S$ 72 Cheap Flights from Chicago to Portland (CHI-PWM)

Cheap Flights from Chicago to Portland

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Cheap Flights from Chicago to Portland starting at S$ 72

Whether you’re going for a one-way or round-trip to Portland, we’ve got you covered! Check out these different flight options from Chicago below.

One way
Round-trip

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Cheapest time to fly from Chicago to Portland

Price trend charts are a great way of tracking how much your flights cost in the lead up to departure and can help you choose when to book your tickets. See how prices to Portland from Chicago have changed and are set to move below.

Displayed prices are calculated based on the lowest average weekly prices of the corresponding route on Trip.com.

Cheapest Airlines flying from Chicago to Portland

Which airline provides the cheapest flights from Chicago to Portland? Discover the option that best suits your travel needs before embarking on your journey.

Frontier Airlines

From S$ 72

American Airlines

From S$ 122

Delta Air Lines

From S$ 141

United Airlines

From S$ 185

Southwest Airlines

From S$ 250

Jetblue Airways

From S$ 299

Spirit Airlines

From S$ 975

Find more flights and airlines

Alternative Routes from Chicago to Portland

Searching for potential routes that might be cheaper and faster? There are a few alternative ways to get to Portland from Chicago which could help you save money and time.

Cheapest
ORD
10:59
8h 13m
1 transfer
PWM
20:12
O'Hare International Airport - Portland International Jetport
Mon, Feb 3Frontier Airlines
S$ 72
MDW
11:33
7h 39m
1 transfer
PWM
20:12
Midway International Airport - Portland International Jetport
Mon, Jan 27Frontier Airlines
S$ 74
MDW
11:33
7h 39m
1 transfer
PWM
20:12
Midway International Airport - Portland International Jetport
Mon, Jan 27Frontier Airlines
S$ 74
Find More Flights

Frequently Asked Questions

When to buy flight tickets from Chicago (CHI) to Portland (PWM) the cheapest?
Airlines adjust prices for flights from Chicago to Portland based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the cheapest flight prices on Tuesdays, Wednesdays, and Saturdays.
How much is a flight from Chicago (CHI) to Portland (PWM) cost?
According to Trip.com's data, the lowest price is around S$ 439.
How long is a flight from Chicago (CHI) to Portland (PWM)?
It takes about 2 hours 27 minutes to fly from Chicago (CHI) to Portland (PWM).
What are the most popular airlines that fly from Chicago (CHI) to Portland (PWM)?
Airlines with flights from Chicago (CHI) to Portland (PWM): Emirates, Air New Zealand and United Airlines.
What's the most popular airline for direct flights from Chicago (CHI) to Portland (PWM)?
United Airlines operates 5 direct flights from Chicago (CHI) to Portland (PWM).
How many airports in Portland?
There are 1 airports near Portland: Portland International Jetport.

How to find a cheap flight from Chicago to Portland

Understanding the common pitfalls when booking your flight tickets can help you save massively when it comes time to fly. We’ve listed our six essential steps to keep in mind when you’re booking flight tickets to help you find the best price.

Book Early

Once prices are gone, they're gone. Lock in deals while you can!

Compare Flight Prices

Compare prices on travel agency and airline websites.

Look Out for Deals

Check airline and travel agency websites for latest flight deals

Check One-way Fares

Buying two cheap one-way flights can sometimes be a better deal than a round-trip.

Try Different Dates

Flying during the week, early in the morning, or late at night can help save money.

Use the Trip.com App

Save up to £10 per person when booking your flights on Trip.com

Find cheapest flight ticket from Chicago to Portland

Cheapest direct flight price	S$ 71
Cheapest return ticket price	S$ 357
Off-season for travel	January
Peak season for travel	March
Flight distance	1,425.81km
Average flight time	2 hours 27 minutes
Popular airline	American Airlines