Which airlines fly to Chicago?

When flying to Chicago from Canada, momondo travellers will most often fly with one of these popular airlines: Air Canada, United Airlines, Porter Airlines or WestJet. Depending on what airport in Canada you fly from, you may be able to find flights with any of these popular airlines.

How long does it take to fly to Chicago?

Flight times from Canada to Chicago vary, but if you’re flying out of Toronto Pearson Intl and flying into Chicago O'Hare Intl (one of the most popular routes), then the duration is 1h 58m on average. Another popular route from Canada to Chicago is flying from Vancouver Intl to Chicago O'Hare Intl, which will take roughly 3h 09m. Keep in mind that layovers or delays could extend your travel time.

C$ 224 Cheap Flights to Chicago in 2026/27

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Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

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2:00 p.m. - 2:55 p.m.YYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

1h 55mdirect

10:15 a.m. - 12:52 p.m.ORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 37mdirect

C$ 312Air Canada

Sat, 24 Oct - Fri, 30 Oct

12:15 p.m. - 1:25 p.m.YTZ Toronto Island-ORD Chicago O'Hare Intl

2h 10mdirect

1:55 p.m. - 4:42 p.m.ORD Chicago O'Hare Intl-YTZ Toronto Island

1h 47mdirect

C$ 323Air Canada

Sat, 24 Oct - Fri, 30 Oct

8:35 a.m. - 9:44 a.m.YYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 09mdirect

6:15 p.m. - 11:52 p.m.ORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

4h 37m1 stop Washington, D.C. Dulles Intl

C$ 331Lufthansa

Sat, 5 Dec - Sat, 5 Dec

7:44 p.m. - 12:01 a.m.YYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

5h 17m1 stop Washington, D.C. Dulles Intl

7:03 a.m. - 9:47 a.m.ORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 44mdirect

C$ 349United Airlines

Fri, 27 Nov - Sat, 28 Nov

2:45 p.m. - 9:44 p.m.YYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

7h 59m1 stop Washington, D.C. Dulles Intl

7:03 a.m. - 9:47 a.m.ORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 44mdirect

C$ 349United Airlines

Fri, 30 Oct - Sat, 31 Oct

1:45 p.m. - 2:35 p.m.YTZ Toronto Island-MDW Chicago Midway

1h 50mdirect

11:45 a.m. - 2:25 p.m.MDW Chicago Midway-YTZ Toronto Island

1h 40mdirect

C$ 359Porter Airlines

Wed, 21 Oct - Sat, 24 Oct

4:35 p.m. - 5:40 p.m.YTZ Toronto Island-ORD Chicago O'Hare Intl

2h 05mdirect

6:20 p.m. - 9:05 p.m.ORD Chicago O'Hare Intl-YTZ Toronto Island

1h 45mdirect

C$ 375Porter Airlines

Thu, 5 Nov - Mon, 9 Nov

1:51 p.m. - 6:36 p.m.YYC Calgary-ORD Chicago O'Hare Intl

3h 45mdirect

5:00 a.m. - 2:11 p.m.ORD Chicago O'Hare Intl-YYC Calgary

9h 11m1 stop Dallas/Fort Worth

C$ 400American Airlines

Fri, 30 Oct - Sun, 1 Nov

1:51 p.m. - 6:36 p.m.YYC Calgary-ORD Chicago O'Hare Intl

3h 45mdirect

12:10 p.m. - 9:45 p.m.ORD Chicago O'Hare Intl-YYC Calgary

10h 35m1 stop Dallas/Fort Worth

C$ 400American Airlines

Thu, 22 Oct - Sat, 31 Oct

6:45 a.m. - 7:54 a.m.YYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 09mdirect

10:15 a.m. - 12:52 p.m.ORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 37mdirect

C$ 435Multiple Airlines

Sat, 28 Nov - Sun, 29 Nov

Cheap last-minute flights

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10:10 a.m. - 11:00 a.m.YTZ Toronto Island-MDW Chicago Midway

1h 50mdirect

11:45 a.m. - 2:25 p.m.MDW Chicago Midway-YTZ Toronto Island

1h 40mdirect

C$ 460Porter Airlines

Sun, 11 Oct - Sat, 17 Oct

1:45 p.m. - 2:35 p.m.YTZ Toronto Island-MDW Chicago Midway

1h 50mdirect

11:45 a.m. - 2:25 p.m.MDW Chicago Midway-YTZ Toronto Island

1h 40mdirect

C$ 473Porter Airlines

Sat, 10 Oct - Thu, 15 Oct

6:35 a.m. - 8:30 p.m.YYC Calgary-ORD Chicago O'Hare Intl

12h 55m2 stops Salt Lake City Detroit Metropolitan Wayne County

12:30 p.m. - 1:10 a.m.ORD Chicago O'Hare Intl-YYC Calgary

12h 40m2 stops Minneapolis St Paul Salt Lake City

C$ 482Delta

Sat, 10 Oct - Thu, 5 Nov

6:35 a.m. - 8:30 p.m.YYC Calgary-ORD Chicago O'Hare Intl

12h 55m2 stops Salt Lake City Detroit Metropolitan Wayne County

12:30 p.m. - 8:40 p.m.ORD Chicago O'Hare Intl-YYC Calgary

9h 10m1 stop Minneapolis St Paul

C$ 486Delta

Sat, 10 Oct - Thu, 15 Oct

7:29 a.m. - 8:39 a.m.YYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 10mdirect

