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Flight Deals from Canada to Chicago from $155

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Top Deals on flights from Toronto to Chicago

Toronto, CA (YTO) - Chicago, US (CHI)

Porter Airlines Logo
Porter Airlines

May 20

YTZ
49m
Direct

May 20

MDW
Porter Airlines Logo
Porter Airlines

May 27

MDW
2h 42m
Direct

May 27

YTZ

as low as

$155

Toronto, CA (YTO) - Chicago, US (CHI)

Air Canada Logo
Air Canada

May 26

YTZ
3h 59m
YUL

May 26

ORD
Air Canada Logo
Air Canada

Jun 10

ORD
2h 54m
Direct

Jun 10

YTZ

as low as

$160

Toronto, CA (YTO) - Chicago, US (CHI)

Air Canada Logo
Air Canada

May 29

YYZ
1h 5m
Direct

May 29

ORD
Air Canada Logo
Air Canada

Jun 12

ORD
2h 44m
Direct

Jun 12

YYZ

as low as

$161

Toronto, CA (YTO) - Chicago, US (CHI)

Air Canada Logo
Air Canada

May 19

YTZ
9h 52m
YOW
YUL

May 19

ORD
Air Canada Logo
Air Canada

Jun 11

ORD
2h 42m
Direct

Jun 11

YTZ

as low as

$165

Toronto, CA (YTO) - Chicago, US (CHI)

Air Transat Logo
Air Transat

Jun 4

YTZ
50m
Direct

Jun 4

MDW
Air Transat Logo
Air Transat

Jun 6

MDW
2h 42m
Direct

Jun 6

YTZ

as low as

$187

Toronto, CA (YTO) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 24

YYZ
55m
Direct

May 24

ORD
American Airlines Logo
American Airlines

May 26

ORD
2h 40m
Direct

May 26

YYZ

as low as

$194

Toronto, CA (YTO) - Chicago, US (CHI)

United Airlines Logo
United Airlines

May 31

YYZ
59m
Direct

May 31

ORD
United Airlines Logo
United Airlines

Jun 13

ORD
2h 44m
Direct

Jun 13

YYZ

as low as

$197

Toronto, CA (YTO) - Chicago, US (CHI)

Air Canada Logo
Air Canada

May 19

YTZ
9h 52m
YOW
YUL

May 19

ORD
Air Canada Logo
Air Canada

Jun 11

ORD
5h 35m
YYZ

Jun 11

YTZ

as low as

$201

Toronto, CA (YTO) - Chicago, US (CHI)

United Airlines Logo
United Airlines

May 14

YYZ
55m
Direct

May 14

ORD
United Airlines Logo
United Airlines

May 14

ORD
7h 29m
BNA

May 14

YYZ

as low as

$204

Toronto, CA (YTO) - Chicago, US (CHI)

United Airlines Logo
United Airlines

May 19

YYZ
3h 56m
IAD

May 19

ORD
United Airlines Logo
United Airlines

Jun 2

ORD
2h 54m
Direct

Jun 2

YYZ

as low as

$213

Toronto, CA (YTO) - Chicago, US (CHI)

Air Canada Logo
Air Canada

May 12

YHM
4h 16m
YYZ

May 12

ORD
Air Canada Logo
Air Canada

May 27

ORD
2h 52m
Direct

May 27

YHM

as low as

$222

Toronto, CA (YTO) - Chicago, US (CHI)

United Airlines Logo
United Airlines

May 28

YYZ
4h 39m
LGA

May 28

ORD
United Airlines Logo
United Airlines

May 29

ORD
2h 59m
Direct

May 29

YYZ

as low as

$228

Top Deals on flights from Vancouver to Chicago

Vancouver, CA (YVR) - Chicago, US (CHI)

WestJet Logo
WestJet

Jun 11

YVR
10h 44m
YYC

Jun 11

ORD
WestJet Logo
WestJet

Jun 17

ORD
5h 5m
YYC

Jun 17

YVR

as low as

$209

Vancouver, CA (YVR) - Chicago, US (CHI)

Air Canada Logo
Air Canada

Jun 13

YVR
14h 10m
YEG
YYZ

Jun 14

ORD
Air Canada Logo
Air Canada

Jun 18

ORD
2h 33m
Direct

Jun 18

YVR

as low as

$305

Vancouver, CA (YVR) - Chicago, US (CHI)

Alaska Airlines Logo
Alaska Airlines

May 20

YVR
8h 29m
SEA

May 20

ORD
Alaska Airlines Logo
Alaska Airlines

Jun 11

ORD
6h 48m
SEA

Jun 11

YVR

as low as

$307

Vancouver, CA (YVR) - Chicago, US (CHI)

