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Cheap flights from Canada to Illinois from $99

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 Illinois departing on 5/4. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Canada to Illinois

Recent round-trip flight deals from Canada to Illinois

Enter your travel dates to find the best prices.
WestJet Logo
12:00 pm - 4:40 pm
YYC
-
ORD
3h 40mnonstop
WestJet Logo
5:30 pm - 8:25 pm
ORD
-
YYC
3h 55mnonstop
$161WestJet
Mon, May 4 - Thu, May 7
WestJet Logo
12:00 pm - 4:40 pm
YYC
-
ORD
3h 40mnonstop
WestJet Logo
5:30 pm - 8:25 pm
ORD
-
YYC
3h 55mnonstop
$162WestJet
Mon, May 4 - Thu, May 7
Air Canada Logo
6:25 pm - 8:10 pm
YUL
-
ORD
2h 45mnonstop
Air Canada Logo
12:50 pm - 4:01 pm
ORD
-
YUL
2h 11mnonstop
$177Air Canada
Mon, Feb 23 - Wed, Feb 25
Air Canada Logo
6:25 pm - 8:10 pm
YUL
-
ORD
2h 45mnonstop
Air Canada Logo
3:35 pm - 6:40 pm
ORD
-
YUL
2h 05mnonstop
$178Air Canada
Tue, Feb 24 - Wed, Mar 4
Porter Airlines Logo
11:25 am - 3:20 pm
YUL
-
MDW
4h 55m
1 stop
Porter Airlines Logo
4:15 pm - 10:45 pm
MDW
-
YUL
5h 30m
1 stop
$179Porter Airlines
Wed, Apr 8 - Sun, Apr 12
Porter Airlines Logo
10:35 am - 4:50 pm
YUL
-
MDW
7h 15m
1 stop
Porter Airlines Logo
10:25 am - 6:15 pm
MDW
-
YUL
6h 50m
1 stop
$180Porter Airlines
Fri, May 1 - Mon, May 4
United Airlines Logo
6:00 am - 8:00 am
YUL
-
ORD
3h 00mnonstop
United Airlines Logo
4:20 pm - 12:13 am
ORD
-
YUL
6h 53m
1 stop
$186United Airlines
Thu, Mar 26 - Mon, Mar 30
United Airlines Logo
4:45 pm - 6:45 pm
YUL
-
ORD
3h 00mnonstop
United Airlines Logo
6:01 pm - 12:13 am
ORD
-
YUL
5h 12m
1 stop
$187United Airlines
Tue, Mar 10 - Tue, Mar 31
Delta Logo
6:00 pm - 11:56 pm
YUL
-
ORD
6h 56m
1 stop
Delta Logo
5:25 am - 4:53 pm
ORD
-
YUL
10h 28m
1 stop
$209Delta
Mon, Feb 23 - Wed, Feb 25
Delta Logo
7:00 am - 1:25 pm
YUL
-
MDW
7h 25m
1 stop
Delta Logo
6:34 pm - 11:13 pm
MDW
-
YUL
3h 39m
1 stop
$218Delta
Wed, Mar 11 - Mon, Mar 16

Air Canada flights from Canada to Illinois

Our best Air Canada deals on Canada to Illinois flight tickets
Air Canada
Feb 23
YUL6:25 pmMontreal Pierre Elliott Trudeau Intl
2h 45m
ORD8:10 pmChicago O'Hare Intl
Feb 25
ORD12:50 pmChicago O'Hare Intl
2h 11m
YUL4:01 pmMontreal Pierre Elliott Trudeau Intl
$177
Air Canada
Feb 24
YUL6:25 pmMontreal Pierre Elliott Trudeau Intl
2h 45m
ORD8:10 pmChicago O'Hare Intl
Mar 4
ORD3:35 pmChicago O'Hare Intl
2h 05m
YUL6:40 pmMontreal Pierre Elliott Trudeau Intl
$178
Air Canada
Feb 26
YYZ6:40 pmToronto Pearson Intl
2h 05m
ORD7:45 pmChicago O'Hare Intl
Mar 1
ORD8:40 pmChicago O'Hare Intl
1h 40m
YYZ11:20 pmToronto Pearson Intl
$193

Delta flights from Canada to Illinois

Our best Delta deals on Canada to Illinois flight tickets
Delta
Feb 23
YUL6:00 pmMontreal Pierre Elliott Trudeau Intl
6h 56m
1 stop
ORD11:56 pmChicago O'Hare Intl
Feb 25
ORD5:25 amChicago O'Hare Intl
10h 28m
1 stop
YUL4:53 pmMontreal Pierre Elliott Trudeau Intl
$209
Delta
Apr 16
YUL7:00 amMontreal Pierre Elliott Trudeau Intl
10h 42m
1 stop
ORD4:42 pmChicago O'Hare Intl
Apr 24
ORD7:00 amChicago O'Hare Intl
3h 59m
1 stop
YUL11:59 amMontreal Pierre Elliott Trudeau Intl
$217
Delta
May 1
YUL7:00 amMontreal Pierre Elliott Trudeau Intl
10h 42m
1 stop
ORD4:42 pmChicago O'Hare Intl
May 4
ORD2:25 pmChicago O'Hare Intl
8h 23m
1 stop
YUL11:48 pmMontreal Pierre Elliott Trudeau Intl
$218

momondo Fare Finder

 
Customize your flight search to find flights from Canada to Illinois that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated February 5, 2026.
Use the filters below to find and compare flights from Canada to Illinois that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 5/4

