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Cheap flights from Portland to Chicago

43 nonstop flights a week, 5 of them today. Operated by 4 airlines, about 4h 45m in the air, 1,755 mi (2,824 km). Tickets from $145.

Flights from Portland to Chicago

Pick a departure date to see flights and seller prices

We search agencies and airlines for your day: nonstop and connecting flights, baggage, departure and arrival times.

Prices by day: Portland to Chicago

Lowest one-way price in dollars from recent searches, cheap days in green. Press a day to see flights and exact prices.

Filters

Best fares from Portland to Chicago

Lowest one-way prices found by recent searches for the next 120 days; press a card to search that date

Cheapest one-way $145 14 November 2026, nonstop Cheapest nonstop $145 14 November 2026, Alaska Airlines Cheapest in the next 7 days $145 14 November, Sat Cheapest weekend departure $145 Sat, 14 November 2026
Cheapest day of the week Saturday $211 on average over the next 120 days
Cheapest month November 2026 tickets from $145

Portland to Chicago at a glance

flight time, from 3h 49m to 9h 25m
4h 45m
straight-line distance
1,755 mi (2,824 km)
flights a week
43
flights today
5
first and last departure
05:50 - 13:19
lowest price, nonstop, 14 November
$145
average across months
$154
airlines
4

Portland to Chicago ticket prices by month

Lowest one-way fare found by recent searches

Cheapest month: November 2026, tickets from $145. Prices come from searches over the last few days; check the search for your exact date.

The most expensive month is December 2026: from $171. The average across months is $154.

Portland to Chicago flight schedule

43 flights a week, 5 today, 48 seasonal or one-off. Departure and arrival times are local.

FlightDepartsArrivesDurationDaysAircraft
WN 507
Southwest Airlines
05:50 Portland International
11:35 Chicago Midway International
4h 45m
Sat
Boeing 737
WN 507
Southwest Airlines
06:00 Portland International
11:50 Chicago Midway International
4h 50m
Mon, Tue, Wed, Thu
Boeing 737
AS 324
Alaska Airlines
07:00 Portland International
13:08 , terminal 2
5h 8m
Mon, Fri, Sat, Sun
Boeing 737
UA 2306
United Airlines
07:00 Portland International
13:07 , terminal 1
5h 7m
Tue, Wed, Thu, Fri
Boeing 737
AS 324
Alaska Airlines
07:01 Portland International
13:09 , terminal 2
5h 8m
Daily
Boeing 737-800
WN 537
Southwest Airlines
07:35 Portland International
17:35 Chicago Midway International
9h
Mon, Thu, Fri, Sun
Boeing 737-800
WN 507
Southwest Airlines
08:30 Portland International
14:15 Chicago Midway International
4h 45m
Sat
Boeing 737-800
UA 1114
United Airlines
09:00 Portland International
20:25 , terminal 1
9h 25m
Daily
Boeing 737-800
UA 1923
United Airlines
10:47 Portland International
16:53 , terminal 1
4h 6m
Daily
Boeing 737-900
WN 696
Southwest Airlines
11:20 Portland International
17:05 Chicago Midway International
4h 45m
Mon, Tue, Wed, Thu
Boeing 737
AA 561
American Airlines
13:19 Portland International
19:40 , terminal 3
5h 21m
Mon, Thu, Fri, Sat, Sun
Airbus A321

Seasonal and one-off flights

Not operating in the next two weeks. The first of them is on 24 November.

