PDX → ORD
Compare one-way, round-trip and flight + hotel packages from Portland to Chicago, a nonstop flight of about 4h, with fares from around 240. Nonstop fares seen from Alaska.
Portland to Chicago is a domestic route covering about 1,734 miles, arriving at O'Hare International Airport (ORD) in United States. Peak travel season in Chicago runs June–August (warm, lakefront festivals), while November–April is usually the quietest and best-value time to visit. Nonstop fares we've tracked on this route come from Alaska.
| Departing from | Portland International Airport (PDX) |
|---|---|
| Arriving at | O'Hare International Airport (ORD) |
| Distance | 1,734 miles (2,792 km) |
| Nonstop flight time | About 4h |
| Nonstop airlines seen | Alaska |
| Round-trip fares from | $240 (estimate) |
| Cheapest months | February, September, October |
| Peak season in Chicago | June–August |
| Cheapest hotel months in Chicago | November–April |
| Best time to book | 1 to 3 months ahead |
| Route info updated | October 16, 2026 |
June–August
Warm, lakefront festivals
May & September–October
Mild and comfortable
November–April
Cold, windy and snowy
| Month | Fares from |
|---|---|
| January | $260 |
| February | $240 |
| March | $305 |
| April | $260 |
| May | $260 |
| June | $330 |
| July | $370 |
| August | $310 |
| September | $245 |
| October | $250 |
| November | $330 |
| December | $375 |
Nonstop fares we've tracked on this route come from Alaska. Ducoffs.com compares full-service and low-cost airlines flying between Portland and Chicago in a single search, including nonstop and one-stop options, so you can weigh price against total travel time.
Fares on this route tend to be lowest in February, September, and October. For the best selection, book about 1 to 3 months before departure and stay flexible by a day or two.
Portland and Chicago are about 1,734 miles apart. A nonstop flight takes roughly 4h; connecting itineraries usually add 2 to 5 hours.
The best way to secure budget rates is by comparing multiple airlines simultaneously and checking flexible dates. Ducoffs.com scans available partner networks to bring you real-time pricing options.
Based on typical seasonal demand, February, September, and October tend to offer the lowest fares on this route, with estimated round-trip prices starting around $240. Live prices change daily, so run a search for your exact dates.
Portland and Chicago are about 1,734 miles apart. A nonstop flight takes roughly 4h, while connecting itineraries usually add 2 to 5 hours depending on the layover.
Recent nonstop fares we've tracked on this route come from Alaska. Schedules change by season, so your live search shows every airline flying your dates.
Hotel rates in Chicago are usually lowest in November–April, when demand is quieter, and highest during peak season (June–August). Booking your flight and hotel together can save up to 30%.
This route arrives at O'Hare International Airport (ORD). Your search results also show nearby airports when they offer a cheaper or faster option.
For this route, booking about 1 to 3 months before departure usually gives the best balance of price and seat selection. Mid-week departures are often cheaper than weekend flights.
Yes. Bundling your travel components can save you up to 30% compared to booking flights and hotels separately, as airlines and properties offer exclusive package discounts.
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