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Cheap flights Chicago — Portland

Chicago (MDW, US) Portland (PDX, US)
from $195 2 824 km ~3h 49m 7 flights found 1 airlines cheapest on Monday
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 20.12.2026
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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Su
December 2026
Mo
Tu
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January 2027
Mo
Tu
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Prices found for 12 of 90 days. Prices update as more travellers search. Click any date to search live.
Depart
—
Return
—
Cheapest flights found
21 Dec 2026, Mon
Southwest Airlines WN 3295
06:30
MDW Chicago Midway International Airport
11:15
PDX Portland International Airport
4h 45m Direct
Farera
$195
View this ticket
14 Nov 2026, Sat
Southwest Airlines WN 1045
19:25
MDW Chicago Midway International Airport
00:00
PDX Portland International Airport
4h 35m Direct
Farera
$260
View this ticket
14 Nov 2026, Sat
Southwest Airlines WN 3295
06:15
MDW Chicago Midway International Airport
10:55
PDX Portland International Airport
4h 40m Direct
Farera
$270
View this ticket
15 Nov 2026, Sun
Southwest Airlines WN 1045
19:10
MDW Chicago Midway International Airport
23:45
PDX Portland International Airport
4h 35m Direct
Farera
$280
View this ticket
20 Nov 2026, Fri
Southwest Airlines WN 1045
19:10
MDW Chicago Midway International Airport
23:45
PDX Portland International Airport
4h 35m Direct
Farera
$285
View this ticket
23 Nov 2026, Mon
Southwest Airlines WN 1045
19:10
MDW Chicago Midway International Airport
23:45
PDX Portland International Airport
4h 35m Direct
Farera
$285
View this ticket
Route characteristics
Distance
2 824 km
Flight time
3h 49m
Time difference
-2h
Minimum price
from $195 (20.12.2026)
Average price
$267
Maximum price
$285
Departures per week
1
Cheapest day
Monday
Departure airports (1)
MDW Chicago Midway International Airport
Arrival airports (1)
PDX Portland International Airport
Airlines (1)
WN Southwest Airlines
Agencies (1)
Farera
Prices by day of week
Monday
$195
avg $240
Cheapest
Friday
$285
avg $285
Saturday
$260
avg $265
Sunday
$280
avg $280
Price trend by month
November 2026
from $260
avg $276
5 flights
December 2026
from $195
avg $195
1 flights
Airlines — cheapest prices 1
Southwest Airlines
Southwest Airlines
Low-cost 7 flights · 6 days
$195
Where to buy tickets 1
Farera
7 tickets · 6 days
from $195
Airports

From — Chicago (1)

  • MDW Chicago Midway International Airport

To — Portland (1)

  • PDX Portland International Airport
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Boston
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Buffalo
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Baltimore
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Frequently asked questions about the route Chicago — Portland
How long is the flight from Chicago to Portland?
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 Chicago to Portland?
The straight-line distance — 2 824 km.
How much do flights from Chicago to Portland cost?
The minimum price over 3 months — from $195 on 20.12.2026.
What is the average ticket price?
The average price — $267. Range: $195 — $285.
What is the time difference between Chicago and Portland?
The difference — -2h.
From which airports does Chicago operate flights?
From Chicago: MDW (Chicago Midway International Airport).
To which airports in Portland do flights arrive?
To Portland: PDX (Portland 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: 6.
Which day of the week is cheapest?
The cheapest day of the week — Monday.
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 Chicago — Portland

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

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

1 airline operate on this route: Southwest Airlines.

The minimum price for the next 3 months — from $195 (20.12.2026). The cheapest dates are highlighted in the calendar above.

The average ticket price — $267, ranging from $195 to $285. Book 1–3 months in advance to get the best deals.

Cheapest day to fly — Monday.

Other destinations in United States from Chicago
Omaha
US
Providence
US
Pittsburgh
US
Phoenix
US
Philadelphia
US
Norfolk
US
Ontario
US
New Orleans
US

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