Air Canada Logo
Air Canada

May 24

YVR
6h 13m
Direct

May 24

ORD
Air Canada Logo
Air Canada

Jun 18

ORD
2h 33m
Direct

Jun 18

YVR

as low as

$321

Vancouver, CA (YVR) - Chicago, US (CHI)

Alaska Airlines Logo
Alaska Airlines

Jun 5

YVR
10h 39m
PDX

Jun 5

ORD
Alaska Airlines Logo
Alaska Airlines

Jun 11

ORD
6h 48m
SEA

Jun 11

YVR

as low as

$323

Vancouver, CA (YVR) - Chicago, US (CHI)

Air Canada Logo
Air Canada

May 17

YVR
6h 13m
Direct

May 17

ORD
Air Canada Logo
Air Canada

Jun 11

ORD
9h 4m
YYZ
YWG

Jun 11

YVR

as low as

$338

Vancouver, CA (YVR) - Chicago, US (CHI)

Delta Air Lines Logo
Delta Air Lines

May 22

YVR
9h 44m
YYC

May 22

ORD
Delta Air Lines Logo
Delta Air Lines

May 25

ORD
6h 40m
YYC

May 26

YVR

as low as

$340

Vancouver, CA (YVR) - Chicago, US (CHI)

Air Canada Logo
Air Canada

May 17

YVR
14h 27m
YYC
YUL

May 18

ORD
Air Canada Logo
Air Canada

Jun 11

ORD
9h 4m
YYZ
YWG

Jun 11

YVR

as low as

$348

Vancouver, CA (YVR) - Chicago, US (CHI)

Delta Air Lines Logo
Delta Air Lines

May 22

YVR
13h 37m
YYC
DTW

May 22

ORD
Delta Air Lines Logo
Delta Air Lines

May 25

ORD
6h 40m
YYC

May 26

YVR

as low as

$356

Vancouver, CA (YVR) - Chicago, US (CHI)

WestJet Logo
WestJet

May 20

YXX
19h 49m
YYC

May 21

ORD
WestJet Logo
WestJet

Jun 11

ORD
6h 48m
SEA

Jun 11

YXX

as low as

$377

Vancouver, CA (YVR) - Chicago, US (CHI)

United Airlines Logo
United Airlines

May 22

YVR
6h 16m
Direct

May 22

ORD
United Airlines Logo
United Airlines

May 24

ORD
7h 43m
LAX

May 24

YVR

as low as

$454

Vancouver, CA (YVR) - Chicago, US (CHI)

JetBlue Logo
JetBlue

May 27

YVR
16h 39m
JFK

May 28

ORD
JetBlue Logo
JetBlue

Jun 4

ORD
14h 50m
JFK

Jun 4

YVR

as low as

$463

Top Deals on flights from Montreal to Chicago

Montreal, CA (YMQ) - Chicago, US (CHI)

Air Canada Logo
Air Canada

May 31

YUL
1h 44m
Direct

May 31

ORD
Air Canada Logo
Air Canada

Jun 7

ORD
3h 31m
Direct

Jun 7

YUL

as low as

$251

Montreal, CA (YMQ) - Chicago, US (CHI)

United Airlines Logo
United Airlines

May 25

YUL
1h 39m
Direct

May 25

ORD
United Airlines Logo
United Airlines

Jun 8

ORD
3h 19m
Direct

Jun 8

YUL

as low as

$251

Montreal, CA (YMQ) - Chicago, US (CHI)

Air Canada Logo
Air Canada

May 21

YUL
1h 47m
Direct

May 21

ORD
Air Canada Logo
Air Canada

May 31

ORD
5h 10m
YOW

May 31

YUL

as low as

$256

Montreal, CA (YMQ) - Chicago, US (CHI)

Porter Airlines Logo
Porter Airlines

May 28

YUL
6h 9m
YTZ

May 28

MDW
Porter Airlines Logo
Porter Airlines

Jun 1

MDW
6h 20m
YTZ

Jun 1

YUL

as low as

$261

Montreal, CA (YMQ) - Chicago, US (CHI)

United Airlines Logo
United Airlines

Jun 6

YUL
1h 32m
Direct

Jun 6

ORD
United Airlines Logo
United Airlines

Jun 20

ORD
6h 44m
LGA

Jun 20

YUL

as low as

$261

Montreal, CA (YMQ) - Chicago, US (CHI)

Air Canada Logo
Air Canada

Jun 11

YUL
1h 32m
Direct

Jun 11

ORD
Air Canada Logo
Air Canada

Jun 18

ORD
7h 21m
YYZ

Jun 18

YUL

as low as

$263

Montreal, CA (YMQ) - Chicago, US (CHI)

