Cheap flights from Portland to Chicago (PDX - CHI)
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The best prices from Portland to Chicago are usually found in October or January, booked 60 days in advance, depart on a Saturday or Wednesday and return on a Wednesday
How to find the cheapest flight from
Portland (PDX) to Chicago (CHI)
All the information you need to plan the best PDX to CHI flight in 2022: compare Portland to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
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PDX - CHI Price
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$246 - $623
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CHI Temperature
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23 - 73.4 °F
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CHI Rainfall
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1.7 - 4.9 inches
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Popular in June High demand for flights, 41% potential price rise |
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Cheapest in October Best time to find cheap flights, 33% potential price drop |
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Round-trip from $246 From Portland to Chicago (CHI) |
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One-way from $129 One-way flight from Portland to Chicago (CHI) |
How far in advance should I book a flight from Portland to Chicago?
Travelers have found it’s best to book a flight 60 days in advance to save up to 58% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 60 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Portland to Chicago 1-2 weeks in advance for as low as $446, or $593 for flights within the next 24 hours.
When is the cheapest time to fly from Portland to Chicago (PDX - CHI)?
A simple way to save on the total cost of your ticket is to fly from Portland to Chicago in the afternoon. If you’re flexible enough to do this you can expect to save up to 39% on your trip compared to booking a flight at noon.
What is the cheapest month to fly from Portland to Chicago?
Due to multiple factors, expect to potentially pay more when booking in June. For low rates, October can be a great choice for travel to Chicago. Flights to Chicago from Portland in October are about $368 on average during October, but can be found for as low as $158.
What is the cheapest day to fly round-trip from Portland to Chicago?
Friday is generally a great day to depart. Flying on this day could help you save up to 34%.
Cheap flights from Portland to Chicago in August, September 2022
The best prices found for PDX to CHI flights for August, September
Portland to Chicago 2022 flight deals
Cheap flights to Chicago from Portland found for this year
Cheap Spirit Airlines flights from Portland to Chicago
If you’re traveling from Portland to Chicago, one of the more common airlines traveling that route is Spirit Airlines. Portland to Chicago flights are typically 56% cheaper than other airlines traveling the same route. Flights from Spirit Airlines typically cost $389.61 RT. The cheapest Spirit Airlines flight found for this route was $118. When traveling from Portland to Chicago on Spirit Airlines, the most popular airport to depart from is Portland Airport and the most popular airport to arrive at is Chicago O'Hare Intl Airport. When flying from Portland to Chicago, Spirit Airlines flights are 23% more popular than any other airline flying that same route.
Cheap United Airlines flights from Portland to Chicago
One of the most popular airlines traveling from Portland to Chicago is Frontier. Flights from Frontier traveling this route typically cost $536.20 RT. This price is typically 30% cheaper than other airlines that offer Portland to Chicago flights. When booking this route, the cheapest RT price found was $159. Portland Airport is the most common Portland airport to take off from when flying to Chicago. Chicago O'Hare Intl Airport is the most popular arrival airport in Chicago. When flying from Portland to Chicago, Frontier flights are 19% more popular than any other airline flying that same route.
Non-stop flights to Chicago from Portland
Save time with Portland to Chicago direct flight deals
Last minute flights from Portland to Chicago
Late deals on round-trip flights to Chicago from Portland, departing today and this week
One-way flights to Chicago from Portland
The cheapest one-way flights from Portland to Chicago
Related info for your journey
Useful info, stats and facts about <span class="emphasized">Portland</span> to <span class="emphasized">Chicago</span> flights.
COVID Restrictions
View COVID Travel Restrictions for Chicago, ILAlternative routes for Portland to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Top 7 airlines flying from Portland to Chicago
The chart below displays the airlines Cheapflights users traveling from Portland to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
| Airline | Cheapest | Average | Flexibility | On-time | COVID-19 safety | |
|---|---|---|---|---|---|---|
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$16 | $22 | No cancel fee | 66% |
We couldn't confirm the COVID-19 safety measures taken by Juneyao Airlines. Please check directly on their website for additional information. |
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$61 | $227 | No cancel fee | 62% | ||
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$99 | $368 | No cancel fee | 65% | ||
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$118 | $390 | No cancel fee | 75% | ||
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$138 | $437 | No cancel fee | N/A | ||
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$158 | $403 | No cancel fee | 71% | ||
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$159 | $536 | No cancel fee | 69% |
Popular flight searches
Check out other popular destinations found by fellow travelers in 2022.
Hourly flight availability from Portland to Chicago
See what time of day planes typically take off from Portland towards Chicago.
| Morning 6 AM to noon | 46% of PDX to CHI departures |
| Early morning Midnight to 6 AM | 36% of PDX to CHI departures |
| Afternoon Noon to 6 PM | 15% of PDX to CHI departures |
| Evening 6 PM to midnight | 3% of PDX to CHI departures |