11:45 a.m. - 2:33 p.m.ORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 48mdirect

C$ 500American Airlines

Sun, 11 Oct - Thu, 15 Oct

8:35 a.m. - 10:12 a.m.YUL Montreal Pierre Elliott Trudeau Intl-ORD Chicago O'Hare Intl

2h 37mdirect

8:45 a.m. - 12:00 p.m.ORD Chicago O'Hare Intl-YUL Montreal Pierre Elliott Trudeau Intl

2h 15mdirect

C$ 509Air Canada

Wed, 7 Oct - Wed, 14 Oct

6:30 p.m. - 8:12 p.m.YUL Montreal Pierre Elliott Trudeau Intl-ORD Chicago O'Hare Intl

2h 42mdirect

2:00 p.m. - 9:45 p.m.ORD Chicago O'Hare Intl-YUL Montreal Pierre Elliott Trudeau Intl

6h 45m1 stop Toronto Island

C$ 517Air Canada

Wed, 7 Oct - Wed, 14 Oct

6:25 p.m. - 7:30 p.m.YYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 05mdirect

8:06 a.m. - 10:59 a.m.ORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 53mdirect

C$ 547American Airlines

Sun, 11 Oct - Fri, 16 Oct

12:30 p.m. - 5:05 p.m.YYC Calgary-ORD Chicago O'Hare Intl

3h 35mdirect

8:40 a.m. - 11:28 a.m.ORD Chicago O'Hare Intl-YYC Calgary

3h 48mdirect

C$ 601United Airlines

Wed, 7 Oct - Sun, 11 Oct

12:30 p.m. - 5:05 p.m.YYC Calgary-ORD Chicago O'Hare Intl

3h 35mdirect

6:00 a.m. - 9:48 p.m.ORD Chicago O'Hare Intl-YYC Calgary

16h 48m1 stop Denver Intl

C$ 615United Airlines

Wed, 7 Oct - Sun, 11 Oct

Recent direct flight deals from Canada to Chicago

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2:00 p.m. - 2:55 p.m.YYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

1h 55mdirect

10:15 a.m. - 12:52 p.m.ORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 37mdirect

C$ 312Air Canada

Sat, 24 Oct - Fri, 30 Oct

12:15 p.m. - 1:25 p.m.YTZ Toronto Island-ORD Chicago O'Hare Intl

2h 10mdirect

1:55 p.m. - 4:42 p.m.ORD Chicago O'Hare Intl-YTZ Toronto Island

1h 47mdirect

C$ 323Air Canada

Sat, 24 Oct - Fri, 30 Oct

1:45 p.m. - 2:35 p.m.YTZ Toronto Island-MDW Chicago Midway

1h 50mdirect

11:45 a.m. - 2:25 p.m.MDW Chicago Midway-YTZ Toronto Island

1h 40mdirect

C$ 359Porter Airlines

Wed, 21 Oct - Sat, 24 Oct

4:35 p.m. - 5:40 p.m.YTZ Toronto Island-ORD Chicago O'Hare Intl

2h 05mdirect

6:20 p.m. - 9:05 p.m.ORD Chicago O'Hare Intl-YTZ Toronto Island

1h 45mdirect

C$ 375Porter Airlines

Thu, 5 Nov - Mon, 9 Nov

1:51 p.m. - 6:36 p.m.YYC Calgary-ORD Chicago O'Hare Intl

3h 45mdirect

10:00 a.m. - 12:51 p.m.ORD Chicago O'Hare Intl-YYC Calgary

3h 51mdirect

C$ 420American Airlines

Thu, 22 Oct - Fri, 30 Oct

2:52 p.m. - 5:39 p.m.YYC Calgary-ORD Chicago O'Hare Intl

2h 47mdirect

9:50 a.m. - 2:54 p.m.ORD Chicago O'Hare Intl-YYC Calgary

5h 04mdirect

C$ 432American Airlines

Wed, 3 Feb - Sat, 6 Feb

8:35 a.m. - 9:44 a.m.YYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 09mdirect

9:21 p.m. - 11:59 p.m.ORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 38mdirect

C$ 435United Airlines

Fri, 4 Dec - Sun, 6 Dec

5:55 p.m. - 7:05 p.m.YYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 10mdirect

