Cheap flights from Canada to Chicago from C$ 176
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Canada to Chicago departing on 24/6. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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1 adult
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Tue 28/5
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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
WestJet![WestJet]()
26 May![WestJet]()
26 Aug.
YYC12:30 p.m.Calgary
3h 35m
ORD5:05 p.m.Chicago O'Hare Intl
ORD5:55 p.m.Chicago O'Hare Intl
3h 45m
YYC8:40 p.m.Calgary
Porter Airlines![Porter Airlines]()
18 Jun.![Porter Airlines]()
24 Jun.
YTZ9:20 a.m.Toronto Island
1h 47m
MDW10:07 a.m.Chicago Midway
MDW8:00 a.m.Chicago Midway
1h 42m
YTZ10:42 a.m.Toronto Island
Multiple Airlines![Multiple Airlines]()
4 Jun.![Multiple Airlines]()
11 Jun.
YYZ6:30 a.m.Toronto Pearson Intl
12h 10m
1 stop
ORD5:40 p.m.Chicago O'Hare Intl
ORD6:40 p.m.Chicago O'Hare Intl
18h 20m
1 stop
YYZ2:00 p.m.Toronto Pearson Intl
Air Canada![Air Canada]()
10 Jul.![Air Canada]()
17 Jul.
YYZ9:00 a.m.Toronto Pearson Intl
1h 54m
ORD9:54 a.m.Chicago O'Hare Intl
ORD6:00 a.m.Chicago O'Hare Intl
1h 48m
YYZ8:48 a.m.Toronto Pearson Intl
American Airlines![American Airlines]()
7 Jun.![American Airlines]()
9 Jun.
YYZ1:20 p.m.Toronto Pearson Intl
1h 55m
ORD2:15 p.m.Chicago O'Hare Intl
ORD9:50 a.m.Chicago O'Hare Intl
1h 50m
YYZ12:40 p.m.Toronto Pearson 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, Porter Airlines and WestJet
Search last-minute flights to Chicago from Canada
Find and compare round-trip flight prices for your last-minute flight from Canada to Chicago
WestJet![WestJet]()
26 May![WestJet]()
26 Aug.
YYC12:30 p.m.Calgary
3h 35m
ORD5:05 p.m.Chicago O'Hare Intl
ORD5:55 p.m.Chicago O'Hare Intl
3h 45m
YYC8:40 p.m.Calgary
American Airlines![American Airlines]()
30 May![American Airlines]()
31 May
YYZ3:10 p.m.Toronto Pearson Intl
1h 55m
ORD4:05 p.m.Chicago O'Hare Intl
ORD9:59 a.m.Chicago O'Hare Intl
1h 35m
YYZ12:34 p.m.Toronto Pearson Intl
Delta![Delta]()
29 May![Delta]()
5 Jun.
YYZ6:04 a.m.Toronto Pearson Intl
4h 16m
1 stop
ORD9:20 a.m.Chicago O'Hare Intl
ORD6:07 a.m.Chicago O'Hare Intl
4h 32m
1 stop
YYZ11:39 a.m.Toronto Pearson Intl
Multiple Airlines![Multiple Airlines]()
26 May![Multiple Airlines]()
26 Aug.
YYC12:05 p.m.Calgary
16h 15m
1 stop
ORD5:20 a.m.Chicago O'Hare Intl
ORD5:55 p.m.Chicago O'Hare Intl
3h 45m
YYC8:40 p.m.Calgary
Air Canada![Air Canada]()
24 May![Air Canada]()
27 May
YVR11:35 p.m.Vancouver Intl
4h 01m
ORD5:36 a.m.Chicago O'Hare Intl
ORD7:40 p.m.Chicago O'Hare Intl
4h 38m
YVR10:18 p.m.Vancouver Intl
WestJet flights from Canada to Chicago
Our best WestJet deals on Canada to Chicago flight tickets
WestJet![WestJet]()
