There are 9 ways to get from Chicago Loop to Boston by plane, train (Amtrak), bus (Greyhound), car, bus, train, or bus (Flixbus)
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Fly Chicago Midway International Airport to Boston Logan Airport
best- Fly from Chicago Midway International Airport (MDW) to Boston Logan Airport (BOS)plane MDW - BOS
3h 56m$102–555Fly Chicago Midway International Airport to Theodore Francis Green State Airport, train
cheapest- Fly from Chicago Midway International Airport (MDW) to Theodore Francis Green State Airport (PVD)plane MDW - PVD
- Take the train from TF Green Airport to South Stationtrain
6h 32m$86–411Train (Amtrak)
- Take the train from Chicago Union Station to Bostontrain Lake Shore Limited
22h 2m$260–600Bus via Brook Park (Greyhound)
- Take the bus from Chicago Bus Station to Cleveland Bus Stationbus Greyhound US0164
- Take the bus from Cleveland Bus Station to Bostonbus Greyhound US0171
22h 5m$153–299Drive 981.1 mi
- Drive from Chicago Loop to Bostoncar 981.1 mi
16h 52m$179–259Fly Chicago O'Hare International Airport to Boston Logan Airport
- Fly from Chicago O'Hare International Airport (ORD) to Boston Logan Airport (BOS)plane ORD - BOS
4h 6m$602–905Fly Chicago Midway International Airport to Manchester Airport, bus
- Fly from Chicago Midway International Airport (MDW) to Manchester Airport (MHT)plane MDW - MHT
- Take the bus from Boston Manchester Airport to Bostonbus
6h 16m$110–570Fly Chicago O'Hare International Airport to Manchester Airport, bus
- Fly from Chicago O'Hare International Airport (ORD) to Manchester Airport (MHT)plane ORD - MHT
- Take the bus from Boston Manchester Airport to Bostonbus
6h 41m$90–430Bus (Flixbus)
- Take the bus from Chicago Bus Station to New York Midtownbus FlixBus N2640 / ...
- Take the bus from New York Midtown to Bostonbus FlixBus 2610 / ...
25h 30m$175–282
Chicago Loop to Boston by train (Amtrak)
Questions & Answers
The cheapest way to get from Chicago Loop to Boston is to bus via Brook Park which costs $150 - $300 and takes 22h 5m.
The fastest way to get from Chicago Loop to Boston is to fly which takes 3h 56m and costs $100 - $600.
No, there is no direct bus from Chicago Loop station to Boston. However, there are services departing from Chicago Bus Station and arriving at Boston via Cleveland Bus Station. The journey, including transfers, takes approximately 22h 5m.
Yes, there is a direct train departing from Chicago Union Station station and arriving at Boston. Services depart once daily, and operate every day. The journey takes approximately 22h 2m.
The distance between Chicago Loop and Boston is 875 miles. The road distance is 986.8 miles.
The best way to get from Chicago Loop to Boston without a car is to train which takes 22h 2m and costs $260 - $600.
It takes approximately 3h 56m to get from Chicago Loop to Boston, including transfers.
Chicago Loop to Boston bus services, operated by Greyhound USA, depart from Chicago Bus Station.
Chicago Loop to Boston train services, operated by Amtrak, depart from Chicago Union Station.
The best way to get from Chicago Loop to Boston is to fly which takes 3h 56m and costs $100 - $600. Alternatively, you can train, which costs $260 - $600 and takes 22h 2m, you could also bus via Brook Park, which costs $150 - $300 and takes 22h 5m.
What companies run services between Chicago Loop, IL, USA and Boston, MA, USA?
Southwest Airlines and Delta fly from Chicago Midway International Airport (MDW) to Boston Logan Airport (BOS) every 4 hours. Alternatively, Amtrak operates a train from Chicago Union Station to Boston once daily. Tickets cost $260–600 and the journey takes 22h 2m.
- Website
- southwest.com
Flights from Chicago Midway International Airport to Boston Logan Airport
- Ave. Duration
- 2h 20m
- When
- Every day
- Estimated price
- $100–550
Flights from Chicago Midway International Airport to Manchester Airport
- Ave. Duration
- 2h 11m
- When
- Every day
- Estimated price
- $100–550
Flights from Chicago Midway International Airport to Manchester Airport via Baltimore
- Ave. Duration
- 4h 25m
- When
- Saturday, Monday, Thursday, Friday, and Sunday
- Estimated price
- $120–600
Flights from Chicago Midway International Airport to Manchester Airport via Nashville
- Ave. Duration
- 4h 55m
- When
- Monday, Thursday, and Friday
- Estimated price
- $150–700
Flights from Chicago Midway International Airport to Theodore Francis Green State Airport
- Ave. Duration
- 2h 16m
- When
- Every day
- Estimated price
- $75–390
Flights from Chicago Midway International Airport to Theodore Francis Green State Airport via Baltimore
- Ave. Duration
- 4h 8m
- When
- Monday, Thursday, Friday, and Saturday
- Estimated price
- $80–410
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Chicago Union Station to Boston
- Ave. Duration
- 22h 2m
- Frequency
- Once daily
- Estimated price
- $260–600
- Website
- Amtrak
Rome2Rio's guide to Greyhound USA
Contact DetailsContact Details
- Phone
- +1 214-849-8100
- ifsr@greyhound.com
- Website
- Greyhound
Bus from Chicago Bus Station to Cleveland Bus Station
- Ave. Duration
- 7h 10m
- Frequency
- Twice daily
- Estimated price
- $50–100
- Website
- Greyhound
Bus from Cleveland Bus Station to Boston
- Ave. Duration
- 13h 55m
- Frequency
- Once daily
- Estimated price
- $100–200
- Website
- Greyhound
Bus from Boston Manchester Airport to Boston
- Ave. Duration
- 1h 30m
- Frequency
- Twice daily
- Estimated price
- $8–15
- Website
- Greyhound
Bus from Boston Manchester Airport to Boston
- Ave. Duration
- 1h 30m
- Frequency
- Twice daily
- Estimated price
- $8–15
- Website
- Greyhound
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More Questions & Answers
Chicago Loop to Boston bus services, operated by Greyhound USA, arrive at Cleveland Bus Station.
Boston is 1h ahead of Chicago Loop. It is currently 9:37 AM in Chicago Loop and 10:37 AM in Boston.
Chicago Loop to Boston train services, operated by Amtrak, arrive at Boston station.
Yes, the driving distance between Chicago Loop to Boston is 987 miles. It takes approximately 16h 52m to drive from Chicago Loop to Boston.
Book your Chicago Loop to Boston train tickets online with Omio.
Book your Chicago Loop to Boston bus tickets online with Omio and FlixBus.
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