There are 10 ways to get from Chicago to Manchester-by-the-Sea by plane, train, train (Amtrak), bus (Greyhound), car, subway, bus, 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 O'Hare International Airport to Boston Logan Airport, train
best- Fly from Chicago O'Hare International Airport (ORD) to Boston Logan Airport (BOS)plane ORD - BOS
- Take the train from Chelsea to Manchestertrain
6h 19m$558–1,020Fly Chicago O'Hare International Airport to Theodore Francis Green State Airport, train
cheapest- Fly from Chicago O'Hare International Airport (ORD) to Theodore Francis Green State Airport (PVD)plane ORD - PVD
- Take the train from TF Green Airport to Rugglestrain
- Take the train from North Station to Manchestertrain
8h 47m$68–295Train
- Take the train from Chicago Union Station to Bostontrain Lake Shore Limited
- Take the train from North Station to Manchestertrain Newburyport/Rockport Line
23h 54m$567–873Bus 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
24h 13m$176–286Drive 1,003.4 mi
- Drive from Chicago to Manchester-by-the-Seacar 1,003.4 mi
17h 29m$184–265Subway to Chicago Midway International Airport, fly to Boston Logan Airport, train
- Take the subway from Adams/Wabash to Midwaysubway
- Fly from Chicago Midway International Airport (MDW) to Boston Logan Airport (BOS)plane MDW - BOS
- Take the train from Chelsea to Manchestertrain
6h 7m$118–620Fly Chicago Midway International Airport to Manchester Airport, bus, train
- Fly from Chicago Midway International Airport (MDW) to Manchester Airport (MHT)plane MDW - MHT
- Take the bus from Boston Manchester Airport to Bostonbus
- Take the train from North Station to Manchestertrain
8h 15m$118–583Fly Chicago Midway International Airport to Theodore Francis Green State Airport, train
- 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 Rugglestrain
- Take the train from North Station to Manchestertrain
8h 19m$94–435Fly Chicago O'Hare International Airport to Manchester Airport, bus, train
- Fly from Chicago O'Hare International Airport (ORD) to Manchester Airport (MHT)plane ORD - MHT
- Take the bus from Boston Manchester Airport to Bostonbus
- Take the train from North Station to Manchestertrain
8h 43m$84–383Bus (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 / ...
27h 37m$193–297
Chicago to Manchester-by-the-Sea by train and subway
Comparing Your Travel Options
The cheapest way to get from Chicago to Manchester-by-the-Sea is to fly and train which costs $65 - $300 and takes 8h 47m.
The fastest way to get from Chicago to Manchester-by-the-Sea is to subway and fly and train which takes 6h 7m and costs $110 - $650.
No, there is no direct bus from Chicago station to Manchester-by-the-Sea. However, there are services departing from Chicago Bus Station and arriving at Chelsea via Cleveland Bus Station and South Station. The journey, including transfers, takes approximately 24h 13m.
No, there is no direct train from Chicago station to Manchester-by-the-Sea. However, there are services departing from Chicago Union Station and arriving at Manchester via Back Bay and North Station. The journey, including transfers, takes approximately 23h 54m.
The distance between Chicago and Manchester-by-the-Sea is 912 miles. The road distance is 1009.2 miles.
The best way to get from Chicago to Manchester-by-the-Sea without a car is to train which takes 23h 54m and costs $550 - $900.
It takes approximately 6h 19m to get from Chicago to Manchester-by-the-Sea, including transfers.
Chicago to Manchester-by-the-Sea bus services, operated by Greyhound USA, depart from Chicago Bus Station.
Chicago to Manchester-by-the-Sea train services, operated by Amtrak, depart from Chicago Union Station.
The best way to get from Chicago to Manchester-by-the-Sea is to train which takes 23h 54m and costs $550 - $900. Alternatively, you can bus via Brook Park, which costs $170 - $290 and takes 24h 13m.
What companies run services between Chicago, IL, USA and Manchester-by-the-Sea, MA, USA?
You can take a train from Chicago Union Station to Manchester via Boston, Back Bay, North Station, and North Station in around 23h 54m. Alternatively, you can take a bus from Chicago Bus Station to Manchester via Cleveland Bus Station, Boston, South Station, Chelsea, and Chelsea in around 24h 13m.
