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Flights to Chicago

C$ 192 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 11/9. 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
1 adult, Economy, 0 bags

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Find the cheapest flights from Canada to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Air Canada Logo
4:00 p.m. - 8:12 p.m.
YYZ
-
ORD
5h 12m
1 stop
Air Canada Logo
3:45 p.m. - 6:30 p.m.
ORD
-
YYZ
1h 45mdirect
C$ 289Air Canada
Wed, 9 Sep - Wed, 16 Sep
Air Canada Logo
8:20 a.m. - 2:52 p.m.
YTZ
-
ORD
7h 32m
2 stops
Air Canada Logo
8:45 a.m. - 3:50 p.m.
ORD
-
YTZ
6h 05m
1 stop
C$ 289Air Canada
Thu, 17 Sep - Tue, 22 Sep
Porter Airlines Logo
8:55 a.m. - 9:45 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
3:20 p.m. - 6:00 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 290Porter Airlines
Mon, 31 Aug - Mon, 21 Sep
Porter Airlines Logo
8:55 a.m. - 9:45 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
11:45 a.m. - 2:25 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 292Porter Airlines
Tue, 25 Aug - Wed, 9 Sep
United Airlines Logo
11:00 a.m. - 12:00 p.m.
YYZ
-
ORD
2h 00mdirect
United Airlines Logo
12:59 p.m. - 3:46 p.m.
ORD
-
YYZ
1h 47mdirect
C$ 294United Airlines
Fri, 4 Sep - Wed, 9 Sep
WestJet Logo
12:00 p.m. - 4:40 p.m.
YYC
-
ORD
3h 40mdirect
WestJet Logo
5:30 p.m. - 8:25 p.m.
ORD
-
YYC
3h 55mdirect
C$ 310WestJet
Sat, 29 Aug - Mon, 31 Aug
WestJet Logo
12:00 p.m. - 4:40 p.m.
YYC
-
ORD
3h 40mdirect
WestJet Logo
5:30 p.m. - 8:25 p.m.
ORD
-
YYC
3h 55mdirect
C$ 313WestJet
Sat, 29 Aug - Mon, 31 Aug
Delta Logo
4:05 p.m. - 6:33 p.m.
YYZ
-
MDW
3h 28m
1 stop
Delta Logo
9:29 a.m. - 1:34 p.m.
MDW
-
YYZ
3h 05m
1 stop
C$ 342Delta
Fri, 25 Sep - Sun, 27 Sep
United Airlines Logo
8:30 a.m. - 1:05 p.m.
YYC
-
ORD
3h 35mdirect
United Airlines Logo
7:45 p.m. - 10:35 p.m.
ORD
-
YYC
3h 50mdirect
C$ 354United Airlines
Sat, 5 Sep - Sun, 13 Sep
Delta Logo
6:45 a.m. - 3:30 p.m.
YYC
-
ORD
7h 45m
1 stop
Delta Logo
2:00 p.m. - 11:04 p.m.
ORD
-
YYC
10h 04m
1 stop
C$ 369Delta
Sat, 29 Aug - Mon, 31 Aug

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 27 July 2026.
Use the filters below to find and compare flights to Chicago that are best for you.

Fly from

Route

Depart

Return

Price

Cheapest round-trip

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 9/9

4:00 p.m.-8:12 p.m.

1 stop5h 12m

Chicago O'Hare Intl

Wed 16/9

3:45 p.m.-6:30 p.m.

Nonstop1h 45m

C$ 289

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Thu 17/9

8:20 a.m.-2:52 p.m.

2 stops7h 32m

Chicago O'Hare Intl

Tue 22/9

8:45 a.m.-3:50 p.m.

1 stop6h 05m

C$ 289
Quickest round-trip

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 31/8

8:55 a.m.-9:45 a.m.

Nonstop1h 50m

Chicago Midway

Mon 21/9

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

C$ 290

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 25/8

8:55 a.m.-9:45 a.m.

Nonstop1h 50m

Chicago Midway

Wed 9/9

11:45 a.m.-2:25 p.m.

Nonstop1h 40m

C$ 292

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 4/9

11:00 a.m.-12:00 p.m.

Nonstop2h 00m

Chicago O'Hare Intl

Wed 9/9

12:59 p.m.-3:46 p.m.

Nonstop1h 47m

C$ 294

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 29/8

12:00 p.m.-4:40 p.m.

Nonstop3h 40m

Chicago O'Hare Intl

Mon 31/8

5:30 p.m.-8:25 p.m.

Nonstop3h 55m

C$ 310

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 29/8

12:00 p.m.-4:40 p.m.

Nonstop3h 40m

Chicago O'Hare Intl

Mon 31/8

5:30 p.m.-8:25 p.m.

Nonstop3h 55m

C$ 313

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 25/9

4:05 p.m.-6:33 p.m.

1 stop3h 28m

Chicago Midway

Sun 27/9

9:29 a.m.-1:34 p.m.

1 stop3h 05m

C$ 342

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 5/9

8:30 a.m.-1:05 p.m.

Nonstop3h 35m

Chicago O'Hare Intl

Sun 13/9

7:45 p.m.-10:35 p.m.

Nonstop3h 50m

C$ 354

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 29/8

6:45 a.m.-3:30 p.m.

1 stop7h 45m

Chicago O'Hare Intl

Mon 31/8

2:00 p.m.-11:04 p.m.

1 stop10h 04m

C$ 369

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 February is another great option to travel to Chicago, with average flight prices from Canada averaging around C$ 354.

What is the absolute cheapest flight to Chicago?

Users booking trips to Chicago from Toronto found flights 39% 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$ 632. 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$ 998. 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 morning is the cheapest time of day to fly from Canada to Chicago when you can find flight prices for as low as C$ 697. Flying to Chicago in the morning 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$ 1,064 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$ 430 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$ 247 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 AIRPORTMarch19% cheaperFlying from Toronto Pearson Intl Airport to Chicago costs on average just C$ 314 in March
MOST EXPENSIVE MONTH TO FLY TO CHICAGO FROM TORONTO PEARSON INTL AIRPORTDecember18% more expensiveIt costs about C$ 457 for flights to Chicago from Toronto Pearson Intl Airport in December
MOST POPULAR MONTH TO FLY TO CHICAGO FROM TORONTO PEARSON INTL AIRPORTAugust161% 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$ 192

Best Round-Trip Price

C$ 289

Fastest flight time

1h 50m

Popular in

July
The best one-way flight price to Chicago from Canada in the last 5 days is C$ 192 (Toronto Pearson Intl to Chicago O'Hare Intl).
Search Deals
The best round-trip flight price to Chicago from Canada in the last 5 days is C$ 289 (Toronto Pearson Intl to Chicago O'Hare Intl).
Search Deals
The fastest flight to Chicago from Canada takes 1h 50m (Toronto Island to Chicago Midway).
Search Deals
July has the highest demand for flights to Chicago, with a 11% price increase on average.
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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 88 days out, which is when prices tend to be around C$ 380. Don’t hesitate to check prices now though, because momondo users recently found tickets for as low as C$ 245.

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$ 388 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 July 2026, there are 8 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
Merrillville
Hammond
Munster
Valparaiso
Portage

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.

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