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Cheap flights from Toronto Region of Waterloo Intl Airport to Chicago from C$ 330

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 28/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Toronto Region of Waterloo Intl Airport to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
6:05 a.m. - 4:40 p.m.YKF  Toronto Region of Waterloo Intl-ORD Chicago O'Hare Intl
11h 35m1 stop Calgary
Multiple Airlines Logo
3:40 p.m. - 3:00 p.m.ORD  Chicago O'Hare Intl-YKF Toronto Region of Waterloo Intl
22h 20m2 stops Montreal Pierre Elliott Trudeau Intl Calgary
C$ 676Multiple Airlines
Fri, 25 Sep - Mon, 28 Sep
Multiple Airlines Logo
6:05 a.m. - 4:40 p.m.YKF  Toronto Region of Waterloo Intl-ORD Chicago O'Hare Intl
11h 35m1 stop Calgary
Multiple Airlines Logo
3:40 p.m. - 3:00 p.m.ORD  Chicago O'Hare Intl-YKF Toronto Region of Waterloo Intl
22h 20m2 stops Montreal Pierre Elliott Trudeau Intl Calgary
C$ 705Multiple Airlines
Fri, 11 Sep - Fri, 18 Sep
Multiple Airlines Logo
6:05 a.m. - 4:40 p.m.YKF  Toronto Region of Waterloo Intl-ORD Chicago O'Hare Intl
11h 35m1 stop Calgary
Multiple Airlines Logo
5:30 p.m. - 7:50 p.m.ORD  Chicago O'Hare Intl-YKF Toronto Region of Waterloo Intl
25h 20m1 stop Calgary
C$ 787Multiple Airlines
Fri, 25 Sep - Sun, 27 Sep
Multiple Airlines Logo
8:40 p.m. - 12:23 a.m.YKF  Toronto Region of Waterloo Intl-ORD Chicago O'Hare Intl
52h 43m3 stops Calgary San Francisco Denver Intl
Multiple Airlines Logo
1:21 p.m. - 7:50 p.m.ORD  Chicago O'Hare Intl-YKF Toronto Region of Waterloo Intl
53h 29m2 stops Las Vegas Harry Reid Intl Calgary
C$ 834Multiple Airlines
Thu, 10 Sep - Wed, 16 Sep
Multiple Airlines Logo
6:05 a.m. - 4:40 p.m.YKF  Toronto Region of Waterloo Intl-ORD Chicago O'Hare Intl
11h 35m1 stop Calgary
Multiple Airlines Logo
8:55 p.m. - 7:50 p.m.ORD  Chicago O'Hare Intl-YKF Toronto Region of Waterloo Intl
21h 55m2 stops Las Vegas Harry Reid Intl Calgary
C$ 835Multiple Airlines
Fri, 25 Sep - Sun, 27 Sep
Multiple Airlines Logo
8:40 p.m. - 12:23 a.m.YKF  Toronto Region of Waterloo Intl-ORD Chicago O'Hare Intl
52h 43m3 stops Calgary San Francisco Denver Intl
Multiple Airlines Logo
6:30 a.m. - 7:50 p.m.ORD  Chicago O'Hare Intl-YKF Toronto Region of Waterloo Intl
60h 20m3 stops Denver Intl Las Vegas Harry Reid Intl Calgary
C$ 891Multiple Airlines
Thu, 10 Sep - Wed, 16 Sep
Multiple Airlines Logo
6:10 a.m. - 4:40 p.m.YKF  Toronto Region of Waterloo Intl-ORD Chicago O'Hare Intl
35h 30m2 stops Edmonton Calgary
Multiple Airlines Logo
5:30 p.m. - 5:20 a.m.ORD  Chicago O'Hare Intl-YKF Toronto Region of Waterloo Intl
10h 50m1 stop Calgary
C$ 895Multiple Airlines
Fri, 4 Sep - Sun, 6 Sep
Multiple Airlines Logo
6:05 a.m. - 4:40 p.m.YKF  Toronto Region of Waterloo Intl-ORD Chicago O'Hare Intl
11h 35m1 stop Calgary
Multiple Airlines Logo
5:30 p.m. - 5:20 a.m.ORD  Chicago O'Hare Intl-YKF Toronto Region of Waterloo Intl
10h 50m1 stop Calgary
C$ 903Multiple Airlines
Fri, 4 Sep - Sun, 6 Sep
Multiple Airlines Logo
8:40 p.m. - 4:40 p.m.YKF  Toronto Region of Waterloo Intl-ORD Chicago O'Hare Intl
21h 00m1 stop Calgary
Multiple Airlines Logo
1:21 p.m. - 7:50 p.m.ORD  Chicago O'Hare Intl-YKF Toronto Region of Waterloo Intl
53h 29m2 stops Las Vegas Harry Reid Intl Calgary
C$ 916Multiple Airlines
Wed, 9 Sep - Wed, 16 Sep
Multiple Airlines Logo
8:40 p.m. - 10:15 a.m.YKF  Toronto Region of Waterloo Intl-ORD Chicago O'Hare Intl
14h 35m2 stops Calgary Montreal Pierre Elliott Trudeau Intl
Multiple Airlines Logo
7:54 p.m. - 7:50 p.m.ORD  Chicago O'Hare Intl-YKF Toronto Region of Waterloo Intl
22h 56m2 stops Winnipeg Calgary
C$ 929Multiple Airlines
Mon, 14 Sep - Tue, 15 Sep

