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Cheap flights from Toronto Region of Waterloo Intl Airport to Chicago from C$ 188

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 6/10. 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

Logo
6:00 a.m. - 5:40 a.m.YKF-ORD
24h 40m2 stops
Logo
1:40 p.m. - 5:30 a.m.ORD-YKF
14h 50m1 stop
C$ 494
Find Deal
Wed, 27 Aug - Wed, 3 Sep
Logo
6:00 a.m. - 4:43 p.m.YKF-ORD
11h 43m1 stop
Logo
5:30 p.m. - 5:15 a.m.ORD-YKF
10h 45m1 stop
C$ 519
Find Deal
Thu, 25 Sep - Mon, 29 Sep
Logo
7:45 p.m. - 5:40 a.m.YKF-ORD
34h 55m2 stops
Logo
7:05 a.m. - 12:46 a.m.ORD-YKF
16h 41m2 stops
C$ 535
Find Deal
Tue, 19 Aug - Wed, 27 Aug
Logo
7:45 p.m. - 4:50 a.m.YKF-ORD
34h 05m3 stops
Logo
7:05 a.m. - 12:46 a.m.ORD-YKF
16h 41m2 stops
C$ 548
Find Deal
Tue, 19 Aug - Wed, 27 Aug
Logo
6:00 a.m. - 5:40 a.m.YKF-ORD
24h 40m2 stops
Logo
7:09 p.m. - 6:55 p.m.ORD-YKF
22h 46m2 stops
C$ 560
Find Deal
Wed, 27 Aug - Wed, 3 Sep
Logo
6:00 a.m. - 4:43 p.m.YKF-ORD
11h 43m1 stop
Logo
5:30 p.m. - 5:15 a.m.ORD-YKF
10h 45m1 stop
C$ 601
Find Deal
Fri, 12 Sep - Fri, 19 Sep
Logo
6:00 a.m. - 4:43 p.m.YKF-ORD
11h 43m1 stop
Logo
5:30 p.m. - 5:15 a.m.ORD-YKF
10h 45m1 stop
C$ 625
Find Deal
Fri, 12 Sep - Fri, 19 Sep
Logo
7:45 p.m. - 5:40 a.m.YKF-ORD
34h 55m2 stops
Logo
1:40 p.m. - 5:30 a.m.ORD-YKF
14h 50m1 stop
C$ 670
Find Deal
Tue, 19 Aug - Wed, 27 Aug
Logo
6:00 a.m. - 4:44 p.m.YKF-ORD
11h 44m1 stop
Logo
5:30 p.m. - 5:15 a.m.ORD-YKF
10h 45m1 stop
C$ 850
Find Deal
Thu, 28 Aug - Thu, 4 Sep
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$ 1,924WestJet
Find Deal
Fri, 24 Oct - Sun, 26 Oct

WestJet flights from Toronto Region of Waterloo Intl Airport to Chicago O'Hare Intl Airport

Our best WestJet deals on Toronto Region of Waterloo Intl Airport to Chicago O'Hare Intl Airport flight tickets
WestJet
24 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$ 1,924
Find similar
WestJet
8 Aug
YKF6:00 a.m.Toronto Region of Waterloo Intl
11h 44m
1 stop
ORD4:44 p.m.Chicago O'Hare Intl
11 Aug
ORD5:30 p.m.Chicago O'Hare Intl
24h 26m
1 stop
YKF6:56 p.m.Toronto Region of Waterloo Intl
C$ 2,116
Find similar
WestJet
8 Aug
YKF6:00 a.m.Toronto Region of Waterloo Intl
11h 44m
1 stop
ORD4:44 p.m.Chicago O'Hare Intl
11 Aug
ORD5:30 p.m.Chicago O'Hare Intl
24h 26m
1 stop
YKF6:56 p.m.Toronto Region of Waterloo Intl
C$ 2,178
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Toronto Region of Waterloo Intl Airport to Chicago O'Hare Intl Airport 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 31 July 2025.
Use the filters below to find and compare flights from Toronto Region of Waterloo Intl Airport to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Wed 27/8

6:00 a.m.-5:40 a.m.

2 stops24h 40m

Chicago O'Hare Intl

Wed 3/9

1:40 p.m.-5:30 a.m.

