PDX - MDW

$150 Find Cheap Flights from Portland to Chicago Midway Airport - Compare and Save

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Everything you should know

Cheapest round-trip
$322
Typical prices: $288-$428
Southwest
Tue 10/16Sat 10/20
PDX - MDW • Non-stop
Cheapest one-way
$150
Typical prices: $157-$334
Southwest
Sat 10/6
PDX - MDW • Non-stop
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 3h 51m
Direct flights
+1
Direct flights
+1
When to book
24 weeks
in advance
Our data shows that travelers who book at least 24 weeks in advance save around 52% compared to booking last minute.
Insights
Insights
When to travel
February
Cheapest • 28% price drop
August
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Denver Intl (DEN)
Cheapest • Avg $274 (round-trip)
Minneapolis St Paul (MSP)
Shortest trip • 7h 38m (one-way)
Insights
Insights
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We hope you love your trip to Chicago Midway Airport!
Flight Deals
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Expert advice
Flight Deals

Cheap Flights from Portland to Midway (PDX-MDW)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Portland to Midway

Fri, Oct 16 - Tue, Oct 20
Southwest Logo
11:35 pm - 5:25 amPDX  Portland-MDW Chicago Midway
3h 50mnonstop
Southwest Logo
8:40 pm - 11:10 pmMDW  Chicago Midway-PDX Portland
4h 30mnonstop
$322Southwest
Wed, Oct 14 - Wed, Oct 21
Southwest Logo
11:35 pm - 5:25 amPDX  Portland-MDW Chicago Midway
3h 50mnonstop
Southwest Logo
12:15 pm - 8:10 pmMDW  Chicago Midway-PDX Portland
9h 55m2 stops Austin Bergstrom Denver Intl
$329Southwest
Tue, Oct 20 - Fri, Oct 23
Delta Logo
6:00 am - 4:47 pmPDX  Portland-MDW Chicago Midway
8h 47m1 stop Minneapolis St Paul
Delta Logo
12:49 pm - 9:49 pmMDW  Chicago Midway-PDX Portland
11h 00m1 stop Atlanta Hartsfield-Jackson
$329Delta
Mon, Oct 19 - Thu, Oct 22
Southwest Logo
11:35 pm - 5:25 amPDX  Portland-MDW Chicago Midway
3h 50mnonstop
Southwest Logo
9:45 pm - 12:15 amMDW  Chicago Midway-PDX Portland
4h 30mnonstop
$331Southwest
Thu, Nov 12 - Mon, Nov 16
Southwest Logo
11:30 pm - 5:15 amPDX  Portland-MDW Chicago Midway
3h 45mnonstop
Southwest Logo
8:40 pm - 11:25 pmMDW  Chicago Midway-PDX Portland
4h 45mnonstop
$331Southwest
Fri, Oct 16 - Tue, Oct 20
Southwest Logo
11:35 pm - 5:25 amPDX  Portland-MDW Chicago Midway
3h 50mnonstop
Southwest Logo
5:45 am - 11:50 amMDW  Chicago Midway-PDX Portland
8h 05m1 stop Phoenix Sky Harbor Intl
$332Southwest
Tue, Oct 20 - Fri, Oct 23
Southwest Logo
2:15 pm - 11:55 pmPDX  Portland-MDW Chicago Midway
7h 40m1 stop Phoenix Sky Harbor Intl
Southwest Logo
9:45 pm - 12:15 amMDW  Chicago Midway-PDX Portland
4h 30mnonstop
$332Southwest
Tue, Dec 22 - Tue, Jan 5
Southwest Logo
10:15 pm - 9:20 amPDX  Portland-MDW Chicago Midway
9h 05m1 stop Phoenix Sky Harbor Intl
Southwest Logo
5:20 am - 10:50 amMDW  Chicago Midway-PDX Portland
7h 30m1 stop Phoenix Sky Harbor Intl
$333Southwest
Sat, Oct 17 - Mon, Oct 19
Southwest Logo
5:55 pm - 5:00 amPDX  Portland-MDW Chicago Midway
9h 05m1 stop San Jose
Southwest Logo
6:05 am - 10:20 amMDW  Chicago Midway-PDX Portland
6h 15m1 stop Denver Intl
$333Southwest
Tue, Oct 20 - Fri, Oct 23
Delta Logo
8:44 pm - 9:32 amPDX  Portland-MDW Chicago Midway
10h 48m2 stops Seattle/Tacoma Intl Detroit Metropolitan Wayne County
Delta Logo
12:49 pm - 9:49 pmMDW  Chicago Midway-PDX Portland
11h 00m1 stop Atlanta Hartsfield-Jackson
$334Delta
Booking Insights

Price, demand and travel trends for Portland to Chicago Midway Airport flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights from Portland to Chicago Midway Airport with more confidence.

