FFL Helper

FFL Helper / Portland / Chicago

PDX → CHI

Portland (PDX) to Chicago (CHI)

Compare one-way fares for flights from Portland to Chicago.

Lowest fare $186
Distance 1,754 mi
Flight time 14h 51m
Airports PDX–ORD
Search this route

Ad. Ticket links are affiliate ads. We may earn a commission if you book. Advertising disclosure

By month: October 2026 from $186

Price calendar

October 2026

From $186 · up to $266

Mon
Tue
Wed
Thu
Fri
Sat
Sun
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23 $186 24 $226 25 $226 26 $226 27 $226 28 $226 29 $226 30 $266
31

November 2026

Mon
Tue
Wed
Thu
Fri
Sat
Sun
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30

Upcoming dates

Chicago CHI

$186

Oct 23, 12:25pm · 14h 51m · 1 stop

PDX → ORD · Frontier Airlines

Tickets

Chicago CHI

$266

Oct 30, 5:20am · 3h 50m · 0 stops

PDX → MDW · Southwest Airlines

Tickets

About this route

This calendar shows dated one-way fares from Portland to Chicago. Use it to see which days are cheaper before you search tickets.

Flight time and airport codes on this page are for the sample itinerary we have on file. Always confirm the live routing when you book Portland to Chicago.