There are 10 ways to get from South Station to Chicago by plane, train (Amtrak), bus (Greyhound, Flixbus), car, bus, or train
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 36m$83–427Train 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
6h 12m$77–371Train (Amtrak)
- Take the train from Boston to Chicago Union Stationtrain Lake Shore Limited
22h 22m$270–600Bus
- Take the bus from Boston to Newark Penn Stationbus Greyhound US0235 / ...
- Take the bus from Newark Penn Station to Chicago Bus Stationbus FlixBus N2641 / ...
22h 40m$146–259Drive 980 mi
- Drive from South Station to Chicagocar 980 mi
16h 47m$179–259Fly 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
4h 57m$603–1,007Bus 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
5h 6m$109–568Bus 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
5h 40m$99–478Train 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
5h 49m$87–421Fly 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 7m$675–1,966
South Station to Chicago by train (Amtrak)
Questions & Answers
The cheapest way to get from South Station to Chicago is to bus which costs $140 - $260 and takes 22h 40m.
The fastest way to get from South Station to Chicago is to fly which takes 4h 36m and costs $80 - $430.
No, there is no direct bus from South Station to Chicago station. However, there are services departing from Boston and arriving at Chicago Bus Station via Newark Penn Station. The journey, including transfers, takes approximately 22h 40m.
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 22m.
The distance between South Station and Chicago is 878 miles. The road distance is 985.8 miles.
The best way to get from South Station to Chicago without a car is to train which takes 22h 22m and costs $270 - $600.
It takes approximately 4h 36m to get from South Station to Chicago, including transfers.
South Station to Chicago bus services, operated by Greyhound USA, depart from Boston station.
South Station to Chicago train services, operated by Amtrak, depart from Boston station.
The best way to get from South Station to Chicago is to fly which takes 4h 36m and costs $80 - $430. Alternatively, you can train, which costs $270 - $600 and takes 22h 22m, you could also bus, which costs $140 - $260 and takes 22h 40m.
What companies run services between South Station, 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 $270–600 and the journey takes 22h 22m.
- 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
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
- $270–600
- Website
- Amtrak
Train from Milwaukee to Chicago Union Station
- Ave. Duration
- 1h 29m
- Frequency
- Every 4 hours
- Estimated price
- $22–50
- Website
- Amtrak
Rome2Rio's guide to Greyhound USA
Contact DetailsContact Details
- Phone
- +1 214-849-8100
- [email protected]
- Website
- Greyhound
Bus from Boston to Newark Penn Station
- Ave. Duration
- 5h 20m
- Frequency
- 4 times a day
- Estimated price
- $35–70
- Website
- Greyhound
Bus from Boston to Boston Manchester Airport
- Ave. Duration
- 1h 5m
- Frequency
- Twice daily
- Estimated price
- $7–14
- Website
- Greyhound
Bus from Boston to Boston Manchester Airport
- Ave. Duration
- 1h 5m
- Frequency
- Twice daily
- Estimated price
- $7–14
- Website
- Greyhound
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More Questions & Answers
South Station to Chicago bus services, operated by Greyhound USA, arrive at Newark Penn Station.
Chicago is 1h behind South Station. It is currently 4:55 PM in South Station and 3:55 PM in Chicago.
South Station to Chicago train services, operated by Amtrak, arrive at Chicago Union Station.
Yes, the driving distance between South Station to Chicago is 986 miles. It takes approximately 16h 47m to drive from South Station to Chicago.
Book your South Station to Chicago train tickets online with Omio.
Book your South Station to Chicago bus tickets online with Omio and FlixBus.
There are 1297+ hotels available in Chicago.