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Cheap flights from Chicago to Portland

42 nonstop flights a week, 5 of them today. Operated by 4 airlines, about 3h 47m in the air, 1,755 mi (2,824 km). Tickets from $183, nonstop from $210.

Flights from Chicago to Portland

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: Chicago to Portland

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 Chicago to Portland

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

Cheapest one-way $183 15 November 2026, with a connection Cheapest nonstop $210 14 November 2026, Southwest Airlines Cheapest in the next 7 days $183 15 November, Sun Cheapest weekend departure $210 Sat, 14 November 2026 Cheapest month November 2026 tickets from $183

Chicago to Portland at a glance

flight time, from 3h 25m to 9h 8m
3h 47m
straight-line distance
1,755 mi (2,824 km)
flights a week
42
flights today
5
first and last departure
09:00 - 13:30
lowest price, with a connection, 15 November
$183
lowest nonstop price
$210
airlines
4

Chicago to Portland flight schedule

42 flights a week, 5 today, 39 seasonal or one-off. Departure and arrival times are local.

FlightDepartsArrivesDurationDaysAircraft
UA 751
United Airlines
09:00 , terminal 1
11:47 Portland International
4h 47m
Wed, Thu, Sun
Boeing 737
UA 751
United Airlines
09:05 , terminal 1
11:52 Portland International
4h 47m
Mon, Tue, Fri, Sat
Boeing 737
AA 561
American Airlines
09:44 , terminal 3
12:26 Portland International
3h 42m
Mon, Thu, Fri, Sat, Sun
Airbus A321
AA 562
American Airlines
09:45 , terminal 3
12:28 Portland International
3h 43m
Daily
Airbus A321
WN 1045
Southwest Airlines
10:00 Chicago Midway International
12:35 Portland International
3h 35m
Mon, Tue, Wed, Thu
Boeing 737
WN 3295
Southwest Airlines
10:05 Chicago Midway International
12:40 Portland International
3h 35m
Sat
Boeing 737
WN 1045
Southwest Airlines
10:10 Chicago Midway International
12:45 Portland International
3h 35m
Mon, Fri, Sun
Boeing 737
WN 1045
Southwest Airlines
10:25 Chicago Midway International
13:00 Portland International
3h 35m
Sat
Boeing 737
WN 162
Southwest Airlines
12:30 Chicago Midway International
19:30 Portland International
8h
Sat
UA 2182
United Airlines
12:49 , terminal 1
15:23 Portland International
3h 34m
Daily
Boeing 737-800
UA 1811
United Airlines
13:30 , terminal 1
20:33 Portland International
9h 3m
Daily
Boeing 737

