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Flights to Chicago

C$ 222 Cheap flights to Chicago

1 adult
1 adult, Economy, 0 bags

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Cheap round-trip flights

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Multiple Airlines Logo
7:35 a.m. - 4:14 p.m.YYZ  Toronto Pearson Intl-ORD Chicago O'Hare Intl
9h 39m1 stop Fort Lauderdale
Multiple Airlines Logo
8:25 a.m. - 3:20 p.m.ORD  Chicago O'Hare Intl-YYZ Toronto Pearson Intl
29h 55m1 stop Fort Lauderdale
C$ 350Multiple Airlines
Wed, 17 Feb - Wed, 24 Feb
Multiple Airlines Logo
7:35 a.m. - 4:14 p.m.YYZ  Toronto Pearson Intl-ORD Chicago O'Hare Intl
9h 39m1 stop Fort Lauderdale
Multiple Airlines Logo
8:25 a.m. - 10:55 p.m.ORD  Chicago O'Hare Intl-YYZ Toronto Pearson Intl
13h 30m1 stop Fort Lauderdale
C$ 358Multiple Airlines
Wed, 17 Feb - Wed, 24 Feb
Porter Airlines Logo
4:35 p.m. - 5:40 p.m.YTZ  Toronto Island-ORD Chicago O'Hare Intl
2h 05mdirect
Porter Airlines Logo
6:20 p.m. - 9:05 p.m.ORD  Chicago O'Hare Intl-YTZ Toronto Island
1h 45mdirect
C$ 387Porter Airlines
Thu, 3 Dec - Sun, 6 Dec
Porter Airlines Logo
4:35 p.m. - 5:40 p.m.YTZ  Toronto Island-ORD Chicago O'Hare Intl
2h 05mdirect
Porter Airlines Logo
12:15 p.m. - 3:00 p.m.ORD  Chicago O'Hare Intl-YTZ Toronto Island
1h 45mdirect
C$ 387Porter Airlines
Tue, 1 Dec - Fri, 4 Dec
United Airlines Logo
5:55 p.m. - 7:05 p.m.YYZ  Toronto Pearson Intl-ORD Chicago O'Hare Intl
2h 10mdirect
United Airlines Logo
5:00 a.m. - 1:43 p.m.ORD  Chicago O'Hare Intl-YYZ Toronto Pearson Intl
7h 43m1 stop Newark
C$ 391United Airlines
Fri, 27 Nov - Sat, 28 Nov
Air Canada Logo
2:35 p.m. - 3:38 p.m.YYZ  Toronto Pearson Intl-ORD Chicago O'Hare Intl
2h 03mdirect
Air Canada Logo
10:15 a.m. - 12:52 p.m.ORD  Chicago O'Hare Intl-YYZ Toronto Pearson Intl
1h 37mdirect
C$ 398Air Canada
Thu, 26 Nov - Sun, 29 Nov
Air Canada Logo
6:55 p.m. - 7:58 p.m.YYZ  Toronto Pearson Intl-ORD Chicago O'Hare Intl
2h 03mdirect
Air Canada Logo
8:50 p.m. - 11:32 p.m.ORD  Chicago O'Hare Intl-YYZ Toronto Pearson Intl
1h 42mdirect
C$ 401Air Canada
Wed, 23 Dec - Wed, 30 Dec
United Airlines Logo
8:35 a.m. - 9:44 a.m.YYZ  Toronto Pearson Intl-ORD Chicago O'Hare Intl
2h 09mdirect
United Airlines Logo
3:47 p.m. - 6:45 p.m.ORD  Chicago O'Hare Intl-YYZ Toronto Pearson Intl
1h 58mdirect
C$ 405United Airlines
Tue, 24 Nov - Sun, 29 Nov
Alaska Airlines Logo
9:07 a.m. - 5:49 p.m.YYC  Calgary-ORD Chicago O'Hare Intl
8h 42m1 stop Seattle/Tacoma Intl
Alaska Airlines Logo
5:29 p.m. - 9:37 p.m.ORD  Chicago O'Hare Intl-YYC Calgary
28h 08m1 stop Seattle/Tacoma Intl
C$ 444Alaska Airlines
Mon, 7 Dec - Fri, 11 Dec
Alaska Airlines Logo
2:35 p.m. - 11:59 p.m.YVR  Vancouver Intl-ORD Chicago O'Hare Intl
8h 24m1 stop Seattle/Tacoma Intl
Alaska Airlines Logo
8:00 a.m. - 1:35 p.m.ORD  Chicago O'Hare Intl-YVR Vancouver Intl
6h 35m1 stop Seattle/Tacoma Intl
C$ 626Alaska Airlines
Wed, 16 Dec - Wed, 6 Jan

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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 Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Wed 17/2

7:35 a.m.-4:14 p.m.

