Flight Deals from Chicago to Canada from $206
Top flight deals from leading airlines:
... and +100s more
Save up to 50% on select flights with Priceline
Save an average of $240 per person when bundling your flight and hotel together with Priceline
If a VIP member finds a better price elsewhere, we'll refund up to 200% of the difference
We’re always here for you - reach us 24 hours a day, 7 days a week
Top Deals on flights from Chicago to Toronto
Chicago, US (CHI) - Toronto, CA (YTO)
May 12
May 12
May 12
May 12
as low as
$206
Chicago, US (CHI) - Toronto, CA (YTO)
May 13
May 13
May 13
May 13
as low as
$222
Chicago, US (CHI) - Toronto, CA (YTO)
May 24
May 24
May 28
May 28
as low as
$254
Chicago, US (CHI) - Toronto, CA (YTO)
Jun 11
Jun 11
Jun 15
Jun 15
as low as
$280
Chicago, US (CHI) - Toronto, CA (YTO)
May 25
May 25
May 28
May 28
as low as
$296
Chicago, US (CHI) - Toronto, CA (YTO)
Jun 15
Jun 15
Jun 19
Jun 19
as low as
$320
Chicago, US (CHI) - Toronto, CA (YTO)
May 25
May 25
May 28
May 28
as low as
$442
Chicago, US (CHI) - Toronto, CA (YTO)
May 24
May 24
May 28
May 28
as low as
$452
Chicago, US (CHI) - Toronto, CA (YTO)
Jun 6
Jun 7
Jun 7
Jun 7
as low as
$480
Chicago, US (CHI) - Toronto, CA (YTO)
May 24
May 25
May 28
May 28
as low as
$504
Chicago, US (CHI) - Toronto, CA (YTO)
May 25
May 25
May 28
May 28
as low as
$1044
Top Deals on flights from Chicago to Vancouver
Chicago, US (CHI) - Vancouver, CA (YVR)
May 8
May 8
May 18
May 18
as low as
$223
Chicago, US (CHI) - Vancouver, CA (YVR)
May 25
May 25
May 28
May 29
as low as
$541
Chicago, US (CHI) - Vancouver, CA (YVR)
Apr 24
Apr 25
Apr 27
Apr 28
as low as
$544
Chicago, US (CHI) - Vancouver, CA (YVR)
Apr 24
Apr 25
Apr 26
Apr 27
as low as
$577
Chicago, US (CHI) - Vancouver, CA (YVR)
Jun 5
Jun 6
Jun 8
Jun 8
as low as
$670
Chicago, US (CHI) - Vancouver, CA (YVR)
Jun 11
Jun 11
Jun 17
Jun 17
as low as
$689
Chicago, US (CHI) - Vancouver, CA (YVR)
Apr 24
Apr 25
Apr 26
Apr 26
as low as
$756
Chicago, US (CHI) - Vancouver, CA (YVR)
Apr 24
Apr 24
Apr 26
Apr 26
as low as
$885
Chicago, US (CHI) - Vancouver, CA (YVR)
Apr 24
Apr 24
Apr 26
Apr 26
as low as
$923
Chicago, US (CHI) - Vancouver, CA (YVR)
Apr 24
Apr 24
Apr 26
Apr 26
as low as
$934
Chicago, US (CHI) - Vancouver, CA (YVR)
Apr 24
Apr 24
Apr 26
Apr 26
as low as
$1225
Chicago, US (CHI) - Vancouver, CA (YVR)
Apr 24
Apr 24
Apr 26
Apr 26
as low as
$1505
Top Deals on flights from Chicago to Montreal
Chicago, US (CHI) - Montreal, CA (YMQ)
Aug 27
Aug 27
Sep 1
Sep 1
as low as
$364
Chicago, US (CHI) - Montreal, CA (YMQ)
Aug 27
Aug 27
Sep 1
Sep 1
as low as
$364
Chicago, US (CHI) - Montreal, CA (YMQ)
Sep 5
Sep 5
Sep 7
Sep 7
as low as
$408
Chicago, US (CHI) - Montreal, CA (YMQ)
Sep 9
Sep 9
Sep 14
Sep 14
as low as
$416
Chicago, US (CHI) - Montreal, CA (YMQ)
Aug 17
Aug 17
Aug 21
Aug 21
as low as
$433
Chicago, US (CHI) - Montreal, CA (YMQ)
Sep 1
Sep 1
Sep 5
Sep 5
as low as
$443
Chicago, US (CHI) - Montreal, CA (YMQ)
Aug 26
Aug 26
Aug 31
Aug 31
as low as
$447
Chicago, US (CHI) - Montreal, CA (YMQ)
Sep 5
Sep 5
Sep 7
Sep 7
as low as
$458
Chicago, US (CHI) - Montreal, CA (YMQ)
Sep 9
Sep 9
Sep 14
Sep 14
as low as
$466
Chicago, US (CHI) - Montreal, CA (YMQ)
Aug 19
Aug 19
Aug 23
Aug 23
as low as
$477
Chicago, US (CHI) - Montreal, CA (YMQ)
