MDW - PWM

$115 Find Cheap Flights from Chicago Midway Airport to Portland

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Portland departing on 4/1. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Portland

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Portland, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Portland, as well as popular online travel agencies
Travelers love KAYAK
41.299.237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$229
Delta
Sat 4/18Sat 4/25
MDW - PWM • 1 stop
Cheapest non-stop
$368
Southwest
Wed 6/10Sun 6/14
MDW - PWM • Non-stop
Top airlines
Delta
Cheapest • from $229 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Portland!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Midway to Portland (MDW-PWM)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Portland that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Portland

Sat, Apr 18 - Sat, Apr 25
Delta Logo
9:27 am - 3:57 pm
MDW
-
PWM
5h 30m
1 stop
Delta Logo
12:46 pm - 5:58 pm
PWM
-
MDW
6h 12m
1 stop
$229Delta
Sat, Apr 18 - Sat, Apr 25
Delta Logo
9:27 am - 3:57 pm
MDW
-
PWM
5h 30m
1 stop
Delta Logo
12:46 pm - 10:28 pm
PWM
-
MDW
10h 42m
2 stops
$234Delta
Sat, Apr 18 - Sun, Apr 26
Delta Logo
9:27 am - 3:57 pm
MDW
-
PWM
5h 30m
1 stop
Delta Logo
12:46 pm - 5:58 pm
PWM
-
MDW
6h 12m
1 stop
$284Delta
Sat, Apr 18 - Sat, Apr 25
Delta Logo
2:12 pm - 11:23 pm
MDW
-
PWM
8h 11m
2 stops
Delta Logo
12:46 pm - 10:28 pm
PWM
-
MDW
10h 42m
2 stops
$294Delta
Wed, Apr 8 - Sat, Apr 11
Southwest Logo
7:00 am - 12:20 pm
MDW
-
PWM
4h 20m
1 stop
Southwest Logo
4:35 pm - 8:40 pm
PWM
-
MDW
5h 05m
1 stop
$296Southwest
Sat, Mar 14 - Fri, Mar 20
Southwest Logo
6:25 pm - 12:10 am
MDW
-
PWM
4h 45m
1 stop
Southwest Logo
2:50 pm - 8:15 pm
PWM
-
MDW
6h 25m
1 stop
$304Southwest
Tue, May 19 - Sun, May 24
Southwest Logo
12:45 pm - 10:20 pm
MDW
-
PWM
8h 35m
2 stops
Southwest Logo
6:00 am - 2:55 pm
PWM
-
MDW
9h 55m
1 stop
$305Southwest
Thu, May 7 - Mon, May 11
Southwest Logo
5:50 pm - 11:25 pm
MDW
-
PWM
4h 35m
1 stop
Southwest Logo
4:50 pm - 10:20 pm
PWM
-
MDW
6h 30m
1 stop
$307Southwest
Wed, Apr 29 - Wed, May 13
Delta Logo
12:53 pm - 11:24 pm
MDW
-
PWM
9h 31m
2 stops
Delta Logo
12:50 pm - 6:31 pm
PWM
-
MDW
6h 41m
1 stop
$309Delta
Thu, May 7 - Mon, May 11
Southwest Logo
2:10 pm - 11:25 pm
MDW
-
PWM
8h 15m
2 stops
Southwest Logo
4:50 pm - 10:20 pm
PWM
-
MDW
6h 30m
1 stop
$312Southwest
Booking Insights

KAYAK's insights & trends for Midway to Portland flights

Get data-powered insights and trends into flights from Midway to Portland to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Chicago Midway Airport to Portland?

The average price of all round-trip flights from Chicago Midway Airport to Portland clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Chicago Midway Airport to Portland, look for departures on Tuesdays and avoid leaving on a Thursday, as it's usually the priciest day. When flying back from Portland, Thursday is the cheapest day to fly and Sunday is the most expensive.

Can I save money by flying with a layover from Chicago Midway Airport to Portland?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $384 on average.

Find deals

Good to know

Cheapest flight$115
Flight from Chicago Midway Airport to Portland

When to book flights from Midway to Portland

Are your dates flexible? Find out the best times to travel from Midway to Portland based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to Portland flights

  • What is the cheapest flight from Chicago Midway Airport to Portland?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Portland was $115 for a one-way ticket and $229 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and Portland?

    No, a passport isn't needed to fly from Chicago Midway Airport to Portland. However, local authorities might ask for an official ID.

  • Which airports will I be using when flying from Chicago Midway Airport to Portland?

    Chicago Midway Airport airport is called Chicago Midway and the only airport in Portland is Portland.

  • Which airlines offer Wi-Fi service onboard planes from Chicago Midway Airport to Portland?

    Only American Airlines offers inflight Wi-Fi service on the Chicago Midway Airport to Portland flight route.

  • Which aircraft models fly most regularly from Chicago Midway Airport to Portland?

    The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the Chicago Midway Airport to Portland flight route.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Portland?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to Portland.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Portland?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Portland from Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to Portland?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Portland with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and PWM can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Portland?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Portland from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Midway to Portland

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Portland. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to Portland? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4267 reviews
8.1Boarding
8.0Comfort
7.5Entertainment
8.6Crew
7.0Food
Airline reviews

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled. No snack or drink on this flight.

10.0 ExcellentJoseph, Jan 2026
BWI - RIC
Read more Southwest reviews

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled. No snack or drink on this flight.

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled.

The wifi on the plane is great. The only issue that I have is that I prefer an aisle seat and on my trips this week, I was either in the middle or window. If we can work to secure aisle seating, I will be thrilled. Nice trip.

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Everything went smoothly and we even arrived a little bit early.

Great vacation. Can't wait till next year for another one.

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

Everything you need to know for your flight from Midway to Portland

Information on your arrival and departure airports

Chicago Midway Airport (MDW)
Portland (PWM)