Cheap flights from Portland to Chicago from $179
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Portland to Chicago departing on 11/16. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Fly from
Fly to
Route
Depart
Return
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Tue 10/27
12:02 pm-12:21 am
1 stop10h 19m
Chicago O'Hare Intl
Thu 10/29
5:15 pm-11:36 am
1 stop20h 21m
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Wed 11/11
11:09 pm-5:07 am
Nonstop3h 58m
Chicago O'Hare Intl
Mon 11/16
5:15 pm-12:01 am
1 stop8h 46m
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Mon 11/9
1:25 pm-10:29 pm
1 stop7h 04m
Chicago O'Hare Intl
Sun 11/15
4:25 pm-7:12 pm
Nonstop4h 47m
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Thu 11/12
3:40 pm-12:59 am
1 stop7h 19m
Chicago O'Hare Intl
Sun 11/15
7:45 pm-10:27 pm
Nonstop4h 42m
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Fri 12/4
5:23 am-2:21 pm
1 stop6h 58m
Chicago O'Hare Intl
Sat 12/12
2:08 pm-5:05 pm
Nonstop4h 57m
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Sat 12/5
7:00 am-1:10 pm
Nonstop4h 10m
Chicago O'Hare Intl
Sun 12/13
6:00 am-1:28 pm
1 stop9h 28m
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Thu 11/19
9:16 am-9:47 pm
2 stops10h 31m
Chicago O'Hare Intl
Mon 11/23
2:03 pm-9:57 pm
2 stops9h 54m
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Wed 10/28
6:00 am-4:32 pm
2 stops8h 32m
Chicago O'Hare Intl
Fri 10/30
7:35 am-12:03 pm
1 stop6h 28m
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Mon 2/1
2:06 pm-8:25 pm
Nonstop4h 19m
Chicago O'Hare Intl
Sun 2/28
10:00 am-6:09 pm
1 stop10h 09m
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Thu 10/29
12:02 pm-12:21 am
1 stop10h 19m
Chicago O'Hare Intl
Sun 11/1
6:30 am-11:12 am
1 stop6h 42m
See travel insights to Chicago from
How to get the cheapest flight ticket from Portland to Chicago
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the typical price of a round-trip flight between Portland and Chicago?
Prices are currently low for flights on this route.
Typical prices usually range from $373 to $525.The lowest price recently found on this route was $352.
What is the cheapest month to fly to Chicago?
The month of January is, on average, the cheapest month to fly to Chicago from Portland, with most prices found around $279. If you’re not able to fly to Chicago in January, then February is your next best option. Flight prices from Portland to Chicago during February average around $290.
What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $450. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Portland to Chicago for around $553.
What is the cheapest time of day to depart on your flight to Chicago?
Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Portland to Chicago during this time can be as low as $367. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $515.
What is the cheapest Portland to Chicago flight route?
Fly from Portland to Chicago O'Hare Intl for the best Portland - Chicago flight prices
How far in advance should I book a flight from Portland to Chicago?
You are more likely to see cheaper flights to Chicago from Portland when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $388 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Portland for as low as $309 on momondo.
What cabin class options are available on Portland to Chicago flights?
There are 4 cabin classes available to choose from on Portland to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
Can stopping save me money on Portland to Chicago flights?
You could potentially save up to 40% on your flight if you consider stops on a Portland to Chicago flight.
How have Portland to Chicago flight prices changed over time?
As of October 2026, prices for Portland to Chicago flights are approximately 18% more expensive when compared to flights at the same time last year.
What is the cheapest airline that flies from Portland to Chicago?
Alaska Airlines, Delta, and United Airlines are the most popular carriers operating from Portland to Chicago
What airlines fly to Chicago?
United Airlines, American Airlines and Alaska Airlines are the top three most popular airlines that fly to Chicago from Portland according to our data. United Airlines is the first choice among our users, with 42% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.
How many flights depart from Portland to Chicago on average per day?
The number of flights available between Portland and Chicago is 27 per day as of October 2026. The most frequent departure time is 7:00AM, with 71% of daily flights leaving at noon.
How many flights depart from Portland to Chicago on average per week?
194 flights are operational weekly from Portland to Chicago as of October 2026. The most popular departure day for this route is Mon, with 15% of flights per week taking off on this day.
When to book flights from Portland to Chicago
Cheap Portland to Chicago (PDX to CHI) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Portland to Chicago
Frequently asked questions about flying from Portland to Chicago
How far is Portland to Chicago by plane?
Portland and Chicago are 1753.4 mi apart from one another. A reasonable flight in good conditions will take 3h 45m.
When did momondo last update prices for flights from Portland Airport to Chicago?
Prices for flights from Portland Airport to Chicago are refreshed on a daily basis.
How many operators does momondo search for flights from Portland Airport to Chicago?
There are 6 operators available for flights from Portland Airport to Chicago as of October 2026.
How old do you have to be to fly from Portland Airport to Chicago?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Portland Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Portland to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Portland to Chicago is Boeing 737-800 (26.78% of total bookings). The next most popular plane models are Airbus A321-100/200 (13.68%), Airbus A321neo (13.51%), and Boeing 737 MAX 8 (11.21%).
What is the most popular airline from Portland to Chicago?
momondo data reveals that the most frequently booked airline on the route from Portland to Chicago is United Airlines, representing 36% of all bookings. The subsequent popular airlines are American Airlines at 31%, Alaska Airlines at 17%, and Southwest at 13%.
Best airlines flying from Portland to Chicago
Compare and see reviews for airlines that fly from Portland to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $125 | Free Cancellation | Rating 7.8 8,634 reviews | |||
| PriceFrom $216 | Free Cancellation | Rating 7.1 3,046 reviews | |||
| PriceFrom $223 | Free Cancellation | Rating 7.0 12,129 reviews | |||
| PriceFrom $232 | Free Cancellation | Rating 7.9 13,027 reviews | |||
| PriceFrom $243 | Free Cancellation | Rating 7.4 10,295 reviews | |||
| PriceFrom $266 | Free Cancellation | Rating 7.9 4,214 reviews |
Southwest Flights From Portland to Chicago
Southwest flies from Portland to Chicago around 9 times per week, with 4,215 momondo users rating the airline 7.9/10. The cheapest Southwest deal from Portland to Chicago in the last 72 hours was $266 (round-trip), much lower than the average airfare cost of $370 for Southwest flights on this route.
Alaska Airlines Flights From Portland to Chicago
Another popular option for Portland to Chicago flights is Alaska Airlines (7.9/10, 13,022 ratings). Alaska Airlines flies from Portland to Chicago around 5 times per week, with deals starting from $232 round-trip and rising to an average price of around $402.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Portland to Chicago?
To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Portland.
Can I find flights from Portland to Chicago with flexible booking policies on momondo?
Flights from Portland to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.
How can momondo help me find flights from Portland to Chicago?
Once all potential Portland to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.
I’m not ready to book a flight from Portland to Chicago right now. Can momondo alert me if prices change?
Yes. momondo can track prices for Portland to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.