Aug 29
Aug 29
Sep 6
Sep 6
as low as
$498
Chicago, US (CHI) - Montreal, CA (YMQ)
Aug 20
Aug 20
Aug 23
Aug 23
as low as
$504
Top Deals on flights from Chicago to Calgary
Chicago, US (CHI) - Calgary, CA (YYC)
May 27
May 27
May 30
May 30
as low as
$219
Chicago, US (CHI) - Calgary, CA (YYC)
May 25
May 25
May 30
May 30
as low as
$219
Chicago, US (CHI) - Calgary, CA (YYC)
May 6
May 6
May 8
May 8
as low as
$233
Chicago, US (CHI) - Calgary, CA (YYC)
May 14
May 14
May 19
May 19
as low as
$457
Chicago, US (CHI) - Calgary, CA (YYC)
May 12
May 12
May 19
May 19
as low as
$571
Chicago, US (CHI) - Calgary, CA (YYC)
Jul 27
Jul 27
Aug 3
Aug 3
as low as
$989
Top Deals on flights from Chicago to Ottawa
Chicago, US (CHI) - Ottawa, CA (YOW)
May 8
May 9
May 9
May 9
as low as
$257
Chicago, US (CHI) - Ottawa, CA (YOW)
May 8
May 9
May 9
May 9
as low as
$257
Chicago, US (CHI) - Ottawa, CA (YOW)
May 8
May 9
May 9
May 9
as low as
$334
Chicago, US (CHI) - Ottawa, CA (YOW)
May 20
May 20
May 21
May 21
as low as
$479
Chicago, US (CHI) - Ottawa, CA (YOW)
May 10
May 10
May 10
May 10
as low as
$508
Chicago, US (CHI) - Ottawa, CA (YOW)
May 8
May 8
May 9
May 9
as low as
$553
Chicago, US (CHI) - Ottawa, CA (YOW)
May 20
May 20
May 21
May 21
as low as
$606
Chicago, US (CHI) - Ottawa, CA (YOW)
May 7
May 7
May 9
May 9
as low as
$617
Chicago, US (CHI) - Ottawa, CA (YOW)
May 8
May 8
May 10
May 10
as low as
$628
Chicago, US (CHI) - Ottawa, CA (YOW)
May 19
May 19
May 26
May 26
as low as
$666
Chicago, US (CHI) - Ottawa, CA (YOW)
May 14
May 14
May 27
May 27
as low as
$674
Chicago, US (CHI) - Ottawa, CA (YOW)
Dec 5
Dec 6
Dec 12
Dec 12
as low as
$674
Top Deals on flights from Chicago to Winnipeg
Chicago, US (CHI) - Winnipeg, CA (YWG)
May 9
May 9
May 10
May 10
as low as
$548
Chicago, US (CHI) - Winnipeg, CA (YWG)
May 9
May 9
May 10
May 10
as low as
$548
Chicago, US (CHI) - Winnipeg, CA (YWG)
May 7
May 7
May 30
May 30
as low as
$572
Chicago, US (CHI) - Winnipeg, CA (YWG)
May 24
May 25
May 29
May 29
as low as
$650
Chicago, US (CHI) - Winnipeg, CA (YWG)
May 9
May 9
May 10
May 10
as low as
$720
Chicago, US (CHI) - Winnipeg, CA (YWG)
May 9
May 9
May 10
May 10
as low as
$734
Chicago, US (CHI) - Winnipeg, CA (YWG)
May 24
May 25
May 29
May 29
as low as
$749
Chicago, US (CHI) - Winnipeg, CA (YWG)
May 16
May 16
May 22
May 22
as low as
$843
Chicago, US (CHI) - Winnipeg, CA (YWG)
May 22
May 22
May 24
May 25
as low as
$848
Chicago, US (CHI) - Winnipeg, CA (YWG)
May 22
May 22
May 24
May 24
as low as
$852
Chicago, US (CHI) - Winnipeg, CA (YWG)
May 16
May 16
May 22
May 22
as low as
$867
Chicago, US (CHI) - Winnipeg, CA (YWG)
May 16
May 16
May 22
May 22
as low as
$982
Top Deals on flights from Chicago to Halifax
Chicago, US (CHI) - Halifax, CA (YHZ)
May 20
May 20
May 26
May 26
as low as
$425
Chicago, US (CHI) - Halifax, CA (YHZ)
May 8
May 8
May 17
May 17
as low as
$492
Chicago, US (CHI) - Halifax, CA (YHZ)
Aug 5
Aug 5
Aug 25
Aug 25
as low as
$507
Chicago, US (CHI) - Halifax, CA (YHZ)
May 29
May 30
Jun 2
Jun 2
as low as
$608
Chicago, US (CHI) - Halifax, CA (YHZ)
May 8
May 9
May 18
May 18
as low as
$645
Chicago, US (CHI) - Halifax, CA (YHZ)
May 8
May 8
May 18
May 18
as low as
$668
Chicago, US (CHI) - Halifax, CA (YHZ)
May 8
May 8
May 18
