Like any major city, it has safe and unsafe areas; stick to tourist zones.

How do I get to downtown?

The CTA Blue Line from O'Hare or Orange Line from Midway.

Is the train worth it?

Only if you enjoy long-distance rail travel and scenic views.

What is the best airport?

O'Hare (ORD) has more flight options, but Midway (MDW) is closer to downtown.

No, Chicago has excellent public transportation.

Kennebunk

Chicago

Train Flight

Kennebunk to Chicago

Updated: 28 May 2026

The distance between Kennebunk and Chicago makes flying the most practical choice for most travelers. You can fly from Portland (PWM) to O'Hare (ORD) with a single connection, usually in under 6 hours. Alternatively, the train journey involves taking the Downeaster to Boston and transferring to the Lake Shore Limited, which takes over 24 hours. Chicago is a major transit hub, making it easy to reach once you land at O'Hare or Midway. Plan for significant travel time if choosing the rail option.

Total Distance: 1,750 km driving distance; 1,550 km straight-line air distance.

Fastest Way

Flying from Portland (PWM) to Chicago (ORD) is the fastest method.

Cheapest Way

Flights are often cheaper than sleeper-car train tickets if booked in advance.

Compare Kennebunk to Chicago Routes

	Train Connecting	Flight Connecting
Duration	26 hours	5 hours 30 mins
Avg Price	$200-$450	$250-$500
Operator	Amtrak	United Airlines
Route	Downeaster to Boston, then Lake Shore Limited to Union Station.	PWM to ORD via Newark or Washington.
Tip	Book a sleeper car if you prefer comfort on this long-haul journey.	Take the Blue Line train from O'Hare directly to downtown Chicago.

Travel Tips

Airport Transit
The CTA Blue Line is the most affordable way to get from O'Hare to downtown.
Weather
Chicago is known as the 'Windy City'; pack layers regardless of the season.
Dining
Try the deep-dish pizza at local institutions like Lou Malnati's.
Museum Passes
Consider a CityPASS if you plan to visit multiple major attractions.
Walking
Chicago's downtown is very grid-based and easy to navigate on foot.

Safety Tips

General Safety
Stay in well-populated areas, especially at night.
Public Transit
Keep your phone and wallet secure while riding the 'L' train.
Emergency
Dial 911 for emergencies; Chicago has a robust emergency response system.
Awareness
Be mindful of your surroundings in busy tourist hubs like Navy Pier.