There are 10 ways to get from Marblehead to Chicago by bus, plane, train (Amtrak), bus (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 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$92–442Train 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 20m$81–378Train (Amtrak)
- Take the train from Boston to Chicago Union Stationtrain Lake Shore Limited
24h 34m$265–607Bus (Flixbus)
- Take the bus from Boston to New York Midtownbus FlixBus 2610 / ...
- Take the bus from New York Midtown to Chicago Bus Stationbus FlixBus N2640 / ...
28h 1m$175–297Drive 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 52m$607–912Bus 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 22m$114–577Train 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
7h 58m$91–438Bus 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 56m$104–497Fly 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, foot, and train (Amtrak)
Questions & Answers
The cheapest way to get from Marblehead to Chicago is to bus which costs $170 - $300 and takes 28h 1m.
The fastest way to get from Marblehead to Chicago is to line 442 bus and fly which takes 5h 31m and costs $90 - $450.
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 28h 1m.
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 34m.
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 train which takes 24h 34m and costs $260 - $650.
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 train which takes 24h 34m and costs $260 - $650. Alternatively, you can bus, which costs $170 - $300 and takes 28h 1m.
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 $260–600 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 New York Midtown in around 28h 1m.
- Website
- southwest.com
Flights from Boston Logan Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 36m
- When
- Every day
- Estimated price
- $85–430
Flights from Manchester Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 22m
- When
- Every day
- Estimated price
- $100–550
Flights from Manchester Airport to Chicago Midway International Airport via Baltimore
- Ave. Duration
- 4h 35m
- When
- Tuesday to Monday
- Estimated price
- $120–600
Flights from Manchester Airport to Chicago Midway International Airport via Nashville
- Ave. Duration
- 5h
- When
- Monday, Thursday, and Friday
- Estimated price
- $150–700
Flights from Theodore Francis Green State Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 26m
- When
- Every day
- Estimated price
- $75–410
Flights from Theodore Francis Green State Airport to Chicago Midway International Airport via Baltimore
- Ave. Duration
- 4h 20m
- When
- Thursday, Friday, and Monday
- Estimated price
- $85–420
Flights from Boston Logan Airport to General Mitchell International Airport via Baltimore
- Ave. Duration
- 4h 47m
- When
- Monday, Thursday, Friday, Tuesday, Wednesday, and Sunday
- Estimated price
- $130–700
Flights from Boston Logan Airport to General Mitchell International Airport via Chicago Midway International Airport
- Ave. Duration
- 4h 32m
- When
- Monday, Thursday, Friday, and Saturday
- Estimated price
- $130–650
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
- $260–600
- 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
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
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 3:07 AM in Marblehead and 2:07 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 1275+ hotels available in Chicago.