Seasonal and one-off flights

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

FlightDepartsArrivesDurationDaysAircraft
WN 1045
Southwest Airlines
10:05 Chicago Midway International
12:45 Portland International
3h 40m
Seasonal
Boeing 737
UA 751
United Airlines
08:48 , terminal 1
11:35 Portland International
3h 47m
Seasonal
Boeing 737
UA 2182
United Airlines
12:48 , terminal 1
15:29 Portland International
3h 41m
Seasonal
Airbus A319
WN 281
Southwest Airlines
10:05 Chicago Midway International
12:35 Portland International
3h 30m
Seasonal
Boeing 737
WN 1045
Southwest Airlines
09:35 Chicago Midway International
12:10 Portland International
3h 35m
Seasonal
Boeing 737
UA 751
United Airlines
08:58 , terminal 1
11:41 Portland International
3h 43m
Seasonal
Boeing 737
UA 2182
United Airlines
12:40 , terminal 1
15:19 Portland International
3h 39m
Seasonal
Boeing 737-800
UA 751
United Airlines
08:59 , terminal 1
11:42 Portland International
3h 43m
Seasonal
Boeing 737
AA 563
American Airlines
10:00 , terminal 3
12:56 Portland International
3h 56m
Seasonal
Airbus A321
AA 563
American Airlines
10:05 , terminal 3
13:01 Portland International
3h 56m
Seasonal
Airbus A321
AA 563
American Airlines
09:55 , terminal 3
12:47 Portland International
3h 52m
Seasonal
Airbus A321
WN 2087
Southwest Airlines
10:15 Chicago Midway International
12:40 Portland International
3h 25m
Seasonal
Boeing 737
AA 819
American Airlines
10:30 , terminal 3
13:16 Portland International
3h 46m
Seasonal
Airbus A321
WN 2087
Southwest Airlines
10:10 Chicago Midway International
12:35 Portland International
3h 25m
Seasonal
Boeing 737
AA 819
American Airlines
10:20 , terminal 3
13:06 Portland International
3h 46m
Seasonal
Airbus A321
UA 751
United Airlines
09:06 , terminal 1
11:53 Portland International
3h 47m
Seasonal
Boeing 737
AA 820
American Airlines
10:00 , terminal 3
12:39 Portland International
3h 39m
Seasonal
Airbus A321
WN 590
Southwest Airlines
10:10 Chicago Midway International
12:35 Portland International
3h 25m
Seasonal
Boeing 737
WN 138
Southwest Airlines
10:10 Chicago Midway International
12:35 Portland International
3h 25m
Seasonal
Boeing 737
UA 1402
United Airlines
07:25 , terminal 1
10:12 Portland International
3h 47m
Seasonal
Boeing 737
WN 2615
Southwest Airlines
10:05 Chicago Midway International
12:40 Portland International
3h 35m
Seasonal
Boeing 737
WN 2615
Southwest Airlines
10:55 Chicago Midway International
13:25 Portland International
3h 30m
Seasonal
Boeing 737
WN 2615
Southwest Airlines
10:25 Chicago Midway International
13:00 Portland International
4h 35m
Seasonal
Boeing 737
UA 751
United Airlines
09:15 , terminal 1
11:35 Portland International
4h 20m
Seasonal
Boeing 737-800
UA 1811
United Airlines
13:25 , terminal 1
20:33 Portland International
9h 8m
Seasonal
Airbus A320
WN 4450
Southwest Airlines
10:10 Chicago Midway International
12:35 Portland International
4h 25m
Seasonal
Boeing 737
AA 937
American Airlines
11:52 , terminal 3
14:24 Portland International
4h 32m
Seasonal
Airbus A321
WN 4450
Southwest Airlines
10:15 Chicago Midway International
12:40 Portland International
4h 25m
Seasonal
Boeing 737
WN 4450
Southwest Airlines
10:25 Chicago Midway International
12:50 Portland International
4h 25m
Seasonal
Boeing 737
AA 3223
American Airlines
07:29 , terminal 3
09:57 Portland International
4h 28m
Seasonal
Boeing 737-800
AA 937
American Airlines
12:09 , terminal 3
14:35 Portland International
4h 26m
Seasonal
Airbus A321
AS 345
Alaska Airlines
07:00 , terminal 2
09:34 Portland International
4h 34m
Seasonal
Boeing 737-900
AA 1774
American Airlines
08:00 , terminal 3
10:25 Portland International
4h 25m
Seasonal
Airbus A321
AA 937
American Airlines
12:15 , terminal 3
14:38 Portland International
4h 23m
Seasonal
Airbus A321
WN 2715
Southwest Airlines
09:55 Chicago Midway International
12:15 Portland International
4h 20m
Seasonal
Boeing 737
WN 2715
Southwest Airlines
10:10 Chicago Midway International
12:35 Portland International
4h 25m
Seasonal
Boeing 737
WN 2715
Southwest Airlines
11:00 Chicago Midway International
13:25 Portland International
4h 25m
Seasonal
Boeing 737
AA 937
American Airlines
12:10 , terminal 3
14:40 Portland International
4h 30m
Seasonal
Airbus A321
AA 1774
American Airlines
09:00 , terminal 3
11:34 Portland International
4h 34m
Seasonal
Boeing 737-800

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

Airlines flying Chicago to Portland

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

United Airlines21 a week American Airlines12 a week Southwest Airlines9 a week Alaska Airlinesfrom 13 May

Airports

Where flights from Chicago to Portland depart and land

Departure from Chicago

Chicago Midway International MDW

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

About the airport

Arrival in Portland

Portland International PDX

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

About the airport

Frequently asked questions

How long is the flight from Chicago to Portland?
A nonstop flight takes 3 hours 47 minutes on average, from 3h 25m to 9h 8m depending on the flight.
How far is Portland from Chicago?
1,755 mi (2,824 km) in a straight line between the cities.
Which airlines fly nonstop from Chicago to Portland?
United Airlines (21 a week), American Airlines (12 a week), Southwest Airlines (9 a week) and Alaska Airlines.
How many flights a day are there from Chicago to Portland?
5 flights today and 42 a week, about 6 a day on average.
When are the first and last flights from Chicago to Portland?
The first departure is at 09:00 (UA751), the last at 13:30 (UA1811). Local time.
What is the cheapest upcoming date to fly from Chicago to Portland?
15 November 2026 (Sunday): from $183 one way, with a connection, by recent searches. The search shows the price for your dates.
Which airline is the cheapest from Chicago to Portland?
Southwest Airlines: nonstop tickets from $210 on 14 November by recent searches. Prices change daily, so compare the sellers in the search.
What is the time difference between Chicago and Portland?
Portland is 2 hours behind Chicago. Schedule times on this page are local to each airport.
Which Chicago airport do flights to Portland leave from?
Chicago Midway International (9 a week).