Air Canada Logo
Air Canada

May 27

YUL
5h 53m
YOW

May 27

ORD
Air Canada Logo
Air Canada

Jun 4

ORD
6h 57m
IAD

Jun 4

YUL

as low as

$266

Montreal, CA (YMQ) - Chicago, US (CHI)

United Airlines Logo
United Airlines

May 24

YUL
6h 27m
DCA

May 24

ORD
United Airlines Logo
United Airlines

Jun 7

ORD
3h 31m
Direct

Jun 7

YUL

as low as

$266

Montreal, CA (YMQ) - Chicago, US (CHI)

Delta Air Lines Logo
Delta Air Lines

May 23

YUL
3h 16m
DTW

May 23

ORD
Delta Air Lines Logo
Delta Air Lines

Jun 6

ORD
7h 15m
DTW

Jun 6

YUL

as low as

$276

Montreal, CA (YMQ) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 23

YUL
1h 35m
Direct

May 23

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
6h 39m
CLT

Jun 6

YUL

as low as

$278

Montreal, CA (YMQ) - Chicago, US (CHI)

Air Canada Logo
Air Canada

Jun 14

YUL
9h 9m
YOW
YYZ

Jun 14

ORD
Air Canada Logo
Air Canada

Jun 16

ORD
5h 26m
YYZ

Jun 17

YUL

as low as

$311

Montreal, CA (YMQ) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 25

YUL
6h 5m
PHL

May 25

ORD
American Airlines Logo
American Airlines

Jun 8

ORD
3h 20m
Direct

Jun 8

YUL

as low as

$316

Top Deals on flights from Calgary to Chicago

Calgary, CA (YYC) - Chicago, US (CHI)

American Airlines Logo
American Airlines

Aug 6

YYC
4h 25m
Direct

Aug 6

ORD
American Airlines Logo
American Airlines

Aug 20

ORD
2h 55m
Direct

Aug 20

YYC

as low as

$206

Calgary, CA (YYC) - Chicago, US (CHI)

Delta Air Lines Logo
Delta Air Lines

Aug 12

YYC
10h 50m
SLC

Aug 12

ORD
Delta Air Lines Logo
Delta Air Lines

Aug 26

ORD
9h 8m
SLC

Aug 26

YYC

as low as

$214

Calgary, CA (YYC) - Chicago, US (CHI)

WestJet Logo
WestJet

Aug 12

YYC
4h 29m
Direct

Aug 12

ORD
WestJet Logo
WestJet

Sep 3

ORD
2h 49m
Direct

Sep 3

YYC

as low as

$215

Calgary, CA (YYC) - Chicago, US (CHI)

Air Canada Logo
Air Canada

Aug 12

YYC
9h 4m
YYZ

Aug 12

ORD
Air Canada Logo
Air Canada

Sep 3

ORD
7h 27m
YYZ

Sep 3

YYC

as low as

$216

Calgary, CA (YYC) - Chicago, US (CHI)

Air Canada Logo
Air Canada

Aug 19

YYC
10h 18m
YUL

Aug 19

ORD
Air Canada Logo
Air Canada

Sep 2

ORD
9h 17m
YYZ

Sep 2

YYC

as low as

$233

Calgary, CA (YYC) - Chicago, US (CHI)

United Airlines Logo
United Airlines

Aug 19

YYC
6h 54m
DEN

Aug 19

ORD
United Airlines Logo
United Airlines

Sep 2

ORD
9h 17m
YYZ

Sep 2

YYC

as low as

$240

Calgary, CA (YYC) - Chicago, US (CHI)

Delta Air Lines Logo
Delta Air Lines

Aug 19

YYC
10h 15m
MSP

Aug 19

ORD
Delta Air Lines Logo
Delta Air Lines

Sep 2

ORD
8h 28m
MSP

Sep 2

YYC

as low as

$270

Calgary, CA (YYC) - Chicago, US (CHI)

American Airlines Logo
American Airlines

Aug 12

YYC
8h 2m
DFW

Aug 12

ORD
American Airlines Logo
American Airlines

Aug 26

ORD
2h 55m
Direct

Aug 26

YYC

as low as

$300

Calgary, CA (YYC) - Chicago, US (CHI)

WestJet Logo
WestJet

Aug 12

YYC
4h 29m
Direct

Aug 12

ORD
WestJet Logo
WestJet

Sep 3

ORD
5h
YEG

Sep 3

YYC

as low as

$379

Calgary, CA (YYC) - Chicago, US (CHI)

