Business Class Flight Deals from Chicago to Canada from $567
Top flight deals from leading airlines:
... and +100s more
Free cancellation for many rates
If a VIP member finds a better price elsewhere, we'll refund up to 200% of the difference
VIP member priority support for seamless bookings and exclusive travel benefits
We’re always here for you - reach us 24 hours a day, 7 days a week
Top Deals on Business Class Flights from Chicago to Toronto
Chicago, US (CHI) - Toronto, CA (YTO)
May 5
May 5
May 7
May 7
as low as
$567
Chicago, US (CHI) - Toronto, CA (YTO)
May 5
May 5
May 7
May 7
as low as
$576
Chicago, US (CHI) - Toronto, CA (YTO)
May 7
May 7
May 11
May 11
as low as
$582
Chicago, US (CHI) - Toronto, CA (YTO)
May 7
May 7
May 11
May 11
as low as
$592
Chicago, US (CHI) - Toronto, CA (YTO)
May 16
May 16
May 30
May 30
as low as
$592
Chicago, US (CHI) - Toronto, CA (YTO)
Jun 23
Jun 23
Jun 25
Jun 25
as low as
$804
Chicago, US (CHI) - Toronto, CA (YTO)
Jun 23
Jun 23
Jun 25
Jun 25
as low as
$813
Chicago, US (CHI) - Toronto, CA (YTO)
May 13
May 13
May 22
May 22
as low as
$869
Chicago, US (CHI) - Toronto, CA (YTO)
Jun 7
Jun 7
Jun 14
Jun 14
as low as
$937
Chicago, US (CHI) - Toronto, CA (YTO)
Jun 12
Jun 12
Jun 15
Jun 15
as low as
$962
Chicago, US (CHI) - Toronto, CA (YTO)
May 25
May 25
May 28
May 28
as low as
$1038
Chicago, US (CHI) - Toronto, CA (YTO)
May 24
May 24
May 28
May 28
as low as
$1038
Top Deals on Business Class Flights from Chicago to Vancouver
Chicago, US (CHI) - Vancouver, CA (YVR)
Jun 7
Jun 7
Jun 16
Jun 17
as low as
$1328
Chicago, US (CHI) - Vancouver, CA (YVR)
Jun 19
Jun 19
Jun 22
Jun 23
as low as
$1774
Chicago, US (CHI) - Vancouver, CA (YVR)
Jun 19
Jun 19
Jun 22
Jun 23
as low as
$1808
Chicago, US (CHI) - Vancouver, CA (YVR)
Jun 18
Jun 18
Jun 22
Jun 23
as low as
$2067
Chicago, US (CHI) - Vancouver, CA (YVR)
Apr 24
Apr 24
Apr 26
Apr 26
as low as
$2169
Chicago, US (CHI) - Vancouver, CA (YVR)
Jun 19
Jun 19
Jun 22
Jun 22
as low as
$2377
Chicago, US (CHI) - Vancouver, CA (YVR)
Jun 18
Jun 18
Jun 22
Jun 22
as low as
$2670
Chicago, US (CHI) - Vancouver, CA (YVR)
Jun 7
Jun 7
Jun 16
Jun 16
as low as
$3925
Chicago, US (CHI) - Vancouver, CA (YVR)
Jun 24
Jun 24
Jun 28
Jun 28
as low as
$8241
Chicago, US (CHI) - Vancouver, CA (YVR)
Jun 18
Jun 18
Jun 21
Jun 21
as low as
$8281
Chicago, US (CHI) - Vancouver, CA (YVR)
Jun 15
Jun 15
Jun 22
Jun 22
as low as
$9101
Chicago, US (CHI) - Vancouver, CA (YVR)
Jun 11
Jun 11
Jun 15
Jun 15
as low as
$9121
Top Deals on Business Class Flights from Chicago to Montreal
Chicago, US (CHI) - Montreal, CA (YMQ)
Jun 29
Jun 29
Jul 2
Jul 2
as low as
$615
Chicago, US (CHI) - Montreal, CA (YMQ)
Jun 19
Jun 19
Jun 24
Jun 24
as low as
$645
Chicago, US (CHI) - Montreal, CA (YMQ)
Jun 19
Jun 19
Jun 24
Jun 24
as low as
$660
Chicago, US (CHI) - Montreal, CA (YMQ)
Jun 19
Jun 19
Jun 24
Jun 24
as low as
$662
Chicago, US (CHI) - Montreal, CA (YMQ)
Jun 29
Jun 29
Jul 2
Jul 2
