There are 6 ways to get from Kennebunk to Chicago by plane, bus (Greyhound), train (Amtrak), 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 to Chicago Midway International Airport
best- Fly from Portland (PWM) to Chicago Midway International Airport (MDW)plane PWM - MDW
3h 40m$183–591Fly to Chicago O'Hare International Airport
cheapest- Fly from Portland (PWM) to Chicago O'Hare International Airport (ORD)plane PWM - ORD
4h 11m$168–511Bus via Brook Park (Greyhound)
- Take the bus from Wells Transportation Center to Bostonbus
- Take the bus from Boston to Cleveland Bus Stationbus
- Take the bus from Cleveland Bus Station to Chicago Bus Stationbus
25h 22m$186–351Train (Amtrak)
- Take the train from Wells to Bostontrain Downeaster
- Take the train from Boston to Chicago Union Stationtrain Lake Shore Limited
25h 30m$384–786Drive 1,013.4 mi
- Drive from Kennebunk to Chicagocar 1,013.4 mi
18h 50m$185–268Bus (Flixbus)
- Take the bus from Portsmouth Bus Stop to New York Midtownbus FlixBus N2615
- Take the bus from New York Midtown to Chicago Bus Stationbus FlixBus N2641 / ...
25h 57m$197–340
Portland (PWM) to Chicago Midway International Airport (MDW) flights
Questions & Answers
The cheapest way to get from Kennebunk to Chicago is to drive which costs $180 - $270 and takes 18h 50m.
The fastest way to get from Kennebunk to Chicago is to fly which takes 3h 40m and costs $180 - $600.
No, there is no direct bus from Kennebunk to Chicago station. However, there are services departing from Wells Transportation Center and arriving at Chicago Bus Station via Boston and Cleveland Bus Station. The journey, including transfers, takes approximately 25h 22m.
No, there is no direct train from Kennebunk to Chicago station. However, there are services departing from Wells and arriving at Chicago Union Station via North Station and Boston. The journey, including transfers, takes approximately 25h 30m.
The distance between Kennebunk and Chicago is 933 miles. The road distance is 1019.3 miles.
The best way to get from Kennebunk to Chicago without a car is to bus via Brook Park which takes 25h 22m and costs $180 - $360.
It takes approximately 3h 40m to get from Kennebunk to Chicago, including transfers.
Kennebunk to Chicago bus services, operated by Greyhound USA, depart from Wells Transportation Center station.
Kennebunk to Chicago train services, operated by Amtrak, depart from Wells station.
The best way to get from Kennebunk to Chicago is to fly which takes 3h 40m and costs $180 - $600. Alternatively, you can bus via Brook Park, which costs $180 - $360 and takes 25h 22m, you could also train, which costs $380 - $800 and takes 25h 30m.
What companies run services between Kennebunk, ME, USA and Chicago, IL, USA?
Southwest Airlines flies from Portland (PWM) to Chicago Midway International Airport (MDW) twice daily. Alternatively, you can take a vehicle from Kennebunk to Chicago Bus Station via Wells Transportation Center, Boston, and Cleveland Bus Station in around 25h 22m.
- Website
- united.com
Flights from Portland to Chicago O'Hare International Airport
- Ave. Duration
- 3h
- When
- Every day
- Estimated price
- $85–410
Flights from Portland to Chicago O'Hare International Airport via Washington Dulles
- Ave. Duration
- 5h 22m
- When
- Every day
- Estimated price
- $95–450
- Website
- southwest.com
Flights from Portland to Chicago Midway International Airport
- Ave. Duration
- 2h 32m
- When
- Every day
- Estimated price
- $100–490
Flights from Portland to Chicago Midway International Airport via Baltimore
- Ave. Duration
- 5h
- When
- Monday, Thursday, Friday, and Sunday
- Estimated price
- $110–550
- Website
- aa.com
Flights from Portland to Chicago O'Hare International Airport
- Ave. Duration
- 3h 10m
- When
- Every day
- Estimated price
- $85–410
- Website
- delta.com
Flights from Portland to Chicago O'Hare International Airport via Detroit
- Ave. Duration
- 4h 35m
- When
- Every day
- Estimated price
- $85–420
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Train from Wells to Boston
- Ave. Duration
- 1h 51m
- Frequency
- Every 4 hours
- Estimated price
- $27–55
- Website
- https://www.amtrak.com/home.html
Train from Boston to Chicago Union Station
- Ave. Duration
- 22h 15m
- Frequency
- Once daily
- Estimated price
- $330–700
- Website
- https://www.amtrak.com/home.html
Rome2Rio's guide to Greyhound USA
Contact DetailsContact Details
- Phone
- +1 214-849-8100
- [email protected]
- Website
- greyhound.com
Bus from Wells Transportation Center to Boston
- Ave. Duration
- 1h 55m
- Frequency
- Once daily
- Estimated price
- $12–23
- Website
- https://www.greyhound.com/
Bus from Boston to Cleveland Bus Station
- Ave. Duration
- 13h 50m
- Frequency
- Once daily
- Estimated price
- $100–200
- Website
- https://www.greyhound.com/
Bus from Cleveland Bus Station to Chicago Bus Station
- Ave. Duration
- 7h 25m
- Frequency
- Twice daily
- Estimated price
- $50–100
- Website
- https://www.greyhound.com/
- Phone
- +1 (855) 626-8585
- Website
- https://www.flixbus.com
Bus from Portsmouth Bus Stop to New York Midtown
- Ave. Duration
- 6h 20m
- Frequency
- Once daily
- Estimated price
- $40–75
- Schedules at
- flixbus.com
Bus from New York Midtown to Chicago Bus Station
- Ave. Duration
- 16h 55m
- Frequency
- Twice daily
- Estimated price
- $130–230
- Schedules at
- flixbus.com
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More Questions & Answers
Kennebunk to Chicago bus services, operated by Greyhound USA, arrive at Boston station.
Chicago is 1h behind Kennebunk. It is currently 12:38 AM in Kennebunk and 11:38 PM in Chicago.
Kennebunk to Chicago train services, operated by Amtrak, arrive at Boston station.
Yes, the driving distance between Kennebunk to Chicago is 1019 miles. It takes approximately 18h 50m to drive from Kennebunk to Chicago.
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Book your Kennebunk to Chicago bus tickets online with Omio.
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