What is the cheapest way to get from Chicago to Kennebunkport?

The cheapest way to get from Chicago to Kennebunkport is to drive which costs $180 - $270 and takes 18h 55m.

What is the fastest way to get from Chicago to Kennebunkport?

The fastest way to get from Chicago to Kennebunkport is to fly and taxi which takes 4h 25m and costs $200 - $750.

Is there a direct bus between Chicago and Kennebunkport?

No, there is no direct bus from Chicago station to Kennebunkport. However, there are services departing from Chicago Bus Station and arriving at Wells Transportation Center via Cleveland Bus Station and Boston. The journey, including transfers, takes approximately 25h.

Is there a direct train between Chicago and Kennebunkport?

No, there is no direct train from Chicago station to Kennebunkport. However, there are services departing from Chicago Union Station and arriving at Wells via Back Bay and Boston. The journey, including transfers, takes approximately 25h 8m.

How far is it from Chicago to Kennebunkport?

The distance between Chicago and Kennebunkport is 935 miles. The road distance is 1020.7 miles.

How do I travel from Chicago to Kennebunkport without a car?

The best way to get from Chicago to Kennebunkport without a car is to bus via Brook Park which takes 25h and costs $190 - $370.

How long does it take to get from Chicago to Kennebunkport?

It takes approximately 4h 25m to get from Chicago to Kennebunkport, including transfers.

Where do I catch the Chicago to Kennebunkport bus from?

Chicago to Kennebunkport bus services, operated by Greyhound USA, depart from Chicago Bus Station.

Where do I catch the Chicago to Kennebunkport train from?

Chicago to Kennebunkport train services, operated by Amtrak, depart from Chicago Union Station.

Train or bus from Chicago to Kennebunkport?

The best way to get from Chicago to Kennebunkport is to bus via Brook Park which takes 25h and costs $190 - $370. Alternatively, you can train, which costs $390 - $800 and takes 25h 8m.

Where does the Chicago to Kennebunkport bus arrive?

Chicago to Kennebunkport bus services, operated by Greyhound USA, arrive at Cleveland Bus Station.

What is the time difference between Chicago and Kennebunkport?

Kennebunkport is 1h ahead of Chicago. It is currently 5:05 AM in Chicago and 6:05 AM in Kennebunkport.

Where does the Chicago to Kennebunkport train arrive?

Chicago to Kennebunkport train services, operated by Amtrak, arrive at Boston station.

Can I drive from Chicago to Kennebunkport?

Yes, the driving distance between Chicago to Kennebunkport is 1021 miles. It takes approximately 18h 55m to drive from Chicago to Kennebunkport.

Where can I stay near Kennebunkport?

There are 477+ hotels available in Kennebunkport.

Chicago to Kennebunkport - 8 ways to travel via train, plane, taxi, bus

How to get fromChicago to Kennebunkport

Travel from

See all options

Search accommodation with Expedia

There are 8 ways to get from Chicago to Kennebunkport by plane, taxi, bus (Greyhound), train (Amtrak), car, train, 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 Chicago Midway International Airport to Portland, taxi
best
1. Fly from Chicago Midway International Airport (MDW) to Portland (PWM)plane MDW - PWM
2. Take the taxi from Portland-Airport-PWM to Kennebunkporttaxi
4h 25m
$208–715
Fly Chicago Midway International Airport to Boston Logan Airport, train
cheapest
1. Fly from Chicago Midway International Airport (MDW) to Boston Logan Airport (BOS)plane MDW - BOS
2. Take the train from Woburn Amtrak Station to Wellstrain
7h 29m
$164–589
Bus via Brook Park (Greyhound)
1. Take the bus from Chicago Bus Station to Cleveland Bus Stationbus
2. Take the bus from Cleveland Bus Station to Bostonbus
3. Take the bus from Boston to Wells Transportation Centerbus
25h
$197–362
Train (Amtrak)
1. Take the train from Chicago Union Station to Bostontrain Lake Shore Limited
2. Take the train from Boston to Wellstrain Downeaster
25h 8m
$392–764
Drive 1,014.8 mi
1. Drive from Chicago to Kennebunkportcar 1,014.8 mi
18h 55m
$186–268
Fly Chicago O'Hare International Airport to Portland, taxi
1. Fly from Chicago O'Hare International Airport (ORD) to Portland (PWM)plane ORD - PWM
2. Take the taxi from Portland-Airport-PWM to Kennebunkporttaxi
4h 50m
$182–585
Fly Chicago O'Hare International Airport to Boston Logan Airport, train
1. Fly from Chicago O'Hare International Airport (ORD) to Boston Logan Airport (BOS)plane ORD - BOS
2. Take the train from Woburn Amtrak Station to Wellstrain
7h 46m
$664–999
Bus (Flixbus)
1. Take the bus from Chicago Bus Station to New York Midtownbus FlixBus N2641 / ...
2. Take the bus from New York Midtown to Portsmouth Bus Stopbus FlixBus N2615
25h 56m
$219–348

Chicago Midway International Airport (MDW) to Portland (PWM) flights

19Weekly Planes

3h 56mAverage Duration

$127Cheapest Price

See schedules

Questions & Answers

Map of how to get from Chicago to Kennebunkport.

Launch map view

Distance: 929.6 mi
Duration: 4h 25m

What companies run services between Chicago, IL, USA and Kennebunkport, ME, USA?

You can take a bus from Chicago Bus Station to Kennebunkport via Cleveland Bus Station, Boston, and Wells Transportation Center in around 25h. Alternatively, you can take a train from Chicago Union Station to Kennebunkport via Boston, Back Bay, North Station, Boston, and Wells in around 25h 8m.

Airlines

Train operators

Bus operators

Other operators

Want to know more about travelling around United States

Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.