- Website
- southwest.com
Flights from Chicago Midway International Airport to Boston Logan Airport
- Ave. Duration
- 2h 20m
- When
- Every day
- Estimated price
- $110–600
Flights from Chicago Midway International Airport to Manchester Airport
- Ave. Duration
- 2h 8m
- When
- Every day
- Estimated price
- $100–550
Flights from Chicago Midway International Airport to Manchester Airport via Baltimore
- Ave. Duration
- 4h 36m
- When
- Sunday, Monday, Thursday, Friday, Tuesday, and Wednesday
- Estimated price
- $110–600
Flights from Chicago Midway International Airport to Manchester Airport via Nashville
- Ave. Duration
- 4h 55m
- When
- Sunday
- Estimated price
- $140–650
Flights from Chicago Midway International Airport to Theodore Francis Green State Airport
- Ave. Duration
- 2h 11m
- When
- Every day
- Estimated price
- $75–400
Flights from Chicago Midway International Airport to Theodore Francis Green State Airport via Baltimore
- Ave. Duration
- 4h 36m
- When
- Every day
- Estimated price
- $80–420
Flights from Chicago Midway International Airport to Theodore Francis Green State Airport via Reagan Washington
- Ave. Duration
- 4h 37m
- When
- Every day
- Estimated price
- $80–420
- Website
- aa.com
Flights from Chicago O'Hare International Airport to Boston Logan Airport
- Ave. Duration
- 2h 39m
- When
- Every day
- Estimated price
- $70–380
Flights from Chicago O'Hare International Airport to Boston Logan Airport via Syracuse
- Ave. Duration
- 4h 15m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $70–380
Flights from Chicago O'Hare International Airport to Manchester Airport
- Ave. Duration
- 2h 27m
- When
- Every day
- Estimated price
- $65–350
Flights from Chicago O'Hare International Airport to Manchester Airport via Philadelphia
- Ave. Duration
- 5h 6m
- When
- Every day
- Estimated price
- $70–370
Flights from Chicago O'Hare International Airport to Manchester Airport via Reagan Washington
- Ave. Duration
- 5h 34m
- When
- Saturday
- Estimated price
- $75–370
Flights from Chicago O'Hare International Airport to Theodore Francis Green State Airport
- Ave. Duration
- 2h 31m
- When
- Every day
- Estimated price
- $50–260
Flights from Chicago O'Hare International Airport to Theodore Francis Green State Airport via Reagan Washington
- Ave. Duration
- 5h 5m
- When
- Every day
- Estimated price
- $50–280
- Website
- united.com
Flights from Chicago O'Hare International Airport to Boston Logan Airport
- Ave. Duration
- 2h 26m
- When
- Every day
- Estimated price
- $70–380
Flights from Chicago O'Hare International Airport to Manchester Airport via Washington Dulles
- Ave. Duration
- 4h 54m
- When
- Monday, Tuesday, Thursday, Friday, Saturday, and Sunday
- Estimated price
- $70–370
Flights from Chicago O'Hare International Airport to Theodore Francis Green State Airport
- Ave. Duration
- 2h 32m
- When
- Every day
- Estimated price
- $50–260
Flights from Chicago O'Hare International Airport to Theodore Francis Green State Airport via Washington Dulles
- Ave. Duration
- 4h 38m
- When
- Monday
- Estimated price
- $50–280
- Website
- delta.com
Flights from Chicago O'Hare International Airport to Boston Logan Airport
- Ave. Duration
- 2h 36m
- When
- Every day
- Estimated price
- $70–380
Flights from Chicago Midway International Airport to Boston Logan Airport via Detroit
- Ave. Duration
- 4h 48m
- When
- Every day
- Estimated price
- $110–600
Flights from Chicago O'Hare International Airport to Theodore Francis Green State Airport via Detroit
- Ave. Duration
- 4h 40m
- When
- Every day
- Estimated price
- $50–260
- Website
- jetblue.com
Flights from Chicago O'Hare International Airport to Boston Logan Airport
- Ave. Duration
- 2h 46m
- When
- Every day
- Estimated price
- $70–380
Train from Chelsea to Manchester
