Cheap Flights from Portland to Chicago in 2019

Flight information Portland to Chicago

Cheapest roundtrip price last month


Non-stop airlines


Flights per week


Average flight time, total distance 1721 miles

3h 36min

Most popular airline last month


Chicago O'Hare International, Chicago Midway, Chicago Pal-Waukee, Chicago Dupage County and others

5 airports

The flight route from Portland, Oregon to Chicago takes you from the green-thinking City of Roses to the buzzing urban vibe of the Windy City, perched on the shore of Lake Michigan. While you’ll soon find that the high winds of Chicago are mainly mythical, these tips from Skyscanner will make sure that your journey is a breeze.

Flight Route Options

Chicago has two airports, and from Portland you can fly to either Chicago O’Hare, or Chicago Midway, which is located just southwest of the city. If you’re flying to O’Hare, your airline carriers will be Spirit, American, United, or Alaska, while if you’re flying to Midway, your journey will be courtesy of Southwest airlines. Depending on your flight route, your journey time will be between 3 and three-quarters hours, and four hours. While most US airlines provide a complimentary drink service, meals are not included for economy passengers on flights within the US, so check with your airline or pack a snack if you think you might get hungry along the way. Happily, airports on both ends offer plenty of dining options.

Heading out from Portland Airport

Portland airport offers interesting diversions for travellers, not the least of which include a new cinema available to passengers once you get through security. The cinema will feature free short films that highlight West Coast talents, and keep you entertained as you wait for your flight. Autumn 2016 will also see the opening of the House Spirits Distillery tasting room, another indulgent way to pass the time before you take off. Wi-Fi is free throughout the airport for all your business and entertainment needs. There is a North and South terminal at the airport, connected by the ‘Concourse Connector’ walkway. If you’re returning to Portland after your trip to Chicago, the airport has Short-Term, Long-Term and Economy lots, as well as parking for motorcycles and bicycles.

If you don’t want to drive or take a taxi, TriMet MAX train will also deliver you to the airport on the Red Line.

What to expect in Chicago

Most flights from Portland to Chicago connect to Chicago O’Hare airport, although Southwest flies to Chicago Midway. Both airports boast a range of features designed to make your journey relaxing. If you need a few moments of peace and quiet before heading out, you can stop in one of the yoga rooms in either airport, and Chicago O’Hare also features an atrium garden, which even supplies fresh herbs and produce to some of the airport’s many eateries.

Getting from either Chicago airport to your journey’s endpoint is easy, thanks to the “L” train service, which connects both O’Hare and Midway to downtown Chicago. Midway is closer to the city’s central hub, and it takes only 25 minutes to get downtown by train, while you can expect a 45-minute train ride into the city from Chicago O’Hare. While train travel is often the best way to avoid city traffic, taxis, curbside pick-up, and rental cars are also available from the airport. If you’re looking to rent, start with Skyscanner’s car rental search to find the best car deals and wind your way through the Windy City in style.

Time Zone and Climate

Chicago, in the Central time zone, is two hours ahead of Portland, so you’ll lose two hours during travel. Depending on which season you’re travelling in, you may notice that Chicago experiences greater temperature variations than Portland, so make sure to button up in winter! While the Windy City may not actually be as breezy as it’s nickname suggests, winter temperatures still go below freezing for most of the winter months, while summers are hot and humid, with average highs in the mid- 80s.

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Prices shown on this page are estimated lowest prices only. Found in the last 45 days.