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$ 179 Cheap Flights to Chicago in 2026/27

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Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

10:35 a.m. - 11:40 a.m.YTZ Toronto Island-ORD Chicago O'Hare Intl

2h 05mdirect

6:20 p.m. - 9:06 p.m.ORD Chicago O'Hare Intl-YTZ Toronto Island

1h 46mdirect

C$ 287Porter Airlines

Wed, 4 Nov - Wed, 11 Nov

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

1h 50mdirect

3:20 p.m. - 6:00 p.m.MDW Chicago Midway-YTZ Toronto Island

1h 40mdirect

C$ 289Porter Airlines

Sun, 4 Oct - Thu, 8 Oct

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

2h 10mdirect

2:00 p.m. - 4:48 p.m.ORD Chicago O'Hare Intl-YTZ Toronto Island

1h 48mdirect

C$ 289Air Canada

Sat, 3 Oct - Sun, 4 Oct

8:20 a.m. - 3:00 p.m.YTZ Toronto Island-ORD Chicago O'Hare Intl

7h 40m2 stops Ottawa Montreal Pierre Elliott Trudeau Intl

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

1h 47mdirect

C$ 290Air Canada

Mon, 2 Nov - Mon, 9 Nov

7:00 a.m. - 8:00 a.m.YYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 00mdirect

7:09 a.m. - 9:54 a.m.ORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 45mdirect

C$ 290Lufthansa

Thu, 8 Oct - Sun, 11 Oct

11:00 a.m. - 12:00 p.m.YYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 00mdirect

8:50 a.m. - 11:49 a.m.ORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 59mdirect

C$ 294Lufthansa

Thu, 8 Oct - Sun, 11 Oct

7:00 p.m. - 11:21 p.m.YYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

5h 21m1 stop Newark

7:09 a.m. - 9:54 a.m.ORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 45mdirect

C$ 299United Airlines

Sat, 3 Oct - Sun, 4 Oct

8:50 a.m. - 9:48 a.m.YYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

1h 58mdirect

4:40 p.m. - 11:26 p.m.ORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

5h 46m1 stop Newark

C$ 299United Airlines

Sat, 24 Oct - Mon, 26 Oct

7:09 a.m. - 8:39 a.m.YYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 30mdirect

9:00 a.m. - 3:10 p.m.ORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

5h 10m1 stop Charlotte Douglas

C$ 299American Airlines

Tue, 3 Nov - Tue, 10 Nov

11:36 a.m. - 1:01 p.m.YYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 25mdirect

6:02 a.m. - 11:59 a.m.ORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

4h 57m1 stop Washington, D.C. Reagan-National

C$ 299American Airlines

Sat, 14 Nov - Tue, 17 Nov

Cheap last-minute flights

Enter your travel dates to find the best prices.

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

1h 50mdirect

3:20 p.m. - 6:00 p.m.MDW Chicago Midway-YTZ Toronto Island

1h 40mdirect

C$ 444Porter Airlines

Sat, 26 Sep - Fri, 2 Oct

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

1h 50mdirect

3:20 p.m. - 6:00 p.m.MDW Chicago Midway-YTZ Toronto Island

1h 40mdirect

C$ 454Porter Airlines

Sat, 26 Sep - Tue, 6 Oct

8:50 a.m. - 9:53 a.m.YYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 03mdirect

12:59 p.m. - 3:46 p.m.ORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 47mdirect

C$ 488United Airlines

Tue, 22 Sep - Sun, 11 Oct

9:00 p.m. - 10:05 p.m.YYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 05mdirect

9:20 p.m. - 11:59 p.m.ORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 39mdirect

C$ 488United Airlines

Wed, 23 Sep - Sun, 18 Oct

5:15 p.m. - 6:18 p.m.YYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 03mdirect

8:40 p.m. - 11:26 p.m.ORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 46mdirect

C$ 488Multiple Airlines

Wed, 23 Sep - Sun, 18 Oct

10:15 a.m. - 11:21 a.m.YYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 06mdirect

2:15 p.m. - 5:01 p.m.ORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 46mdirect

C$ 488Multiple Airlines

Tue, 22 Sep - Thu, 15 Oct

10:45 a.m. - 2:52 p.m.YTZ Toronto Island-ORD Chicago O'Hare Intl

5h 07m1 stop Montreal Pierre Elliott Trudeau Intl

2:00 p.m. - 4:48 p.m.ORD Chicago O'Hare Intl-YTZ Toronto Island

1h 48mdirect

C$ 489Air Canada

Sat, 26 Sep - Tue, 6 Oct

10:45 a.m. - 2:52 p.m.YTZ Toronto Island-ORD Chicago O'Hare Intl

5h 07m1 stop Montreal Pierre Elliott Trudeau Intl

7:25 a.m. - 10:13 a.m.ORD Chicago O'Hare Intl-YTZ Toronto Island

1h 48mdirect

C$ 489Air Canada

Sat, 26 Sep - Fri, 2 Oct

6:35 a.m. - 4:59 p.m.YYC Calgary-ORD Chicago O'Hare Intl

9h 24m1 stop Minneapolis St Paul

2:05 p.m. - 11:06 p.m.ORD Chicago O'Hare Intl-YYC Calgary

10h 01m1 stop Salt Lake City

C$ 507Delta

Fri, 25 Sep - Tue, 29 Sep

6:35 a.m. - 4:59 p.m.YYC Calgary-ORD Chicago O'Hare Intl

9h 24m1 stop Minneapolis St Paul

8:25 a.m. - 1:00 p.m.ORD Chicago O'Hare Intl-YYC Calgary

5h 35m1 stop Minneapolis St Paul

C$ 507Delta

Fri, 25 Sep - Tue, 29 Sep

Recent direct flight deals from Canada to Chicago

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10:35 a.m. - 11:40 a.m.YTZ Toronto Island-ORD Chicago O'Hare Intl

