Cheapest flight routes found to Chicago, Illinois
From Calgary (YYC), Canada to Chicago, United States (ORD):
C$191
Depart: 23 Oct 2025 · Return: 26 Oct 2025
Price found 13 Jul 2025, 23:31
From Montreal (YUL), Canada to Chicago, United States (ORD):
C$228
Depart: 31 Oct 2025 · Return: 02 Nov 2025
Price found 13 Jul 2025, 00:43
From Edmonton (YEG), Canada to Chicago, United States (ORD):
C$247
Depart: 20 Sep 2025 · Return: 21 Sep 2025
Price found 14 Jul 2025, 02:50
From Vancouver (YVR), Canada to Chicago, United States (ORD):
C$274
Depart: 17 Oct 2025 · Return: 20 Oct 2025
Price found 12 Jul 2025, 03:21
From Saskatoon (YXE), Canada to Chicago, United States (ORD):
C$287
Depart: 17 Sep 2025 · Return: 24 Sep 2025
Price found 14 Jul 2025, 19:32
From Winnipeg (YWG), Canada to Chicago, United States (ORD):
C$295
Depart: 02 Oct 2025 · Return: 04 Oct 2025
Price found 11 Jul 2025, 03:56
From Victoria (YYJ), Canada to Chicago, United States (ORD):
C$296
Depart: 05 Sep 2025 · Return: 08 Sep 2025
Price found 14 Jul 2025, 18:47
From Regina (YQR), Canada to Chicago, United States (ORD):
C$325
Depart: 03 Nov 2025 · Return: 10 Nov 2025
Price found 11 Jul 2025, 15:39
From Thunder Bay (YQT), Canada to Chicago, United States (MDW):
C$347
Depart: 04 Sep 2025 · Return: 08 Sep 2025
Price found 13 Jul 2025, 19:12
From Halifax (YHZ), Canada to Chicago, United States (MDW):
C$379
Depart: 18 Oct 2025 · Return: 21 Oct 2025
Price found 14 Jul 2025, 10:45
From Ottawa (YOW), Canada to Chicago, United States (MDW):
C$413
Depart: 19 Sep 2025 · Return: 22 Sep 2025
Price found 11 Jul 2025, 16:23
From Quebec (YQB), Canada to Chicago, United States (ORD):
C$424
Depart: 04 Nov 2025 · Return: 19 Nov 2025
Price found 14 Jul 2025, 17:23
From Kelowna (YLW), Canada to Chicago, United States (ORD):
C$459
Depart: 24 Aug 2025 · Return: 31 Aug 2025
Price found 10 Jul 2025, 23:18
From St John's (YYT), Canada to Chicago, United States (MDW):
C$531
Depart: 20 Sep 2025 · Return: 21 Sep 2025
Price found 14 Jul 2025, 02:01
From Moncton (YQM), Canada to Chicago, United States (ORD):
C$575
Depart: 15 Aug 2025 · Return: 16 Aug 2025
Price found 10 Jul 2025, 23:10