There are 7 ways to get from Maine to Chicago by plane, bus (Amtrak, Greyhound), bus, train, car, 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 Portland to Chicago Midway International Airport
best- Fly from Portland (PWM) to Chicago Midway International Airport (MDW)plane PWM - MDW
3h 11m$107–521Fly Portland to Chicago O'Hare International Airport
cheapest- Fly from Portland (PWM) to Chicago O'Hare International Airport (ORD)plane PWM - ORD
3h 42m$91–443Bus via Brook Park
- Take the bus from Portland, ME to Boston, MA - South Stationbus
- Take the bus from Boston to Cleveland Bus Stationbus
- Take the bus from Cleveland Bus Station to Chicago Bus Stationbus
25h 48m$173–339Bus, train
- Take the bus from Portland, ME to Boston, MA - South Stationbus Portland / ...
- Take the train from Boston to Chicago Union Stationtrain Lake Shore Limited
25h 55m$323–699Drive 1,036.4 mi
- Drive from Portland to Chicagocar 1,036.4 mi
19h 16m$190–274Fly Bangor to Chicago O'Hare International Airport
- Fly from Bangor (BGR) to Chicago O'Hare International Airport (ORD)plane BGR - ORD
4h 56m$124–656Bus (Flixbus)
- Take the bus from City of Portland to New York Midtownbus FlixBus N2615
- Take the bus from New York Midtown to Chicago Bus Stationbus FlixBus N2641 / ...
26h 19m$182–309
Maine to Chicago by bus
Questions & Answers
The cheapest way to get from Maine to Chicago is to bus via Brook Park which costs $170 - $340 and takes 25h 48m.
The fastest way to get from Maine to Chicago is to fly which takes 3h 11m and costs $100 - $550.
No, there is no direct bus from Maine to Chicago station. However, there are services departing from Portland Public Library and arriving at Chicago Bus Station via Portland, ME, Boston and Cleveland Bus Station. The journey, including transfers, takes approximately 25h 48m.
The distance between Maine and Chicago is 909 miles. The road distance is 1042.4 miles.
The best way to get from Maine to Chicago without a car is to bus via Brook Park which takes 25h 48m and costs $170 - $340.
It takes approximately 3h 11m to get from Maine to Chicago, including transfers.
Maine to Chicago bus services, operated by Concord Coach Lines, depart from Portland, ME station.
The best way to get from Maine to Chicago is to fly which takes 3h 11m and costs $100 - $550. Alternatively, you can bus via Brook Park, which costs $170 - $340 and takes 25h 48m.
Maine to Chicago bus services, operated by Concord Coach Lines, arrive at Boston, MA - South Station.
Chicago is 1h behind Maine. It is currently 9:05 AM in Maine and 8:05 AM in Chicago.
What companies run services between Maine, USA and Chicago, IL, USA?
Southwest Airlines flies from Portland (PWM) to Chicago Midway International Airport (MDW) twice daily. Alternatively, you can take a bus from Portland Public Library to Chicago Bus Station via Portland, ME, Boston, MA - South Station, Boston, and Cleveland Bus Station in around 25h 48m.
- Website
- aa.com
Flights from Portland to Chicago O'Hare International Airport
- Ave. Duration
- 3h 10m
- When
- Every day
- Estimated price
- $85–440
Flights from Bangor to Chicago O'Hare International Airport
- Ave. Duration
- 3h 21m
- When
- Every day
- Estimated price
- $120–650
Flights from Bangor to Chicago O'Hare International Airport via Reagan Washington
- Ave. Duration
- 5h 30m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $140–700
Flights from Bangor to Chicago O'Hare International Airport via Philadelphia
- Ave. Duration
- 5h 58m
- When
- Tuesday, Wednesday, Monday, Thursday, Friday, and Sunday
- Estimated price
- $140–700
Flights from Bangor to Chicago O'Hare International Airport via New York La Guardia
- Ave. Duration
- 6h 16m
- When
- Every day
- Estimated price
- $130–650
- Website
- united.com
Flights from Portland to Chicago O'Hare International Airport
- Ave. Duration
- 2h 59m
- When
- Every day
- Estimated price
- $85–440
Flights from Portland to Chicago O'Hare International Airport via Washington Dulles
- Ave. Duration
- 5h 22m
- When
- Every day
- Estimated price
- $100–480
Flights from Bangor to Chicago O'Hare International Airport
- Ave. Duration
- 3h 1m
- When
- Every day
- Estimated price
- $120–650
Flights from Bangor to Chicago O'Hare International Airport via Newark
- Ave. Duration
- 5h 58m
- When
- Every day
- Estimated price
- $130–650
- Website
- southwest.com
Flights from Portland to Chicago Midway International Airport
- Ave. Duration
- 2h 32m
- When
- Every day
- Estimated price
- $100–550
Flights from Portland to Chicago Midway International Airport via Baltimore
- Ave. Duration
- 5h
- When
- Monday, Thursday, Friday, and Sunday
- Estimated price
- $110–600
- Website
- delta.com
Flights from Portland to Chicago O'Hare International Airport via Detroit
- Ave. Duration
- 5h 17m
- When
- Every day
- Estimated price
- $85–440
Flights from Bangor to Chicago O'Hare International Airport via New York La Guardia
- Ave. Duration
- 6h 3m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- 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
- $300–650
- Website
- Amtrak
- Phone
- +1 800 639 3317
- [email protected]
- Website
- Concord Coach Lines
Bus from Portland, ME to Boston, MA - South Station
- Ave. Duration
- 1h 55m
- Frequency
- Hourly
- Estimated price
- $23–30
- Website
- Concord Coach Lines
Bus from Portland, ME to Boston, MA - South Station
- Ave. Duration
- 1h 55m
- Frequency
- Hourly
- Estimated price
- $23–30
- Website
- Concord Coach Lines
Rome2Rio's guide to Amtrak Thruway
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Bus from Portland, ME to Boston, MA - South Station
- Ave. Duration
- 1h 55m
- Frequency
- Hourly
- Estimated price
- $21–45
- Website
- Amtrak
- Adult
- $21–45
Bus from Portland, ME to Boston, MA - South Station
- Ave. Duration
- 1h 55m
- Frequency
- Hourly
- Estimated price
- $21–45
- Website
- Amtrak
- Adult
- $21–45
Rome2Rio's guide to Greyhound USA
Contact DetailsContact Details
- Phone
- +1 214-849-8100
- [email protected]
- Website
- Greyhound
Bus from Boston to Cleveland Bus Station
- Ave. Duration
- 13h 50m
- Frequency
- Once daily
- Estimated price
- $100–190
- Website
- Greyhound
Bus from Cleveland Bus Station to Chicago Bus Station
- Ave. Duration
- 7h 25m
- Frequency
- Twice daily
- Estimated price
- $50–100
- Website
- Greyhound
- Phone
- +1 (855) 626-8585
- Website
- Flixbus USA
Bus from City of Portland to New York Midtown
- Ave. Duration
- 7h 16m
- Frequency
- Once daily
- Estimated price
- $50–85
- Schedules at
- Flixbus USA
Bus from New York Midtown to Chicago Bus Station
- Ave. Duration
- 16h 55m
- Frequency
- Twice daily
- Estimated price
- $130–220
- Schedules at
- Flixbus USA
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More Questions & Answers
Yes, the driving distance between Maine to Chicago is 1042 miles. It takes approximately 19h 16m to drive from Maine to Chicago.
There are 1080+ hotels available in Chicago.








