$44 Cheap flight deals from Chicago (CHI) to Portland (PWM)

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This Weekend's Flight Deals from Chicago to Portland

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Airfares from $44 One Way, $88 Round Trip from Chicago to Portland

Prices starting at $88 for return flights and $44 for one-way flights to Portland were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Portland economy flight packages

Prices and availability subject to change. Additional terms may apply.
Portland Harbor Hotel
Portland Regency Hotel & Spa
Inn at Diamond Cove
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More About Flying To Portland from Chicago

Route Information for Flights from Chicago to Portland

Origin Airport IATA Code
CHI
Destination Airport IATA Code
PWM
Distance
897 mi
Direct Flight Airlines
Air New Zealand, United Airlines
Earliest Flight Arrival
6:51PM UTC
Latest Flight Arrival
1:43AM UTC

Flights from Chicago to Portland

Airports in Chicago

The city of Chicago is primarily served by two international airports. Travelers looking for low-fare flights from Chicago can use Orbitz.com to find flights from both O'Hare and Midway. O'Hare International Airport is located approximately 17 miles northwest of downtown Chicago. Midway International Airport is located on the city's southwest side, approximately eight miles from Chicago's Loop. O'Hare serves as a hub for American Airlines and United Airlines, and Midway is a hub for Southwest Airlines.

Chicago Airport Parking

Daily, hourly, and valet parking are available at O'Hare. Rates vary from $2.00 to $10.00 per hour. An economy parking lot is also available at a rate of $2.00 per hour. Similar parking options and rates apply at Midway.

Chicago Airport Transportation

There are numerous transportation options for getting to and from both O'Hare and Midway. O'Hare can be accessed via regional trains, buses, and local mass transit lines. The CTA Blue Line offers a fast and convenient transportation option to and from this airport. Midway is served by the CTA Orange Line. Car rental services are available at both airports, and travelers can quickly book car rental services at either airport using Orbitz.com.

Chicago Airport Restaurants

Both O'Hare and Midway offer a variety of restaurant options for travelers. Restaurants located in both airports include Starbuck's Coffee, Chicago Style Hot Dogs, McDonald's, Auntie Anne's, Chili's, Cinnabon, and Dunkin Donuts, making it easy for visitors to grab a quick breakfast, snack, or meal. By using Orbitz.com, travelers can quickly and easily find low-fare flights from Chicago.

Vacation in Portland

Whether you are on a business trip or taking a vacation to "The City of Roses," Orbitz.com can help you find cheap flights to Portland by comparing most of the airlines that provide service to the airport. For those on a budget, this is a great way to compare and save money when traveling by air.

Portland Airport

The Portland International Airport provides air service to the Portland area. Airlines providing service to Portland include Southwest, Delta, Alaska, American, Jet Blue, Frontier, Hawaiian, Air Canada, Sea Port, United, Spirit, US Airways, and Virgin America. The airport is located about nine miles from downtown Portland.

Transportation From the Airport

Transportation from the airport is provided by taxis, shuttle buses, hotel vans, and car rentals. Most of these services can be prearranged at Orbitz.com when you're booking your flight. The cost of a taxi from the airport to downtown is about $32, and you can expect to find even lower fares to nearby hotels.

Portland Weather

The average high temperature in Portland is 80 degrees in the summer and 48 degrees in the winter. Portland is known for receiving abundant rainfall, so having an umbrella handy is always a good idea.

Portland Attractions

Portland offers a wide variety of activities for individuals and families, including museums, parks, breweries, and plenty of rainy day activities. Orbitz.com offers several ideas on activities to do in Portland, while providing the best discounts available, all at the same time you are searching for cheap flights to Portland. Everyone will find Orbitz.com to be a great tool for locating discounts and staying within your budget.

Frequently asked questions

Are there non-stop flights from Chicago to Portland?
Yes, there are two airlines that offer direct flights from O’Hare Airport to Portland Intl. Jetport. Look for a bargain fare and take to the skies with United Airlines or American Airlines.
What is the shortest flight from Chicago to Portland?
The journey from Chicago to Portland can be as fast as 2 hours and 54 minutes. With a leisurely flight time like this, why not book a spur-of-the-moment getaway?
What airlines fly from Chicago to Portland most frequently?
There are a couple of airlines offering frequent flights from Chicago, IL (ORD-O’Hare Intl.) to Portland Intl. Jetport Airport (PWM), including United Airlines (UA). Popular with travelers, it operates 91 flights on this route each month. If you need a few more options, look up the prices with American Airlines (AA), which operates 82 flights from Chicago to Portland each month.
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won’t keep you guessing, according to Orbitz data from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.