There are 10 ways to get from Marblehead to Chicago by bus, plane, train (Amtrak), bus (Greyhound, Flixbus), car, 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.
Line 442 bus to Boston Logan Airport, fly to Chicago O'Hare International Airport
best- Take the bus from Pleasant St @ Bessom St to Wonderlandbus
- Fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD)plane BOS - ORD
6h 1m$557–1,012Bus to Manchester Airport, fly to Chicago O'Hare International Airport
cheapest- Take the bus from Boston to Boston Manchester Airportbus
- Fly from Manchester Airport (MHT) to Chicago O'Hare International Airport (ORD)plane MHT - ORD
8h 16m$76–346Train (Amtrak)
- Take the train from Boston to Chicago Union Stationtrain Lake Shore Limited
24h 37m$555–907Bus
- Take the bus from Boston to Newark Penn Stationbus Greyhound US0235 / ...
- Take the bus from Newark Penn Station to Chicago Bus Stationbus FlixBus N2640 / ...
28h 7m$195–302Drive 995.1 mi
- Drive from Marblehead to Chicagocar 995.1 mi
17h 14m$176–254Line 442 bus to Boston Logan Airport, fly to Chicago Midway International Airport
- Take the bus from Pleasant St @ Bessom St to Wonderlandbus
- Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane BOS - MDW
5h 48m$107–562Bus 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
7h 42m$101–476Train 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
8h 11m$111–518Fly 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
8h 2m$182–796Train to Theodore Francis Green State Airport, fly to Chicago O'Hare International Airport
- 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
8h 44m$86–388
Marblehead to Chicago by bus, subway, foot, and train (Amtrak)
Comparing Your Travel Options
The cheapest way to get from Marblehead to Chicago is to bus and fly which costs $75 - $350 and takes 8h 16m.
The fastest way to get from Marblehead to Chicago is to line 442 bus and fly which takes 5h 48m and costs $100 - $600.
No, there is no direct bus from Marblehead to Chicago station. However, there are services departing from Pleasant St @ Bessom St and arriving at Chicago Bus Station via Boston and Newark Penn Station. The journey, including transfers, takes approximately 28h 7m.
No, there is no direct train from Marblehead to Chicago station. However, there are services departing from Wonderland and arriving at Chicago Union Station via Boston. The journey, including transfers, takes approximately 24h 37m.
The distance between Marblehead and Chicago is 903 miles. The road distance is 1000.9 miles.
The best way to get from Marblehead to Chicago without a car is to train which takes 24h 37m and costs $550 - $950.
It takes approximately 6h 1m to get from Marblehead to Chicago, including transfers.
Marblehead to Chicago bus services, operated by Greyhound USA, depart from Boston station.
Marblehead to Chicago train services, operated by Amtrak, depart from Boston station.
The best way to get from Marblehead to Chicago is to train which takes 24h 37m and costs $550 - $950. Alternatively, you can bus, which costs $190 - $310 and takes 28h 7m.
What companies run services between Marblehead, MA, USA and Chicago, IL, USA?
Amtrak operates a train from Boston to Chicago Union Station once daily. Tickets cost $550–900 and the journey takes 22h 22m. Alternatively, you can take a bus from Pleasant St @ Bessom St to Chicago Bus Station via Wonderland, Wonderland, Aquarium, Boston, and Newark Penn Station in around 28h 7m.
- Website
- aa.com
Flights from Boston Logan Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h 12m
- When
- Every day
- Estimated price
- $70–380
Flights from Manchester Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h 4m
- When
- Every day
- Estimated price
- $60–320
Flights from Manchester Airport to Chicago O'Hare International Airport via Reagan Washington
- Ave. Duration
- 5h 58m
- When
- Monday, Tuesday, Wednesday, Thursday, Sunday, and Friday
- Estimated price
- $70–350
Flights from Manchester Airport to Chicago O'Hare International Airport via Philadelphia
- Ave. Duration
- 5h 57m
- When
- Every day
- Estimated price
- $65–340
Flights from Manchester Airport to Chicago O'Hare International Airport via Charlotte
- Ave. Duration
- 6h 18m
- When
- Every day
- Estimated price
- $85–390
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 Theodore Francis Green State Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h 8m
- When
- Every day
- Estimated price
- $70–360
Flights from Theodore Francis Green State Airport to Chicago O'Hare International Airport via Philadelphia
- Ave. Duration
- 5h 23m
- When
- Every day
- Estimated price
- $70–370
- Website
- southwest.com
Flights from Boston Logan Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 45m
- When
- Every day
- Estimated price
- $100–550
Flights from Manchester Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 37m
- When
- Every day
- Estimated price
- $85–450
Flights from Manchester Airport to Chicago Midway International Airport via Baltimore
- Ave. Duration
- 5h 17m
- When
- Every day
- Estimated price
- $95–470
Flights from Manchester Airport to Chicago Midway International Airport via Nashville
- Ave. Duration
- 5h 45m
- When
- Thursday, Monday, Friday, and Sunday
