There are 9 ways to get from Chicago Station (CTA Logan Square branch) to Kennebunkport by plane, train, bus, bus (Flixbus, Greyhound), 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 Chicago O'Hare International Airport to Boston Logan Airport, train
best- Fly from Chicago O'Hare International Airport (ORD) to Boston Logan Airport (BOS)ORD - BOS
- Take the train from Woburn Amtrak Station to Wells
8h 26m$132–358Fly Chicago O'Hare International Airport to Portland, train
cheapest- Fly from Chicago O'Hare International Airport (ORD) to Portland (PWM)ORD - PWM
- Take the train from Portland to Wells
8h 22m$110–528Train, bus
- Take the train from Chicago Union Station to BostonLake Shore Limited
- Take the bus from Boston to Wells Transportation CenterGreyhound US0265s
27h 25m$152–630Bus
- Take the bus from Chicago Bus Station to New York Midtown
- Take the bus from New York Midtown to Boston
- Take the bus from Boston to Wells Transportation Center
30h 42m$152–315Drive 1,018.3 mi
- Drive from Chicago Station (CTA Logan Square branch) to Kennebunkport1,018.3 mi
18h 46m$186–269Fly Chicago Midway International Airport to Boston Logan Airport, train
- Fly from Chicago Midway International Airport (MDW) to Boston Logan Airport (BOS)MDW - BOS
- Take the train from Woburn Amtrak Station to Wells
8h 31m$131–595Fly Chicago Midway International Airport to Portland, train
- Fly from Chicago Midway International Airport (MDW) to Portland (PWM)MDW - PWM
- Take the train from Portland to Wells
8h 23m$135–675Fly Chicago Midway International Airport to Manchester Airport, bus, train
- Fly from Chicago Midway International Airport (MDW) to Manchester Airport (MHT)MDW - MHT
- Take the bus from Boston Manchester Airport to Boston
- Take the train from Boston to Wells
10h 34m$143–679Fly Chicago O'Hare International Airport to Manchester Airport, bus, train
- Fly from Chicago O'Hare International Airport (ORD) to Manchester Airport (MHT)ORD - MHT
- Take the bus from Boston Manchester Airport to Boston
- Take the train from Boston to Wells
10h 42m$124–522
Chicago O'Hare International Airport (ORD) to Boston Logan Airport (BOS) flights
Questions & Answers
The cheapest way to get from Chicago Station (CTA Logan Square branch) to Kennebunkport is to drive which costs $180 - $270 and takes 18h 46m.
The fastest way to get from Chicago Station (CTA Logan Square branch) to Kennebunkport is to fly and train which takes 8h 22m and costs $110 - $550.
No, there is no direct bus from Chicago Station (CTA Logan Square branch) to Kennebunkport. However, there are services departing from Milwaukee & Thomas and arriving at Lower Village/Old Vines Wine Bar via Madison & Canal, Chicago Bus Station, New York Midtown, Boston and Wells Regional Transportation Center. The journey, including transfers, takes approximately 30h 42m.
The distance between Chicago Station (CTA Logan Square branch) and Kennebunkport is 981 miles. The road distance is 1024.2 miles.
The best way to get from Chicago Station (CTA Logan Square branch) to Kennebunkport without a car is to train and bus which takes 27h 25m and costs $150 - $650.
It takes approximately 8h 26m to get from Chicago Station (CTA Logan Square branch) to Kennebunkport, including transfers.
Chicago Station (CTA Logan Square branch) to Kennebunkport bus services, operated by Flixbus USA, depart from Chicago Bus Station.
Chicago Station (CTA Logan Square branch) to Kennebunkport bus services, operated by Flixbus USA, arrive at New York Midtown station.
Yes, the driving distance between Chicago Station (CTA Logan Square branch) to Kennebunkport is 1024 miles. It takes approximately 18h 46m to drive from Chicago Station (CTA Logan Square branch) to Kennebunkport.
There are 405+ hotels available in Kennebunkport.
What companies run services between Chicago Station (CTA Logan Square branch), IL, USA and Kennebunkport, ME, USA?
You can take a vehicle from Chicago Station (CTA Logan Square branch) to Lower Village/Old Vines Wine Bar via Milwaukee & Thomas, Washington & Canal, Madison & Canal, Harrison & Jefferson, Chicago Bus Station, New York Midtown, Boston, and Wells Regional Transportation Center in around 30h 42m.
