There are 9 ways to get from Wrentham 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 Theodore Francis Green State Airport, fly to Chicago Midway International Airport
best- Take the train from Mansfield to TF Green Airporttrain
- Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)plane PVD - MDW
5h 34m$125–540Train to Theodore Francis Green State Airport, fly to Chicago O'Hare International Airport
cheapest- Take the train from Mansfield to TF Green Airporttrain
- Fly from Theodore Francis Green State Airport (PVD) to Chicago O'Hare International Airport (ORD)plane PVD - ORD
6h 12m$100–400Train (Amtrak)
- Take the train from Framingham Amtrak to Chicago Union Stationtrain Lake Shore Limited
22h 18m$559–920Bus
- Take the bus from Mansfield Station to Newton - Riverside MBTA Stationbus
- Take the bus from Newton, MA to Manhattan, NYbus
- Take the bus from New York Midtown to Chicago Bus Stationbus
27h 4m$246–345Drive 972.7 mi
- Drive from Wrentham to Chicagocar 972.7 mi
16h 39m$161–232Bus to Boston Logan Airport, fly to Chicago Midway International Airport
- Take the bus from Mansfield Station to Boston Airportbus
- Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane BOS - MDW
5h 45m$147–610Bus to Boston Logan Airport, fly to Chicago O'Hare International Airport
- Take the bus from Mansfield Station to Boston Airportbus
- Fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD)plane BOS - ORD
6h 2m$122–430Train, bus to Manchester Airport, fly to Chicago Midway International Airport
- Take the train from Mansfield 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 22m$128–524Bus to Boston Logan Airport, fly to General Mitchell International Airport, train
- Take the bus from Mansfield Station to Boston Airportbus
- 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$227–844
Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW) flights
Comparing Your Travel Options
The cheapest way to get from Wrentham to Chicago is to drive which costs $160 - $240 and takes 16h 39m.
The fastest way to get from Wrentham to Chicago is to train and fly which takes 5h 34m and costs $120 - $550.
No, there is no direct bus from Wrentham station to Chicago station. However, there are services departing from Mansfield Station and arriving at Chicago Bus Station via Newton, MA and New York Midtown. The journey, including transfers, takes approximately 27h 4m.
No, there is no direct train from Wrentham to Chicago station. However, there are services departing from Framingham Amtrak and arriving at Chicago Union Station via . The journey, including transfers, takes approximately 22h 18m.
The distance between Wrentham and Chicago is 892 miles. The road distance is 978.4 miles.
The best way to get from Wrentham to Chicago without a car is to train which takes 22h 18m and costs $550 - $950.
It takes approximately 5h 34m to get from Wrentham to Chicago, including transfers.
Wrentham to Chicago bus services, operated by Blue Apple Bus, depart from Mansfield Station.
Wrentham to Chicago train services, operated by Amtrak, depart from Framingham Amtrak station.
The best way to get from Wrentham to Chicago is to train which takes 22h 18m and costs $550 - $950. Alternatively, you can bus, which costs $240 - $350 and takes 27h 4m.
What companies run services between Wrentham, MA, USA and Chicago, IL, USA?
Amtrak operates a train from Framingham Amtrak to Chicago Union Station once daily. Tickets cost $500–850 and the journey takes 21h 47m. Alternatively, you can take a vehicle from Wrentham to Chicago Bus Station via Mansfield Station, Newton - Riverside MBTA Station, Newton, MA, Manhattan, NY, and New York Midtown in around 27h 4m.
- Website
- southwest.com
Flights from Theodore Francis Green State Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 36m
- When
- Every day
- Estimated price
- $90–490
Flights from Theodore Francis Green State Airport to Chicago Midway International Airport via Baltimore
- Ave. Duration
- 4h 51m
- When
- Every day
- Estimated price
- $100–500
Flights from Boston Logan Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 45m
- When
- Every day
- Estimated price
- $95–550
Flights from Manchester Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 35m
- When
- Every day
- Estimated price
- $85–460
Flights from Manchester Airport to Chicago Midway International Airport via Baltimore
- Ave. Duration
- 5h 28m
- When
- Every day
- Estimated price
- $95–480
Flights from Manchester Airport to Chicago Midway International Airport via Nashville
- Ave. Duration
- 5h 57m
- When
- Saturday, Monday, Thursday, Friday, and Sunday
- Estimated price
- $110–550
Flights from Boston Logan Airport to General Mitchell International Airport via Chicago Midway International Airport
- Ave. Duration
- 4h 45m
- When
- Saturday, Monday, Tuesday, Wednesday, and Thursday
- Estimated price
- $130–700
Flights from Boston Logan Airport to General Mitchell International Airport via Baltimore
- Ave. Duration
- 4h 56m
- When
- Monday to Thursday
- Estimated price
- $140–750
- Website
- aa.com
Flights from Boston Logan Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h 14m
- When
- Every day
- Estimated price
- $70–370
