Cheap flights from Chicago Midway Airport to Portland from $90
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Portland departing on 8/31. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
Discover deals from 900+ travel sites with momondo.
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.Price Alerts
Price Alerts
Not ready to book? to track prices.Find the cheapest flights from Chicago Midway Airport to Portland
Cheap round-trip flights
Cheap one-way flights
Cheap last minute flights
Cheap direct flights
Southwest flights from Chicago Midway Airport to Portland
Our best Southwest deals on Chicago Midway Airport to Portland flight tickets
Delta flights from Chicago Midway Airport to Portland
Our best Delta deals on Chicago Midway Airport to Portland flight tickets
See travel insights to Portland from
How to get the cheapest flight ticket from Chicago Midway Airport to Portland
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 cheapest month to fly to Portland?
The cheapest month to fly to Portland from Chicago Midway Airport is in January. Flight prices, which tend to average around $266, are often lower during this time because this is during the off-season. If you don’t want to visit Portland in January, then you should wait until February to fly from Chicago Midway Airport, when ticket prices are also cheap, with an average price of $288.
What is the cheapest day to depart on your flight to Portland?
The cheapest day to depart on your flight to Portland is on a Wednesday when prices can be found for as low as $322. This is often the case because there is less demand to fly during this day of the week. The most expensive day to fly to Portland is Sunday, with ticket prices averaging around $394.
What is the cheapest time of day to depart on your flight to Portland?
The cheapest time of day to fly to Portland is in the evening when flights can be purchased for as low as $256. At noon is when there is more demand to fly to Portland, so prices are often more expensive at around $384 per ticket.
What is the cheapest Chicago Midway to Portland flight route?
Fly from Chicago Midway to Portland for the best Chicago Midway - Portland flight prices
What cabin class options are available on Chicago Midway to Portland flights?
There are 1 cabin classes available to choose from on Chicago Midway to Portland 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 Chicago Midway Airport to Portland flights?
No. A direct flight is the cheapest option for a flight between Chicago Midway Airport to Portland.
How many flights depart from Chicago Midway Airport to Portland on average per day?
As of June 2025, 2 flights take off from Chicago Midway Airport and land in Portland each day. The most common flight departure time for this route is 10:00PM, with 40% of daily flights taking off at noon.
How many flights depart from Chicago Midway Airport to Portland on average per week?
As of June 2025, there are 15 flights per week flying from Chicago Midway Airport to Portland. The most common day of the week flights depart is Mon, with 20% of flights taking off on this day.
When to book flights from Chicago Midway Airport to Portland
Cheap Chicago Midway Airport to Portland (MDW to PDX) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Portland
How far is Chicago Midway to Portland by plane?
The distance between Chicago Midway and Portland is about 1749.8 mi. A reasonable flight in good conditions will take 4h 10m.
When did momondo last update prices for flights from Chicago Midway Airport to Portland Airport?
Prices for flights from Chicago Midway Airport to Portland Airport are refreshed on a daily basis.
How many operators does momondo search for flights from Chicago Midway Airport to Portland Airport?
As of June 2025, there are 2 operators available to choose from for flights from Chicago Midway Airport to Portland Airport.
How old do you have to be to fly from Chicago Midway Airport to Portland Airport?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Portland Airport.
What documentation or ID do you need to fly to Portland Airport?
The necessary travel and health documents for your Portland Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago Midway Airport to Portland?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago Midway Airport to Portland is Boeing 737-800 (17.45% of total bookings). The next most popular plane models are Boeing 737 MAX 8 (12.31%), Boeing 737 MAX 9 (12.31%), and Boeing 737-900 (11.99%).
What is the most popular airline from Chicago Midway Airport to Portland?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Chicago Midway Airport to Portland is Southwest (83% of total bookings). The next most popular airline is Frontier (17%).
Best airlines flying from Chicago Midway Airport to Portland
Compare and see reviews for airlines that fly from Chicago Midway Airport to Portland with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $108 | Free Cancellation | Rating 5.9 3,295 reviews | |||
| PriceFrom $237 | Free Cancellation | Rating 8.0 4,287 reviews |
Southwest Flights From Chicago Midway Airport to Portland
Southwest is one of the most popular airlines flying from Chicago Midway Airport to Portland, operating 15 flights/week on average for this route. A good Southwest flight deal for Chicago Midway Airport to Portland starts from $237 round-trip, up to an average price of $444. Our users have rated Southwest at 8.0/10.
Traveling to a place near Portland?
Book flights to Portland if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Chicago to Portland?
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 Portland from Chicago.
Can I find flights from Chicago to Portland with flexible booking policies on momondo?
Flights from Chicago to Portland 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 Chicago to Portland?
momondo provides multiple filters to help you find the best flight to Portland from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.
I’m not ready to book a flight from Chicago to Portland right now. Can momondo alert me if prices change?
If you are not ready to book a flight from Chicago to Portland now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Portland and let you know when they change.