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Flights to Chicago

C$ 190 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 15/8. 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.
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$ 269WestJet
Fri, 28 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$ 282WestJet
Fri, 28 Aug - Mon, 31 Aug
Porter Airlines Logo
1:45 p.m. - 2:35 p.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
3:20 p.m. - 6:00 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 285Porter Airlines
Wed, 2 Sep - Wed, 16 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$ 286Porter Airlines
Thu, 27 Aug - Tue, 1 Sep
Porter Airlines Logo
1:45 p.m. - 2:35 p.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
3:15 p.m. - 5:55 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 288Porter Airlines
Wed, 5 Aug - Wed, 12 Aug
Air Canada Logo
10:45 a.m. - 2:44 p.m.
YTZ
-
ORD
4h 59m
1 stop
Air Canada Logo
7:25 a.m. - 10:18 a.m.
ORD
-
YTZ
1h 53mdirect
C$ 289Air Canada
Thu, 20 Aug - Mon, 24 Aug
Porter Airlines Logo
8:55 a.m. - 9:45 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
10:25 a.m. - 1:05 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 289Porter Airlines
Fri, 14 Aug - Mon, 17 Aug
Air Canada Logo
7:35 p.m. - 8:41 p.m.
YTZ
-
ORD
2h 06mdirect
Air Canada Logo
7:25 a.m. - 10:18 a.m.
ORD
-
YTZ
1h 53mdirect
C$ 290Air Canada
Wed, 19 Aug - Tue, 25 Aug
United Airlines Logo
12:37 p.m. - 5:10 p.m.
YYC
-
ORD
3h 33mdirect
United Airlines Logo
8:40 a.m. - 11:35 a.m.
ORD
-
YYC
3h 55mdirect
C$ 350United Airlines
Mon, 26 Oct - Fri, 30 Oct
American Airlines Logo
4:15 p.m. - 10:30 p.m.
YUL
-
ORD
7h 15m
1 stop
American Airlines Logo
8:18 a.m. - 11:43 a.m.
ORD
-
YUL
2h 25mdirect
C$ 381American Airlines
Wed, 5 Aug - Wed, 12 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 15 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

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 28/8

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$ 269

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 28/8

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$ 282
Quickest round-trip

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 2/9

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Wed 16/9

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

Nonstop1h 40m

C$ 285

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 27/8

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

Nonstop1h 50m

Chicago Midway

Tue 1/9

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

Nonstop1h 40m

C$ 286

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 5/8

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Wed 12/8

3:15 p.m.-5:55 p.m.

Nonstop1h 40m

C$ 288

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Thu 20/8

10:45 a.m.-2:44 p.m.

1 stop4h 59m

Chicago O'Hare Intl

Mon 24/8

7:25 a.m.-10:18 a.m.

Nonstop1h 53m

C$ 289

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 14/8

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

Nonstop1h 50m

Chicago Midway

Mon 17/8

10:25 a.m.-1:05 p.m.

Nonstop1h 40m

C$ 289

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Wed 19/8

7:35 p.m.-8:41 p.m.

Nonstop2h 06m

Chicago O'Hare Intl

Tue 25/8

7:25 a.m.-10:18 a.m.

Nonstop1h 53m

C$ 290

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 26/10

12:37 p.m.-5:10 p.m.

Nonstop3h 33m

Chicago O'Hare Intl

Fri 30/10

8:40 a.m.-11:35 a.m.

Nonstop3h 55m

C$ 350

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Wed 5/8

4:15 p.m.-10:30 p.m.

1 stop7h 15m

Chicago O'Hare Intl

Wed 12/8

8:18 a.m.-11:43 a.m.

Nonstop2h 25m

C$ 381

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$ 364.

What is the absolute cheapest flight to Chicago?

Users booking trips to Chicago from Toronto found flights 47% 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$ 634. 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$ 1,024. 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$ 703. 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$ 1,063 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$ 427 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 AIRPORTDecember19% 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 AIRPORTAugust237% 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$ 190

Best Round-Trip Price

C$ 269

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$ 190 (Toronto Island to Chicago Midway).
Search Deals
The best round-trip flight price to Chicago from Canada in the last 5 days is C$ 269 (Calgary 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 10% 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 88 days out, which is when prices tend to be around C$ 379. 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$ 450 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 9 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.

An easier way to manage your Chicago trip

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