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Cheap flights from Toronto Region of Waterloo Intl Airport to Chicago from C$ 229

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 13/8. 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

Enter your travel dates to find the best prices.
Multiple Airlines Logo
8:40 p.m. - 8:43 p.m.
YKF
-
ORD
25h 03m
2 stops
Multiple Airlines Logo
5:30 p.m. - 3:00 p.m.
ORD
-
YKF
20h 30m
1 stop
C$ 916Multiple Airlines
Sat, 13 Jun - Mon, 15 Jun
Multiple Airlines Logo
8:40 p.m. - 8:43 p.m.
YKF
-
ORD
25h 03m
2 stops
Multiple Airlines Logo
5:30 p.m. - 7:50 p.m.
ORD
-
YKF
25h 20m
1 stop
C$ 947Multiple Airlines
Sun, 21 Jun - Fri, 26 Jun
Multiple Airlines Logo
6:05 a.m. - 4:40 p.m.
YKF
-
ORD
11h 35m
1 stop
Multiple Airlines Logo
5:30 p.m. - 5:20 a.m.
ORD
-
YKF
10h 50m
1 stop
C$ 957Multiple Airlines
Thu, 20 Aug - Sun, 23 Aug
Multiple Airlines Logo
6:05 a.m. - 4:40 p.m.
YKF
-
ORD
11h 35m
1 stop
Multiple Airlines Logo
8:06 p.m. - 3:00 p.m.
ORD
-
YKF
41h 54m
2 stops
C$ 970Multiple Airlines
Fri, 29 May - Sun, 31 May
Multiple Airlines Logo
6:05 a.m. - 4:40 p.m.
YKF
-
ORD
11h 35m
1 stop
Multiple Airlines Logo
5:30 p.m. - 7:50 p.m.
ORD
-
YKF
25h 20m
1 stop
C$ 1,021Multiple Airlines
Fri, 4 Sep - Mon, 7 Sep
Multiple Airlines Logo
8:40 p.m. - 4:40 p.m.
YKF
-
ORD
21h 00m
1 stop
Multiple Airlines Logo
7:17 p.m. - 3:20 p.m.
ORD
-
YKF
43h 03m
2 stops
C$ 1,028Multiple Airlines
Fri, 19 Jun - Fri, 26 Jun
WestJet Logo
8:40 p.m. - 4:40 p.m.
YKF
-
ORD
21h 00m
1 stop
WestJet Logo
5:30 p.m. - 7:50 p.m.
ORD
-
YKF
25h 20m
1 stop
C$ 1,053WestJet
Fri, 19 Jun - Fri, 26 Jun
Multiple Airlines Logo
8:40 p.m. - 11:36 p.m.
YKF
-
ORD
27h 56m
2 stops
Multiple Airlines Logo
5:30 p.m. - 3:00 p.m.
ORD
-
YKF
20h 30m
1 stop
C$ 1,077Multiple Airlines
Wed, 17 Jun - Wed, 24 Jun
Multiple Airlines Logo
8:40 p.m. - 4:40 p.m.
YKF
-
ORD
21h 00m
1 stop
Multiple Airlines Logo
6:39 p.m. - 3:00 p.m.
ORD
-
YKF
43h 21m
2 stops
C$ 1,082Multiple Airlines
Mon, 1 Jun - Sun, 7 Jun
Multiple Airlines Logo
6:05 a.m. - 4:40 p.m.
YKF
-
ORD
11h 35m
1 stop
Multiple Airlines Logo
5:30 p.m. - 5:20 a.m.
ORD
-
YKF
10h 50m
1 stop
C$ 1,101Multiple Airlines
Fri, 21 Aug - Sun, 23 Aug

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
19 Jun
YKF8:40 p.m.Toronto Region of Waterloo Intl
21h 00m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
26 Jun
ORD5:30 p.m.Chicago O'Hare Intl
25h 20m
1 stop
YKF7:50 p.m.Toronto Region of Waterloo Intl
C$ 1,053
WestJet
29 May
YKF8:40 p.m.Toronto Region of Waterloo Intl
21h 00m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
31 May
ORD5:30 p.m.Chicago O'Hare Intl
25h 20m
1 stop
YKF7:50 p.m.Toronto Region of Waterloo Intl
C$ 1,320
WestJet
20 May
YKF8:40 p.m.Toronto Region of Waterloo Intl
21h 00m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
24 May
ORD5:30 p.m.Chicago O'Hare Intl
25h 20m
1 stop
YKF7:50 p.m.Toronto Region of Waterloo Intl
C$ 1,499

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 7 May 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 - ORD

YKFORD

Toronto Region of Waterloo Intl

Sat 13/6

8:40 p.m.-8:43 p.m.

2 stops25h 03m

Chicago O'Hare Intl

Mon 15/6

5:30 p.m.-3:00 p.m.

1 stop20h 30m

C$ 916

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Sun 21/6

8:40 p.m.-8:43 p.m.

2 stops25h 03m

Chicago O'Hare Intl

Fri 26/6

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

1 stop25h 20m

C$ 947
Quickest round-trip

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Thu 20/8

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

1 stop11h 35m

Chicago O'Hare Intl

Sun 23/8

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

1 stop10h 50m

C$ 957

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Fri 29/5

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

1 stop11h 35m

Chicago O'Hare Intl

Sun 31/5

8:06 p.m.-3:00 p.m.

2 stops41h 54m

C$ 970

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Fri 4/9

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

1 stop11h 35m

Chicago O'Hare Intl

Mon 7/9

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

1 stop25h 20m

C$ 1,021

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Fri 19/6

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

1 stop21h 00m

Chicago O'Hare Intl

Fri 26/6

7:17 p.m.-3:20 p.m.

2 stops43h 03m

C$ 1,028

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Fri 19/6

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

1 stop21h 00m

Chicago O'Hare Intl

Fri 26/6

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

1 stop25h 20m

C$ 1,053

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Wed 17/6

8:40 p.m.-11:36 p.m.

2 stops27h 56m

Chicago O'Hare Intl

Wed 24/6

5:30 p.m.-3:00 p.m.

1 stop20h 30m

C$ 1,077

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Mon 1/6

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

1 stop21h 00m

Chicago O'Hare Intl

Sun 7/6

6:39 p.m.-3:00 p.m.

2 stops43h 21m

C$ 1,082

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Fri 21/8

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

1 stop11h 35m

Chicago O'Hare Intl

Sun 23/8

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

1 stop10h 50m

C$ 1,101

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$ 597. 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$ 1,028. 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$ 671. Flying to Chicago in the morning is an ideal time because this is during off-peak travel hours. At noon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 1,114 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

Fastest flight time

11h 35m

Direct flights

None
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

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