There are 5 ways to get from Portland Airport (PWM) to Chicago by plane, bus, train, bus (Flixbus), or car
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Fly to Chicago Midway International Airport
best- Fly from Portland (PWM) to Chicago Midway International Airport (MDW)plane PWM - MDW
3h 16m$104–525Fly to Chicago O'Hare International Airport
cheapest- Fly from Portland (PWM) to Chicago O'Hare International Airport (ORD)plane PWM - ORD
3h 44m$84–420Bus, 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
26h 25m$295–803Bus (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 / ...
30h 2m$202–314Drive 1,034.1 mi
- Drive from Portland Airport (PWM) to Chicagocar 1,034.1 mi
19h 14m$189–273
Portland Airport (PWM) to Chicago by bus and train
Comparing Your Travel Options
The cheapest way to get from Portland Airport (PWM) to Chicago is to drive which costs $180 - $280 and takes 19h 14m.
The fastest way to get from Portland Airport (PWM) to Chicago is to fly which takes 3h 16m and costs $100 - $550.
No, there is no direct bus from Portland Airport (PWM) to Chicago station. However, there are services departing from Portland Jetport and arriving at Chicago Bus Station via City of Portland and New York Midtown. The journey, including transfers, takes approximately 30h 2m.
The distance between Portland Airport (PWM) and Chicago is 909 miles. The road distance is 1040.2 miles.
The best way to get from Portland Airport (PWM) to Chicago without a car is to bus and train which takes 26h 25m and costs $290 - $850.
It takes approximately 3h 16m to get from Portland Airport (PWM) to Chicago, including transfers.
Portland Airport (PWM) to Chicago bus services, operated by Flixbus USA, depart from City of Portland station.
The best way to get from Portland Airport (PWM) to Chicago is to fly which takes 3h 16m and costs $100 - $550. Alternatively, you can bus, which costs $200 - $320 and takes 30h 2m.
Portland Airport (PWM) to Chicago bus services, operated by Flixbus USA, arrive at New York Midtown station.
Chicago is 1h behind Portland Airport (PWM). It is currently 12:58 PM in Portland Airport (PWM) and 11:58 AM in Chicago.
What companies run services between Portland Airport (PWM), 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 Jetport to Chicago Bus Station via City of Portland and New York Midtown in around 30h 2m.
- Website
- southwest.com
Flights from Portland to Chicago Midway International Airport
- Ave. Duration
- 2h 35m
- When
- Every day
- Estimated price
- $100–550
Flights from Portland to Chicago Midway International Airport via Baltimore
- Ave. Duration
- 5h 38m
- 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 26m
- When
- Every day
- Estimated price
- $80–420
Flights from Portland to Chicago O'Hare International Airport via New York La Guardia
- Ave. Duration
- 5h 46m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $85–440
- Website
- aa.com
Flights from Portland to Chicago O'Hare International Airport
- Ave. Duration
- 3h 5m
- When
- Every day
- Estimated price
- $80–420
Flights from Portland to Chicago O'Hare International Airport via New York La Guardia
- Ave. Duration
- 6h 8m
- When
- Every day
- Estimated price
- $85–440
- Website
- united.com
Flights from Portland to Chicago O'Hare International Airport
- Ave. Duration
- 2h 59m
- When
- Every day
- Estimated price
- $80–420
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
- $270–750
- 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
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
- Phone
- +1 (855) 626-8585
- Website
- Flixbus USA
Bus from City of Portland to New York Midtown
- Ave. Duration
- 7h 16m
- Frequency
- 6 times a week
- Estimated price
- $50–80
- Schedules at
- Flixbus USA
Bus from New York Midtown to Chicago Bus Station
- Ave. Duration
- 20h 25m
- Frequency
- Twice daily
- Estimated price
- $150–230
- Schedules at
- Flixbus USA
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Booking & Getting There
Yes, the driving distance between Portland Airport (PWM) to Chicago is 1040 miles. It takes approximately 19h 14m to drive from Portland Airport (PWM) to Chicago.
There are 1303+ hotels available in Chicago.