Boston to Boston Manchester Airportbus
- Fly from Manchester Airport (MHT) to Chicago Midway International Airport (MDW)plane MHT - MDW
7h 31m$145–691Bus to Bradley International Airport, fly to Chicago Midway International Airport
- Take the bus from Worcester to Hartfordbus
- Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane BDL - MDW
7h 31m$105–470Train, train to Theodore Francis Green State Airport, fly to Chicago Midway International Airport
- Take the train from Westborough to Back Baytrain
- Take the train from Back Bay to TF Green Airporttrain
- Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)plane PVD - MDW
7h 57m$106–454Train to Boston Logan Airport, fly to General Mitchell International Airport, train
- Take the train from Westborough to Back Baytrain
- Fly from Boston Logan Airport (BOS) to General Mitchell International Airport (MKE)plane BOS - MKE
- Take the train from Milwaukee to Chicago Union Stationtrain
8h 45m$698–1,996
Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW) flights
Comparing Your Travel Options
The cheapest way to get from Westborough to Chicago is to drive which costs $170 - $250 and takes 16h 20m.
The fastest way to get from Westborough to Chicago is to train and fly which takes 6h 14m and costs $110 - $480.
No, there is no direct bus from Westborough station to Chicago station. However, there are services departing from Worcester Union Station and arriving at Chicago Bus Station via Newark Penn Station. The journey, including transfers, takes approximately 24h 35m.
No, there is no direct train from Westborough to Chicago station. However, there are services departing from Westborough and arriving at Chicago Union Station via Worcester Union Station. The journey, including transfers, takes approximately 22h 31m.
The distance between Westborough and Chicago is 914 miles. The road distance is 955.7 miles.
The best way to get from Westborough to Chicago without a car is to train which takes 22h 31m and costs $260 - $650.
It takes approximately 6h 14m to get from Westborough to Chicago, including transfers.
Westborough to Chicago bus services, operated by Greyhound USA, depart from Worcester Union Station.
Westborough to Chicago train services, operated by Amtrak, depart from Worcester Union Station.
The best way to get from Westborough to Chicago is to train which takes 22h 31m and costs $260 - $650. Alternatively, you can bus, which costs $200 - $310 and takes 24h 35m.
What companies run services between Westborough, MA, USA and Chicago, IL, USA?
Amtrak operates a train from Worcester Union Station to Chicago Union Station once daily. Tickets cost $250–600 and the journey takes 21h 6m. Alternatively, you can take a vehicle from Westborough to Chicago Bus Station via Worcester Union Station and Newark Penn Station in around 24h 35m.
- Website
- southwest.com
Flights from Boston Logan Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 38m
- When
- Every day
- Estimated price
- $85–440
Flights from Manchester Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 24m
- When
- Every day
- Estimated price
- $120–650
Flights from Manchester Airport to Chicago Midway International Airport via Baltimore
- Ave. Duration
- 4h 46m
- When
- Every day
- Estimated price
- $130–650
Flights from Bradley International Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 22m
- When
- Every day
- Estimated price
- $80–420
Flights from Bradley International Airport to Chicago Midway International Airport via Baltimore
- Ave. Duration
- 4h 17m
- When
- Tuesday to Friday
- Estimated price
- $85–440
Flights from Theodore Francis Green State Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 28m
- When
- Every day
- Estimated price
- $80–410
Flights from Theodore Francis Green State Airport to Chicago Midway International Airport via Baltimore
- Ave. Duration
- 4h 28m
- When
- Every day
- Estimated price
- $85–430
Flights from Boston Logan Airport to General Mitchell International Airport via Chicago Midway International Airport
- Ave. Duration
- 4h 41m
- When
- Sunday and Saturday
- Estimated price
- $130–700
Flights from Boston Logan Airport to General Mitchell International Airport via Baltimore
- Ave. Duration
- 4h 36m
- When
- Sunday, Tuesday, and Wednesday
- Estimated price
- $140–700
Train from Westborough to Back Bay
- Ave. Duration
- 1h 14m
- Frequency
- Hourly
- Estimated price
- $6–12
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Adult
- $6–12
Train from Westborough to Back Bay
- Ave. Duration
- 1h 14m
- Frequency
- Hourly
- Estimated price
- $6–12
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Adult
- $6–12
Train from Westborough to South Station
- Ave. Duration
- 1h 20m
- Frequency
- Hourly
- Estimated price
- $6–12
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Adult
- $6–12
Train from Westborough to Back Bay
- Ave. Duration
- 1h 14m
- Frequency
- Hourly
- Estimated price
- $6–12
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Adult
- $6–12
Train from Back Bay to TF Green Airport
- Ave. Duration
- 1h 20m
- Frequency
- Every 4 hours
- Estimated price
- $9–16
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Adult
- $9–16
Train from Westborough to Back Bay
- Ave. Duration
- 1h 14m
- Frequency
- Hourly
- Estimated price
- $6–12
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Adult
- $6–12
Train from Back Bay to TF Green Airport
- Ave. Duration
- 1h 20m
- Frequency
- Every 4 hours
- Estimated price
- $9–16
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Adult
- $9–16
Train from Westborough to Back Bay
- Ave. Duration
- 1h 14m
- Frequency
- Hourly
- Estimated price
- $6–12
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Adult
- $6–12
Rome2Rio's guide to Greyhound USA
Contact DetailsContact Details
- Phone
- +1 214-849-8100
- [email protected]
- Website
- Greyhound
Bus from Worcester Union Station to Newark Penn Station
- Ave. Duration
- 3h 40m
- Frequency
- Twice daily
- Estimated price
- $30–55
- Website
- Greyhound
Bus from Boston to Boston Manchester Airport
- Ave. Duration
- 1h 5m
- Frequency
- Twice daily
- Estimated price
- $8–13
- Website
- Greyhound
Want to know more about travelling around United States
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Booking & Getting There
Westborough to Chicago bus services, operated by Greyhound USA, arrive at Newark Penn Station.
Chicago is 1h behind Westborough. It is currently 5:29 PM in Westborough and 4:29 PM in Chicago.
Westborough to Chicago train services, operated by Amtrak, arrive at Chicago Union Station.
Yes, the driving distance between Westborough to Chicago is 956 miles. It takes approximately 16h 20m to drive from Westborough to Chicago.
Book your Westborough to Chicago bus tickets online with Omio.
There are 1285+ hotels available in Chicago.