How much is a round-trip flight from Portland to Chicago Midway Airport?

Round-trip flights from Portland to Chicago Midway Airport start at $322. Prices are typical for this route right now, with typical round-trip fares ranging from $288 to $428. The lowest price found in the past 5 days was $322 on Southwest.

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

Wednesday is the cheapest day of the week to fly from Portland to Chicago Midway Airport, it is 11% cheaper than the average day. Monday is the most expensive day with flight prices 12% higher than average. Based on deals found by KAYAK users in the last 12 months.

What is the cheapest month to fly from Portland to Chicago Midway Airport?

  • February is the cheapest month to fly from Portland to Chicago Midway Airport at $253 round-trip.
  • December ($499) and November ($492) are the most expensive months.
  • The price difference between flying in the cheapest and most expensive months is 97% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are prices from Portland to Chicago Midway Airport the cheapest?

Flights from Portland to Chicago Midway Airport are cheapest 24 weeks before departure. Booking in this window typically costs about 52% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

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Expert advice

Expert advice for your flight from Portland to Midway

 
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on MDW

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Gabriel Leigh

Gabriel Leigh

Expert on PDX

Gabriel is a writer and video creator. As senior content producer for Flightradar24 and Monocle’s transport correspondent, he keeps a close eye on aviation in particular. He has also written travel articles for the likes of The New York Times. Born in New York but raised around the world, he now lives in Sweden. He’s been to 75 countries, flying 2.3 million miles on 113 airlines and through 234 airports in the process.

Read more

Key details for Portland to Chicago Midway Airport flights

Low season

December

Cheapest flight

$150
Best time to beat the crowds but there is an average 41% increase in price.
Most popular time to fly with an average 9% increase in price.
Flight from Portland to Chicago Midway Airport

When to book flights from Portland to Midway

Are your dates flexible? Find out the best times to travel from Portland to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Portland to Chicago Midway Airport flight questions, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • Which airlines offer extra legroom and free seat selection on Portland to Chicago Midway Airport flights?

    Among airlines operating Portland to Chicago Midway Airport flights:

    • Southwest: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • What airlines are available from Portland to Chicago Midway Airport?

    Only Southwest operates flights between Portland and Chicago Midway Airport.

  • Which airports can I use when flying from Portland to Chicago Midway Airport?

    Flights from Portland to Chicago Midway Airport usually depart from Portland (PDX) and arrive at Chicago Midway (MDW).

  • Which airlines include bags at no extra cost on Portland to Chicago Midway Airport flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • Southwest: a cabin bag and a checked bag in Economy Class
    • JetBlue: a cabin bag in Economy Class class

    Bag allowance can vary by ticket type, cabin class, route and airline, so travelers should check the fare details before booking.

  • What cabin classes can I book on flights from Portland to Chicago Midway Airport?

    Two cabin classes are available on flights from Portland to Chicago Midway Airport:

    • Economy Class
    • First Class

  • How much can I save by taking a layover when flying from Portland to Chicago Midway Airport?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $274 round-trip via Denver Intl (DEN), compared to $355 for nonstop.

  • What is the standard checked-bag allowance on flights from Portland to Chicago Midway Airport?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$90 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Which aircraft model is used most often on flights from Portland to Chicago Midway Airport?

    The Boeing 737-800 family is used most often on this route, operated mainly by United Airlines and American Airlines. Other aircraft seen on the route include Boeing 737 MAX 8 variants.

  • Which airports do connecting flights from Portland to Chicago Midway Airport pass through?

    One-stop flights from Portland to Chicago Midway Airport most commonly connect through:

    • Denver Intl (DEN) - 36% of one-stop connections
    • Minneapolis St Paul (MSP) - 29% of one-stop connections
    • Phoenix Sky Harbor Intl (PHX) - 21% of one-stop connections
    • Oakland (OAK) - 14% of one-stop connections

    Denver Intl (DEN) handles the largest share of one-stop connections on this route.