FlightDepartsArrivesDurationDaysAircraft
WN 507
Southwest Airlines
05:25 Portland International
11:15 Chicago Midway International
4h 50m
Seasonal
Boeing 737
WN 507
Southwest Airlines
07:00 Portland International
12:45 Chicago Midway International
4h 45m
Seasonal
Boeing 737-800
WN 507
Southwest Airlines
05:45 Portland International
11:30 Chicago Midway International
4h 45m
Seasonal
Boeing 737
WN 507
Southwest Airlines
05:20 Portland International
11:05 Chicago Midway International
4h 45m
Seasonal
Boeing 737
UA 1923
United Airlines
10:43 Portland International
16:49 , terminal 1
5h 6m
Seasonal
Boeing 737-900
UA 1923
United Airlines
10:49 Portland International
16:57 , terminal 1
5h 8m
Seasonal
Airbus A320
UA 2306
United Airlines
07:02 Portland International
13:06 , terminal 1
5h 4m
Seasonal
Boeing 737-800
UA 1923
United Airlines
10:45 Portland International
16:51 , terminal 1
5h 6m
Seasonal
Boeing 737-800
UA 1923
United Airlines
10:52 Portland International
17:00 , terminal 1
5h 8m
Seasonal
Airbus A320
UA 2306
United Airlines
07:10 Portland International
13:15 , terminal 1
5h 5m
Seasonal
Boeing 737
UA 1923
United Airlines
10:46 Portland International
16:53 , terminal 1
5h 7m
Seasonal
Boeing 737
WN 4309
Southwest Airlines
06:50 Portland International
12:40 Chicago Midway International
4h 50m
Seasonal
Boeing 737
WN 3059
Southwest Airlines
10:50 Portland International
16:40 Chicago Midway International
4h 50m
Seasonal
Boeing 737-800
WN 3059
Southwest Airlines
08:35 Portland International
14:25 Chicago Midway International
4h 50m
Seasonal
Boeing 737-800
WN 4309
Southwest Airlines
06:10 Portland International
12:00 Chicago Midway International
4h 50m
Seasonal
Boeing 737-800
WN 3059
Southwest Airlines
10:55 Portland International
16:45 Chicago Midway International
4h 50m
Seasonal
Boeing 737-800
WN 3216
Southwest Airlines
05:35 Portland International
11:25 Chicago Midway International
4h 50m
Seasonal
Boeing 737
AS 324
Alaska Airlines
07:02 Portland International
13:09 , terminal 2
5h 7m
Seasonal
Boeing 737-900
WN 2532
Southwest Airlines
12:15 Portland International
18:05 Chicago Midway International
4h 50m
Seasonal
Boeing 737
WN 3216
Southwest Airlines
06:20 Portland International
12:10 Chicago Midway International
4h 50m
Seasonal
Boeing 737
UA 2812
United Airlines
08:46 Portland International
14:50 , terminal 1
5h 4m
Seasonal
Boeing 737
WN 4559
Southwest Airlines
06:00 Portland International
11:55 Chicago Midway International
4h 55m
Seasonal
Boeing 737
WN 2901
Southwest Airlines
11:20 Portland International
17:15 Chicago Midway International
4h 55m
Seasonal
Boeing 737-800
WN 354
Southwest Airlines
06:00 Portland International
11:55 Chicago Midway International
4h 55m
Seasonal
Boeing 737
WN 4754
Southwest Airlines
05:35 Portland International
11:30 Chicago Midway International
3h 55m
Selected dates
Boeing 737
UA 2306
United Airlines
07:11 Portland International
13:00 , terminal 1
3h 49m
Seasonal
Boeing 737-800
UA 1114
United Airlines
10:57 Portland International
20:25 , terminal 1
7h 28m
Seasonal
Airbus A319
UA 1923
United Airlines
11:07 Portland International
16:59 , terminal 1
3h 52m
Seasonal
Boeing 737-800
WN 2190
Southwest Airlines
05:40 Portland International
11:40 Chicago Midway International
4h
Seasonal
Boeing 737-800
AA 1397
American Airlines
06:22 Portland International
12:32 , terminal 3
4h 10m
Seasonal
Airbus A321
WN 2523
Southwest Airlines
10:00 Portland International
15:55 Chicago Midway International
3h 55m
Seasonal
Boeing 737
WN 2807
Southwest Airlines
05:55 Portland International
11:55 Chicago Midway International
4h
Seasonal
Boeing 737
WN 2523
Southwest Airlines
12:00 Portland International
17:55 Chicago Midway International
3h 55m
Seasonal
WN 2797
Southwest Airlines
05:55 Portland International
11:55 Chicago Midway International
4h
Seasonal
Boeing 737
WN 2523
Southwest Airlines
08:35 Portland International
14:35 Chicago Midway International
4h
Seasonal
Boeing 737
WN 2577
Southwest Airlines
06:10 Portland International
12:10 Chicago Midway International
4h
Seasonal
Boeing 737
AA 1397
American Airlines
06:15 Portland International
12:31 , terminal 3
4h 16m
Seasonal
Boeing 737-800
AA 3223
American Airlines
11:20 Portland International
17:36 , terminal 3
4h 16m
Seasonal
Boeing 737-800
AA 1774
American Airlines
11:20 Portland International
17:39 , terminal 3
4h 19m
Seasonal
Airbus A321
WN 644
Southwest Airlines
05:15 Portland International
11:10 Chicago Midway International
3h 55m
Seasonal
Boeing 737
WN 4957
Southwest Airlines
11:50 Portland International
17:45 Chicago Midway International
3h 55m
Seasonal
Boeing 737
WN 644
Southwest Airlines
06:05 Portland International
12:00 Chicago Midway International
3h 55m
Seasonal
Boeing 737
WN 644
Southwest Airlines
05:20 Portland International
11:15 Chicago Midway International
3h 55m
Seasonal
Boeing 737
WN 4957
Southwest Airlines
11:30 Portland International
17:25 Chicago Midway International
3h 55m
Seasonal
Boeing 737
AA 1397
American Airlines
06:07 Portland International
12:17 , terminal 3
4h 10m
Seasonal
Boeing 737-800
AA 1774
American Airlines
11:26 Portland International
17:42 , terminal 3
4h 16m
Seasonal
Airbus A321
AA 1397
American Airlines
05:59 Portland International
12:12 , terminal 3
4h 13m
Seasonal
Boeing 737-800
AA 1774
American Airlines
12:24 Portland International
18:45 , terminal 3
4h 21m
Seasonal
Boeing 737-800

