$89 Cheap Delta flights from Portland to Chicago (PDX to MDW)

Find The Best Day To Fly from Portland to Chicago

Amazing Delta PDX to MDW Flight Deals

The cheapest flights to Midway Intl. found within the past 7 days were $177 round trip and $89 one way. Prices and availability subject to change. Additional terms may apply.

Sat, Aug 23 - Sat, Aug 23
PDX
Portland
MDW
Chicago
$177 Roundtrip, found 2 days ago
$177
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Aug 23 from Portland to Chicago, returning Sat, Aug 23, priced at $177 found 2 days ago
Sun, Aug 24 - Tue, Aug 26
PDX
Portland
MDW
Chicago
$179 Roundtrip, found 2 days ago
$179
Roundtrip
found 2 days ago
Select Delta flight, departing Sun, Aug 24 from Portland to Chicago, returning Tue, Aug 26, priced at $179 found 2 days ago
Sat, Sep 6 - Mon, Sep 8
PDX
Portland
MDW
Chicago
$252 Roundtrip, found 6 hours ago
$252
Roundtrip
found 6 hours ago
Select Delta flight, departing Sat, Sep 6 from Portland to Chicago, returning Mon, Sep 8, priced at $252 found 6 hours ago

MDW From PDX Economy Coach Packages on Similar Airlines

Price found within the past 48 hours. Click for updated prices.
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
per person
Aug 8 - Aug 12
found 9 hours ago
Roundtrip non-stop flight included
Portland (PDX) to Chicago (ORD)
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
Save 100% on your flight
per person
Aug 8 - Aug 12
found 9 hours ago
Roundtrip non-stop flight included
Portland (PDX) to Chicago (ORD)
Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

4 out of 5
per person
Aug 8 - Aug 12
found 9 hours ago
Roundtrip non-stop flight included
Portland (PDX) to Chicago (ORD)
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Frequently asked questions

Can I catch a flight from Portland Intl. Airport (PDX) to Midway Airport right now?
For information on any present Chicago Airport quarantine requirements and travel advice, visit the Covid-19 Travel Advisor. Look before you book your flight, so you don't get caught up en route.
What terminal is Delta Air Lines at PDX Airport?
Once you've received your ticket for your flight from PDX to Chicago Airport, you should be able to identify which terminals Delta Air Lines flies in and out of. If not, contact your airline or do some research online for that information.
Are there Delta Air Lines non-stop flights from PDX to MDW?
Expect at least one stopover when traveling from PDX to Chicago Airport, as Delta Air Lines doesn't offer any direct flights between these two locations. While in transit, you might like to pick up the local newspaper or an interesting magazine from the airport bookstore to help pass the time.
How long is a Delta Air Lines flight from PDX to MDW?
Your Delta Air Lines flight from PDX to Midway Intl. Airport (MDW) will take roughly 6 hours and 24 minutes. But there are plenty of things you can do to keep yourself occupied. Talking to the passenger beside you about their amazing travel experiences is one of them. If you'd prefer a different sort of in-flight entertainment, you could always watch a film.
How many direct and indirect flights does Delta Air Lines fly from PDX to MDW?
You can choose from about 3 Delta Air Lines flights each day from PDX to MDW.
If I am not able to travel due to COVID-19, can I change my booking to a later date?
For more info about changing your flight to Chicago Airport, please visit our Customer Service Portal.
What is the best day to buy a plane ticket?
This just in! Airfares offered on Thursdays tend to be the cheapest, according to flight demand on Travelocity in 2021. Tuesday and Wednesday prices are also good, but you may want to prepare your budget if booking during the weekend, as data shows that is when prices are generally at their highest.
What are the cheapest days to fly?
Frequent travelers may already know this, but earlier in the week can be the cheapest time to fly. In 2021, flights departing on a Monday were generally the cheapest of the week, whereas you may pay a premium for weekend flights when demand is usually high. On average, tickets were most expensive for Saturday departures, so if you need to fly out on a weekend, you might look for deals ahead of time.
How far in advance can you book a flight?
Trying to figure out how early you should book your flight? It's possible to start comparing international airfares on Travelocity up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2021 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 0-2 weeks prior to their travel dates.*According to flight demand on Travelocity.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

Discover our best Delta flight from Portland PDX to Chicago MDW 

To find the best deals on flights to Portland from Chicago with Delta, just enter your travel dates, filter by Delta, and hit search. You’ll find flights to choose from and can sort by price, flight duration, and arrival or departure time.  

 

Return flights from Portland PDX to Chicago MDW with Delta 

If you’re planning a round trip, booking return flights with Delta is usually the most cost-effective option. With airfares ranging from $177 to $252, it’s easy to find a flight that suits your budget. Prices and availability subject to change. Additional terms may apply. 

 

Book one-way Delta flights from Portland PDX to Chicago MDW 

A one-way ticket gives you much greater flexibility—allowing you to choose your return date, destination, and time whenever you’re ready. By booking in advance you can find great deals on one-way tickets too. Right now, a one-way Delta flight from Portland to Chicago costs from $89. Prices and availability subject to change. Additional terms may apply. 

 

The easy way to find cheap flights to Chicago MDW from  Portland PDX with Delta 

To find a cheap Delta flight from Portland PDX to Chicago MDW, sort your search results by price or filter by budget. Thanks to Travelocity’s Price Match Promise, if you find a better airfare deal anywhere else within 24 hours, we’ll credit or refund the difference. 

 

How to find our best airfare deals on Delta flights from Portland PDX to Chicago MDW 

If you’re looking for cheap flights, it helps to be flexible when it comes to your travel dates. You’ll usually find lower cost tickets when you travel during quieter months such as August, or if you book a flight with a stopover. 

 

Find nonstop flights from Portland PDX to Chicago MDW with Delta 

If you’re keen to be on Chicago soil fast, don’t waste time with a stopover—filter your search results to show direct Delta flights only. The journey takes around hour(s) min(s) – so you’ll be there before you know it. 

 

Flexible airline tickets for Delta flights from Portland PDX to Chicago MDW 

Make sure you’re not out of pocket if plans change by choosing a flexible ticket with penalty-free amendment and cancellation options. Use our ‘no change fee’ filter to see which flights have this option.  

 

There are a lot of reasons to book your flights to Chicago MDW from  Portland PDX with Delta on Travelocity 

At Travelocity our vast and up-to-the-minute inventory puts all of our best flight deals in one place. So, whether you’re traveling on business or jetting off with friends and family, you can trust Travelocity to get you there.

Delta Airports
Hop on a(n) Delta flight today by flying to many destinations out of these domestic and international airports:
Airport code
Country
Airport name
Number of flights
ATLUSAHartsfield-Jackson Atlanta Intl.252
DTWUSADetroit Metropolitan Wayne County156
MSPUSAMinneapolis - St. Paul Intl.131
SLCUSASalt Lake City Intl.116
SEAUSASeattle - Tacoma Intl.57
LAXUSALos Angeles Intl.41
AMSNLDSchiphol31
YYCCANCalgary Intl.26
YYZCANPearson Intl.24
JFKUSAJohn F. Kennedy Intl.23

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