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 54m on average. Another popular route from Canada to Chicago is flying from Vancouver Intl to Chicago O'Hare Intl, which will take roughly 4h 11m. Keep in mind that layovers or delays could extend your travel time.

C$ 136 Cheap Flights to Chicago in 2025/26

1 adult

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Early arrival? Instantly customize your results

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Canada to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

7:00 a.m. - 4:43 p.m.YVR-ORD

7h 43m1 stop

5:30 p.m. - 10:36 p.m.ORD-YVR

7h 06m1 stop

C$ 205WestJet

Find Deal

Fri, 17 Oct - Sat, 18 Oct

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

3h 28mdirect

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

3h 49mdirect

C$ 208WestJet

Find Deal

Fri, 17 Oct - Sun, 19 Oct

8:30 a.m. - 2:41 p.m.YVR-ORD

4h 11mdirect

3:40 p.m. - 6:15 p.m.ORD-YVR

4h 35mdirect

C$ 230Air Canada

Find Deal

Sat, 1 Nov - Sat, 8 Nov

1:45 p.m. - 8:04 p.m.YVR-ORD

4h 19mdirect

8:51 a.m. - 11:33 a.m.ORD-YVR

4h 42mdirect

C$ 231United Airlines

Find Deal

Tue, 30 Sep - Sun, 12 Oct

12:35 p.m. - 5:10 p.m.YYC-ORD

3h 35mdirect

7:10 a.m. - 9:53 p.m.ORD-YYC

15h 43m1 stop

C$ 237United Airlines

Find Deal

Thu, 11 Dec - Mon, 15 Dec

5:35 a.m. - 3:10 p.m.YYC-ORD

8h 35m1 stop

2:00 p.m. - 8:39 p.m.ORD-YYC

7h 39m1 stop

C$ 241Air Canada

Find Deal

Sat, 1 Nov - Sat, 8 Nov

1:28 p.m. - 7:43 p.m.YVR-ORD

4h 15mdirect

9:53 a.m. - 12:33 p.m.ORD-YVR

4h 40mdirect

C$ 242American Airlines

Find Deal

Fri, 24 Oct - Mon, 27 Oct

12:54 p.m. - 9:49 a.m.YYC-ORD

19h 55m1 stop

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

7h 59m1 stop

C$ 270American Airlines

Find Deal

Fri, 24 Oct - Wed, 29 Oct

1:10 p.m. - 4:24 p.m.YUL-MDW

4h 14m1 stop

9:35 a.m. - 4:00 p.m.MDW-YUL

5h 25m1 stop

C$ 322Porter Airlines

Find Deal

Fri, 17 Oct - Mon, 20 Oct

6:45 a.m. - 10:05 a.m.YUL-MDW

4h 20m1 stop

4:15 p.m. - 10:45 p.m.MDW-YUL

5h 30m1 stop

C$ 323Porter Airlines

Find Deal

Thu, 30 Oct - Thu, 6 Nov

Fly from

Route

Depart

Return

Price

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 17/10

7:00 a.m.-4:43 p.m.

1 stop7h 43m

Chicago O'Hare Intl

Sat 18/10

5:30 p.m.-10:36 p.m.

1 stop7h 06m

C$ 205

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$ 208

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Sat 1/11

8:30 a.m.-2:41 p.m.

Nonstop4h 11m

Chicago O'Hare Intl

Sat 8/11

3:40 p.m.-6:15 p.m.

Nonstop4h 35m

C$ 230

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Tue 30/9

1:45 p.m.-8:04 p.m.

Nonstop4h 19m

Chicago O'Hare Intl

Sun 12/10

8:51 a.m.-11:33 a.m.

Nonstop4h 42m

C$ 231

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 11/12

12:35 p.m.-5:10 p.m.

Nonstop3h 35m

Chicago O'Hare Intl

Mon 15/12

7:10 a.m.-9:53 p.m.

1 stop15h 43m

C$ 237

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 1/11

5:35 a.m.-3:10 p.m.

1 stop8h 35m

Chicago O'Hare Intl

Sat 8/11

2:00 p.m.-8:39 p.m.

1 stop7h 39m

C$ 241

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 24/10

1:28 p.m.-7:43 p.m.

Nonstop4h 15m

Chicago O'Hare Intl

Mon 27/10

9:53 a.m.-12:33 p.m.

Nonstop4h 40m

C$ 242

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 24/10

12:54 p.m.-9:49 a.m.

1 stop19h 55m

Chicago O'Hare Intl

Wed 29/10

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

1 stop7h 59m

C$ 270

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 17/10

1:10 p.m.-4:24 p.m.

1 stop4h 14m

Chicago Midway

Mon 20/10

9:35 a.m.-4:00 p.m.

1 stop5h 25m

C$ 322

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 30/10

6:45 a.m.-10:05 a.m.

1 stop4h 20m

Chicago Midway

Thu 6/11

4:15 p.m.-10:45 p.m.

1 stop5h 30m

C$ 323

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 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 Nashville found flights 74% 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$ 643. 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$ 1,148. 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$ 620. 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$ 1,158 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$ 401 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$ 297 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	August	13% cheaper	Flying from Toronto Pearson Intl Airport to Chicago costs on average just C$ 330 in August
MOST EXPENSIVE MONTH TO FLY TO CHICAGO FROM TORONTO PEARSON INTL AIRPORT	December	22% more expensive	It costs about C$ 465 for flights to Chicago from Toronto Pearson Intl Airport in December
MOST POPULAR MONTH TO FLY TO CHICAGO FROM TORONTO PEARSON INTL AIRPORT	December	75% more users visited	More momondo users searched in flights to Chicago from Toronto Pearson Intl Airport in December than any other month

Cheap Chicago flight deals and tips

Summary info about Chicago flight prices, duration and airlines

Best One-Way Price	C$ 136
Best Round-Trip Price	C$ 205
Fastest flight time	3h 33m
Popular in	November

The best one-way flight price to Chicago from Canada in the last 72 hours is C$ 136 (Vancouver 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$ 205 (Vancouver Intl to Chicago O'Hare Intl).

Search Deals

The fastest flight to Chicago from Canada takes 3h 33m (Calgary to Chicago O'Hare Intl).

Search Deals

November has the highest demand for flights to Chicago, with a 5% 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 68 days out, which is when prices tend to be around C$ 350. Don’t hesitate to check prices now though, because momondo users recently found tickets for as low as C$ 250.

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$ 402 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 O'Hare Intl in Chicago which is the closest available airport to Downtown (25.3 km away).

What’s the closest airport to Magnificent Mile?

The closest airport to Magnificent Mile is Chicago O'Hare Intl, 25.0 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 2025, there are 11 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.

Munster

Hammond

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.