as low as
$708
Chicago, US (CHI) - Montreal, CA (YMQ)
Jun 29
Jun 29
Jul 2
Jul 2
as low as
$783
Chicago, US (CHI) - Montreal, CA (YMQ)
Jun 27
Jun 27
Jun 30
Jun 30
as low as
$783
Chicago, US (CHI) - Montreal, CA (YMQ)
Jun 29
Jun 29
Jul 2
Jul 2
as low as
$797
Chicago, US (CHI) - Montreal, CA (YMQ)
Jun 29
Jun 29
Jul 2
Jul 2
as low as
$810
Chicago, US (CHI) - Montreal, CA (YMQ)
Jun 27
Jun 28
Jun 30
Jun 30
as low as
$1368
Chicago, US (CHI) - Montreal, CA (YMQ)
Jun 29
Jun 29
Jul 2
Jul 2
as low as
$1383
Chicago, US (CHI) - Montreal, CA (YMQ)
Jul 23
Jul 23
Jul 26
Jul 26
as low as
$5456
Top Deals on Business Class Flights from Chicago to Calgary
Chicago, US (CHI) - Calgary, CA (YYC)
Sep 10
Sep 10
Sep 15
Sep 15
as low as
$1051
Chicago, US (CHI) - Calgary, CA (YYC)
Sep 10
Sep 10
Sep 15
Sep 15
as low as
$1067
Chicago, US (CHI) - Calgary, CA (YYC)
Aug 28
Aug 28
Sep 2
Sep 2
as low as
$1079
Chicago, US (CHI) - Calgary, CA (YYC)
Sep 12
Sep 12
Sep 24
Sep 25
as low as
$1079
Chicago, US (CHI) - Calgary, CA (YYC)
Sep 9
Sep 9
Sep 15
Sep 15
as low as
$1089
Chicago, US (CHI) - Calgary, CA (YYC)
Sep 12
Sep 12
Sep 24
Sep 24
as low as
$1200
Chicago, US (CHI) - Calgary, CA (YYC)
Sep 12
Sep 12
Sep 24
Sep 24
as low as
$1214
Chicago, US (CHI) - Calgary, CA (YYC)
Sep 12
Sep 12
Sep 24
Sep 24
as low as
$1489
Chicago, US (CHI) - Calgary, CA (YYC)
Sep 12
Sep 12
Sep 24
Sep 24
as low as
$1690
Chicago, US (CHI) - Calgary, CA (YYC)
Sep 12
Sep 12
Sep 24
Sep 24
as low as
$1690
Chicago, US (CHI) - Calgary, CA (YYC)
Sep 12
Sep 12
Sep 24
Sep 24
as low as
$1919
Chicago, US (CHI) - Calgary, CA (YYC)
Sep 12
Sep 12
Sep 24
Sep 24
as low as
$3215
Top Deals on Business Class Flights from Chicago to Ottawa
Chicago, US (CHI) - Ottawa, CA (YOW)
Aug 19
Aug 19
Aug 26
Aug 26
as low as
$1039
Chicago, US (CHI) - Ottawa, CA (YOW)
Aug 19
Aug 19
Aug 26
Aug 26
as low as
$1039
Chicago, US (CHI) - Ottawa, CA (YOW)
Aug 19
Aug 19
Aug 26
Aug 26
as low as
$1039
Chicago, US (CHI) - Ottawa, CA (YOW)
Aug 19
Aug 19
Aug 26
Aug 26
as low as
$1044
Chicago, US (CHI) - Ottawa, CA (YOW)
Aug 19
Aug 19
Aug 26
Aug 26
as low as
$1044
Chicago, US (CHI) - Ottawa, CA (YOW)
Aug 19
Aug 20
Aug 26
Aug 26
as low as
$1044
Chicago, US (CHI) - Ottawa, CA (YOW)
Aug 19
Aug 19
Aug 26
Aug 26
as low as
$1118
Chicago, US (CHI) - Ottawa, CA (YOW)
Aug 19
Aug 19
Aug 26
Aug 26
as low as
$1118
Chicago, US (CHI) - Ottawa, CA (YOW)
Aug 19
Aug 19
Aug 26
Aug 26
as low as
$1118
Chicago, US (CHI) - Ottawa, CA (YOW)
Aug 19
Aug 19
Aug 26
Aug 26
as low as
$1118
Chicago, US (CHI) - Ottawa, CA (YOW)
Aug 19
Aug 19
Aug 26
Aug 26
as low as
$1127
Chicago, US (CHI) - Ottawa, CA (YOW)
Aug 19
Aug 19
Aug 26
Aug 26
as low as
$1135
Top Deals on Business Class Flights from Chicago to Winnipeg
Chicago, US (CHI) - Winnipeg, CA (YWG)
May 23
May 23
May 30
May 30
as low as
$1114
Chicago, US (CHI) - Winnipeg, CA (YWG)
May 23
May 23
May 30
May 30
as low as
$1128
Chicago, US (CHI) - Winnipeg, CA (YWG)
May 23