Alaska Airlines Logo
Alaska Airlines

Aug 12

YYC
10h 40m
SEA

Aug 13

ORD
Alaska Airlines Logo
Alaska Airlines

Sep 3

ORD
2h 49m
Direct

Sep 3

YYC

as low as

$448

Calgary, CA (YYC) - Chicago, US (CHI)

Aeromexico Logo
Aeromexico

Aug 8

YYC
4h 29m
Direct

Aug 8

ORD
Aeromexico Logo
Aeromexico

Sep 3

ORD
13h 31m
MEX

Sep 4

YYC

as low as

$470

Calgary, CA (YYC) - Chicago, US (CHI)

Air Canada Logo
Air Canada

Jul 29

YYC
13h 59m
YUL
YYZ

Jul 29

ORD
Air Canada Logo
Air Canada

Aug 20

ORD
6h 35m
YYZ

Aug 21

YYC

as low as

$495

Top Deals on flights from Ottawa to Chicago

Ottawa, CA (YOW) - Chicago, US (CHI)

Porter Airlines Logo
Porter Airlines

Jun 6

YOW
4h 19m
YTZ

Jun 6

MDW
Porter Airlines Logo
Porter Airlines

Jun 13

MDW
6h 53m
YTZ

Jun 13

YOW

as low as

$316

Ottawa, CA (YOW) - Chicago, US (CHI)

Air Canada Logo
Air Canada

Jun 20

YOW
3h 52m
YUL

Jun 20

ORD
Air Canada Logo
Air Canada

Jun 22

ORD
5h 50m
YYZ

Jun 23

YOW

as low as

$461

Ottawa, CA (YOW) - Chicago, US (CHI)

United Airlines Logo
United Airlines

Jun 21

YOW
1h 28m
Direct

Jun 21

ORD
United Airlines Logo
United Airlines

Jun 25

ORD
3h 20m
Direct

Jun 25

YOW

as low as

$476

Ottawa, CA (YOW) - Chicago, US (CHI)

Air Canada Logo
Air Canada

Jun 21

YOW
1h 22m
Direct

Jun 21

ORD
Air Canada Logo
Air Canada

Jun 25

ORD
3h 20m
Direct

Jun 25

YOW

as low as

$476

Ottawa, CA (YOW) - Chicago, US (CHI)

United Airlines Logo
United Airlines

Jun 6

YOW
1h 28m
Direct

Jun 6

ORD
United Airlines Logo
United Airlines

Jun 22

ORD
8h 27m
DCA

Jun 22

YOW

as low as

$487

Ottawa, CA (YOW) - Chicago, US (CHI)

WestJet Logo
WestJet

Jun 6

YOW
25h 9m
YYC

Jun 7

ORD
WestJet Logo
WestJet

Jun 9

ORD
31h 11m
YYC

Jun 11

YOW

as low as

$743

Ottawa, CA (YOW) - Chicago, US (CHI)

WestJet Logo
WestJet

Jul 1

YOW
30h 29m
YEG

Jul 2

ORD
WestJet Logo
WestJet

Jul 3

ORD
13h 15m
YYC

Jul 4

YOW

as low as

$829

Ottawa, CA (YOW) - Chicago, US (CHI)

WestJet Logo
WestJet

Jul 1

YOW
30h 29m
YEG

Jul 2

ORD
WestJet Logo
WestJet

Jul 3

ORD
10h 37m
ATL
YYZ

Jul 4

YOW

as low as

$855

Ottawa, CA (YOW) - Chicago, US (CHI)

WestJet Logo
WestJet

Jul 5

YOW
15h 44m
YVR
ATL

Jul 5

ORD
WestJet Logo
WestJet

Jul 7

ORD
13h 36m
MSP
YYC

Jul 8

YOW

as low as

$891

Ottawa, CA (YOW) - Chicago, US (CHI)

WestJet Logo
WestJet

Jun 27

YOW
14h 19m
YYC
SLC

Jun 27

ORD
WestJet Logo
WestJet

Jul 1

ORD
10h 37m
ATL
YYZ

Jul 2

YOW

as low as

$898

Ottawa, CA (YOW) - Chicago, US (CHI)

WestJet Logo
WestJet

Jul 1

YOW
9h 17m
YWG
MSP

Jul 1

ORD
WestJet Logo
WestJet

Jul 3

ORD
14h 15m
SLC
YYC

Jul 4

YOW

as low as

$925

Ottawa, CA (YOW) - Chicago, US (CHI)

WestJet Logo
WestJet

Jun 21

YOW
7h
YYZ
DTW

Jun 21

ORD
WestJet Logo
WestJet

Jun 25

ORD
21h 26m
YYC

Jun 26

YOW

as low as

$937

Top Deals on flights from Winnipeg to Chicago

Winnipeg, CA (YWG) - Chicago, US (CHI)

