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Home / Portland — Chicago

Cheap flights Portland — Chicago

Portland (PDX, US) Chicago (MDW, US)
from $195 2 824 km ~3h 49m 11 flights found 1 airlines cheapest on Friday
Reverse route
How many travellers?
Adults
12+ years
1
Children
2–11 years
0
Infants
under 2
0
Choose your departure date
Cheapest: $195 on 18.12.2026
Prices shown are from searches by other travellers over the last 24 hours. Missing a date? Click any day — we'll find tickets anyway.
November 2026
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Th
Fr
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Su
December 2026
Mo
Tu
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January 2027
Mo
Tu
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Prices found for 17 of 90 days. Prices update as more travellers search. Click any date to search live.
Depart
—
Return
—
Cheapest flights found
18 Dec 2026, Fri
Southwest Airlines WN 507
16:25
PDX Portland International Airport
20:15
MDW Chicago Midway International Airport
3h 50m Direct
Tickets
$195
View this ticket
21 Nov 2026, Sat
Southwest Airlines WN 3350
10:30
PDX Portland International Airport
14:15
MDW Chicago Midway International Airport
3h 45m Direct
Skytripfare
$273
View this ticket
22 Nov 2026, Sun
Southwest Airlines WN 3350
10:30
PDX Portland International Airport
14:15
MDW Chicago Midway International Airport
3h 45m Direct
Farera
$274
View this ticket
16 Nov 2026, Mon
Southwest Airlines WN 3350
10:30
PDX Portland International Airport
14:15
MDW Chicago Midway International Airport
3h 45m Direct
Farera
$278
View this ticket
30 Nov 2026, Mon
Southwest Airlines WN 3436
07:00
PDX Portland International Airport
12:20
MDW Chicago Midway International Airport
5h 20m 1 stop
Farera
$331
View this ticket
30 Nov 2026, Mon
Southwest Airlines WN 3350
10:30
PDX Portland International Airport
14:15
MDW Chicago Midway International Airport
3h 45m Direct
Farera
$340
View this ticket
Route characteristics
Distance
2 824 km
Flight time
3h 49m
Time difference
+2h
Minimum price
from $195 (18.12.2026)
Average price
$297
Maximum price
$371
Departures per week
1
Cheapest day
Friday
Departure airports (1)
PDX Portland International Airport
Arrival airports (1)
MDW Chicago Midway International Airport
Airlines (1)
WN Southwest Airlines
Agencies (3)
Tickets Farera Skytripfare
Prices by day of week
Monday
$278
avg $316
Friday
$195
avg $195
Cheapest
Saturday
$273
avg $273
Sunday
$274
avg $274
Price trend by month
November 2026
from $273
avg $299
5 flights
December 2026
from $195
avg $195
1 flights
Airlines — cheapest prices 1
Southwest Airlines
Southwest Airlines
Low-cost 11 flights · 9 days
$195
Where to buy tickets 3
Tickets
1 tickets · 1 days
from $195
Farera
9 tickets · 7 days
from $257
Skytripfare
1 tickets · 1 days
from $273
Airports

From — Portland (1)

  • PDX Portland International Airport

To — Chicago (1)

  • MDW Chicago Midway International Airport
Other destinations from Portland
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Billings
US
Bangkok
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Nashville
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Banja Luka
BA
Boise
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Frequently asked questions about the route Portland — Chicago
How long is the flight from Portland to Chicago?
Approximate flight time — 3h 49m. This is an average for a direct flight. With connections, the time may be longer.
What is the distance from Portland to Chicago?
The straight-line distance — 2 824 km.
How much do flights from Portland to Chicago cost?
The minimum price over 3 months — from $195 on 18.12.2026.
What is the average ticket price?
The average price — $297. Range: $195 — $371.
What is the time difference between Portland and Chicago?
The difference — +2h.
From which airports does Portland operate flights?
From Portland: PDX (Portland International Airport).
To which airports in Chicago do flights arrive?
To Chicago: MDW (Chicago Midway International Airport).
Which airlines fly this route?
This route is served by 1 airline: Southwest Airlines.
Are there direct flights?
Yes, there are direct flights. Minimum direct price — from $195. Total direct flights found: 5.
Which day of the week is cheapest?
The cheapest day of the week — Friday.
When is the best time to buy tickets?
Optimal — 1–3 months before departure. Check the calendar above — it shows the best dates.
How do I book flights?
Click "View this ticket" on any flight card — you'll be redirected to the booking page with this specific ticket pre-selected.
About the route Portland — Chicago

Flights Portland — Chicago is a popular route. The straight-line distance is 2 824 km. Flight time 3h 49m. Time difference +2h.

From Portland (PDX) flights depart from 1 airport: PDX. To Chicago (MDW) — 1 arrival airport: MDW.

1 airline operate on this route: Southwest Airlines.

The minimum price for the next 3 months — from $195 (18.12.2026). The cheapest dates are highlighted in the calendar above.

The average ticket price — $297, ranging from $195 to $371. Book 1–3 months in advance to get the best deals.

Cheapest day to fly — Friday.

Other destinations in United States from Portland
Pierre
US
Everett
US
Pendleton
US
Phoenix
US
Palm Springs
US
Redmond
US
North Bend
US
Pasco
US

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