Skip to content

United flights from Portland, OR to Chicago starting at

Select journey type

Enter to select travel class and passengers

Book with confidence with United

Low fare calendar for flights from Portland, OR (PDX) to Chicago (ORD)

Sunday
Monday
Tuesday
Wednesday
Thursday
Friday
Saturday
from
$411 Price subject to changes
Viewed:17 hours ago
Economy
Return:
from
$391 Price subject to changes
Viewed:17 hours ago
Economy
Return:
from
$337 Price subject to changes
Viewed:17 hours ago
Economy
Return:
from
$391 Price subject to changes
Viewed:8 hours ago
Economy
Return:
1
from
$446 Price subject to changes
Viewed:17 hours ago
Economy
Return:
2
from
$391 Price subject to changes
Viewed:17 hours ago
Economy
Return:
3
from
$327 Price subject to changes
Viewed:17 hours ago
Economy
Return:
4
from
$337 Price subject to changes
Viewed:17 hours ago
Economy
Return:
5
from
$381 Price subject to changes
Viewed:17 hours ago
Economy
Return:
6
from
$327 Price subject to changes
Viewed:17 hours ago
Economy
Return:
7
from
$327 Price subject to changes
Viewed:17 hours ago
Economy
Return:
8
from
$414 Price subject to changes
Viewed:17 hours ago
Economy
Return:
9
from
$231 Price subject to changes
Viewed:17 hours ago
Economy
Return:
10
from
$209 Price subject to changes
Viewed:17 hours ago
Economy
Return:
11
from
$231 Price subject to changes
Viewed:17 hours ago
Economy
Return:
12
from
$221 Price subject to changes
Viewed:17 hours ago
Economy
Return:
13
from
$209 Price subject to changes
Viewed:17 hours ago
Economy
Return:
14
from
$167 Price subject to changes
Viewed:17 hours ago
Economy
Return:
15
from
$221 Price subject to changes
Viewed:17 hours ago
Economy
Return:
16
from
$177 Price subject to changes
Viewed:17 hours ago
Economy
Return:
17
from
$189 Price subject to changes
Viewed:17 hours ago
Economy
Return:
18
from
$221 Price subject to changes
Viewed:8 hours ago
Economy
Return:
19
from
$189 Price subject to changes
Viewed:17 hours ago
Economy
Return:
20
from
$157 Price subject to changes
Viewed:17 hours ago
Economy
Return:
21
from
$157 Price subject to changes
Viewed:17 hours ago
Economy
Return:
22
from
$189 Price subject to changes
Viewed:17 hours ago
Economy
Return:
23
from
$177 Price subject to changes
Viewed:17 hours ago
Economy
Return:
24
from
$157 Price subject to changes
Viewed:17 hours ago
Economy
Return:
25
from
$219 Price subject to changes
Viewed:8 hours ago
Economy
Return:
26
from
$189 Price subject to changes
Viewed:17 hours ago
Economy
Return:
27
from
$157 Price subject to changes
Viewed:17 hours ago
Economy
Return:
28
from
$157 Price subject to changes
Viewed:17 hours ago
Economy
Return:
29
from
$189 Price subject to changes
Viewed:17 hours ago
Economy
Return:
30
from
$177 Price subject to changes
Viewed:8 hours ago
Economy
Return:
31
from
$157 Price subject to changes
Viewed:17 hours ago
Economy
Return:
Lowest PriceToday
*Prices have been available for round trips within the last 48 hours and may not be currently available. For Economy class, fares listed may be Basic Economy, which is our most restrictive fare option and subject to additional restrictions. Additional baggage charges and fees for other optional service may apply. Other terms and conditions may apply.

More United deals on Portland, OR (PDX) to Chicago (ORD) flights

FromToDatesFare TypePrice

Portland, OR (PDX)

Chicago (ORD)

Depart: 10/27/20

Return: 11/10/20

Roundtrip
from
$157*
Viewed:17hoursago

Portland, OR (PDX)

Chicago (ORD)

Depart: 10/28/20

Return: 11/11/20

Roundtrip
from
$157*
Viewed:17hoursago

Portland, OR (PDX)

Chicago (ORD)

Depart: 10/31/20

Return: 11/14/20

Roundtrip
from
$157*
Viewed:17hoursago

Portland, OR (PDX)

Chicago (ORD)

Depart: 11/02/20

Return: 11/16/20

Roundtrip
from
$157*
Viewed:17hoursago

Portland, OR (PDX)

Chicago (ORD)

Depart: 11/03/20

Return: 11/17/20

Roundtrip
from
$157*
Viewed:17hoursago

Portland, OR (PDX)

Chicago (ORD)

Depart: 11/04/20

Return: 11/18/20

Roundtrip
from
$157*
Viewed:17hoursago

Portland, OR (PDX)

Chicago (ORD)

Depart: 11/05/20

Return: 11/19/20

Roundtrip
from
$157*
Viewed:17hoursago

Portland, OR (PDX)

Chicago (ORD)

Depart: 11/07/20

Return: 11/21/20

Roundtrip
from
$157*
Viewed:17hoursago

Portland, OR (PDX)

Chicago (ORD)

Depart: 11/09/20

Return: 11/23/20

Roundtrip
from
$157*
Viewed:17hoursago

Portland, OR (PDX)

Chicago (ORD)

Depart: 11/10/20

Return: 11/24/20

Roundtrip
from
$157*
Viewed:17hoursago

*Prices have been available for round trips within the last 48 hours and may not be currently available. For Economy class, fares listed may be Basic Economy, which is our most restrictive fare option and subject to additional restrictions. Additional baggage charges and fees for other optional service may apply. Other terms and conditions may apply.

Weather in Chicago

Friday sky is clear
76°F 09/25/20
Saturday scattered clouds
79°F 09/26/20
Sunday light rain
74°F 09/27/20
Monday heavy intensity rain
56°F 09/28/20
Tuesday light rain
60°F 09/29/20
Wednesday few clouds
63°F 09/30/20
Thursday light rain
53°F 10/01/20
Powered by: OpenWeatherMap.org