Flights from Theodore Francis Green State Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h 9m
- When
- Every day
- Estimated price
- $65–350
Flights from Boston Logan Airport to General Mitchell International Airport via Chicago O'Hare International Airport
- Ave. Duration
- 5h 2m
- When
- Every day
- Estimated price
- $130–700
Flights from Boston Logan Airport to General Mitchell International Airport via Philadelphia
- Ave. Duration
- 5h 2m
- When
- Every day
- Estimated price
- $140–700
- Website
- united.com
Flights from Boston Logan Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h 3m
- When
- Every day
- Estimated price
- $70–370
Flights from Theodore Francis Green State Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h 9m
- When
- Every day
- Estimated price
- $65–350
Flights from Theodore Francis Green State Airport to Chicago O'Hare International Airport via Washington Dulles
- Ave. Duration
- 5h 9m
- When
- Every day
- Estimated price
- $70–370
Flights from Boston Logan Airport to General Mitchell International Airport via Chicago O'Hare International Airport
- Ave. Duration
- 5h 2m
- When
- Every day
- Estimated price
- $130–700
- Website
- delta.com
Flights from Theodore Francis Green State Airport to Chicago Midway International Airport via Detroit
- Ave. Duration
- 5h 47m
- When
- Every day
- Estimated price
- $90–490
Flights from Boston Logan Airport to Chicago Midway International Airport via Detroit
- Ave. Duration
- 5h 18m
- When
- Every day
- Estimated price
- $95–550
Flights from Boston Logan Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h 1m
- When
- Every day
- Estimated price
- $70–370
Flights from Theodore Francis Green State Airport to Chicago O'Hare International Airport via Detroit
- Ave. Duration
- 6h 26m
- When
- Every day
- Estimated price
- $65–350
Flights from Boston Logan Airport to General Mitchell International Airport
- Ave. Duration
- 2h 51m
- When
- Every day
- Estimated price
- $130–700
Flights from Boston Logan Airport to General Mitchell International Airport via New York La Guardia
- Ave. Duration
- 5h 8m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $130–700
- Website
- jetblue.com
Flights from Boston Logan Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h 4m
- When
- Every day
- Estimated price
- $70–370
Flights from Boston Logan Airport to General Mitchell International Airport
- Ave. Duration
- 2h 36m
- When
- Every day
- Estimated price
- $130–700
Train from Mansfield to TF Green Airport
- Ave. Duration
- 51 min
- Frequency
- Every 4 hours
- Estimated price
- $5–11
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Adult
- $5–11
Train from Mansfield to TF Green Airport
- Ave. Duration
- 51 min
- Frequency
- Every 4 hours
- Estimated price
- $5–11
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Adult
- $5–11
Train from Mansfield to South Station
- Ave. Duration
- 47 min
- Frequency
- Hourly
- Estimated price
- $4–11
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Adult
- $4–11
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Framingham Amtrak to Chicago Union Station
- Ave. Duration
- 21h 47m
- Frequency
- Once daily
- Estimated price
- $500–850
- Website
- Amtrak
Train from Milwaukee to Chicago Union Station
- Ave. Duration
- 1h 29m
- Frequency
- Every 4 hours
- Estimated price
- $45–75
- Website
- Amtrak
- Phone
- 617 773 9403
- [email protected]
- Website
- Blue Apple Bus
Bus from Mansfield Station to Newton - Riverside MBTA Station
- Ave. Duration
- 35 min
- Frequency
- Hourly
- Estimated price
- $22
- Website
- Blue Apple Bus
Bus from Mansfield Station to Boston Airport
- Ave. Duration
- 1h 5m
- Frequency
- Hourly
- Estimated price
- $22
- Website
- Blue Apple Bus
Bus from Mansfield Station to Boston Airport
- Ave. Duration
- 1h 5m
- Frequency
- Hourly
- Estimated price
- $22
- Website
- Blue Apple Bus
Bus from Mansfield Station to Boston Airport
- Ave. Duration
- 1h 5m
- Frequency
- Hourly
- Estimated price
- $22
- Website
- Blue Apple Bus
- [email protected]
- Website
- Go Buses
Bus from Newton, MA to Manhattan, NY
- Ave. Duration
- 3h 45m
- Frequency
- Twice daily
- Estimated price
- $36–40
- Website
- Go Buses
- Phone
- +1 (855) 626-8585
- Website
- Flixbus USA
Bus from New York Midtown to Chicago Bus Station
- Ave. Duration
- 20h 25m
- Frequency
- Twice daily
- Estimated price
- $160–250
- Schedules at
- Flixbus USA
Rome2Rio's guide to Greyhound USA
Contact Details
- Phone
- +1 214-849-8100
- [email protected]
- Website
- Greyhound
Bus from Boston to Boston Manchester Airport
- Ave. Duration
- 1h 5m
- Frequency
- Twice daily
- Estimated price
- $9–14
- Website
- Greyhound
Want to know more about travelling around United States
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Booking & Getting There
Wrentham to Chicago bus services, operated by Blue Apple Bus, arrive at Newton - Riverside MBTA Station.
Chicago is 1h behind Wrentham. It is currently 2:55 PM in Wrentham and 1:55 PM in Chicago.
Wrentham to Chicago train services, operated by Amtrak, arrive at Chicago Union Station.
Yes, the driving distance between Wrentham to Chicago is 978 miles. It takes approximately 16h 39m to drive from Wrentham to Chicago.
There are 1313+ hotels available in Chicago.

