May 23
May 30
May 30
as low as
$1141
Chicago, US (CHI) - Winnipeg, CA (YWG)
May 11
May 11
May 12
May 12
as low as
$1177
Chicago, US (CHI) - Winnipeg, CA (YWG)
May 10
May 10
May 14
May 14
as low as
$1182
Chicago, US (CHI) - Winnipeg, CA (YWG)
Apr 27
Apr 27
May 4
May 4
as low as
$1294
Chicago, US (CHI) - Winnipeg, CA (YWG)
Apr 27
Apr 27
May 4
May 4
as low as
$1299
Chicago, US (CHI) - Winnipeg, CA (YWG)
Apr 27
Apr 27
May 4
May 4
as low as
$1360
Chicago, US (CHI) - Winnipeg, CA (YWG)
Apr 27
Apr 27
May 4
May 4
as low as
$1360
Chicago, US (CHI) - Winnipeg, CA (YWG)
Apr 27
Apr 27
May 4
May 4
as low as
$1360
Chicago, US (CHI) - Winnipeg, CA (YWG)
Apr 27
Apr 27
May 4
May 4
as low as
$1389
Chicago, US (CHI) - Winnipeg, CA (YWG)
Apr 27
Apr 27
May 4
May 4
as low as
$1394
Top Deals on Business Class Flights from Chicago to Halifax
Chicago, US (CHI) - Halifax, CA (YHZ)
May 27
May 27
Jun 3
Jun 3
as low as
$1001
Chicago, US (CHI) - Halifax, CA (YHZ)
May 27
May 27
Jun 3
Jun 3
as low as
$1001
Chicago, US (CHI) - Halifax, CA (YHZ)
May 27
May 27
Jun 3
Jun 3
as low as
$1006
Chicago, US (CHI) - Halifax, CA (YHZ)
May 27
May 28
Jun 3
Jun 3
as low as
$1006
Chicago, US (CHI) - Halifax, CA (YHZ)
May 27
May 27
Jun 3
Jun 3
as low as
$1048
Chicago, US (CHI) - Halifax, CA (YHZ)
May 27
May 27
Jun 3
Jun 3
as low as
$1048
Chicago, US (CHI) - Halifax, CA (YHZ)
May 15
May 15
May 20
May 20
as low as
$1077
Chicago, US (CHI) - Halifax, CA (YHZ)
May 27
May 27
Jun 3
Jun 3
as low as
$1077
Chicago, US (CHI) - Halifax, CA (YHZ)
May 27
May 27
Jun 3
Jun 3
as low as
$1077
Chicago, US (CHI) - Halifax, CA (YHZ)
May 27
May 27
Jun 3
Jun 3
as low as
$1082
Chicago, US (CHI) - Halifax, CA (YHZ)
May 27
May 27
Jun 3
Jun 3
as low as
$1082
Chicago, US (CHI) - Halifax, CA (YHZ)
May 8
May 8
May 18
May 18
as low as
$1426
Top Deals on Business Class Flights from Chicago to Edmonton
Chicago, US (CHI) - Edmonton, CA (YEA)
Jun 2
Jun 2
Jun 9
Jun 9
as low as
$1083
Chicago, US (CHI) - Edmonton, CA (YEA)
Jun 2
Jun 2
Jun 9
Jun 9
as low as
$1088
Chicago, US (CHI) - Edmonton, CA (YEA)
Jun 2
Jun 2
Jun 9
Jun 9
as low as
$1088
Chicago, US (CHI) - Edmonton, CA (YEA)
Jun 2
Jun 3
Jun 9
Jun 9
as low as
$1113
Chicago, US (CHI) - Edmonton, CA (YEA)
Jun 2
Jun 2
Jun 9
Jun 9
as low as
$1133
Chicago, US (CHI) - Edmonton, CA (YEA)
Jun 2
Jun 2
Jun 9
Jun 9
as low as
$1133
Chicago, US (CHI) - Edmonton, CA (YEA)
Jun 2
Jun 2
Jun 9
Jun 9
as low as
$1136
Chicago, US (CHI) - Edmonton, CA (YEA)
Jun 2
Jun 2
Jun 9
Jun 9
as low as
$1138
Chicago, US (CHI) - Edmonton, CA (YEA)
Jun 2
Jun 2
Jun 9
Jun 9
as low as
$1138
Chicago, US (CHI) - Edmonton, CA (YEA)
Jun 2
Jun 2
Jun 9
Jun 9
as low as
$1186
Chicago, US (CHI) - Edmonton, CA (YEA)
May 9
May 9
May 16
May 16
as low as
$1216
Chicago, US (CHI) - Edmonton, CA (YEA)
May 23
May 23
May 30
May 30
as low as
$1278
Top Deals on Business Class Flights from Chicago to Quebec
Chicago, US (CHI) - Quebec, CA (YQB)
Sep 3
Sep 3
Sep 10
Sep 10