WestJet Logo
WestJet

May 27

YWG
8h 14m
YYC

May 27

ORD
WestJet Logo
WestJet

Jun 29

ORD
7h 46m
YEG

Jun 29

YWG

as low as

$321

Winnipeg, CA (YWG) - Chicago, US (CHI)

WestJet Logo
WestJet

Jun 3

YWG
8h 14m
YYC

Jun 3

ORD
WestJet Logo
WestJet

Jun 8

ORD
15h
MSP

Jun 8

YWG

as low as

$412

Winnipeg, CA (YWG) - Chicago, US (CHI)

Air Canada Logo
Air Canada

Jun 24

YWG
6h 41m
YUL

Jun 24

ORD
Air Canada Logo
Air Canada

Jul 16

ORD
6h 24m
YUL

Jul 16

YWG

as low as

$414

Winnipeg, CA (YWG) - Chicago, US (CHI)

WestJet Logo
WestJet

Jun 3

YWG
8h 14m
YYC

Jun 3

ORD
WestJet Logo
WestJet

Jun 8

ORD
12h 57m
MSP
YEG

Jun 8

YWG

as low as

$417

Winnipeg, CA (YWG) - Chicago, US (CHI)

Air Canada Logo
Air Canada

Jun 10

YWG
7h 55m
YYZ

Jun 10

ORD
Air Canada Logo
Air Canada

Jul 2

ORD
7h 38m
YYZ

Jul 2

YWG

as low as

$428

Winnipeg, CA (YWG) - Chicago, US (CHI)

United Airlines Logo
United Airlines

Jun 14

YWG
2h 31m
Direct

Jun 14

ORD
United Airlines Logo
United Airlines

Jun 21

ORD
2h 29m
Direct

Jun 21

YWG

as low as

$437

Winnipeg, CA (YWG) - Chicago, US (CHI)

United Airlines Logo
United Airlines

Jun 14

YWG
2h 31m
Direct

Jun 14

ORD
United Airlines Logo
United Airlines

Jun 21

ORD
8h 7m
DEN

Jun 21

YWG

as low as

$446

Winnipeg, CA (YWG) - Chicago, US (CHI)

WestJet Logo
WestJet

May 22

YWG
11h 5m
MSP

May 22

MDW
WestJet Logo
WestJet

May 25

MDW
17h 1m
MSP

May 25

YWG

as low as

$477

Winnipeg, CA (YWG) - Chicago, US (CHI)

WestJet Logo
WestJet

May 22

YWG
11h 15m
YEG
MSP

May 22

MDW
WestJet Logo
WestJet

May 25

MDW
11h 26m
DTW
YYC

May 26

YWG

as low as

$488

Winnipeg, CA (YWG) - Chicago, US (CHI)

Delta Air Lines Logo
Delta Air Lines

May 23

YWG
3h 46m
MSP

May 23

ORD
Delta Air Lines Logo
Delta Air Lines

May 25

ORD
7h 25m
MSP

May 25

YWG

as low as

$510

Winnipeg, CA (YWG) - Chicago, US (CHI)

WestJet Logo
WestJet

Jun 16

YWG
12h 45m
ATL

Jun 16

MDW
WestJet Logo
WestJet

Jun 23

MDW
4h 8m
MSP

Jun 23

YWG

as low as

$510

Winnipeg, CA (YWG) - Chicago, US (CHI)

WestJet Logo
WestJet

May 16

YWG
13h 48m
YVR
ATL

May 17

ORD
WestJet Logo
WestJet

May 20

ORD
13h 44m
MSP

May 20

YWG

as low as

$548

Top Deals on flights from Halifax to Chicago

Halifax, CA (YHZ) - Chicago, US (CHI)

Air Canada Logo
Air Canada

May 21

YHZ
4h 7m
YUL

May 21

ORD
Air Canada Logo
Air Canada

May 24

ORD
13h 14m
YYZ

May 25

YHZ

as low as

$321

Halifax, CA (YHZ) - Chicago, US (CHI)

Air Canada Logo
Air Canada

May 26

YHZ
4h 7m
YUL

May 26

ORD
Air Canada Logo
Air Canada

Jun 2

ORD
14h 29m
YYZ

Jun 3

YHZ

as low as

$321

Halifax, CA (YHZ) - Chicago, US (CHI)

Porter Airlines Logo
Porter Airlines

May 26

YHZ
7h 39m
YUL
YTZ

May 26

MDW
Porter Airlines Logo
Porter Airlines

Jun 2

MDW
13h 44m
YTZ
YOW

Jun 2

YHZ

as low as

$329

Halifax, CA (YHZ) - Chicago, US (CHI)

