Flights from Chicago to Portland from $288

Compare All CHI to PWM Flights

Prices are per person for one-way travel. Click “Book” to complete your reservation on the partner site.

1 of 1 flight

Airline	Schedule	Stops	Duration	Price
AA AA · 4504	19:10 CHI 00:46 PWM	0 stop(s)	5h 36m	$288 Best	Book →

Airport Information

Key details about departure and arrival airports for this route

PWM

Portland International Jetport

City: Portland
Country: US
Type: Large Airport
Elevation: 76 ft

PWM Airport Guide →

Tips for Chicago to Portland Flights

Save money and travel smarter with these route-specific tips

📅 When to Book

Book CHI–PWM flights 6–8 weeks in advance for the best prices. Last-minute fares are typically 40–60% more expensive on this route.

💰 Price Trends

The average fare is $288, but prices as low as $288 are available.

✈ Direct vs Connecting

No direct flights currently listed. Consider flexible dates or nearby airports for better connections.

📍 Flexible Dates

Flying midweek (Tuesday–Thursday) on CHI–PWM is typically 15–30% cheaper. Use our price comparison to spot the best day to fly.

Top Hotels in Portland

Book accommodation at your destination — top-rated stays near PWM airport

Annesley House

Portland, 4.5★

10.0 $180/night

NRMA Portland Bay Holiday Park

Portland, 3★

9.8 Check Price

Lorelei Bed & Breakfast

Portland, 4★

9.5 $103/night

Seascape Accommodation

Portland, 4★

9.5 Check Price

Cape Nelson Lighthouse

Portland, 5★

9.2 $180/night

Victoria Lodge Motor Inn & Apartments

Portland, 4★

9.1 $88/night

Frequently Asked Questions

Everything you need to know about flying CHI to PWM

What is the cheapest flight from Chicago to Portland?

The cheapest flight from Chicago (CHI) to Portland (PWM) currently starts at $288 with AA. Prices are updated regularly and may vary by date and availability.

How many airlines fly from CHI to PWM?

We found 1 airline(s) operating on the CHI–PWM route, including AA.

Are there direct flights from Chicago to Portland?

No direct flights are currently listed on this route. All available options involve at least one stop. Consider flexible dates or nearby airports for better connection options.

What is the average flight price on this route?

The average flight price from Chicago to Portland is approximately $288. Prices range from $288 to $288 depending on airline, time, and class.

How long is the flight from CHI to PWM?

The average flight duration from Chicago to Portland is approximately 5 hours 36 minutes. Direct flights are typically shorter than connecting options.

What is the baggage allowance on CHI–PWM flights?

Baggage allowance varies by airline and fare class. Most economy fares on this route include 1 carry-on (7–8 kg) and 1 checked bag (20–23 kg). Always confirm baggage rules on the airline's site at booking — low-cost carriers may charge for checked bags.