May 18
as low as
$746
Chicago, US (CHI) - Halifax, CA (YHZ)
May 8
May 8
May 18
May 18
as low as
$758
Chicago, US (CHI) - Halifax, CA (YHZ)
May 7
May 8
May 17
May 18
as low as
$779
Chicago, US (CHI) - Halifax, CA (YHZ)
May 7
May 8
May 17
May 18
as low as
$779
Chicago, US (CHI) - Halifax, CA (YHZ)
May 8
May 9
May 17
May 17
as low as
$1426
Chicago, US (CHI) - Halifax, CA (YHZ)
May 8
May 9
May 18
May 18
as low as
$1622
Top Deals on flights from Chicago to Edmonton
Chicago, US (CHI) - Edmonton, CA (YEA)
May 7
May 7
May 11
May 11
as low as
$431
Chicago, US (CHI) - Edmonton, CA (YEA)
May 16
May 16
May 24
May 24
as low as
$515
Chicago, US (CHI) - Edmonton, CA (YEA)
May 16
May 17
May 23
May 23
as low as
$531
Chicago, US (CHI) - Edmonton, CA (YEA)
May 16
May 17
May 23
May 23
as low as
$532
Chicago, US (CHI) - Edmonton, CA (YEA)
May 16
May 16
May 23
May 23
as low as
$568
Chicago, US (CHI) - Edmonton, CA (YEA)
May 16
May 16
May 23
May 23
as low as
$596
Chicago, US (CHI) - Edmonton, CA (YEA)
May 5
May 5
May 7
May 8
as low as
$648
Chicago, US (CHI) - Edmonton, CA (YEA)
May 16
May 16
May 23
May 23
as low as
$729
Chicago, US (CHI) - Edmonton, CA (YEA)
Jul 13
Jul 13
Jul 21
Jul 21
as low as
$753
Chicago, US (CHI) - Edmonton, CA (YEA)
May 16
May 17
May 23
May 23
as low as
$787
Top Deals on flights from Chicago to Quebec
Chicago, US (CHI) - Quebec, CA (YQB)
Jun 10
Jun 10
Jun 10
Jun 10
as low as
$474
Chicago, US (CHI) - Quebec, CA (YQB)
Jun 10
Jun 10
Jun 10
Jun 10
as low as
$474
Chicago, US (CHI) - Quebec, CA (YQB)
May 31
May 31
Jun 5
Jun 5
as low as
$520
Chicago, US (CHI) - Quebec, CA (YQB)
May 30
May 30
Jun 3
Jun 3
as low as
$528
Chicago, US (CHI) - Quebec, CA (YQB)
May 28
May 28
Jun 3
Jun 3
as low as
$533
Chicago, US (CHI) - Quebec, CA (YQB)
Jun 13
Jun 13
Jun 17
Jun 17
as low as
$533
Chicago, US (CHI) - Quebec, CA (YQB)
Jun 10
Jun 10
Jun 13
Jun 13
as low as
$535
Chicago, US (CHI) - Quebec, CA (YQB)
May 30
May 30
Jun 3
Jun 3
as low as
$541
Chicago, US (CHI) - Quebec, CA (YQB)
Jun 3
Jun 3
Jun 7
Jun 7
as low as
$546
Chicago, US (CHI) - Quebec, CA (YQB)
Sep 18
Sep 18
Sep 21
Sep 21
as low as
$560
Chicago, US (CHI) - Quebec, CA (YQB)
May 30
May 30
Jun 3
Jun 3
as low as
$596
Chicago, US (CHI) - Quebec, CA (YQB)
Jun 7
Jun 7
Jun 11
Jun 11
as low as
$606
Good to Know
Essential information to help you plan your flight from Chicago to Canada
Cheapest Flight
$206
The lowest price we found in the last two weeks, departing May 12 and returning May 12
1h 50m ‧ economyFastest Flights
$296
The fastest flight that we found in the last two weeks, departing May 25 and returning May 28
1h 39m ‧ economyCheapest Flight Round-trip
$206
Cheapest price found in the last 14 days, departing May 12 and returning May 12
1h 50m ‧ economyCheapest Layover airport
$474
The cheapest layover airport to Quebec is currently $474
1 stop ‧ 5h 2m ‧ economyBest Arrival airport
$206
The best arrival airport to Toronto is currently $206
1h 50m ‧ economyBest Departure airport
$206
The best departure airport to Toronto is currently $206
1h 50m ‧ economyCheapest Airline
$206
The cheapest airline to Toronto is currently $206
1h 50m ‧ economyFlights to Canada
- Flights
- North America
- Canada
- Flights
- North America
- United States
- Illinois
- Chicago