1 stop9h 39m

Chicago O'Hare Intl

Wed 24/2

8:25 a.m.-3:20 p.m.

1 stop29h 55m

C$ 350

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Wed 17/2

7:35 a.m.-4:14 p.m.

1 stop9h 39m

Chicago O'Hare Intl

Wed 24/2

8:25 a.m.-10:55 p.m.

1 stop13h 30m

C$ 358

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Thu 3/12

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

Nonstop2h 05m

Chicago O'Hare Intl

Sun 6/12

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

Nonstop1h 45m

C$ 387

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Tue 1/12

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

Nonstop2h 05m

Chicago O'Hare Intl

Fri 4/12

12:15 p.m.-3:00 p.m.

Nonstop1h 45m

C$ 387

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Fri 27/11

5:55 p.m.-7:05 p.m.

Nonstop2h 10m

Chicago O'Hare Intl

Sat 28/11

5:00 a.m.-1:43 p.m.

1 stop7h 43m

C$ 391
Quickest round-trip

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Thu 26/11

2:35 p.m.-3:38 p.m.

Nonstop2h 03m

Chicago O'Hare Intl

Sun 29/11

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

Nonstop1h 37m

C$ 398

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Wed 23/12

6:55 p.m.-7:58 p.m.

Nonstop2h 03m

Chicago O'Hare Intl

Wed 30/12

8:50 p.m.-11:32 p.m.

Nonstop1h 42m

C$ 401

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Tue 24/11

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

Nonstop2h 09m

Chicago O'Hare Intl

Sun 29/11

3:47 p.m.-6:45 p.m.

Nonstop1h 58m

C$ 405

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Mon 7/12

9:07 a.m.-5:49 p.m.

1 stop8h 42m

Chicago O'Hare Intl

Fri 11/12

5:29 p.m.-9:37 p.m.

1 stop28h 08m

C$ 444

VancouverChicago

YVR Vancouver Intl - ORD Chicago O'Hare Intl

YVRORD

Vancouver Intl

Wed 16/12

2:35 p.m.-11:59 p.m.

1 stop8h 24m

Chicago O'Hare Intl

Wed 6/1

8:00 a.m.-1:35 p.m.

1 stop6h 35m

C$ 626

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 March is another great option to travel to Chicago, with average flight prices from Canada averaging around C$ 372.

What is the absolute cheapest flight to Chicago?

Users booking trips to Chicago from Fort Lauderdale found flights 64% 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$ 650. 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$ 912. 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$ 1,134 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$ 451 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$ 341 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 AIRPORTMarch26% cheaperFlying from Toronto Pearson Intl Airport to Chicago costs on average just C$ 309 in March
MOST EXPENSIVE MONTH TO FLY TO CHICAGO FROM TORONTO PEARSON INTL AIRPORTDecember21% more expensiveIt costs about C$ 507 for flights to Chicago from Toronto Pearson Intl Airport in December
MOST POPULAR MONTH TO FLY TO CHICAGO FROM TORONTO PEARSON INTL AIRPORTSeptember114% more users visitedMore 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$ 222

Best Round-Trip Price

C$ 350

Fastest flight time

2h 05m

Popular in

July
The best one-way flight price to Chicago from Canada in the last 5 days is C$ 222 (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$ 350 (Toronto Pearson Intl to Chicago O'Hare Intl).
Search Deals
The fastest flight to Chicago from Canada takes 2h 05m (Toronto Island to Chicago O'Hare Intl).
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$ 397.

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$ 502 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 O'Hare Intl in Chicago which is the closest available airport to Lake View (20.7 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 November 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.

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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.

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