12:00 pm-4:40 pm

Nonstop3h 40m

Chicago O'Hare Intl

Thu 5/7

5:30 pm-8:25 pm

Nonstop3h 55m

$161

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 5/4

12:00 pm-4:40 pm

Nonstop3h 40m

Chicago O'Hare Intl

Thu 5/7

5:30 pm-8:25 pm

Nonstop3h 55m

$162

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Mon 2/23

6:25 pm-8:10 pm

Nonstop2h 45m

Chicago O'Hare Intl

Wed 2/25

12:50 pm-4:01 pm

Nonstop2h 11m

$177

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Tue 2/24

6:25 pm-8:10 pm

Nonstop2h 45m

Chicago O'Hare Intl

Wed 3/4

3:35 pm-6:40 pm

Nonstop2h 05m

$178

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 4/8

11:25 am-3:20 pm

1 stop4h 55m

Chicago Midway

Sun 4/12

4:15 pm-10:45 pm

1 stop5h 30m

$179

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 5/1

10:35 am-4:50 pm

1 stop7h 15m

Chicago Midway

Mon 5/4

10:25 am-6:15 pm

1 stop6h 50m

$180

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 3/26

6:00 am-8:00 am

Nonstop3h 00m

Chicago O'Hare Intl

Mon 3/30

4:20 pm-12:13 am

1 stop6h 53m

$186

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Tue 3/10

4:45 pm-6:45 pm

Nonstop3h 00m

Chicago O'Hare Intl

Tue 3/31

6:01 pm-12:13 am

1 stop5h 12m

$187

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Mon 2/23

6:00 pm-11:56 pm

1 stop6h 56m

Chicago O'Hare Intl

Wed 2/25

5:25 am-4:53 pm

1 stop10h 28m

$209

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 3/11

7:00 am-1:25 pm

1 stop7h 25m

Chicago Midway

Mon 3/16

6:34 pm-11:13 pm

1 stop3h 39m

$218

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Illinois from

How to get the cheapest flight ticket from Canada to Illinois

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 month to fly to Illinois?

The cheapest month to fly to Illinois from Canada is in July. Flight prices, which tend to average around $217, are often lower during this time because this is during the off-season. If you aren’t able to travel to Illinois during the month of July, then flying in June is also cheap. Prices for this month can be found on momondo for an average of $225.

What is the cheapest day to depart on your flight to Illinois?

The cheapest day to depart from Canada to Illinois is on a Friday when prices can be found for as low as $458. Flights from Canada to Illinois on a Monday will generally be more expensive and average around $725. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Illinois?

Our most recent data shows that the best time of day to fly to Illinois is in the evening. Flights from Canada to Illinois during this time can be as low as $369. Flights in the afternoon are often more expensive with an average ticket price of $679.

What is the cheapest Canada to Illinois flight route?

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

How far in advance should I book a flight to Illinois?

You are more likely to see cheaper flights to Illinois from Canada when booking weeks ahead of your departure date. In general, you can expect to find flights to Illinois for around $286 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Illinois from Canada for as low as $195 on momondo.

What cabin class options are available on Canada to Illinois flights?

There are 4 cabin classes available to choose from on Canada to Illinois 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 Illinois flights?

You could potentially save up to 2% on your flight if you consider stops on a Canada to Illinois flight.

Cheap Canada to Illinois flight deals and tips

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

Best Price Found

$122

Fastest flight time

1h 50m

Direct flights

Every day

Airports in Illinois

98 airports
The best one-way flight to Illinois from Canada in the past 72 hours is $122. The best round-trip flight deal from Canada to Illinois found on momondo in the last 72 hours is $195.
The fastest flight from Canada to Illinois takes 1h 50m
Direct flights go from Canada to Illinois every day.
There are 98 airports in Illinois. From Canada there are direct flights to Chicago Midway (MDW).
Search flight deals

  • When did momondo last update prices for flights from Canada to Illinois?

    Prices for flights from Canada to Illinois were last updated today.

  • How many operators does momondo search for flights from Canada to Illinois?

  • How old do you have to be to fly from Canada to Illinois?

    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 Illinois.

  • What documentation or ID do you need to fly to Illinois?

    The travel and health documents required for your trip to Illinois can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Illinois. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Canada to Illinois?

Best airlines flying from Canada to Illinois

Compare and see reviews for airlines that fly from Canada to Illinois with momondo
Airline
Rating
Free Cancellation
Price
Porter AirlinesPriceFrom $80Free CancellationRating
7.9
412 reviews
Search Porter Airlines flights
Air CanadaPriceFrom $83Free CancellationRating
7.1
10,694 reviews
Search Air Canada flights
United AirlinesPriceFrom $90Free CancellationRating
7.4
9,241 reviews
Search United Airlines flights
WestJetPriceFrom $138Free CancellationRating
7.2
3,255 reviews
Search WestJet flights
American AirlinesPriceFrom $167Free CancellationRating
7.2
11,238 reviews
Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Canada to Illinois?

It is quick and easy to find Canada to Illinois flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Illinois that suits you.

Can I find flights from Canada to Illinois with flexible booking policies on momondo?

momondo does allow users to show only those flights to Illinois from Canada which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Canada to Illinois?

momondo provides multiple filters to help you find the best flight to Illinois from Canada. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Canada to Illinois right now. Can momondo alert me if prices change?

Price alerts on flights to Illinois from Canada are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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