- Estimated price
- $110–550
Flights from Theodore Francis Green State Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 35m
- When
- Every day
- Estimated price
- $95–490
Flights from Theodore Francis Green State Airport to Chicago Midway International Airport via Baltimore
- Ave. Duration
- 4h 59m
- When
- Every day
- Estimated price
- $100–550
Flights from Boston Logan Airport to General Mitchell International Airport via Baltimore
- Ave. Duration
- 4h 56m
- When
- Tuesday, Wednesday, Monday, Thursday, Friday, and Sunday
- Estimated price
- $140–750
Flights from Boston Logan Airport to General Mitchell International Airport via Chicago Midway International Airport
- Ave. Duration
- 4h 57m
- When
- Monday, Thursday, Friday, Sunday, and Saturday
- Estimated price
- $130–700
- Website
- delta.com
Flights from Boston Logan Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 57m
- When
- Every day
- Estimated price
- $70–380
Flights from Boston Logan Airport to Chicago Midway International Airport via Detroit
- Ave. Duration
- 5h 11m
- When
- Every day
- Estimated price
- $100–550
Flights from Theodore Francis Green State Airport to Chicago Midway International Airport via Detroit
- Ave. Duration
- 5h 46m
- When
- Every day
- Estimated price
- $95–490
Flights from Boston Logan Airport to General Mitchell International Airport
- Ave. Duration
- 2h 43m
- When
- Every day
- Estimated price
- $130–700
Flights from Boston Logan Airport to General Mitchell International Airport via Detroit
- Ave. Duration
- 4h 29m
- 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 3m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $130–700
Flights from Theodore Francis Green State Airport to Chicago O'Hare International Airport via Detroit
- Ave. Duration
- 6h 20m
- When
- Every day
- Estimated price
- $70–360
- Website
- united.com
Flights from Boston Logan Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h 3m
- When
- Every day
- Estimated price
- $70–380
Flights from Manchester Airport to Chicago O'Hare International Airport via Washington Dulles
- Ave. Duration
- 5h 42m
- When
- Every day
- Estimated price
- $70–350
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 Theodore Francis Green State Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h 9m
- When
- Every day
- Estimated price
- $70–360
- Website
- jetblue.com
Flights from Boston Logan Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h 6m
- When
- Every day
- Estimated price
- $70–380
Flights from Boston Logan Airport to General Mitchell International Airport
- Ave. Duration
- 2h 36m
- When
- Every day
- Estimated price
- $130–700
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Boston to Chicago Union Station
- Ave. Duration
- 22h 22m
- Frequency
- Once daily
- Estimated price
- $550–900
- Website
- Amtrak
Train from Milwaukee to Chicago Union Station
- Ave. Duration
- 1h 29m
- Frequency
- Every 4 hours
- Estimated price
- $45–75
- Website
- Amtrak
Train from South Station to TF Green Airport
- Ave. Duration
- 1h 25m
- Frequency
- Every 4 hours
- Estimated price
- $9–16
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Adult
- $9–16
Train from South Station to TF Green Airport
- Ave. Duration
- 1h 25m
- Frequency
- Every 4 hours
- Estimated price
- $9–16
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Adult
- $9–16
Bus from Pleasant St @ Bessom St to Wonderland
- Ave. Duration
- 45 min
- Frequency
- Every 30 minutes
- Estimated price
- $1–5
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
Bus from Pleasant St @ Bessom St to Wonderland
- Ave. Duration
- 45 min
- Frequency
- Every 30 minutes
- Estimated price
- $1–5
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
Rome2Rio's guide to Greyhound USA
Contact Details
- Phone
- +1 214-849-8100
- ifsr@greyhound.com
- Website
- Greyhound
Bus from Boston to Newark Penn Station
- Ave. Duration
- 5h 20m
- Frequency
- Every 3 hours
- Estimated price
- $45–75
- Website
- Greyhound
Bus from Boston to Boston Manchester Airport
- Ave. Duration
- 1h 5m
- Frequency
- 4 times a day
- Estimated price
- $9–14
- Website
- Greyhound
Bus from Boston to Boston Manchester Airport
- Ave. Duration
- 1h 5m
- Frequency
- 4 times a day
- Estimated price
- $9–14
- Website
- Greyhound
- Phone
- +1 (855) 626-8585
- Website
- Flixbus USA
Bus from Boston to Newark Penn Station
- Ave. Duration
- 4h 50m
- Frequency
- Every 4 hours
- Estimated price
- $40–65
- Schedules at
- Flixbus USA
Bus from Newark Penn Station to Chicago Bus Station
- Ave. Duration
- 19h 40m
- Frequency
- 4 times a day
- Estimated price
- $150–220
- Schedules at
- Flixbus USA
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.
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Booking & Getting There
Marblehead to Chicago bus services, operated by Greyhound USA, arrive at Newark Penn Station.
Chicago is 1h behind Marblehead. It is currently 2:59 PM in Marblehead and 1:59 PM in Chicago.
Marblehead to Chicago train services, operated by Amtrak, arrive at Chicago Union Station.
Yes, the driving distance between Marblehead to Chicago is 1001 miles. It takes approximately 17h 14m to drive from Marblehead to Chicago.
There are 114+ hotels available in Chicago.










