There are 10 ways to get from Marblehead to Chicago by bus, plane, bus (Flixbus), train (Amtrak), 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 Midway International Airport
best- 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 31m$87–432Train 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
8h 30m$81–378Bus (Flixbus)
- Take the bus from Boston to New York Midtownbus FlixBus 2610 / ...
- Take the bus from New York Midtown to Chicago Bus Stationbus FlixBus N2641 / ...
24h 25m$154–257Train (Amtrak)
- Take the train from Boston to Chicago Union Stationtrain Lake Shore Limited
24h 35m$275–607Drive 995.1 mi
- Drive from Marblehead to Chicagocar 995.1 mi
17h 14m$182–263Line 442 bus to Boston Logan Airport, fly to Chicago O'Hare International Airport
- 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
5h 54m$607–1,012Bus 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 23m$114–576Bus 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 57m$104–486Train 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 4m$91–428Fly 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$679–1,971
Marblehead to Chicago by bus, subway, and foot (Flixbus)
Questions & Answers
The cheapest way to get from Marblehead to Chicago is to bus which costs $150 - $260 and takes 24h 25m.
The fastest way to get from Marblehead to Chicago is to line 442 bus and fly which takes 5h 31m and costs $85 - $440.
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 New York Midtown. The journey, including transfers, takes approximately 24h 25m.
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 35m.
The distance between Marblehead and Chicago is 889 miles. The road distance is 1000.9 miles.
The best way to get from Marblehead to Chicago without a car is to bus which takes 24h 25m and costs $150 - $260.
It takes approximately 5h 31m to get from Marblehead to Chicago, including transfers.
Marblehead to Chicago bus services, operated by Flixbus 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 bus which takes 24h 25m and costs $150 - $260. Alternatively, you can train, which costs $270 - $650 and takes 24h 35m.
What companies run services between Marblehead, MA, USA and Chicago, IL, USA?
You can take a bus from Pleasant St @ Bessom St to Chicago Bus Station via Wonderland, Wonderland, Aquarium, Boston, and New York Midtown in around 24h 25m. 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
Bus from Pleasant St @ Bessom St to Wonderland
- Ave. Duration
- 43 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
- 43 min
- Frequency
- Every 30 minutes
- Estimated price
- $1–5
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
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More Questions & Answers
Marblehead to Chicago bus services, operated by Flixbus USA, arrive at New York Midtown station.
Chicago is 1h behind Marblehead. It is currently 5:16 AM in Marblehead and 4:16 AM 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 1297+ hotels available in Chicago.







