MDW - PWM

$154 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 8/25. 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
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Everything you should know

Cheapest round-trip
$307
Southwest
Wed 7/8Wed 7/15
MDW - PWM • Non-stop
Cheapest one-way
$154
Southwest
Tue 8/25
MDW - PWM • Non-stop
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 2h 15m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Avoid delays
Southwest
Most punctual • 94% on-time
Afternoon flights
Best time • Fewest delays
Insights
Insights
Insights
Insights
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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

Wed, Jul 8 - Wed, Jul 15
Southwest Logo
6:15 pm - 9:35 pm
MDW
-
PWM
2h 20mnonstop
Southwest Logo
7:30 am - 9:05 am
PWM
-
MDW
2h 35mnonstop
$307Southwest
Sat, Aug 29 - Sat, Sep 5
Southwest Logo
3:20 pm - 6:35 pm
MDW
-
PWM
2h 15mnonstop
Southwest Logo
3:40 pm - 5:15 pm
PWM
-
MDW
2h 35mnonstop
$312Southwest
Wed, Jul 8 - Wed, Jul 15
Southwest Logo
4:10 pm - 11:00 pm
MDW
-
PWM
5h 50m
1 stop
Southwest Logo
7:30 am - 9:05 am
PWM
-
MDW
2h 35mnonstop
$317Southwest
Fri, Jul 3 - Wed, Jul 8
Southwest Logo
5:30 pm - 12:05 am
MDW
-
PWM
5h 35m
1 stop
Southwest Logo
7:30 am - 9:05 am
PWM
-
MDW
2h 35mnonstop
$322Southwest
Wed, Jul 8 - Tue, Jul 14
Southwest Logo
5:30 pm - 11:00 pm
MDW
-
PWM
4h 30m
1 stop
Southwest Logo
7:10 pm - 11:15 pm
PWM
-
MDW
5h 05m
1 stop
$327Southwest
Fri, Jul 3 - Wed, Jul 8
Delta Logo
11:05 am - 12:52 am
MDW
-
PWM
12h 47m
2 stops
Delta Logo
11:47 am - 6:18 pm
PWM
-
MDW
7h 31m
1 stop
$332Delta
Wed, Jul 8 - Wed, Jul 15
Southwest Logo
10:10 am - 6:30 pm
MDW
-
PWM
7h 20m
2 stops
Southwest Logo
5:30 am - 11:00 am
PWM
-
MDW
6h 30m
1 stop
$337Southwest
Mon, Aug 31 - Tue, Sep 1
Delta Logo
6:05 am - 1:07 pm
MDW
-
PWM
6h 02m
1 stop
Delta Logo
11:50 am - 6:01 pm
PWM
-
MDW
7h 11m
1 stop
$342Delta
Tue, Sep 1 - Thu, Sep 17
Southwest Logo
6:50 pm - 10:05 pm
MDW
-
PWM
2h 15mnonstop
Southwest Logo
10:30 am - 4:15 pm
PWM
-
MDW
6h 45m
1 stop
$347Southwest
Wed, Sep 2 - Tue, Sep 8
Southwest Logo
6:50 pm - 10:05 pm
MDW
-
PWM
2h 15mnonstop
Southwest Logo
7:45 am - 9:20 am
PWM
-
MDW
2h 35mnonstop
$352Southwest
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 Wednesdays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Portland, Tuesday 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 $397 on average.

Find deals

Good to know

Cheapest flight$154
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 5 days, the lowest price for a flight from Chicago Midway Airport to Portland was $154 for a one-way ticket and $307 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.

  • On which days can I fly direct from Chicago Midway Airport to Portland?

    There are nonstop flights from Chicago Midway Airport to Portland on a daily basis.

  • 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.

KAYAK’s top tips for finding a cheap flight from Chicago Midway Airport to Portland

  • Looking for a cheap flight? 25% of our users found flights on this route for $158 or less one-way.

Prefer to fly direct from Chicago Midway Airport to Portland?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago Midway to Portland.
Find which airlines fly direct from Chicago Midway Airport to Portland Airport, which days they fly and book direct flights.

Direct departures

Chicago Midway to Portland

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Portland to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

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)