as low as
$805
Chicago, US (CHI) - Quebec, CA (YQB)
Sep 3
Sep 3
Sep 10
Sep 10
as low as
$805
Chicago, US (CHI) - Quebec, CA (YQB)
Sep 3
Sep 3
Sep 10
Sep 10
as low as
$887
Chicago, US (CHI) - Quebec, CA (YQB)
Sep 3
Sep 3
Sep 10
Sep 10
as low as
$892
Chicago, US (CHI) - Quebec, CA (YQB)
Sep 3
Sep 3
Sep 10
Sep 10
as low as
$923
Chicago, US (CHI) - Quebec, CA (YQB)
Sep 3
Sep 3
Sep 10
Sep 10
as low as
$927
Chicago, US (CHI) - Quebec, CA (YQB)
Sep 3
Sep 3
Sep 10
Sep 10
as low as
$928
Chicago, US (CHI) - Quebec, CA (YQB)
Sep 3
Sep 3
Sep 10
Sep 11
as low as
$928
Chicago, US (CHI) - Quebec, CA (YQB)
Sep 3
Sep 3
Sep 10
Sep 10
as low as
$928
Chicago, US (CHI) - Quebec, CA (YQB)
Sep 3
Sep 3
Sep 10
Sep 10
as low as
$934
Chicago, US (CHI) - Quebec, CA (YQB)
Sep 3
Sep 3
Sep 10
Sep 10
as low as
$958
Chicago, US (CHI) - Quebec, CA (YQB)
Sep 3
Sep 3
Sep 10
Sep 10
as low as
$963
Top Deals on Business Class Flights from Chicago to Windsor
Chicago, US (CHI) - Windsor, CA (YQG)
May 25
May 26
Jun 1
Jun 1
as low as
$854
Chicago, US (CHI) - Windsor, CA (YQG)
May 25
May 25
Jun 1
Jun 1
as low as
$867
Chicago, US (CHI) - Windsor, CA (YQG)
May 25
May 25
Jun 1
Jun 1
as low as
$867
Chicago, US (CHI) - Windsor, CA (YQG)
May 25
May 26
Jun 1
Jun 1
as low as
$892
Chicago, US (CHI) - Windsor, CA (YQG)
May 25
May 26
Jun 1
Jun 1
as low as
$892
Chicago, US (CHI) - Windsor, CA (YQG)
May 25
May 26
Jun 1
Jun 1
as low as
$892
Chicago, US (CHI) - Windsor, CA (YQG)
May 25
May 25
Jun 1
Jun 2
as low as
$892
Chicago, US (CHI) - Windsor, CA (YQG)
May 24
May 24
May 31
May 31
as low as
$905
Chicago, US (CHI) - Windsor, CA (YQG)
May 23
May 23
May 30
May 30
as low as
$905
Chicago, US (CHI) - Windsor, CA (YQG)
May 23
May 23
May 30
May 30
as low as
$1157
Chicago, US (CHI) - Windsor, CA (YQG)
May 24
May 24
May 31
May 31
as low as
$1363
Chicago, US (CHI) - Windsor, CA (YQG)
May 23
May 23
May 30
May 30
as low as
$1972
Good to Know
Essential information to help you plan your flight Business Class from Chicago to Canada
Cheapest Flight
$567
The lowest price we found in the last two weeks, departing May 5 and returning May 7
1 stop ‧ 2h 45m ‧ businessFastest Flights
$1038
The fastest flight that we found in the last two weeks, departing May 25 and returning May 28
1h 39m ‧ businessCheapest Flight Round-trip
$567
Cheapest price found in the last 14 days, departing May 5 and returning May 7
1 stop ‧ 2h 45m ‧ businessCheapest Layover airport
$905
The cheapest layover airport to Windsor is currently $905
2 stops ‧ 5h 29m ‧ businessBest Arrival airport
$1038
The best arrival airport to Toronto is currently $1038
2 stops ‧ 11h ‧ firstBest Departure airport
$1038
The best departure airport to Toronto is currently $1038
2 stops ‧ 11h ‧ firstCheapest Airline
$1038
The cheapest airline to Toronto is currently $1038
2 stops ‧ 11h ‧ firstFlights to Canada
- Flights
- North America
- Canada
- Flights
- North America
- United States
- Illinois
- Chicago