Cheap flights from Canada to Chicago from C$ 169
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 27/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
Return
1 adult
Economy
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Wed 24/4
Wed 1/5
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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
Porter Airlines![Porter Airlines]()
8 May![Porter Airlines]()
15 May
YTZ8:50 p.m.Toronto Island
1h 47m
MDW9:37 p.m.Chicago Midway
MDW11:05 a.m.Chicago Midway
1h 42m
YTZ1:47 p.m.Toronto Island
WestJet![WestJet]()
23 May![WestJet]()
30 May
YYC12:30 p.m.Calgary
3h 35m
ORD5:05 p.m.Chicago O'Hare Intl
ORD5:55 p.m.Chicago O'Hare Intl
3h 27m
YYC8:22 p.m.Calgary
American Airlines![American Airlines]()
13 May![American Airlines]()
15 May
YYZ6:30 a.m.Toronto Pearson Intl
1h 56m
ORD7:26 a.m.Chicago O'Hare Intl
ORD8:35 a.m.Chicago O'Hare Intl
1h 40m
YYZ11:15 a.m.Toronto Pearson Intl
Air Canada![Air Canada]()
8 May![Air Canada]()
15 May
YYZ1:00 p.m.Toronto Pearson Intl
2h 04m
ORD2:04 p.m.Chicago O'Hare Intl
ORD6:00 a.m.Chicago O'Hare Intl
1h 45m
YYZ8:45 a.m.Toronto Pearson Intl
United Airlines![United Airlines]()
8 May![United Airlines]()
9 May
YUL6:15 a.m.Montreal Pierre Elliott Trudeau Intl
2h 46m
ORD8:01 a.m.Chicago O'Hare Intl
ORD9:37 p.m.Chicago O'Hare Intl
14h 35m
1 stop
YUL1:12 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 American Airlines and Porter Airlines
Search last-minute flights to Chicago from Canada
Find and compare round-trip flight prices for your last-minute flight from Canada to Chicago
Porter Airlines![Porter Airlines]()
28 Apr.![Porter Airlines]()
11 May
YTZ8:50 p.m.Toronto Island
1h 47m
MDW9:37 p.m.Chicago Midway
MDW8:00 a.m.Chicago Midway
1h 42m
YTZ10:42 a.m.Toronto Island
American Airlines![American Airlines]()
28 Apr.![American Airlines]()
11 May
YYZ6:30 a.m.Toronto Pearson Intl
1h 55m
ORD7:25 a.m.Chicago O'Hare Intl
ORD6:00 a.m.Chicago O'Hare Intl
5h 04m
1 stop
YYZ12:04 p.m.Toronto Pearson Intl
Air Canada![Air Canada]()
28 Apr.![Air Canada]()
11 May
YYZ8:00 a.m.Toronto Pearson Intl
1h 54m
ORD8:54 a.m.Chicago O'Hare Intl
ORD6:00 a.m.Chicago O'Hare Intl
1h 45m
YYZ8:45 a.m.Toronto Pearson Intl
Multiple Airlines![Multiple Airlines]()
26 Apr.![Multiple Airlines]()
28 May
YYZ12:35 p.m.Toronto Pearson Intl
12h 45m
1 stop
ORD12:20 a.m.Chicago O'Hare Intl
ORD6:40 p.m.Chicago O'Hare Intl
18h 20m
1 stop
YYZ2:00 p.m.Toronto Pearson Intl
United Airlines![United Airlines]()
1 May![United Airlines]()
3 May
YYC6:25 a.m.Calgary
16h 51m
1 stop
ORD12:16 a.m.Chicago O'Hare Intl
ORD8:51 a.m.Chicago O'Hare Intl
3h 46m
YYC11:37 a.m.Calgary
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$ 266 | Free Cancellation | Rating 7.4 11,333 reviews | |||
| PriceFrom C$ 266 | Free Cancellation | Rating 7.4 439 reviews | |||
| PriceFrom C$ 268 | Free Cancellation | Rating 7.5 3,011 reviews | |||
| PriceFrom C$ 290 | Free Cancellation | Rating 7.0 6,841 reviews | |||
| PriceFrom C$ 301 | Free Cancellation | Rating 8.2 664 reviews | |||
| PriceFrom C$ 321 | Free Cancellation | Rating 8.0 11,102 reviews | |||
| PriceFrom C$ 326 | Free Cancellation | Rating 8.4 951 reviews | |||
| PriceFrom C$ 330 | Free Cancellation | Rating 7.3 14,954 reviews | |||
| PriceFrom C$ 332 | Free Cancellation | Rating 8.1 9,108 reviews | |||
| PriceFrom C$ 465 | Free Cancellation | Rating 8.8 4 reviews |
WestJet Encore flights from Canada to Chicago
Our best WestJet Encore deals on Canada to Chicago flight tickets
Delta flights from Canada to Chicago
Our best Delta deals on Canada to Chicago flight tickets
Delta![Delta]()
11 May![Delta]()
15 May
YUL1:05 p.m.Montreal Pierre Elliott Trudeau Intl
4h 26m
1 stop
ORD4:31 p.m.Chicago O'Hare Intl
ORD7:00 a.m.Chicago O'Hare Intl
9h 36m
1 stop
YUL5:36 p.m.Montreal Pierre Elliott Trudeau Intl
Delta![Delta]()
9 May![Delta]()
15 May
YUL7:00 a.m.Montreal Pierre Elliott Trudeau Intl
8h 20m
1 stop
ORD2:20 p.m.Chicago O'Hare Intl
ORD7:00 a.m.Chicago O'Hare Intl
9h 36m
1 stop
YUL5:36 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?
Montreal Pierre Elliott Trudeau Intl - Chicago Midway. Fly from Montreal Pierre Elliott Trudeau Intl 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$ 169 |
|---|---|
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 April 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.
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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