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Cheap flights Portland — Chicago

Portland (PDX, US) Chicago (CHI, US)
from $145 2 824 km ~3h 49m 10 flights found 5 airlines cheapest on Sunday
Reverse route
How many travellers?
Adults
12+ years
1
Children
2–11 years
0
Infants
under 2
0
Choose your departure date
Cheapest: $145 on 14.11.2026
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 20 of 90 days. Prices update as more travellers search. Click any date to search live.
Depart
—
Return
—
Cheapest flights found
14 Nov 2026, Sat
Alaska Airlines AS 324
18:01
PDX Portland International Airport
22:09
ORD O'Hare International Airport
4h 8m Direct
Clickavia
$145
View this ticket
22 Nov 2026, Sun
Frontier Airlines F9 1104
09:10
PDX Portland International Airport
15:11
ORD O'Hare International Airport
6h 1m 1 stop
Farera
$167
View this ticket
19 Dec 2026, Sat
American Airlines AA 3329
10:31
PDX Portland International Airport
14:25
ORD O'Hare International Airport
3h 54m Direct
Wingie
$175
View this ticket
21 Nov 2026, Sat
Frontier Airlines F9 1106
00:58
PDX Portland International Airport
07:00
ORD O'Hare International Airport
6h 2m 1 stop
Farera
$189
View this ticket
14 Nov 2026, Sat
American Airlines AA 519
10:09
PDX Portland International Airport
14:07
ORD O'Hare International Airport
3h 58m Direct
Tickets
$195
View this ticket
22 Nov 2026, Sun
American Airlines AA 3329
10:11
PDX Portland International Airport
14:15
ORD O'Hare International Airport
4h 4m Direct
Wingie
$259
View this ticket
Route characteristics
Distance
2 824 km
Flight time
3h 49m
Time difference
+2h
Minimum price
from $145 (14.11.2026)
Average price
$214
Maximum price
$331
Departures per week
1
Cheapest day
Sunday
Departure airports (1)
PDX Portland International Airport
Arrival airports (2)
MDW Chicago Midway International Airport ORD O'Hare International Airport
Airlines (5)
AS Alaska Airlines F9 Frontier Airlines AA American Airlines UA United Airlines WN Southwest Airlines
Agencies (6)
Clickavia Farera Wingie Tickets Kiwi.com Wowtickets
Prices by day of week
Saturday
$145
avg $176
Sunday
$167
avg $213
Cheapest
Price trend by month
November 2026
from $145
avg $191
5 flights
December 2026
from $175
avg $175
1 flights
Airlines — cheapest prices 5
Alaska Airlines
Alaska Airlines
2 flights · 2 days
$145
Frontier Airlines
Frontier Airlines
Low-cost 2 flights · 2 days
$167
American Airlines
American Airlines
3 flights · 3 days
$175
United Airlines
United Airlines
2 flights · 2 days
$262
Southwest Airlines
Southwest Airlines
Low-cost 1 flights · 1 days
$331
Where to buy tickets 6
Clickavia
1 tickets · 1 days
from $145
Farera
4 tickets · 3 days
from $167
Wingie
2 tickets · 2 days
from $175
Tickets
1 tickets · 1 days
from $195
Kiwi.com
1 tickets · 1 days
from $322
Wowtickets
1 tickets · 1 days
from $337
Airports

From — Portland (1)

  • PDX Portland International Airport

To — Chicago (2)

  • MDW Chicago Midway International Airport
  • ORD O'Hare International Airport
Other destinations from Portland
Albuquerque
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US
Adler/Sochi
RU
Almaty
KZ
Amsterdam
NL · Hub
Anchorage
US
Atlanta
US · Hub
Billings
US
Bangkok
TH · Hub
Nashville
US
Banja Luka
BA
Boise
US
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 $145 on 14.11.2026.
What is the average ticket price?
The average price — $214. Range: $145 — $331.
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), ORD (O'Hare International Airport).
Which airlines fly this route?
This route is served by 5 airlines: Alaska Airlines, Frontier Airlines, American Airlines, United Airlines, Southwest Airlines.
Are there direct flights?
Yes, there are direct flights. Minimum direct price — from $145. Total direct flights found: 4.
Which day of the week is cheapest?
The cheapest day of the week — Sunday.
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 (CHI) — 2 arrival airports: MDW, ORD.

5 airlines operate on this route: Alaska Airlines, Frontier Airlines, American Airlines, United Airlines, Southwest Airlines.

The minimum price for the next 3 months — from $145 (14.11.2026). The cheapest dates are highlighted in the calendar above.

The average ticket price — $214, ranging from $145 to $331. Book 1–3 months in advance to get the best deals.

Cheapest day to fly — Sunday.

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

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