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Cheap flights from Toronto Region of Waterloo Intl Airport to Chicago from C$ 208

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Toronto Region of Waterloo Intl Airport to Chicago departing on 18/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Toronto Region of Waterloo Intl Airport to Chicago

Cheap round-trip flights

WestJet Logo
6:00 a.m. - 4:43 p.m.YKF-ORD
11h 43m1 stop
WestJet Logo
2:20 p.m. - 5:28 a.m.ORD-YKF
14h 08m1 stop
C$ 455WestJet
Find Deal
Fri, 17 Oct - Sun, 26 Oct
Logo
6:15 a.m. - 12:39 p.m.YKF-ORD
31h 24m1 stop
Logo
2:20 p.m. - 5:28 a.m.ORD-YKF
14h 08m1 stop
C$ 473
Find Deal
Fri, 10 Oct - Mon, 27 Oct
Logo
6:00 a.m. - 8:29 p.m.YKF-ORD
39h 29m2 stops
Logo
2:20 p.m. - 5:28 a.m.ORD-YKF
14h 08m1 stop
C$ 485
Find Deal
Fri, 10 Oct - Mon, 27 Oct
Logo
6:00 a.m. - 4:43 p.m.YKF-ORD
11h 43m1 stop
Logo
5:30 p.m. - 12:45 a.m.ORD-YKF
30h 15m1 stop
C$ 520
Find Deal
Sun, 12 Oct - Sun, 19 Oct
Logo
6:15 a.m. - 10:49 p.m.YKF-ORD
17h 34m2 stops
Logo
5:30 p.m. - 12:45 a.m.ORD-YKF
30h 15m1 stop
C$ 580
Find Deal
Sun, 12 Oct - Sun, 19 Oct
Logo
6:00 a.m. - 4:43 p.m.YKF-ORD
11h 43m1 stop
Logo
9:00 p.m. - 12:45 a.m.ORD-YKF
26h 45m3 stops
C$ 686
Find Deal
Sun, 12 Oct - Sun, 19 Oct
Logo
6:00 a.m. - 8:00 a.m.YKF-ORD
27h 00m2 stops
Logo
5:30 p.m. - 5:15 a.m.ORD-YKF
10h 45m1 stop
C$ 696
Find Deal
Sun, 12 Oct - Sun, 19 Oct
Logo
6:15 a.m. - 10:49 p.m.YKF-ORD
17h 34m2 stops
Logo
9:00 p.m. - 12:45 a.m.ORD-YKF
26h 45m3 stops
C$ 741
Find Deal
Sun, 12 Oct - Sun, 19 Oct
Logo
6:15 a.m. - 3:56 p.m.YKF-ORD
34h 41m3 stops
Logo
9:00 p.m. - 12:45 a.m.ORD-YKF
26h 45m3 stops
C$ 814
Find Deal
Sun, 12 Oct - Sun, 19 Oct
Logo
6:00 a.m. - 8:00 a.m.YKF-ORD
27h 00m2 stops
Logo
3:45 p.m. - 5:15 a.m.ORD-YKF
12h 30m2 stops
C$ 847
Find Deal
Sun, 12 Oct - Sun, 19 Oct

WestJet flights from Toronto Region of Waterloo Intl Airport to Chicago

Our best WestJet deals on Toronto Region of Waterloo Intl Airport to Chicago flight tickets
WestJet
17 Oct
YKF6:00 a.m.Toronto Region of Waterloo Intl
11h 43m
1 stop
ORD4:43 p.m.Chicago O'Hare Intl
26 Oct
ORD2:20 p.m.Chicago O'Hare Intl
14h 08m
1 stop
YKF5:28 a.m.Toronto Region of Waterloo Intl
C$ 455
Find similar
WestJet
8 Sep
YKF6:00 a.m.Toronto Region of Waterloo Intl
16h 35m
2 stops
ORD9:35 p.m.Chicago O'Hare Intl
11 Sep
ORD6:15 a.m.Chicago O'Hare Intl
17h 30m
2 stops
YKF12:45 a.m.Toronto Region of Waterloo Intl
C$ 2,338
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Toronto Region of Waterloo Intl Airport to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 96,600 searches. Data last updated 30 August 2025.
Use the filters below to find and compare flights from Toronto Region of Waterloo Intl Airport to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Fri 17/10

6:00 a.m.-4:43 p.m.

