There are 8 ways to get from Portland, ME 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 56m$105–533Fly Portland to Chicago O'Hare International Airport
cheapest- Fly from Portland (PWM) to Chicago O'Hare International Airport (ORD)plane PWM - ORD
4h 24m$84–424Bus 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 10m$171–298Bus, 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 17m$271–643Drive 1,034.7 mi
- Drive from Portland, ME to Chicagocar 1,034.7 mi
19h 13m$189–273Bus to Boston Logan Airport, fly to Chicago Midway International Airport
- Take the bus from Portland, ME to Logan International Airportbus
- Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane BOS - MDW
6h 18m$111–486Bus to Boston Logan Airport, fly to Chicago O'Hare International Airport
- Take the bus from Portland, ME to Logan International Airportbus
- Fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD)plane BOS - ORD
6h 35m$626–936Bus (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 N2640 / ...
28h 57m$190–294
Portland, ME to Chicago by bus
Comparing Your Travel Options
The cheapest way to get from Portland, ME to Chicago is to bus via Brook Park which costs $170 - $300 and takes 25h 10m.
The fastest way to get from Portland, ME to Chicago is to fly which takes 3h 56m and costs $100 - $550.
No, there is no direct bus from Portland, ME to Chicago station. However, there are services departing from Portland, ME and arriving at Chicago Bus Station via Boston and Cleveland Bus Station. The journey, including transfers, takes approximately 25h 10m.
The distance between Portland, ME and Chicago is 911 miles. The road distance is 1040.8 miles.
The best way to get from Portland, ME to Chicago without a car is to bus via Brook Park which takes 25h 10m and costs $170 - $300.
It takes approximately 3h 56m to get from Portland, ME to Chicago, including transfers.
Portland, ME to Chicago bus services, operated by Flixbus USA, depart from City of Portland station.
The best way to get from Portland, ME to Chicago is to fly which takes 3h 56m and costs $100 - $550. Alternatively, you can bus via Brook Park, which costs $170 - $300 and takes 25h 10m.
Portland, ME to Chicago bus services, operated by Flixbus USA, arrive at New York Midtown station.
Chicago is 1h behind Portland, ME. It is currently 6:34 AM in Portland, ME and 5:34 AM in Chicago.
What companies run services between Portland, ME, USA and Chicago, IL, USA?
Southwest Airlines flies from Portland (PWM) to Chicago Midway International Airport (MDW) 3 times a day. Alternatively, you can take a bus from Portland, ME to Chicago Bus Station via Boston, MA - South Station, Boston, and Cleveland Bus Station in around 25h 10m.
- Website
- united.com
Flights from Portland to Chicago O'Hare International Airport
- Ave. Duration
- 2h 59m
- When
- Every day
- Estimated price
- $80–420
Flights from Portland to Chicago O'Hare International Airport via Washington Dulles
- Ave. Duration
- 5h 17m
- When
- Every day
- Estimated price
- $90–460
Flights from Boston Logan Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 51m
- When
- Every day
- Estimated price
- $65–360
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
- $250–600
- 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
- $23–35
- Website
- Concord Coach Lines
Bus from Portland, ME to Boston, MA - South Station
- Ave. Duration
- 1h 55m
- Frequency
- Hourly
- Estimated price
- $23–35
- Website
- Concord Coach Lines
Bus from Portland, ME to Logan International Airport
- Ave. Duration
- 1h 55m
- Frequency
- Hourly
- Estimated price
- $23–35
- Website
- Concord Coach Lines
Bus from Portland, ME to Logan International Airport
- Ave. Duration
- 1h 55m
- Frequency
- Hourly
- Estimated price
- $23–35
- Website
- Concord Coach Lines
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Booking & Getting There
Yes, the driving distance between Portland, ME to Chicago is 1041 miles. It takes approximately 19h 13m to drive from Portland, ME to Chicago.
Book your Portland, ME to Chicago bus tickets online with Omio and FlixBus.
There are 1301+ hotels available in Chicago.