Days of the week are taken from the schedule for the next 14 days; schedules change by season. Chicago is 2 hours ahead of Portland. The search shows seat availability and the price for your date.

Airlines flying Portland to Chicago

Flights a week by schedule and the cheapest nonstop fare of each airline found by recent searches

United Airlines18 a week Southwest Airlines13 a week Alaska Airlines7 a week American Airlines5 a week

Airports

Where flights from Portland to Chicago depart and land

Departure from Portland

Portland International PDX

43 flights a week, 7 mi (11 km) from the city centre

About the airport

Arrival in Chicago

Chicago Midway International MDW

13 flights a week, 9 mi (14 km) from the city centre

About the airport

When to visit Chicago

Weather by month

Best time to visit: May, June, July, August, September and October, +18° to +27° by day. In November it is +10° by day and +2° at night, with 7 rainy days.

Jan
0° −7° 10 days
Feb
+2° −6° 7 days
Mar
+9° 0° 12 days
Apr
+14° +5° 13 days
May
+19° +10° 11 days
Jun
+27° +17° 9 days
Jul
+27° +19° 12 days
Aug
+27° +19° 10 days
Sep
+24° +16° 7 days
Oct
+18° +10° 11 days
Nov
+10° +2° 7 days
Dec
+4° −3° 10 days

Daytime and night temperatures in °C, rainy days. Months with the most comfortable weather are in green. Long-term averages.

Frequently asked questions

How long is the flight from Portland to Chicago?
A nonstop flight takes 4 hours 45 minutes on average, from 3h 49m to 9h 25m depending on the flight.
How far is Chicago from Portland?
1,755 mi (2,824 km) in a straight line between the cities.
Which airlines fly nonstop from Portland to Chicago?
United Airlines (18 a week), Southwest Airlines (13 a week), Alaska Airlines (7 a week) and American Airlines (5 a week).
How many flights a day are there from Portland to Chicago?
5 flights today and 43 a week, about 6.1 a day on average.
When are the first and last flights from Portland to Chicago?
The first departure is at 05:50 (WN507), the last at 13:19 (AA561). Local time.
What is the cheapest month to fly from Portland to Chicago?
November 2026: tickets from $145. The most expensive is December 2026, from $171.
What is the cheapest upcoming date to fly from Portland to Chicago?
14 November 2026 (Saturday): from $145 one way, nonstop, by recent searches. The search shows the price for your dates.
Which airline is the cheapest from Portland to Chicago?
Alaska Airlines: nonstop tickets from $145 on 14 November by recent searches. Prices change daily, so compare the sellers in the search.
What is the time difference between Portland and Chicago?
Chicago is 2 hours ahead of Portland. Schedule times on this page are local to each airport.
Which Portland airport do flights to Chicago leave from?
Portland International (43 a week).