- Ave. Duration
- 41 min
- Frequency
- Hourly
- Estimated price
- $4–10
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Adult
- $4–10
Train from North Station to Manchester
- Ave. Duration
- 52 min
- Frequency
- Hourly
- Estimated price
- $4–11
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Adult
- $4–11
Train from Chelsea to Manchester
- Ave. Duration
- 41 min
- Frequency
- Hourly
- Estimated price
- $4–10
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Adult
- $4–10
Train from North Station to Manchester
- Ave. Duration
- 52 min
- Frequency
- Hourly
- Estimated price
- $4–11
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Adult
- $4–11
Train from TF Green Airport to Ruggles
- Ave. Duration
- 1h 19m
- Frequency
- Every 4 hours
- Estimated price
- $9–16
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Adult
- $9–16
Train from North Station to Manchester
- Ave. Duration
- 52 min
- Frequency
- Hourly
- Estimated price
- $4–11
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Adult
- $4–11
Train from North Station to Manchester
- Ave. Duration
- 52 min
- Frequency
- Hourly
- Estimated price
- $4–11
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Adult
- $4–11
Train from TF Green Airport to Ruggles
- Ave. Duration
- 1h 19m
- Frequency
- Every 4 hours
- Estimated price
- $9–16
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Adult
- $9–16
Train from North Station to Manchester
- Ave. Duration
- 52 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 DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Chicago Union Station to Boston
- Ave. Duration
- 21h 54m
- Frequency
- Once daily
- Estimated price
- $550–900
- Website
- Amtrak
- Phone
- +1 888-968-7282
- Website
- Chicago Transit Authority
Subway from Adams/Wabash to Midway
- Ave. Duration
- 23 min
- Frequency
- Every 15 minutes
- Estimated price
- $2–5
- Website
- Chicago Transit Authority
- Schedules at
- Chicago Transit Authority Schedules & Routes
- Adult
- $2–5
Rome2Rio's guide to Greyhound USA
Contact DetailsContact Details
- Phone
- +1 214-849-8100
- [email protected]
- Website
- Greyhound
Bus from Chicago Bus Station to Cleveland Bus Station
- Ave. Duration
- 7h 10m
- Frequency
- Twice daily
- Estimated price
- $60–95
- Website
- Greyhound
Bus from Cleveland Bus Station to Boston
- Ave. Duration
- 13h 55m
- Frequency
- Once daily
- Estimated price
- $110–180
- Website
- Greyhound
Bus from Boston Manchester Airport to Boston
- Ave. Duration
- 1h 30m
- Frequency
- Twice daily
- Estimated price
- $9–14
- Website
- Greyhound
Bus from Boston Manchester Airport to Boston
- Ave. Duration
- 1h 30m
- Frequency
- Twice daily
- Estimated price
- $9–14
- Website
- Greyhound
- Phone
- +1 (855) 626-8585
- Website
- Flixbus USA
Bus from Chicago Bus Station to New York Midtown
- Ave. Duration
- 20h 10m
- Frequency
- Twice daily
- Estimated price
- $150–240
- Schedules at
- Flixbus USA
Bus from New York Midtown to Boston
- Ave. Duration
- 4h 20m
- Frequency
- Every 2 hours
- Estimated price
- $30–50
- Schedules at
- Flixbus USA
Want to know more about travelling around United States
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Booking & Getting There
Chicago to Manchester-by-the-Sea bus services, operated by Greyhound USA, arrive at Cleveland Bus Station.
Manchester-by-the-Sea is 1h ahead of Chicago. It is currently 3:22 PM in Chicago and 4:22 PM in Manchester-by-the-Sea.
Chicago to Manchester-by-the-Sea train services, operated by Amtrak, arrive at Boston station.
Yes, the driving distance between Chicago to Manchester-by-the-Sea is 1009 miles. It takes approximately 17h 29m to drive from Chicago to Manchester-by-the-Sea.
There are 275+ hotels available in Manchester-by-the-Sea.















