There are 10 ways to get from Malden to Chicago by plane, train (Amtrak), bus (Greyhound, Flixbus), car, bus, 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.
Fly Boston Logan Airport to Chicago Midway International Airport
best- Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane BOS - MDW
5h 3m$102–510Bus 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
7h 12m$73–351Train (Amtrak)
- Take the train from Boston to Chicago Union Stationtrain Lake Shore Limited
23h 34m$552–902Bus
- Take the bus from Boston to Newark Penn Stationbus Greyhound US0235 / ...
- Take the bus from Newark Penn Station to Chicago Bus Stationbus FlixBus N2640 / ...
27h 27m$182–294Drive 982.7 mi
- Drive from Malden to Chicagocar 982.7 mi
16h 54m$180–259Fly Boston Logan Airport to Chicago O'Hare International Airport
- Fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD)plane BOS - ORD
5h 26m$557–1,010Bus 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
6h 36m$93–461Train to Theodore Francis Green State Airport, fly to Chicago Midway International Airport
- Take the train from Ruggles to TF Green Airporttrain
- Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)plane PVD - MDW
7h 8m$108–572Train to Theodore Francis Green State Airport, fly to Chicago O'Hare International Airport
- Take the train from Ruggles to TF Green Airporttrain
- Fly from Theodore Francis Green State Airport (PVD) to Chicago O'Hare International Airport (ORD)plane PVD - ORD
7h 33m$88–412Fly 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
7h 28m$702–1,994
Malden to Chicago by subway and train (Amtrak)
Comparing Your Travel Options
The cheapest way to get from Malden to Chicago is to bus and fly which costs $70 - $360 and takes 7h 12m.
The fastest way to get from Malden to Chicago is to fly which takes 5h 3m and costs $100 - $550.
No, there is no direct bus from Malden to Chicago station. However, there are services departing from Chelsea and arriving at Chicago Bus Station via Boston and Newark Penn Station. The journey, including transfers, takes approximately 27h 27m.
No, there is no direct train from Malden to Chicago station. However, there are services departing from Malden Center and arriving at Chicago Union Station via Boston. The journey, including transfers, takes approximately 23h 34m.
The distance between Malden and Chicago is 882 miles. The road distance is 988.4 miles.
The best way to get from Malden to Chicago without a car is to train which takes 23h 34m and costs $550 - $900.
It takes approximately 5h 3m to get from Malden to Chicago, including transfers.
Malden to Chicago bus services, operated by Greyhound USA, depart from Boston station.
Malden to Chicago train services, operated by Amtrak, depart from Boston station.
The best way to get from Malden to Chicago is to fly which takes 5h 3m and costs $100 - $550. Alternatively, you can train, which costs $550 - $900 and takes 23h 34m, you could also bus, which costs $180 - $300 and takes 27h 27m.
What companies run services between Malden, MA, USA and Chicago, IL, USA?
Southwest Airlines and Delta fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW) every 3 hours. Alternatively, Amtrak operates a train from Boston to Chicago Union Station once daily. Tickets cost $550–900 and the journey takes 22h 15m.
