Is there a direct train from Oregon to Connecticut?

No, you must transfer in Chicago at Union Station.

How far is Hartford from the airport?

Bradley International Airport is approximately 20 minutes from downtown Hartford.

What is the best way to get around Hartford?

Hartford is walkable, but a rental car is recommended for exploring the surrounding Connecticut countryside.

Are there direct flights from PDX to BDL?

No, all flights require at least one connection, usually in a hub like Chicago or Newark.

What is the cheapest month to fly?

February and November typically offer the lowest airfares for this route.

Milwaukie

Hartford

Train Flight

Milwaukie to Hartford

Updated: 31 May 2026

Traveling from Milwaukie to Hartford covers approximately 4,800 kilometers across the United States. The most efficient route involves driving 15 minutes to Portland International Airport (PDX) for a flight to Bradley International Airport (BDL). Alternatively, you can take the Amtrak Empire Builder from Portland Union Station to Chicago, then transfer to the Lake Shore Limited to Hartford. This journey traverses diverse landscapes, from the Pacific Northwest forests to the industrial corridors of the Northeast. Expect a total travel time of at least 8 hours by air or 72 hours by rail. Planning your connection in Chicago is essential for a smooth cross-country rail experience.

Total Distance: Driving distance 4,850 km, straight-line air distance 4,100 km.

Fastest Way

Flight from PDX to BDL with a single layover.

Cheapest Way

Flight booked during off-peak mid-week hours.

Compare Milwaukie to Hartford Routes

	Train Connecting	Flight Connecting
Duration	72 hours	8 hours 30 mins
Avg Price	$500 - $1200	$400 - $800
Operator	Amtrak	Alaska Airlines
Route	Empire Builder to Chicago, then Lake Shore Limited to Hartford.	PDX to BDL via ORD or EWR.
Tip	Upgrade to a Roomette for a bed and included meals on the long-haul segments.	Book your flight at least 21 days in advance to secure lower fares.

Travel Tips

Airport Transit
Use the MAX Light Rail Red Line to reach PDX from the Portland area efficiently.
Rail Booking
Always book Amtrak tickets through the official website to manage your reservation easily.
Time Zones
Prepare for a three-hour time difference when traveling from Pacific to Eastern Time.
Luggage
Check airline baggage policies carefully, as fees for checked bags can add up quickly.
Connectivity
Download offline maps for Hartford, as cellular service can be spotty in rural transit corridors.

Safety Tips

Public Transit
Stay aware of your surroundings when using public transportation in major transit hubs.
Weather Awareness
Check local forecasts for Hartford, as New England weather can change rapidly.
Valuables
Keep your passport and travel documents in a secure, zipped pocket at all times.
Emergency
Save the local non-emergency police number for Hartford in your phone contacts.