Air Canada Logo
Air Canada

Jun 9

YHZ
4h 7m
YUL

Jun 9

ORD
Air Canada Logo
Air Canada

Jun 11

ORD
7h 39m
YYZ

Jun 11

YHZ

as low as

$330

Halifax, CA (YHZ) - Chicago, US (CHI)

Air Canada Logo
Air Canada

May 26

YHZ
7h 50m
YOW
YYZ

May 26

ORD
Air Canada Logo
Air Canada

Jun 2

ORD
13h 14m
YYZ

Jun 3

YHZ

as low as

$333

Halifax, CA (YHZ) - Chicago, US (CHI)

Air Canada Logo
Air Canada

May 21

YHZ
7h 50m
YOW
YYZ

May 21

ORD
Air Canada Logo
Air Canada

May 24

ORD
13h 14m
YYZ

May 25

YHZ

as low as

$333

Halifax, CA (YHZ) - Chicago, US (CHI)

Porter Airlines Logo
Porter Airlines

Jun 9

YHZ
7h 39m
YUL
YTZ

Jun 9

MDW
Porter Airlines Logo
Porter Airlines

Jun 11

MDW
13h 44m
YTZ
YOW

Jun 11

YHZ

as low as

$334

Halifax, CA (YHZ) - Chicago, US (CHI)

Porter Airlines Logo
Porter Airlines

May 12

YHZ
7h 39m
YUL
YTZ

May 12

MDW
Porter Airlines Logo
Porter Airlines

May 14

MDW
13h 34m
YTZ
YOW

May 14

YHZ

as low as

$340

Halifax, CA (YHZ) - Chicago, US (CHI)

WestJet Logo
WestJet

May 26

YHZ
8h
YYZ
DTW

May 26

ORD
WestJet Logo
WestJet

May 31

ORD
15h 30m
MSP
YYC

Jun 1

YHZ

as low as

$378

Halifax, CA (YHZ) - Chicago, US (CHI)

WestJet Logo
WestJet

May 21

YHZ
9h 15m
YYZ
MSP

May 21

MDW
WestJet Logo
WestJet

May 24

MDW
15h 20m
SLC
YYZ

May 24

YHZ

as low as

$385

Halifax, CA (YHZ) - Chicago, US (CHI)

WestJet Logo
WestJet

Jun 9

YHZ
13h 36m
YYC
ATL

Jun 10

MDW
WestJet Logo
WestJet

Jun 13

MDW
26h 42m
LGA

Jun 14

YHZ

as low as

$399

Halifax, CA (YHZ) - Chicago, US (CHI)

WestJet Logo
WestJet

May 23

YHZ
7h 51m
YWG
MSP

May 23

ORD
WestJet Logo
WestJet

May 27

ORD
20h 8m
ATL
YYC

May 28

YHZ

as low as

$405

Top Deals on flights from Edmonton to Chicago

Edmonton, CA (YEA) - Chicago, US (CHI)

WestJet Logo
WestJet

Jul 13

YEG
4h 34m
Direct

Jul 13

ORD
WestJet Logo
WestJet

Jul 27

ORD
2h 48m
Direct

Jul 27

YEG

as low as

$180

Edmonton, CA (YEA) - Chicago, US (CHI)

WestJet Logo
WestJet

Jul 12

YEG
4h 34m
Direct

Jul 12

ORD
WestJet Logo
WestJet

Jul 20

ORD
2h 48m
Direct

Jul 20

YEG

as low as

$211

Edmonton, CA (YEA) - Chicago, US (CHI)

Air Canada Logo
Air Canada

Jun 17

YEG
8h 50m
YYZ

Jun 17

ORD
Air Canada Logo
Air Canada

Jul 2

ORD
12h 2m
YYZ

Jul 3

YEG

as low as

$259

Edmonton, CA (YEA) - Chicago, US (CHI)

WestJet Logo
WestJet

Jun 29

YEG
4h 34m
Direct

Jun 29

ORD
WestJet Logo
WestJet

Jul 23

ORD
6h 57m
YYC

Jul 24

YEG

as low as

$279

Edmonton, CA (YEA) - Chicago, US (CHI)

WestJet Logo
WestJet

Jul 6

YEG
4h 34m
Direct

Jul 6

ORD
WestJet Logo
WestJet

Jul 30

ORD
6h 57m
YYC

Jul 31

YEG

as low as

$282

Edmonton, CA (YEA) - Chicago, US (CHI)

Air Canada Logo
Air Canada

Jul 1

YEG
13h 14m
YYZ

Jul 2

ORD
Air Canada Logo
Air Canada

Jul 23

ORD
12h 2m
YYZ

Jul 24

YEG

as low as

$293

Edmonton, CA (YEA) - Chicago, US (CHI)