2h 05mdirect

6:20 p.m. - 9:06 p.m.ORD Chicago O'Hare Intl-YTZ Toronto Island

1h 46mdirect

C$ 287Porter Airlines

Wed, 4 Nov - Wed, 11 Nov

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

1h 50mdirect

3:20 p.m. - 6:00 p.m.MDW Chicago Midway-YTZ Toronto Island

1h 40mdirect

C$ 289Porter Airlines

Sun, 11 Oct - Sat, 17 Oct

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

2h 10mdirect

2:00 p.m. - 4:48 p.m.ORD Chicago O'Hare Intl-YTZ Toronto Island

1h 48mdirect

C$ 289Air Canada

Sat, 3 Oct - Sun, 4 Oct

7:00 a.m. - 8:00 a.m.YYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 00mdirect

7:09 a.m. - 9:54 a.m.ORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 45mdirect

C$ 290Lufthansa

Thu, 8 Oct - Sun, 11 Oct

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

2h 10mdirect

2:00 p.m. - 4:48 p.m.ORD Chicago O'Hare Intl-YTZ Toronto Island

1h 48mdirect

C$ 292Air Canada

Thu, 1 Oct - Sun, 4 Oct

11:00 a.m. - 12:00 p.m.YYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 00mdirect

8:50 a.m. - 11:49 a.m.ORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 59mdirect

C$ 294Lufthansa

Thu, 8 Oct - Sun, 11 Oct

11:00 a.m. - 12:00 p.m.YYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 00mdirect

6:17 p.m. - 9:15 p.m.ORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 58mdirect

C$ 324United Airlines

Thu, 22 Oct - Sun, 25 Oct

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

2h 09mdirect

1:57 p.m. - 4:47 p.m.ORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 50mdirect

C$ 324United Airlines

Fri, 6 Nov - Fri, 6 Nov

7:09 a.m. - 8:39 a.m.YYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 30mdirect

9:42 a.m. - 12:32 p.m.ORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 50mdirect

C$ 324American Airlines

Mon, 7 Dec - Sun, 13 Dec

7:09 a.m. - 8:39 a.m.YYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 30mdirect

9:42 a.m. - 12:32 p.m.ORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 50mdirect

C$ 324American Airlines

Thu, 5 Nov - Sun, 8 Nov

Fly from

Route

Depart

Return

Price

Cheapest round-trip

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Wed 4/11

10:35 a.m.-11:40 a.m.

Nonstop2h 05m

Chicago O'Hare Intl

Wed 11/11

6:20 p.m.-9:06 p.m.

Nonstop1h 46m

C$ 287

Quickest round-trip

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Sun 4/10

10:10 a.m.-11:00 a.m.

Nonstop1h 50m

Chicago Midway

Thu 8/10

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

Nonstop1h 40m

C$ 289

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Sat 3/10

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

Nonstop2h 10m

Chicago O'Hare Intl

Sun 4/10

2:00 p.m.-4:48 p.m.

Nonstop1h 48m

C$ 289

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Mon 2/11

8:20 a.m.-3:00 p.m.

2 stops7h 40m

Chicago O'Hare Intl

Mon 9/11

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

Nonstop1h 47m

C$ 290

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Thu 8/10

7:00 a.m.-8:00 a.m.

Nonstop2h 00m

Chicago O'Hare Intl

Sun 11/10

7:09 a.m.-9:54 a.m.

Nonstop1h 45m

C$ 290

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Thu 8/10

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

Nonstop2h 00m

Chicago O'Hare Intl

Sun 11/10

8:50 a.m.-11:49 a.m.

Nonstop1h 59m

C$ 294

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Sat 3/10

7:00 p.m.-11:21 p.m.

1 stop5h 21m

Chicago O'Hare Intl

Sun 4/10

7:09 a.m.-9:54 a.m.

Nonstop1h 45m

C$ 299

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Sat 24/10

8:50 a.m.-9:48 a.m.

Nonstop1h 58m

Chicago O'Hare Intl

Mon 26/10

4:40 p.m.-11:26 p.m.

1 stop5h 46m

C$ 299

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Tue 3/11

7:09 a.m.-8:39 a.m.

Nonstop2h 30m

Chicago O'Hare Intl

Tue 10/11

9:00 a.m.-3:10 p.m.

1 stop5h 10m

C$ 299

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Sat 14/11

11:36 a.m.-1:01 p.m.

Nonstop2h 25m

Chicago O'Hare Intl

Tue 17/11

6:02 a.m.-11:59 a.m.

1 stop4h 57m

C$ 299

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 September is another great option to travel to Chicago, with average flight prices from Canada averaging around C$ 353.

What is the absolute cheapest flight to Chicago?

Users booking trips to Chicago from Minneapolis found flights 59% 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$ 633. 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$ 930. 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$ 698. 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$ 1,090 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$ 438 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$ 317 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$ 313 in March
MOST EXPENSIVE MONTH TO FLY TO CHICAGO FROM TORONTO PEARSON INTL AIRPORT	December	20% more expensive	It costs about C$ 493 for flights to Chicago from Toronto Pearson Intl Airport in December
MOST POPULAR MONTH TO FLY TO CHICAGO FROM TORONTO PEARSON INTL AIRPORT	September	160% 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$ 179
Best Round-Trip Price	C$ 287
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$ 179 (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$ 287 (Toronto Island 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 9% 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$ 388.

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$ 419 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 September 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.