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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
6 Sep
YKF8:40 p.m.Toronto Region of Waterloo Intl
21h 00m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
11 Sep
ORD6:25 p.m.Chicago O'Hare Intl
24h 25m
2 stops
YKF7:50 p.m.Toronto Region of Waterloo Intl
C$ 1,218
WestJet
4 Sep
YKF8:40 p.m.Toronto Region of Waterloo Intl
21h 00m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
8 Sep
ORD6:25 p.m.Chicago O'Hare Intl
24h 25m
2 stops
YKF7:50 p.m.Toronto Region of Waterloo Intl
C$ 1,261
WestJet
4 Sep
YKF8:40 p.m.Toronto Region of Waterloo Intl
21h 00m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
8 Sep
ORD6:25 p.m.Chicago O'Hare Intl
24h 25m
2 stops
YKF7:50 p.m.Toronto Region of Waterloo Intl
C$ 1,438

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 17 August 2026.
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

Cheapest round-trip

TorontoChicago

YKF Toronto Region of Waterloo Intl - ORD Chicago O'Hare Intl

YKFORD

Toronto Region of Waterloo Intl

Fri 25/9

6:05 a.m.-4:40 p.m.

1 stop11h 35m

Chicago O'Hare Intl

Mon 28/9

3:40 p.m.-3:00 p.m.

2 stops22h 20m

C$ 676

TorontoChicago

YKF Toronto Region of Waterloo Intl - ORD Chicago O'Hare Intl

YKFORD

Toronto Region of Waterloo Intl

Fri 11/9

6:05 a.m.-4:40 p.m.

1 stop11h 35m

Chicago O'Hare Intl

Fri 18/9

3:40 p.m.-3:00 p.m.

2 stops22h 20m

C$ 705

TorontoChicago

YKF Toronto Region of Waterloo Intl - ORD Chicago O'Hare Intl

YKFORD

Toronto Region of Waterloo Intl

Fri 25/9

6:05 a.m.-4:40 p.m.

1 stop11h 35m

Chicago O'Hare Intl

Sun 27/9

5:30 p.m.-7:50 p.m.

1 stop25h 20m

C$ 787

TorontoChicago

YKF Toronto Region of Waterloo Intl - ORD Chicago O'Hare Intl

YKFORD

Toronto Region of Waterloo Intl

Thu 10/9

8:40 p.m.-12:23 a.m.

3 stops52h 43m

Chicago O'Hare Intl

Wed 16/9

1:21 p.m.-7:50 p.m.

2 stops53h 29m

C$ 834

TorontoChicago

YKF Toronto Region of Waterloo Intl - ORD Chicago O'Hare Intl

YKFORD

Toronto Region of Waterloo Intl

Fri 25/9

6:05 a.m.-4:40 p.m.

1 stop11h 35m

Chicago O'Hare Intl

Sun 27/9

8:55 p.m.-7:50 p.m.

2 stops21h 55m

C$ 835

TorontoChicago

YKF Toronto Region of Waterloo Intl - ORD Chicago O'Hare Intl

YKFORD

Toronto Region of Waterloo Intl

Thu 10/9

8:40 p.m.-12:23 a.m.

3 stops52h 43m

Chicago O'Hare Intl

Wed 16/9

6:30 a.m.-7:50 p.m.

3 stops60h 20m

C$ 891

TorontoChicago

YKF Toronto Region of Waterloo Intl - ORD Chicago O'Hare Intl

YKFORD

Toronto Region of Waterloo Intl

Fri 4/9

6:10 a.m.-4:40 p.m.

2 stops35h 30m

Chicago O'Hare Intl

Sun 6/9

5:30 p.m.-5:20 a.m.

1 stop10h 50m

C$ 895
Quickest round-trip

TorontoChicago

YKF Toronto Region of Waterloo Intl - ORD Chicago O'Hare Intl

YKFORD

Toronto Region of Waterloo Intl

Fri 4/9

6:05 a.m.-4:40 p.m.

1 stop11h 35m

Chicago O'Hare Intl

Sun 6/9

5:30 p.m.-5:20 a.m.

1 stop10h 50m

C$ 903

TorontoChicago

YKF Toronto Region of Waterloo Intl - ORD Chicago O'Hare Intl

YKFORD

Toronto Region of Waterloo Intl

Wed 9/9

8:40 p.m.-4:40 p.m.

1 stop21h 00m

Chicago O'Hare Intl

Wed 16/9

1:21 p.m.-7:50 p.m.

2 stops53h 29m

C$ 916

TorontoChicago

YKF Toronto Region of Waterloo Intl - ORD Chicago O'Hare Intl

YKFORD

Toronto Region of Waterloo Intl

Mon 14/9

8:40 p.m.-10:15 a.m.

2 stops14h 35m

Chicago O'Hare Intl

Tue 15/9

7:54 p.m.-7:50 p.m.

2 stops22h 56m

C$ 929

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$ 632. 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$ 966. 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 morning 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$ 691. Flying to Chicago in the morning 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$ 1,056 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

Best price found

C$ 330

Fastest flight time

11h 35m

Direct flights

None
The best one-way flight to Chicago from Toronto Region of Waterloo Intl Airport in the past 72 hours is C$ 330. The best round-trip flight deal from Toronto Region of Waterloo Intl Airport to Chicago found on momondo in the last 72 hours is C$ 676.
The fastest flight from Toronto Region of Waterloo Intl Airport to Chicago takes 11h 35m
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

Frequently asked questions about flying from Toronto Region of Waterloo Intl Airport to Chicago

  • 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 35m 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 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?

Travelling to a place near Chicago?

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

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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.

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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