Air Canada Logo
Air Canada

Jun 21

YEG
15h 24m
YYZ

Jun 22

ORD
Air Canada Logo
Air Canada

Jul 16

ORD
7h 14m
YUL

Jul 16

YEG

as low as

$394

Edmonton, CA (YEA) - Chicago, US (CHI)

Air Canada Logo
Air Canada

Jun 23

YEG
15h 24m
YYZ

Jun 24

ORD
Air Canada Logo
Air Canada

Jul 16

ORD
7h 14m
YUL

Jul 16

YEG

as low as

$394

Edmonton, CA (YEA) - Chicago, US (CHI)

Alaska Airlines Logo
Alaska Airlines

Jun 23

YEG
11h 30m
SEA

Jun 24

ORD
Alaska Airlines Logo
Alaska Airlines

Jul 16

ORD
13h 59m
SEA

Jul 17

YEG

as low as

$420

Edmonton, CA (YEA) - Chicago, US (CHI)

WestJet Logo
WestJet

Jul 13

YEG
4h 34m
Direct

Jul 13

ORD
WestJet Logo
WestJet

Jul 27

ORD
11h 27m
DTW
YYC

Jul 27

YEG

as low as

$425

Edmonton, CA (YEA) - Chicago, US (CHI)

WestJet Logo
WestJet

Jul 2

YEG
4h 34m
Direct

Jul 2

ORD
WestJet Logo
WestJet

Jul 12

ORD
11h 49m
ATL
YYC

Jul 13

YEG

as low as

$433

Edmonton, CA (YEA) - Chicago, US (CHI)

WestJet Logo
WestJet

Jul 16

YEG
8h 44m
YYC

Jul 16

ORD
WestJet Logo
WestJet

Jul 28

ORD
8h 48m
MSP
YVR

Jul 28

YEG

as low as

$433

Top Deals on flights from Quebec to Chicago

Quebec, CA (YQB) - Chicago, US (CHI)

American Airlines Logo
American Airlines

Jun 3

YQB
1h 50m
Direct

Jun 3

ORD
American Airlines Logo
American Airlines

Jun 17

ORD
3h 35m
Direct

Jun 17

YQB

as low as

$399

Quebec, CA (YQB) - Chicago, US (CHI)

United Airlines Logo
United Airlines

Jun 4

YQB
1h 56m
Direct

Jun 4

ORD
United Airlines Logo
United Airlines

Jun 18

ORD
5h 46m
YOW

Jun 18

YQB

as low as

$405

Quebec, CA (YQB) - Chicago, US (CHI)

United Airlines Logo
United Airlines

Jun 3

YQB
1h 56m
Direct

Jun 3

ORD
United Airlines Logo
United Airlines

Jun 17

ORD
5h 45m
YOW

Jun 17

YQB

as low as

$405

Quebec, CA (YQB) - Chicago, US (CHI)

Air Canada Logo
Air Canada

Jun 4

YQB
1h 56m
Direct

Jun 4

ORD
Air Canada Logo
Air Canada

Jun 18

ORD
5h 46m
YOW

Jun 18

YQB

as low as

$405

Quebec, CA (YQB) - Chicago, US (CHI)

Air Canada Logo
Air Canada

Jun 3

YQB
1h 56m
Direct

Jun 3

ORD
Air Canada Logo
Air Canada

Jun 17

ORD
5h 45m
YOW

Jun 17

YQB

as low as

$405

Quebec, CA (YQB) - Chicago, US (CHI)

American Airlines Logo
American Airlines

Jun 3

YQB
1h 50m
Direct

Jun 3

ORD
American Airlines Logo
American Airlines

Jun 17

ORD
7h 25m
PHL

Jun 17

YQB

as low as

$409

Quebec, CA (YQB) - Chicago, US (CHI)

American Airlines Logo
American Airlines

Jun 5

YQB
1h 50m
Direct

Jun 5

ORD
American Airlines Logo
American Airlines

Jun 19

ORD
8h 29m
PHL

Jun 19

YQB

as low as

$409

Quebec, CA (YQB) - Chicago, US (CHI)

United Airlines Logo
United Airlines

Jun 3

YQB
5h 34m
YYZ

Jun 3

ORD
United Airlines Logo
United Airlines

Jun 17

ORD
5h 45m
YOW

Jun 17

YQB

as low as

$416

Quebec, CA (YQB) - Chicago, US (CHI)

