Is there a direct train from Portland to Chicago?

No, you must transfer in Boston to the Lake Shore Limited line.

How long is the flight from PWM to ORD?

The flight is approximately 2 hours and 30 minutes, plus airport transit.

What is the best way to get around Chicago?

The 'L' train system and the extensive bus network are the best ways to navigate the city.

Are there direct flights from Portland to Chicago?

Yes, United Airlines typically offers direct flights from PWM to ORD.

What should I pack for Chicago?

Pack comfortable walking shoes and weather-appropriate clothing for the season.

Portland

Chicago

Train Flight

Portland to Chicago

Updated: 30 May 2026

The trip from Portland to Chicago spans over 1,000 miles. The most practical way to travel is by air, with direct or connecting flights from Portland International Jetport (PWM) to O'Hare International Airport (ORD). Alternatively, you can take the Amtrak Downeaster to Boston and transfer to the Lake Shore Limited train, which travels directly to Chicago Union Station. While the train journey is long, it offers a scenic cross-country experience through the Northeast and Midwest. Flying is significantly faster, taking approximately 4 hours of flight time.

Total Distance: 1,750 km driving distance; 1,600 km straight-line air distance.

Fastest Way

Direct flight from PWM to ORD, taking about 4 hours total.

Cheapest Way

Amtrak, if booked well in advance, can be cheaper than last-minute airfare.

Compare Portland to Chicago Routes

	Train Connecting	Flight Direct
Duration	26 hours	4 hours
Avg Price	$200 - $400	$250 - $500
Operator	Amtrak	United Airlines
Route	Downeaster to Boston, transfer to Lake Shore Limited to Chicago Union Station.	PWM to ORD
Tip	Book a sleeper car if you prefer comfort for the overnight portion of the trip.	Take the Blue Line 'L' train from O'Hare directly into downtown Chicago.

Travel Tips

O'Hare Transit
The Blue Line train is the most cost-effective way to reach downtown from O'Hare.
Union Station
Chicago Union Station is centrally located; use the nearby bus lines to reach your hotel.
Weather
Chicago weather changes quickly; pack layers regardless of the season.
Dining
Try deep-dish pizza at a local institution like Lou Malnati's or Giordano's.
Booking
Book your flight at least 21 days in advance to secure the best rates.

Safety Tips

City Awareness
Stay in well-populated tourist areas, especially at night.
Public Transit
Keep your belongings secure while riding the 'L' train or buses.
Emergency
Dial 911 for any emergency; Chicago has a robust emergency response system.
Walking
Avoid walking alone in unfamiliar or isolated areas after dark.