1 stop14h 50m

C$ 494

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Thu 25/9

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

1 stop11h 43m

Chicago O'Hare Intl

Mon 29/9

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

1 stop10h 45m

C$ 519

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Tue 19/8

7:45 p.m.-5:40 a.m.

2 stops34h 55m

Chicago O'Hare Intl

Wed 27/8

7:05 a.m.-12:46 a.m.

2 stops16h 41m

C$ 535

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Tue 19/8

7:45 p.m.-4:50 a.m.

3 stops34h 05m

Chicago O'Hare Intl

Wed 27/8

7:05 a.m.-12:46 a.m.

2 stops16h 41m

C$ 548

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Wed 27/8

6:00 a.m.-5:40 a.m.

2 stops24h 40m

Chicago O'Hare Intl

Wed 3/9

7:09 p.m.-6:55 p.m.

2 stops22h 46m

C$ 560

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Fri 12/9

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

1 stop11h 43m

Chicago O'Hare Intl

Fri 19/9

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

1 stop10h 45m

C$ 601

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Fri 12/9

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

1 stop11h 43m

Chicago O'Hare Intl

Fri 19/9

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

1 stop10h 45m

C$ 625

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Tue 19/8

7:45 p.m.-5:40 a.m.

2 stops34h 55m

Chicago O'Hare Intl

Wed 27/8

1:40 p.m.-5:30 a.m.

1 stop14h 50m

C$ 670

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Thu 28/8

6:00 a.m.-4:44 p.m.

1 stop11h 44m

Chicago O'Hare Intl

Thu 4/9

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

1 stop10h 45m

C$ 850

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Fri 24/10

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$ 1,924

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 O'Hare Intl Airport

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 O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Friday when prices can be found for as low as C$ 787. This is often the case because there is less demand to fly during this day of the week. When flying out on a Tuesday, the most expensive travel day of the week, you can expect to see flight prices from Toronto Region of Waterloo Intl Airport to Chicago O'Hare Intl Airport for around C$ 1,248.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

In the evening is the cheapest time of day to fly from Toronto Region of Waterloo Intl Airport to Chicago O'Hare Intl Airport when you can find flight prices for as low as C$ 608. Flying to Chicago O'Hare Intl Airport in the evening is an ideal time because this is during off-peak travel hours. If you have a flexible travel schedule, then try to avoid flying in the afternoon when prices are C$ 1,489 on average. Flights to Chicago O'Hare Intl Airport from Toronto Region of Waterloo Intl Airport in the afternoon are generally more expensive because this time of day is more convenient for travellers’ schedules.

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

Are you open to changing your travel dates? Check out the ideal times to fly from Toronto Region of Waterloo Intl Airport to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport (YKF to ORD) 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 O'Hare Intl Airport

Best price found

C$ 188

Fastest flight time

11h 43m

Direct flights

None
The best one-way flight to Chicago O'Hare Intl Airport from Toronto Region of Waterloo Intl Airport in the past 72 hours is C$ 188. The best round-trip flight deal from Toronto Region of Waterloo Intl Airport to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is C$ 494.
The fastest flight from Toronto Region of Waterloo Intl Airport to Chicago O'Hare Intl Airport takes 11h 43m
There are no direct flights from Toronto Region of Waterloo Intl Airport to Chicago O'Hare Intl Airport. Popular non-direct route for this connection is Toronto Region of Waterloo Intl Airport - Chicago O'Hare Intl Airport.
Search flight deals

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

    There are 635.1 km between Toronto Region of Waterloo Intl and Chicago O'Hare Intl. 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 O'Hare Intl Airport?

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

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

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

    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 from Toronto Region of Waterloo Intl Airport to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The travel and health documents you'll need for your trip to Chicago O'Hare Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago O'Hare Intl Airport. It is always advisable to seek 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 O'Hare Intl Airport?

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

Compare and see reviews for airlines that fly from Toronto Region of Waterloo Intl Airport to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
Air CanadaPriceFrom C$ 329Free CancellationRating
7.1
9,851 reviews
Search Air Canada flights

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Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Toronto to Chicago for you.

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

Flights from Toronto to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

momondo provides multiple filters to help you find the best flight to Chicago from Toronto. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Toronto and alert you when they change.

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