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Flights to Chicago

C$ 142 Cheap flights to Chicago

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight to Chicago departing on 2/10. 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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Find the cheapest flights from Canada to Chicago

Cheap round-trip flights

United Airlines Logo
6:52 a.m. - 7:58 a.m.YYZ-ORD
2h 06mdirect
United Airlines Logo
11:15 a.m. - 2:01 p.m.ORD-YYZ
1h 46mdirect
C$ 203United Airlines
Find Deal
Tue, 4 Nov - Tue, 11 Nov
WestJet Logo
12:15 p.m. - 4:43 p.m.YYC-ORD
3h 28mdirect
WestJet Logo
5:30 p.m. - 8:19 p.m.ORD-YYC
3h 49mdirect
C$ 216WestJet
Find Deal
Fri, 17 Oct - Sun, 19 Oct
Air Canada Logo
2:10 p.m. - 3:04 p.m.YYZ-ORD
1h 54mdirect
Air Canada Logo
8:25 p.m. - 11:08 p.m.ORD-YYZ
1h 43mdirect
C$ 218Air Canada
Find Deal
Wed, 1 Oct - Wed, 8 Oct
Air Canada Logo
6:30 p.m. - 7:30 p.m.YYZ-ORD
2h 00mdirect
Air Canada Logo
8:15 p.m. - 10:54 p.m.ORD-YYZ
1h 39mdirect
C$ 220Air Canada
Find Deal
Fri, 31 Oct - Mon, 3 Nov
American Airlines Logo
6:29 a.m. - 10:54 a.m.YYC-ORD
3h 25mdirect
American Airlines Logo
5:00 a.m. - 11:59 a.m.ORD-YYC
7h 59m1 stop
C$ 229American Airlines
Find Deal
Tue, 30 Sep - Tue, 7 Oct
Porter Airlines Logo
3:35 p.m. - 4:24 p.m.YTZ-MDW
1h 49mdirect
Porter Airlines Logo
9:35 a.m. - 12:17 p.m.MDW-YTZ
1h 42mdirect
C$ 239Porter Airlines
Find Deal
Fri, 19 Sep - Sun, 21 Sep
Porter Airlines Logo
7:50 a.m. - 8:39 a.m.YTZ-MDW
1h 49mdirect
Porter Airlines Logo
9:35 a.m. - 12:17 p.m.MDW-YTZ
1h 42mdirect
C$ 242Porter Airlines
Find Deal
Thu, 25 Sep - Sun, 28 Sep
American Airlines Logo
3:11 p.m. - 4:05 p.m.YYZ-ORD
1h 54mdirect
American Airlines Logo
9:48 a.m. - 3:39 p.m.ORD-YYZ
4h 51m1 stop
C$ 250American Airlines
Find Deal
Thu, 2 Oct - Sun, 5 Oct
Air Transat Logo
7:50 a.m. - 8:39 a.m.YTZ-MDW
1h 49mdirect
Air Transat Logo
5:20 p.m. - 8:02 p.m.MDW-YTZ
1h 42mdirect
C$ 289Air Transat
Find Deal
Wed, 1 Oct - Wed, 8 Oct
Air Transat Logo
7:50 a.m. - 8:39 a.m.YTZ-MDW
1h 49mdirect
Air Transat Logo
9:35 a.m. - 12:17 p.m.MDW-YTZ
1h 42mdirect
C$ 290Air Transat
Find Deal
Sat, 27 Sep - Mon, 29 Sep

momondo Fare Finder

 
Locate flights to Chicago that fit your budget, with regularly updated fares and availability. In the last 7 days, momondo users made a total of 96,600 searches and data was last updated on 18 August 2025.
Use the filters below to find and compare flights to Chicago that are best for you.

Fly from

Route

Depart

Return

Price

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 4/11

6:52 a.m.-7:58 a.m.

Nonstop2h 06m

Chicago O'Hare Intl

Tue 11/11

11:15 a.m.-2:01 p.m.

Nonstop1h 46m

C$ 203

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 17/10

12:15 p.m.-4:43 p.m.

Nonstop3h 28m

Chicago O'Hare Intl

Sun 19/10

5:30 p.m.-8:19 p.m.

Nonstop3h 49m

C$ 216

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 1/10

2:10 p.m.-3:04 p.m.

Nonstop1h 54m

Chicago O'Hare Intl

Wed 8/10

8:25 p.m.-11:08 p.m.

Nonstop1h 43m

C$ 218

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 31/10

6:30 p.m.-7:30 p.m.

Nonstop2h 00m

Chicago O'Hare Intl

Mon 3/11

8:15 p.m.-10:54 p.m.

Nonstop1h 39m

C$ 220

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 30/9

6:29 a.m.-10:54 a.m.

Nonstop3h 25m

Chicago O'Hare Intl

Tue 7/10

5:00 a.m.-11:59 a.m.

1 stop7h 59m

C$ 229

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 19/9

3:35 p.m.-4:24 p.m.

