Flights from Chicago to Portland
CHI
Chicago
5h 36m avg
PWM
Portland
Flights from
$288
Compare 1 options across 1 airline
Updated 3 months ago
$288
Cheapest Flight
$288
Average Price
0
Direct Flights
1
Airlines
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 → |
No flights match the current filters. Try clearing them.
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 →
Country: US
Type: Large Airport
Elevation: 76 ft
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
Lorelei Bed & Breakfast
Portland, 4★
9.5
$103/night
Cape Nelson Lighthouse
Portland, 5★
9.2
$180/night
Victoria Lodge Motor Inn & Apartments
Portland, 4★
9.1
$88/night
Portland Retro Motel
Portland, 3★
9.0
$66/night
Mariner Motel
Portland, 3★
9.0
$99/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.
From
$288
Book Cheapest →
Other Flights from Chicago
Explore more destinations departing from CHI