9:21 p.m. - 11:59 p.m.ORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 38mdirect

C$ 435United Airlines

Tue, 1 Dec - Wed, 9 Dec

6:45 a.m. - 7:54 a.m.YYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 09mdirect

10:15 a.m. - 12:52 p.m.ORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 37mdirect

C$ 435Multiple Airlines

Sat, 28 Nov - Sun, 29 Nov

3:35 p.m. - 4:44 p.m.YYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 09mdirect

4:30 p.m. - 7:10 p.m.ORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 40mdirect

C$ 435Multiple Airlines

Fri, 27 Nov - Wed, 2 Dec

Fly from

Route

Depart

Return

Price

Cheapest round-trip

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Sat 24/10

2:00 p.m.-2:55 p.m.

Nonstop1h 55m

Chicago O'Hare Intl

Fri 30/10

10:15 a.m.-12:52 p.m.

Nonstop1h 37m

C$ 312

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Sat 24/10

12:15 p.m.-1:25 p.m.

Nonstop2h 10m

Chicago O'Hare Intl

Fri 30/10

1:55 p.m.-4:42 p.m.

Nonstop1h 47m

C$ 323

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Sat 5/12

8:35 a.m.-9:44 a.m.

Nonstop2h 09m

Chicago O'Hare Intl

Sat 5/12

6:15 p.m.-11:52 p.m.

1 stop4h 37m

C$ 331

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Fri 27/11

7:44 p.m.-12:01 a.m.

1 stop5h 17m

Chicago O'Hare Intl

Sat 28/11

7:03 a.m.-9:47 a.m.

Nonstop1h 44m

C$ 349

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Fri 30/10

2:45 p.m.-9:44 p.m.

1 stop7h 59m

Chicago O'Hare Intl

Sat 31/10

7:03 a.m.-9:47 a.m.

Nonstop1h 44m

C$ 349

Quickest round-trip

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Wed 21/10

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

Nonstop1h 50m

Chicago Midway

Sat 24/10

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

Nonstop1h 40m

C$ 359

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Thu 5/11

4:35 p.m.-5:40 p.m.

Nonstop2h 05m

Chicago O'Hare Intl

Mon 9/11

6:20 p.m.-9:05 p.m.

Nonstop1h 45m

C$ 375

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Fri 30/10

1:51 p.m.-6:36 p.m.

Nonstop3h 45m

Chicago O'Hare Intl

Sun 1/11

5:00 a.m.-2:11 p.m.

1 stop9h 11m

C$ 400

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Thu 22/10

1:51 p.m.-6:36 p.m.

Nonstop3h 45m

Chicago O'Hare Intl

Sat 31/10

12:10 p.m.-9:45 p.m.

1 stop10h 35m

C$ 400

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Sat 28/11

6:45 a.m.-7:54 a.m.

Nonstop2h 09m

Chicago O'Hare Intl

Sun 29/11

10:15 a.m.-12:52 p.m.

Nonstop1h 37m

C$ 435

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

Chicago flights insights and trends

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

Prices

Other information

What is the cheapest month to fly to Chicago?

The month of January is another great option to travel to Chicago, with average flight prices from Canada averaging around C$ 366.

What is the absolute cheapest flight to Chicago?

Users booking trips to Chicago from Orlando found flights 41% 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$ 649. 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$ 939. 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$ 713. 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$ 1,108 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$ 445 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$ 322 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 AIRPORT	March	24% cheaper	Flying from Toronto Pearson Intl Airport to Chicago costs on average just C$ 318 in March
MOST EXPENSIVE MONTH TO FLY TO CHICAGO FROM TORONTO PEARSON INTL AIRPORT	December	21% more expensive	It costs about C$ 504 for flights to Chicago from Toronto Pearson Intl Airport in December
MOST POPULAR MONTH TO FLY TO CHICAGO FROM TORONTO PEARSON INTL AIRPORT	September	124% more users visited	More momondo users searched in flights to Chicago from Toronto Pearson Intl Airport in September than any other month

Cheap Chicago flight deals and tips

Summary info about Chicago flight prices, duration and airlines

Best One-Way Price	C$ 224
Best Round-Trip Price	C$ 312
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$ 224 (Toronto Pearson Intl to Chicago O'Hare Intl).

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The best round-trip flight price to Chicago from Canada in the last 5 days is C$ 312 (Toronto Pearson Intl to Chicago O'Hare Intl).

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The fastest flight to Chicago from Canada takes 1h 50m (Toronto Island to Chicago Midway).

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July has the highest demand for flights to Chicago, with a 10% 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$ 394.

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$ 413 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 Lake View?

Yes, if you fly to Chicago Midway in Chicago which is the closest available airport to Lake View (18.8 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 October 2026, there are 7 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.

Merrillville

Benton Harbor

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.