Nonstop1h 49m

Chicago Midway

Sun 21/9

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 239

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 25/9

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

Sun 28/9

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 242

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 2/10

3:11 p.m.-4:05 p.m.

Nonstop1h 54m

Chicago O'Hare Intl

Sun 5/10

9:48 a.m.-3:39 p.m.

1 stop4h 51m

C$ 250

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 1/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

Wed 8/10

5:20 p.m.-8:02 p.m.

Nonstop1h 42m

C$ 289

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 27/9

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

Mon 29/9

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 290

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 Chicago from

Chicago flights insights and trends

Explore insights for your Chicago flight to craft the best travel plan

What is the cheapest month to fly to Chicago?

The month of June is another great option to travel to Chicago, with average flight prices from Canada averaging around C$ 310.

What is the absolute cheapest flight to Chicago?

Users booking trips to Chicago from Orlando found flights 63% cheaper than the average price of flights to Chicago. To find the cheapest price to Chicago from your area, use momondo’s Airport-to-Airport Pricing Tool.
See prices from:

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

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as C$ 680. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Tuesday because tickets tend to average around C$ 1,216. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

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

In the evening is the cheapest time of day to fly from Canada to Chicago when you can find flight prices for as low as C$ 607. Flying to Chicago in the evening is an ideal time because this is during off-peak travel hours. In the afternoon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 1,379 per ticket.

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

You are more likely to see cheaper flights to Chicago from Canada when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around C$ 408 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Canada for as low as C$ 330 on momondo.

Cheapest flights to Chicago

Find the cheapest flights to Chicago from your nearest city or airport
Find Flights from Toronto Pearson Intl Airport to Chicago Midway Airport
CHEAPEST MONTH TO FLY TO CHICAGO FROM TORONTO PEARSON INTL AIRPORTMay12% cheaperFlying from Toronto Pearson Intl Airport to Chicago costs on average just C$ 350 in May
MOST EXPENSIVE MONTH TO FLY TO CHICAGO FROM TORONTO PEARSON INTL AIRPORTDecember18% more expensiveIt costs about C$ 467 for flights to Chicago from Toronto Pearson Intl Airport in December
MOST POPULAR MONTH TO FLY TO CHICAGO FROM TORONTO PEARSON INTL AIRPORTAugust147% more users visitedMore momondo users searched in flights to Chicago from Toronto Pearson Intl Airport in August than any other month

Cheap Chicago flight deals and tips

Summary info about Chicago flight prices, duration and airlines

Best One-Way Price

C$ 142

Best Round-Trip Price

C$ 203

Fastest flight time

1h 49m

Popular in

November
The best one-way flight price to Chicago from Canada in the last 72 hours is C$ 142 (Toronto Pearson Intl to Chicago O'Hare Intl).
Search Deals
The best round-trip flight price to Chicago from Canada in the last 72 hours is C$ 203 (Toronto Pearson Intl to Chicago O'Hare Intl).
Search Deals
The fastest flight to Chicago from Canada takes 1h 49m (Toronto Island to Chicago Midway).
Search Deals
November has the highest demand for flights to Chicago, with a 7% price increase on average.
Search Deals

Frequently asked questions about flying to Chicago

When is it best to fly to Chicago to go sightseeing?

The best time to plan to fly to Chicago to go sightseeing would be when the temperature is not unbearable and the chance of rain is only moderate. Considering those guidelines, May or June seem like the best times of year to plan your visit.

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

The best time to book a flight to Chicago from Canada is 85 days out, which is when prices tend to be around C$ 355.

Is there an alternative airport near Chicago?

Those flying to Chicago could potentially find better pricing at Chicago Midway Airport (14 km from Chicago city centre) or Chicago Greater Rockford Airport (126 km from Chicago city centre) depending on the month and departure airport.

Is there a cheaper alternative to flying into Chicago?

Chicago Midway Airport has an average price of C$ 345 per person and is typically the cheapest airport to fly into when visiting Chicago. This average price does vary based on departure city. Try momondo’s Airport-to-Airport Pricing Tool to find the cheapest flight.

Are there flights to Downtown?

Yes, if you fly to Chicago Midway in Chicago which is the closest available airport to Downtown (14.3 km away).

What’s the closest airport to Magnificent Mile?

The closest airport to Magnificent Mile is Chicago Midway, 15.7 km away.

When did momondo last update prices for flights to Chicago?

Prices for flights to Chicago are updated daily.

How many operators does momondo search for flights to Chicago?

As of August 2025, there are 10 operators available to choose from for flights to Chicago.

How old do you have to be to fly 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 to Chicago.

What documentation or ID do you need to fly to Chicago?

The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Hammond
Munster
Benton Harbor
Merrillville

Why use momondo?

Why should I use momondo to find a flight deal to Chicago?

It is quick and easy to find flights to Chicago 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 Chicago that suits you.

Can I find flights to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights to Chicago?

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

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

Yes momondo offers price alerts on flights to Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Chicago trip

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Find better results for your trip to Chicago

Popular Flights to Chicago

Popular routes according to searches in the past day on momondo
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