There are 10 ways to get from Back Bay to Chicago by plane, train (Amtrak), bus (Greyhound, 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 40m$96–464Train to Theodore Francis Green State Airport, fly to Chicago O'Hare International Airport
cheapest- 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
6h 2m$82–390Train (Amtrak)
- Take the train from Boston to Chicago Union Stationtrain Lake Shore Limited
22h 15m$270–750Bus
- Take the bus from Boston to Newark Penn Stationbus Greyhound US0235 / ...
- Take the bus from Newark Penn Station to Chicago Bus Stationbus FlixBus N2640 / ...
26h$179–275Drive 978.7 mi
- Drive from Back Bay to Chicagocar 978.7 mi
16h 45m$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
5h 1m$611–1,014Train to Theodore Francis Green State Airport, fly to Chicago Midway International Airport
- 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
5h 44m$97–480Bus 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 26m$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 2m$107–570Fly 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$684–1,983
Back Bay to Chicago by train (Amtrak)
Comparing Your Travel Options
The cheapest way to get from Back Bay to Chicago is to train and fly which costs $80 - $390 and takes 6h 2m.
The fastest way to get from Back Bay to Chicago is to fly which takes 4h 40m and costs $95 - $470.
No, there is no direct bus from Back Bay 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 26h.
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 Back Bay and Chicago is 879 miles. The road distance is 984.4 miles.
The best way to get from Back Bay to Chicago without a car is to train which takes 22h 15m and costs $270 - $750.
It takes approximately 4h 40m to get from Back Bay to Chicago, including transfers.
Back Bay to Chicago bus services, operated by Greyhound USA, depart from Boston station.
Back Bay to Chicago train services, operated by Amtrak, depart from Boston station.
The best way to get from Back Bay to Chicago is to fly which takes 4h 40m and costs $95 - $470. Alternatively, you can train, which costs $270 - $750 and takes 22h 15m, you could also bus, which costs $170 - $280 and takes 26h.
What companies run services between Back Bay, 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 $270–750 and the journey takes 22h 15m.
- Website
- southwest.com
Flights from Boston Logan Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 36m
- When
- Every day
- Estimated price
- $85–450
Flights from Theodore Francis Green State Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 30m
- When
- Every day
- Estimated price
- $85–460
Flights from Theodore Francis Green State Airport to Chicago Midway International Airport via Baltimore
- Ave. Duration
- 4h 42m
- When
- Every day
- Estimated price
- $95–480
Flights from Manchester Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 25m
- When
- Every day
- Estimated price
- $120–650
Flights from Manchester Airport to Chicago Midway International Airport via Baltimore
- Ave. Duration
- 5h 4m
- When
- Monday, Thursday, Friday, Tuesday, Wednesday, and Sunday
- Estimated price
- $130–700
Flights from Manchester Airport to Chicago Midway International Airport via Nashville
- Ave. Duration
- 5h 5m
- When
- Monday, Thursday, and Friday
- Estimated price
- $160–800
Flights from Boston Logan Airport to General Mitchell International Airport via Chicago Midway International Airport
- Ave. Duration
- 4h 42m
- When
- Monday to Saturday
- Estimated price
- $130–700
Flights from Boston Logan Airport to General Mitchell International Airport via Baltimore
- Ave. Duration
- 4h 43m
- When
- Monday, Thursday, Friday, Sunday, and Saturday
- Estimated price
- $140–700
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 15m
- Frequency
- Once daily
- Estimated price
- $270–750
- Website
- Amtrak
Train from Milwaukee to Chicago Union Station
- Ave. Duration
- 1h 29m
- Frequency
- Every 4 hours
- Estimated price
- $23–60
- 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
- $40–65
- Website
- Greyhound
Bus from Boston to Boston Manchester Airport
- Ave. Duration
- 1h 5m
- Frequency
- Twice daily
- Estimated price
- $8–13
- 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
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
Booking & Getting There
Back Bay to Chicago bus services, operated by Greyhound USA, arrive at Newark Penn Station.
Chicago is 1h behind Back Bay. It is currently 6:28 PM in Back Bay and 5:28 PM in Chicago.
Back Bay to Chicago train services, operated by Amtrak, arrive at Chicago Union Station.
Yes, the driving distance between Back Bay to Chicago is 984 miles. It takes approximately 16h 45m to drive from Back Bay to Chicago.
Book your Back Bay to Chicago train tickets online with Omio.
Book your Back Bay to Chicago bus tickets online with Omio and FlixBus.
There are 1306+ hotels available in Chicago.