  • Can I save money by using flexible dates for flights from Portland to Chicago Midway Airport?

    Yes. Being flexible with your travel dates can save you up to 21% on the Portland to Chicago Midway Airport route. Wednesday is the cheapest departure day at $316 round-trip on average, while Monday is the most expensive at $397, a difference of $81. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • How are flight departures from Portland to Chicago Midway Airport spread across the day?

    Morning is the busiest departure period on Portland to Chicago Midway Airport flights, with 50% of flights leaving in that window. Night departures account for 50%, afternoon flights for 0%, and evening flights for 0%.

  • What popular places can I visit in Chicago Midway Airport?

    Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, Grant Park and River North. These are among the most viewed places in Chicago Midway Airport on KAYAK.

  • What are the earliest and latest flights from Portland to Chicago Midway Airport?

    These are the earliest and latest flight times available from Portland to Chicago Midway Airport:

    • Earliest: departs at 5:20 am and lands at 9:11 am
    • Latest: departs at 11:35 pm and lands at 3:26 am.

    The flight takes about 3h 51m.

  • How expensive are last-minute Portland to Chicago Midway Airport flights?

    Last-minute fares on this route - booked within 2 weeks of departure - run 62% above the route average of $353. Book 24 weeks before departure for the lowest fares.

  • How long is a flight from Portland to Chicago Midway Airport?

    A nonstop flight from Portland to Chicago Midway Airport takes 3h 51m, covering 1,746 miles.

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

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID, or another TSA-accepted form of identification.

  • Have flight prices from Portland to Chicago Midway Airport changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $322 to $1,994. That means the highest observed fare was about 6x higher than the lowest one.

  • How are flight prices from Portland to Chicago Midway Airport looking right now?

    One-way fares from Portland to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $176, which is 20% below the typical average for this route.

  • How much time can I save by choosing a different layover airport from Portland to Chicago Midway Airport?

    Flying via Minneapolis St Paul (MSP) gives the shortest average 1-stop total travel time at 7h 38m, compared with 8h 51m via Oakland (OAK) and 10h 43m via Phoenix Sky Harbor Intl (PHX).

  • What is the time difference between Portland and Chicago Midway Airport?

    Chicago Midway Airport is 2 hours ahead of Portland (Central Time vs Pacific Time). Plan for the time shift when scheduling connections or first-day activities.

  • What car rental options are available at Chicago Midway Airport (MDW)?

    Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates starting from around $32 for economy cars. Top options include:
    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

  • How much should I expect to pay for a Portland to Chicago Midway Airport flight?

    Round-trip flights from Portland to Chicago Midway Airport range from $288 to $428, with an average of $353 over the past 12 months. Anything below $288 counts as a good deal.

  • Which airlines offer Wi-Fi on Portland to Chicago Midway Airport flights?

    JetBlue is the only airline on the Portland to Chicago Midway Airport route offering in-flight Wi-Fi. Pricing depends on fare class.

Your guide to booking Portland to Chicago Midway Airport flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates can be flexible, aim for a Wednesday departure instead of Monday. On this route, Wednesday flights average $316 - about $81 less than Monday (20% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 24 weeks before you fly. On this route, that window historically saves about 52% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Portland to Chicago Midway Airport trip for February. Fares historically average $253 round-trip in that month - typically $246 less than the most expensive month, which is December (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Denver Intl Airport (DEN) can be cheaper than flying direct. The cheapest layover option averages $274 round-trip on this route - about $81 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.
    - DoubleTree by Hilton Chicago Midway Airport
    - Holiday Inn Chicago - Midway Airport S by IHG
    - Skylark Motel

Prefer to fly direct from Portland to Chicago Midway Airport?

 
Find which airlines fly direct from Portland Airport to Chicago Midway Airport, which days they fly and book direct flights.

Direct departures

Portland to Chicago Midway

Monday

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Tuesday

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Wednesday

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Thursday

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Friday

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Saturday

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Sunday

Southwest

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See more direct flights

Direct returns

Chicago Midway to Portland

Monday

Southwest

Southwest

Tuesday

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Wednesday

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Thursday

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Friday

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Saturday

Southwest

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Sunday

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See more direct flights

More options for your flight from Portland to Midway

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