Transport is disrupted due to the Russia-Ukraine war. Read more
- Website
- aa.com
Flights from Chicago O'Hare International Airport to Boston Logan Airport
- Ave. Duration
- 2h 26m
- When
- Every day
- Estimated price
- $75–410
Flights from Chicago O'Hare International Airport to Boston Logan Airport via Buffalo
- Ave. Duration
- 4h 45m
- When
- Every day
- Estimated price
- $75–410
Flights from Chicago O'Hare International Airport to Portland
- Ave. Duration
- 2h 25m
- When
- Every day
- Estimated price
- $95–500
Flights from Chicago O'Hare International Airport to Portland via Philadelphia
- Ave. Duration
- 4h 54m
- When
- Every day
- Estimated price
- $100–550
Flights from Chicago O'Hare International Airport to Portland via Reagan Washington
- Ave. Duration
- 4h 48m
- When
- Every day
- Estimated price
- $110–550
Flights from Chicago O'Hare International Airport to Manchester Airport
- Ave. Duration
- 2h 18m
- When
- Every day
- Estimated price
- $80–440
Flights from Chicago O'Hare International Airport to Manchester Airport via Reagan Washington
- Ave. Duration
- 5h 2m
- When
- Every day
- Estimated price
- $95–480
Flights from Chicago O'Hare International Airport to Manchester Airport via Philadelphia
- Ave. Duration
- 5h 10m
- When
- Every day
- Estimated price
- $90–470
- Website
- southwest.com
Flights from Chicago Midway International Airport to Boston Logan Airport
- Ave. Duration
- 2h 15m
- When
- Every day
- Estimated price
- $95–550
Flights from Chicago Midway International Airport to Portland
- Ave. Duration
- 2h 15m
- When
- Monday, Thursday, and Friday
- Estimated price
- $120–650
Flights from Chicago Midway International Airport to Portland via Baltimore
- Ave. Duration
- 4h 41m
- When
- Every day
- Estimated price
- $130–700
Flights from Chicago Midway International Airport to Manchester Airport
- Ave. Duration
- 2h 5m
- When
- Every day
- Estimated price
- $100–600
Flights from Chicago Midway International Airport to Manchester Airport via Baltimore
- Ave. Duration
- 4h 40m
- When
- Monday, Tuesday, Wednesday, Thursday, and Saturday
- Estimated price
- $110–600
- Website
- united.com
Flights from Chicago O'Hare International Airport to Boston Logan Airport
- Ave. Duration
- 2h 20m
- When
- Every day
- Estimated price
- $75–410
Flights from Chicago O'Hare International Airport to Portland
- Ave. Duration
- 2h 27m
- When
- Every day
- Estimated price
- $95–500
- Website
- delta.com
Flights from Chicago O'Hare International Airport to Boston Logan Airport
- Ave. Duration
- 2h 26m
- When
- Every day
- Estimated price
- $75–410
Flights from Chicago O'Hare International Airport to Portland via Detroit
- Ave. Duration
- 4h 22m
- When
- Every day
- Estimated price
- $95–500
Flights from Chicago O'Hare International Airport to Portland via New York La Guardia
- Ave. Duration
- 5h 5m
- When
- Every day
- Estimated price
- $100–550
Flights from Chicago Midway International Airport to Boston Logan Airport via Detroit
- Ave. Duration
- 5h 23m
- When
- Every day
- Estimated price
- $95–550
- Website
- jetblue.com
Flights from Chicago O'Hare International Airport to Boston Logan Airport
- Ave. Duration
- 2h 28m
- When
- Every day
- Estimated price
- $75–410
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Train from Woburn Amtrak Station to Wells
- Ave. Duration
- 1h 30m
- Frequency
- Every 4 hours
- Estimated price
- $23–29
- Website
- https://www.amtrak.com/home.html
Train from Chicago Union Station to Boston
- Ave. Duration
- 22h 2m
- Frequency
- Once daily
- Estimated price
- $130–600
- Website
- https://www.amtrak.com/home.html
Train from Portland to Wells
- Ave. Duration
- 41 min
- Frequency
- Every 4 hours
- Estimated price
- $7–10
- Website
- https://www.amtrak.com/home.html
Train from Boston to Wells
- Ave. Duration
- 1h 48m
- Frequency
- Every 4 hours
- Estimated price
- $23–29
- Website
- https://www.amtrak.com/home.html
Rome2Rio's guide to Greyhound USA
Contact Details
- Phone
- +1 214-849-8100
- ifsr@greyhound.com
- Website
- greyhound.com
Bus from Boston to Wells Transportation Center
- Ave. Duration
- 1h 40m
- Frequency
- Once daily
- Estimated price
- $17–25
- Website
- https://www.greyhound.com/
Bus from Boston Manchester Airport to Boston
- Ave. Duration
- 1h 30m
- Frequency
- Twice daily
- Estimated price
- $13–40
- Website
- https://www.greyhound.com/
- Phone
- +1 (855) 626-8585
- Website
- flixbus.com
Bus from Chicago Bus Station to New York Midtown
- Ave. Duration
- 20h 10m
- Frequency
- Once daily
- Estimated price
- $100–220
- Schedules at
- flixbus.com
Bus from New York Midtown to Boston
- Ave. Duration
- 4h 20m
- Frequency
- Every 3 hours
- Estimated price
- $30–65
- Schedules at
- flixbus.com
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