Air Canada Logo
Air Canada

Jun 3

YQB
5h 34m
YYZ

Jun 3

ORD
Air Canada Logo
Air Canada

Jun 17

ORD
5h 45m
YOW

Jun 17

YQB

as low as

$416

Quebec, CA (YQB) - Chicago, US (CHI)

Air Canada Logo
Air Canada

May 30

YQB
7h 40m
YOW
YYZ

May 30

ORD
Air Canada Logo
Air Canada

Jun 7

ORD
6h 15m
YYZ

Jun 7

YQB

as low as

$425

Quebec, CA (YQB) - Chicago, US (CHI)

Air Canada Logo
Air Canada

May 18

YQB
7h 40m
YOW
YYZ

May 18

ORD
Air Canada Logo
Air Canada

Jun 11

ORD
6h 55m
YYZ

Jun 11

YQB

as low as

$425

Quebec, CA (YQB) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 27

YQB
1h 50m
Direct

May 27

ORD
American Airlines Logo
American Airlines

Jun 10

ORD
3h 35m
Direct

Jun 10

YQB

as low as

$429

Top Deals on flights from Windsor to Chicago

Windsor, CA (YQG) - Chicago, US (CHI)

Air Canada Logo
Air Canada

May 29

YQG
4h 46m
YYZ

May 29

ORD
Air Canada Logo
Air Canada

Jun 5

ORD
12h 4m
YYZ

Jun 6

YQG

as low as

$331

Windsor, CA (YQG) - Chicago, US (CHI)

Air Canada Logo
Air Canada

May 29

YQG
5h 50m
YYZ

May 29

ORD
Air Canada Logo
Air Canada

Jun 5

ORD
12h 4m
YYZ

Jun 6

YQG

as low as

$331

Windsor, CA (YQG) - Chicago, US (CHI)

Air Canada Logo
Air Canada

May 29

YQG
6h 35m
YYZ

May 29

ORD
Air Canada Logo
Air Canada

Jun 5

ORD
12h 4m
YYZ

Jun 6

YQG

as low as

$331

Windsor, CA (YQG) - Chicago, US (CHI)

Air Canada Logo
Air Canada

May 29

YQG
6h 35m
YYZ

May 29

ORD
Air Canada Logo
Air Canada

Jun 5

ORD
4h 26m
YYZ

Jun 5

YQG

as low as

$340

Windsor, CA (YQG) - Chicago, US (CHI)

Air Canada Logo
Air Canada

May 29

YQG
4h 46m
YYZ

May 29

ORD
Air Canada Logo
Air Canada

Jun 5

ORD
4h 26m
YYZ

Jun 5

YQG

as low as

$340

Windsor, CA (YQG) - Chicago, US (CHI)

Air Canada Logo
Air Canada

May 29

YQG
5h 50m
YYZ

May 29

ORD
Air Canada Logo
Air Canada

Jun 5

ORD
4h 26m
YYZ

Jun 5

YQG

as low as

$340

Windsor, CA (YQG) - Chicago, US (CHI)

Air Canada Logo
Air Canada

May 29

YQG
4h 46m
YYZ

May 29

ORD
Air Canada Logo
Air Canada

Jun 5

ORD
18h 13m
YOW
YYZ

Jun 6

YQG

as low as

$341

Windsor, CA (YQG) - Chicago, US (CHI)

Air Canada Logo
Air Canada

May 29

YQG
5h 50m
YYZ

May 29

ORD
Air Canada Logo
Air Canada

Jun 5

ORD
18h 13m
YOW
YYZ

Jun 6

YQG

as low as

$341

Windsor, CA (YQG) - Chicago, US (CHI)

Air Canada Logo
Air Canada

May 29

YQG
6h 35m
YYZ

May 29

ORD
Air Canada Logo
Air Canada

Jun 5

ORD
18h 13m
YOW
YYZ

Jun 6

YQG

as low as

$341

Windsor, CA (YQG) - Chicago, US (CHI)

Air Canada Logo
Air Canada

May 29

YQG
8h 9m
YYZ

May 29

ORD
Air Canada Logo
Air Canada

Jun 5

ORD
12h 4m
YYZ

Jun 6

YQG

as low as

$354

Windsor, CA (YQG) - Chicago, US (CHI)

Air Canada Logo
Air Canada

May 29

YQG
8h 9m
YYZ

May 29

ORD
Air Canada Logo
Air Canada

Jun 5

ORD
4h 26m
YYZ

Jun 5

YQG

as low as

$363

Windsor, CA (YQG) - Chicago, US (CHI)

Air Canada Logo
Air Canada

May 29

YQG
9h
YYZ

May 29

ORD
Air Canada Logo
Air Canada

Jun 5

ORD
4h 26m
YYZ

Jun 5

YQG

as low as

$363