Cheapest flight routes found to Chicago, Illinois
From Toronto (YYZ), Canada to Chicago, United States (ORD):
C$200
Depart: 25 Nov 2025 · Return: 30 Nov 2025
Price found 23 Jul 2025, 13:56
From Montreal (YUL), Canada to Chicago, United States (ORD):
C$219
Depart: 04 Nov 2025 · Return: 12 Nov 2025
Price found 22 Jul 2025, 22:58
From Calgary (YYC), Canada to Chicago, United States (ORD):
C$222
Depart: 17 Nov 2025 · Return: 24 Nov 2025
Price found 21 Jul 2025, 17:42
From Vancouver (YVR), Canada to Chicago, United States (ORD):
C$307
Depart: 16 Sep 2025 · Return: 23 Sep 2025
Price found 23 Jul 2025, 10:04
From Edmonton (YEG), Canada to Chicago, United States (ORD):
C$324
Depart: 02 Sep 2025 · Return: 06 Sep 2025
Price found 22 Jul 2025, 06:16
From Victoria (YYJ), Canada to Chicago, United States (ORD):
C$333
Depart: 16 Oct 2025 · Return: 24 Oct 2025
Price found 23 Jul 2025, 09:54
From Winnipeg (YWG), Canada to Chicago, United States (ORD):
C$343
Depart: 06 Sep 2025 · Return: 13 Sep 2025
Price found 23 Jul 2025, 16:04
From Kelowna (YLW), Canada to Chicago, United States (ORD):
C$361
Depart: 03 Sep 2025 · Return: 08 Sep 2025
Price found 20 Jul 2025, 18:25
From Ottawa (YOW), Canada to Chicago, United States (MDW):
C$399
Depart: 08 Sep 2025 · Return: 18 Sep 2025
Price found 23 Jul 2025, 01:33
From Saskatoon (YXE), Canada to Chicago, United States (ORD):
C$412
Depart: 08 Sep 2025 · Return: 12 Sep 2025
Price found 21 Jul 2025, 07:32
From Quebec (YQB), Canada to Chicago, United States (MDW):
C$435
Depart: 04 Sep 2025 · Return: 11 Sep 2025
Price found 23 Jul 2025, 01:52
From Regina (YQR), Canada to Chicago, United States (ORD):
C$449
Depart: 03 Nov 2025 · Return: 10 Nov 2025
Price found 23 Jul 2025, 01:03
From Halifax (YHZ), Canada to Chicago, United States (MDW):
C$473
Depart: 25 Nov 2025 · Return: 27 Nov 2025
Price found 22 Jul 2025, 23:21
From Comox (YQQ), Canada to Chicago, United States (ORD):
C$475
Depart: 28 Aug 2025 · Return: 03 Sep 2025
Price found 20 Jul 2025, 23:03
From Fort Mcmurray (YMM), Canada to Chicago, United States (ORD):
C$487
Depart: 08 Sep 2025 · Return: 12 Sep 2025
Price found 23 Jul 2025, 18:12
From Thunder Bay (YQT), Canada to Chicago, United States (MDW):
C$518
Depart: 07 Nov 2025 · Return: 10 Nov 2025
Price found 22 Jul 2025, 12:31
From Timmins (YTS), Canada to Chicago, United States (ORD):
C$557
Depart: 24 Sep 2025 · Return: 03 Oct 2025
Price found 21 Jul 2025, 03:12
From Moncton (YQM), Canada to Chicago, United States (MDW):
C$575
Depart: 08 Sep 2025 · Return: 12 Sep 2025
Price found 22 Jul 2025, 16:02
From St John's (YYT), Canada to Chicago, United States (MDW):
C$591
Depart: 29 Aug 2025 · Return: 07 Sep 2025
Price found 21 Jul 2025, 17:22
From Yellowknife (YZF), Canada to Chicago, United States (MDW):
C$1,042
Depart: 07 Mar 2026 · Return: 14 Mar 2026
Price found 21 Jul 2025, 20:28