- Website
- southwest.com
Flights from Boston Logan Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 37m
- When
- Every day
- Estimated price
- $95–500
Flights from Manchester Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 30m
- When
- Every day
- Estimated price
- $80–440
Flights from Manchester Airport to Chicago Midway International Airport via Baltimore
- Ave. Duration
- 5h 10m
- When
- Monday to Saturday
- Estimated price
- $90–460
Flights from Theodore Francis Green State Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 31m
- When
- Every day
- Estimated price
- $95–550
Flights from Theodore Francis Green State Airport to Chicago Midway International Airport via Baltimore
- Ave. Duration
- 4h 30m
- When
- Monday to Wednesday
- Estimated price
- $100–550
Flights from Boston Logan Airport to General Mitchell International Airport via Chicago Midway International Airport
- Ave. Duration
- 4h 35m
- When
- Saturday to Wednesday
- Estimated price
- $140–750
Flights from Boston Logan Airport to General Mitchell International Airport via Baltimore
- Ave. Duration
- 4h 45m
- When
- Monday to Wednesday
- Estimated price
- $140–750
- Website
- aa.com
Flights from Boston Logan Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h 9m
- When
- Every day
- Estimated price
- $70–380
Flights from Manchester Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 58m
- When
- Every day
- Estimated price
- $60–330
Flights from Manchester Airport to Chicago O'Hare International Airport via Reagan Washington
- Ave. Duration
- 5h 26m
- When
- Every day
- Estimated price
- $70–350
Flights from Manchester Airport to Chicago O'Hare International Airport via Philadelphia
- Ave. Duration
- 5h 50m
- When
- Every day
- Estimated price
- $65–350
Flights from Manchester Airport to Chicago O'Hare International Airport via Charlotte
- Ave. Duration
- 6h 5m
- When
- Every day
- Estimated price
- $85–400
Flights from Theodore Francis Green State Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h 2m
- When
- Every day
- Estimated price
- $75–390
Flights from Theodore Francis Green State Airport to Chicago O'Hare International Airport via Philadelphia
- Ave. Duration
- 5h 3m
- When
- Monday, Wednesday, Friday, Saturday, Sunday, and Tuesday
- Estimated price
- $75–400
- 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 44m
- When
- Every day
- Estimated price
- $70–350
Flights from Theodore Francis Green State Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h 9m
- When
- Every day
- Estimated price
- $75–390
Flights from Theodore Francis Green State Airport to Chicago O'Hare International Airport via Washington Dulles
- Ave. Duration
- 5h 8m
- When
- Monday, Friday, and Saturday
- Estimated price
- $80–410
Flights from Boston Logan Airport to General Mitchell International Airport via Chicago O'Hare International Airport
- Ave. Duration
- 4h 57m
- When
- Every day
- Estimated price
- $140–750
- Website
- delta.com
Flights from Boston Logan Airport to Chicago Midway International Airport via Detroit
- Ave. Duration
- 5h 6m
- When
- Every day
- Estimated price
- $95–500
Flights from Boston Logan Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 55m
- When
- Every day
- Estimated price
- $70–380
Flights from Theodore Francis Green State Airport to Chicago Midway International Airport via Detroit
- Ave. Duration
- 4h 57m
- When
- Every day
- Estimated price
- $95–550
Flights from Theodore Francis Green State Airport to Chicago O'Hare International Airport via Detroit
- Ave. Duration
- 4h 28m
- When
- Every day
- Estimated price
- $75–390
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
- 4h 56m
- When
- Monday to Friday
- Estimated price
- $140–750
- 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 DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Boston to Chicago Union Station
- Ave. Duration
- 22h 15m
- 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 Ruggles to TF Green Airport
- Ave. Duration
- 1h 22m
- Frequency
- Every 4 hours
- Estimated price
- $9–15
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Adult
- $9–15
Train from Ruggles to TF Green Airport
- Ave. Duration
- 1h 22m
- Frequency
- Every 4 hours
- Estimated price
- $9–15
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Adult
- $9–15
Rome2Rio's guide to Greyhound USA
Contact DetailsContact Details
- Phone
- +1 214-849-8100
- [email protected]
- Website
- Greyhound
Bus from Boston to Newark Penn Station
- Ave. Duration
- 5h 20m
- Frequency
- 4 times a day
- Estimated price
- $45–70
- Website
- Greyhound
Bus from Boston to Boston Manchester Airport
- Ave. Duration
- 1h 5m
- Frequency
- Twice daily
- Estimated price
- $9–14
- Website
- Greyhound
Bus from Boston to Boston Manchester Airport
- Ave. Duration
- 1h 5m
- Frequency
- Twice daily
- 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
- 3 times a day
- Estimated price
- $40–65
- Schedules at
- Flixbus USA
Bus from Newark Penn Station to Chicago Bus Station
- Ave. Duration
- 19h 40m
- Frequency
- Twice daily
- Estimated price
- $140–220
- 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.
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
Booking & Getting There
Malden to Chicago bus services, operated by Greyhound USA, arrive at Newark Penn Station.
Chicago is 1h behind Malden. It is currently 6:34 PM in Malden and 5:34 PM in Chicago.
Malden to Chicago train services, operated by Amtrak, arrive at Chicago Union Station.
Yes, the driving distance between Malden to Chicago is 988 miles. It takes approximately 16h 54m to drive from Malden to Chicago.
There are 1294+ hotels available in Chicago.