26 May![WestJet]()
26 Aug.
YYC12:30 p.m.Calgary
3h 35m
ORD5:05 p.m.Chicago O'Hare Intl
ORD5:55 p.m.Chicago O'Hare Intl
3h 45m
YYC8:40 p.m.Calgary
WestJet![WestJet]()
6 Sep.![WestJet]()
13 Sep.
YYC12:30 p.m.Calgary
3h 27m
ORD4:57 p.m.Chicago O'Hare Intl
ORD5:55 p.m.Chicago O'Hare Intl
3h 45m
YYC8:40 p.m.Calgary
Air Canada flights from Canada to Chicago
Our best Air Canada deals on Canada to Chicago flight tickets
Air Canada![Air Canada]()
10 Jul.![Air Canada]()
17 Jul.
YYZ9:00 a.m.Toronto Pearson Intl
1h 54m
ORD9:54 a.m.Chicago O'Hare Intl
ORD6:00 a.m.Chicago O'Hare Intl
1h 48m
YYZ8:48 a.m.Toronto Pearson Intl
Air Canada![Air Canada]()
5 Sep.![Air Canada]()
8 Sep.
YUL6:15 a.m.Montreal Pierre Elliott Trudeau Intl
2h 43m
ORD7:58 a.m.Chicago O'Hare Intl
ORD7:25 a.m.Chicago O'Hare Intl
5h 46m
1 stop
YUL2:11 p.m.Montreal Pierre Elliott Trudeau Intl
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?
Air New Zealand. ANA, Air Canada, and Air New Zealand 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
What cabin class options are available on Canada to Chicago flights?
There are 4 cabin classes available to choose from on Canada to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
Can stopping save me money on Canada to Chicago flights?
No. A direct flight is the cheapest option for a flight between Canada to Chicago.
Cheap Canada to Chicago flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Canada to Chicago
Best price found | C$ 176 |
|---|---|
Fastest flight time | 1h 47m |
Direct flights | Every day |
Airports in Chicago | 2 airports |
When did momondo last update prices for flights from Canada to Chicago?
Prices for flights from Canada to Chicago were last updated today.
How many operators does momondo search for flights from Canada to Chicago?
The number of operators available for flights from Canada to Chicago is 12 as of May 2024.
How old do you have to be to fly from Canada to Chicago?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Canada to Chicago.
What documentation or ID do you need to fly to Chicago?
The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
Best airlines flying from Canada to Chicago
Compare and see reviews for airlines that fly from Canada to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom C$ 263 | Free Cancellation | Rating 7.5 2,919 reviews | |||
| PriceFrom C$ 264 | Free Cancellation | Rating 7.4 415 reviews | |||
| PriceFrom C$ 289 | Free Cancellation | Rating 7.0 6,947 reviews | |||
| PriceFrom C$ 294 | Free Cancellation | Rating 7.4 10,924 reviews | |||
| PriceFrom C$ 298 | Free Cancellation | Rating 8.2 626 reviews | |||
| PriceFrom C$ 317 | Free Cancellation | Rating 8.0 10,673 reviews | |||
| PriceFrom C$ 323 | Free Cancellation | Rating 8.4 921 reviews | |||
| PriceFrom C$ 327 | Free Cancellation | Rating 7.3 14,514 reviews | |||
| PriceFrom C$ 329 | Free Cancellation | Rating 8.0 9,157 reviews | |||
| PriceFrom C$ 460 | Free Cancellation | Rating 8.8 4 reviews |
Why use momondo?
Why should I use momondo to find a flight deal from Canada to Chicago?
momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Canada to Chicago . Millions of users trust and use momondo every year so you are in good hands.
Can I find flights from Canada to Chicago with flexible booking policies on momondo?
Yes. momondo enables you to select and highlight flights to Chicago from Canada with this policy.
How can momondo help me find flights from Canada to Chicago?
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.
I’m not ready to book a flight from Canada to Chicago right now. Can momondo alert me if prices change?
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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