Cheap flights from Canada to Chicago from C$ 161

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1 adult
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0 bags
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Sat 25/3
Sat 1/4

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Flight information for Canada to Chicago

Find info about flight duration, direct flights, and airports for your flight from Canada to Chicago

Fastest flight time

1h 35m

Direct flights

Every day

Airports in Chicago

3 airports
The fastest flight from Canada to Chicago takes 1h 35m
Direct flights go from Canada to Chicago every day.
There are 3 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW), Chicago Greater Rockford (RFD)

How to get the cheapest flight ticket from Canada to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies to Chicago from Canada?

Swoop. ANA, Air New Zealand, and Egypt Air are the most popular carriers operating from Canada to Chicago

What is the cheapest Canada to Chicago flight route?

Toronto Island - Chicago Midway. Fly from Toronto Island to Chicago Midway for the best Canada - Chicago flight prices

Easily compare round-trip flights from Canada to Chicago

Below you can see the best fares for your round-trip flight route over the next three months. All fares were found on momondo this week. Browse the quickest and cheapest flights from Canada to Chicago by changing tabs
Porter Airlines
15 Apr.
YTZ6:45 a.m.Toronto Island
1h 47m
MDW8:32 a.m.Chicago Midway
22 Apr.
MDW8:30 a.m.Chicago Midway
1h 42m
YTZ10:12 a.m.Toronto Island
Air Canada
21 Apr.
YYZ3:44 p.m.Toronto Pearson Intl
4h 18m
1 stop
ORD8:02 p.m.Chicago O'Hare Intl
22 Apr.
ORD2:40 a.m.Chicago O'Hare Intl
1h 37m
YYZ4:17 a.m.Toronto Pearson Intl
United Airlines
10 Apr.
YYZ5:15 p.m.Toronto Pearson Intl
2h 02m
ORD7:17 p.m.Chicago O'Hare Intl
14 Apr.
ORD3:13 a.m.Chicago O'Hare Intl
1h 42m
YYZ4:55 a.m.Toronto Pearson Intl
American Airlines
21 Apr.
YYZ3:42 p.m.Toronto Pearson Intl
12h 26m
1 stop
ORD4:08 a.m.Chicago O'Hare Intl
22 Apr.
ORD5:36 a.m.Chicago O'Hare Intl
4h 40m
1 stop
YYZ10:16 a.m.Toronto Pearson Intl
Multiple Airlines
18 Apr.
YUL2:50 p.m.Montreal Pierre Elliott Trudeau Intl
2h 31m
ORD5:21 p.m.Chicago O'Hare Intl
25 Apr.
ORD3:15 a.m.Chicago O'Hare Intl
2h 04m
YUL5:19 a.m.Montreal Pierre Elliott Trudeau Intl
Delta
18 Apr.
YUL8:44 a.m.Montreal Pierre Elliott Trudeau Intl
7h 36m
1 stop
ORD4:20 p.m.Chicago O'Hare Intl
25 Apr.
ORD8:20 a.m.Chicago O'Hare Intl
5h 41m
1 stop
YUL2:01 p.m.Montreal Pierre Elliott Trudeau Intl

Find the cheapest one-way flights from Canada to Chicago

If you're looking for one-way flights from Canada to Chicago, view some of our deals below provided by Air Canada and Porter Airlines
Porter Airlines
9 Apr.
YTZ6:45 a.m.Toronto Island
1h 47m
MDW8:32 a.m.Chicago Midway
Air Canada
9 Jun.
YYZ3:00 a.m.Toronto Pearson Intl
12h 03m
1 stop
ORD3:03 p.m.Chicago O'Hare Intl
Multiple Airlines
26 Apr.
YYZ5:10 a.m.Toronto Pearson Intl
16h 49m
1 stop
MDW9:59 p.m.Chicago Midway

Search last-minute flights to Chicago from Canada

Find and compare round-trip flight prices for your last-minute flight from Canada to Chicago
Multiple Airlines
26 Mar.
YYZ1:40 p.m.Toronto Pearson Intl
15h 27m
1 stop
ORD5:07 a.m.Chicago O'Hare Intl
29 Mar.
ORD4:45 a.m.Chicago O'Hare Intl
13h 40m
1 stop
YYZ6:25 p.m.Toronto Pearson Intl
United Airlines
30 Mar.
YQB1:00 a.m.Québec City
5h 54m
1 stop
ORD6:54 a.m.Chicago O'Hare Intl
2 Apr.
ORD5:30 p.m.Chicago O'Hare Intl
12h 47m
1 stop
YQB6:17 a.m.Québec City
Porter Airlines
30 Mar.
YTZ5:30 a.m.Toronto Island
1h 47m
MDW7:17 a.m.Chicago Midway
2 Apr.
MDW8:30 a.m.Chicago Midway
1h 42m
YTZ10:12 a.m.Toronto Island
American Airlines
30 Mar.
YYZ11:00 a.m.Toronto Pearson Intl
2h 08m
ORD1:08 p.m.Chicago O'Hare Intl
3 Apr.
ORD7:06 a.m.Chicago O'Hare Intl
6h 19m
1 stop
YYZ1:25 p.m.Toronto Pearson Intl
Delta
30 Mar.
YYZ9:40 a.m.Toronto Pearson Intl
5h 38m
1 stop
ORD3:18 p.m.Chicago O'Hare Intl
3 Apr.
ORD2:10 a.m.Chicago O'Hare Intl
6h 32m
1 stop
YYZ8:42 a.m.Toronto Pearson Intl
Air Canada
30 Mar.
YYZ10:30 a.m.Toronto Pearson Intl
1h 50m
ORD12:20 p.m.Chicago O'Hare Intl
3 Apr.
ORD2:45 p.m.Chicago O'Hare Intl
1h 38m
YYZ4:23 p.m.Toronto Pearson Intl

Best airlines flying from Canada to Chicago

Compare and see reviews for airlines that fly from Canada to Chicago with momondo
AirlineRatingFree CancellationPrice
WestJetPriceFrom C$ 131Free CancellationRating
7.3
161 reviews
Search WestJet flights
DeltaPriceFrom C$ 170Free CancellationRating
7.8
783 reviews
Search Delta flights
SwoopPriceFrom C$ 176Free CancellationRating
0.0
0 reviews
Search Swoop flights
Flair AirlinesPriceFrom C$ 189Free CancellationRating
6.1
17 reviews
Search Flair Airlines flights
American AirlinesPriceFrom C$ 216Free CancellationRating
7.2
2,055 reviews
Search American Airlines flights
Endeavor AirlinesPriceFrom C$ 224Free CancellationRating
10.0
1 review
Search Endeavor Airlines flights
Porter AirlinesPriceFrom C$ 230Free CancellationRating
8.2
53 reviews
Search Porter Airlines flights
Air CanadaPriceFrom C$ 260Free CancellationRating
7.3
325 reviews
Search Air Canada flights
United AirlinesPriceFrom C$ 283Free CancellationRating
7.2
1,676 reviews
Search United Airlines flights
Air New ZealandPriceFrom C$ 291Free CancellationRating
7.7
113 reviews
Search Air New Zealand flights

Air Canada flights from Canada to Chicago

Our best Air Canada deals on Canada to Chicago flight tickets
Air Canada
21 Apr.
YYZ3:44 p.m.Toronto Pearson Intl
4h 18m
1 stop
ORD8:02 p.m.Chicago O'Hare Intl
22 Apr.
ORD2:40 a.m.Chicago O'Hare Intl
1h 37m
YYZ4:17 a.m.Toronto Pearson Intl
Air Canada
21 Apr.
YYZ3:44 p.m.Toronto Pearson Intl
4h 18m
1 stop
ORD8:02 p.m.Chicago O'Hare Intl
22 Apr.
ORD3:15 a.m.Chicago O'Hare Intl
5h 11m
1 stop
YYZ8:26 a.m.Toronto Pearson Intl
Air Canada
22 Apr.
YYZ12:00 p.m.Toronto Pearson Intl
5h 21m
1 stop
ORD5:21 p.m.Chicago O'Hare Intl
23 Apr.
ORD2:40 a.m.Chicago O'Hare Intl
1h 37m
YYZ4:17 a.m.Toronto Pearson Intl

United Airlines flights from Canada to Chicago

Our best United Airlines deals on Canada to Chicago flight tickets
United Airlines
10 Apr.
YYZ5:15 p.m.Toronto Pearson Intl
2h 02m
ORD7:17 p.m.Chicago O'Hare Intl
14 Apr.
ORD3:13 a.m.Chicago O'Hare Intl
1h 42m
YYZ4:55 a.m.Toronto Pearson Intl
United Airlines
20 Apr.
YYZ5:15 p.m.Toronto Pearson Intl
2h 02m
ORD7:17 p.m.Chicago O'Hare Intl
22 Apr.
ORD9:55 a.m.Chicago O'Hare Intl
7h 14m
1 stop
YYZ5:09 p.m.Toronto Pearson Intl
United Airlines
11 Apr.
YUL2:19 a.m.Montreal Pierre Elliott Trudeau Intl
2h 46m
ORD5:05 a.m.Chicago O'Hare Intl
15 Apr.
ORD5:00 a.m.Chicago O'Hare Intl
7h 39m
1 stop
YUL12:39 p.m.Montreal Pierre Elliott Trudeau Intl

Alternative routes for Canada to Chicago

Compare alternative flights to and from nearby airports and cities to discover the best prices and most convenient flight times
Vancouver to Chicago Flights
Fastest flight time4h 01m
Cheapest priceC$ 313
Toronto to Chicago Flights
Fastest flight time1h 47m
Cheapest priceC$ 268
Montreal to Chicago Flights
Fastest flight time3h 47m
Cheapest priceC$ 283
Québec City to Chicago Flights
Fastest flight time2h 20m
Cheapest priceC$ 409
Calgary to Chicago Flights
Fastest flight time3h 21m
Cheapest priceC$ 415
Toronto to St. Louis Flights
Fastest flight time2h 06m
Cheapest priceC$ 522
Winnipeg to Chicago Flights
Fastest flight time6h 07m
Cheapest priceC$ 423
Ottawa to Chicago Flights
Fastest flight time4h 02m
Cheapest priceC$ 406
Vancouver to St. Louis Flights
Fastest flight time7h 25m
Cheapest priceC$ 573
Edmonton to Chicago Flights
Fastest flight time8h 13m
Cheapest priceC$ 435
Halifax to Chicago Flights
Fastest flight time5h 50m
Cheapest priceC$ 472
Montreal to St. Louis Flights
Fastest flight time5h 35m
Cheapest priceC$ 589

Similar Canada to Chicago flights

Flexible with your destination? Broaden your search and find flights similar to your Canada to Chicago route

Why use momondo?

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Yes. momondo enables you to select and highlight flights to Chicago from Canada with this policy.

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Canada to Chicago.

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Canada and alert you when they change.


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