1 stop11h 43m

Chicago O'Hare Intl

Sun 26/10

2:20 p.m.-5:28 a.m.

1 stop14h 08m

C$ 455

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Fri 10/10

6:15 a.m.-12:39 p.m.

1 stop31h 24m

Chicago O'Hare Intl

Mon 27/10

2:20 p.m.-5:28 a.m.

1 stop14h 08m

C$ 473

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Fri 10/10

6:00 a.m.-8:29 p.m.

2 stops39h 29m

Chicago O'Hare Intl

Mon 27/10

2:20 p.m.-5:28 a.m.

1 stop14h 08m

C$ 485

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Sun 12/10

6:00 a.m.-4:43 p.m.

1 stop11h 43m

Chicago O'Hare Intl

Sun 19/10

5:30 p.m.-12:45 a.m.

1 stop30h 15m

C$ 520

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Sun 12/10

6:15 a.m.-10:49 p.m.

2 stops17h 34m

Chicago O'Hare Intl

Sun 19/10

5:30 p.m.-12:45 a.m.

1 stop30h 15m

C$ 580

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Sun 12/10

6:00 a.m.-4:43 p.m.

1 stop11h 43m

Chicago O'Hare Intl

Sun 19/10

9:00 p.m.-12:45 a.m.

3 stops26h 45m

C$ 686

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Sun 12/10

6:00 a.m.-8:00 a.m.

2 stops27h 00m

Chicago O'Hare Intl

Sun 19/10

5:30 p.m.-5:15 a.m.

1 stop10h 45m

C$ 696

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Sun 12/10

6:15 a.m.-10:49 p.m.

2 stops17h 34m

Chicago O'Hare Intl

Sun 19/10

9:00 p.m.-12:45 a.m.

3 stops26h 45m

C$ 741

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Sun 12/10

6:15 a.m.-3:56 p.m.

3 stops34h 41m

Chicago O'Hare Intl

Sun 19/10

9:00 p.m.-12:45 a.m.

3 stops26h 45m

C$ 814

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Sun 12/10

6:00 a.m.-8:00 a.m.

2 stops27h 00m

Chicago O'Hare Intl

Sun 19/10

3:45 p.m.-5:15 a.m.

2 stops12h 30m

C$ 847

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

How to get the cheapest flight ticket from Toronto Region of Waterloo Intl Airport to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

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$ 662. 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$ 1,182. 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 Toronto Region of Waterloo Intl Airport to Chicago when you can find flight prices for as low as C$ 611. 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$ 1,304 per ticket.

When to book flights from Toronto Region of Waterloo Intl Airport to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Toronto Region of Waterloo Intl Airport to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Toronto Region of Waterloo Intl Airport to Chicago (YKF to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Toronto Region of Waterloo Intl Airport to Chicago

Direct flights

None
There are no direct flights from Toronto Region of Waterloo Intl Airport to Chicago. There are no popular flight routes from Toronto Region of Waterloo Intl Airport to Chicago.
Search flight deals

  • How far is Toronto Region of Waterloo Intl to Chicago by plane?

    The straight-line distance from Toronto Region of Waterloo Intl to Chicago is 617.0 km. Typically, this will take 11h 43m by plane in normal conditions.

  • When did momondo last update prices for flights from Toronto Region of Waterloo Intl Airport to Chicago?

    Prices for flights from Toronto Region of Waterloo Intl Airport to Chicago were last updated today.

  • How many operators does momondo search for flights from Toronto Region of Waterloo Intl Airport to Chicago?

  • How old do you have to be to fly from Toronto Region of Waterloo Intl Airport to Chicago?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Toronto Region of Waterloo Intl Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Toronto Region of Waterloo Intl Airport to Chicago?

Best airlines flying from Toronto Region of Waterloo Intl Airport to Chicago

Compare and see reviews for airlines that fly from Toronto Region of Waterloo Intl Airport to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Air CanadaPriceFrom C$ 328Free CancellationRating
7.1
10,000 reviews
Search Air Canada flights

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Munster
Hammond
Merrillville

Why use momondo?

Why should I use momondo to find a flight deal from Toronto to Chicago?

Finding the right flight to Chicago from Toronto is quick and easy when you have a range of options in front of you, from reputable agents and recognizable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Toronto to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Toronto with this policy.

How can momondo help me find flights from Toronto to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Toronto to Chicago.

I’m not ready to book a flight from Toronto to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Toronto are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 25.6 km from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport