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Cheap flights from Toronto Region of Waterloo Intl Airport to Chicago from C$ 192

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 1/5. 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

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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
6:20 a.m. - 1:35 p.m.
YKF
-
ORD
32h 15m1 stop
Multiple Airlines Logo
8:00 a.m. - 5:29 a.m.
ORD
-
YKF
20h 29m2 stops
C$ 570Multiple Airlines
Thu, 5 Feb - Wed, 11 Feb
Multiple Airlines Logo
6:20 a.m. - 12:30 a.m.
YKF
-
ORD
19h 10m2 stops
Multiple Airlines Logo
8:43 p.m. - 5:28 a.m.
ORD
-
YKF
31h 45m3 stops
C$ 1,427Multiple Airlines
Mon, 5 Jan - Thu, 8 Jan
Multiple Airlines Logo
6:20 a.m. - 1:10 p.m.
YKF
-
ORD
31h 50m3 stops
Multiple Airlines Logo
8:43 p.m. - 5:28 a.m.
ORD
-
YKF
31h 45m3 stops
C$ 1,623Multiple Airlines
Mon, 5 Jan - Thu, 8 Jan

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
20 Dec
YKF7:00 p.m.Toronto Region of Waterloo Intl
17h 27m
2 stops
ORD11:27 a.m.Chicago O'Hare Intl
22 Dec
ORD2:20 p.m.Chicago O'Hare Intl
14h 08m
1 stop
YKF5:28 a.m.Toronto Region of Waterloo Intl
C$ 2,995
Find similar
WestJet
20 Dec
YKF7:00 p.m.Toronto Region of Waterloo Intl
24h 59m
2 stops
ORD6:59 p.m.Chicago O'Hare Intl
22 Dec
ORD10:00 a.m.Chicago O'Hare Intl
18h 28m
2 stops
YKF5:28 a.m.Toronto Region of Waterloo Intl
C$ 3,323
Find similar
WestJet
20 Dec
YKF7:00 p.m.Toronto Region of Waterloo Intl
17h 27m
2 stops
ORD11:27 a.m.Chicago O'Hare Intl
21 Dec
ORD4:01 p.m.Chicago O'Hare Intl
12h 27m
2 stops
YKF5:28 a.m.Toronto Region of Waterloo Intl
C$ 3,987
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 18 December 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

Thu 5/2

6:20 a.m.-1:35 p.m.

1 stop32h 15m

Chicago O'Hare Intl

Wed 11/2

8:00 a.m.-5:29 a.m.

2 stops20h 29m

C$ 570

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Mon 5/1

6:20 a.m.-12:30 a.m.

2 stops19h 10m

Chicago O'Hare Intl

Thu 8/1

8:43 p.m.-5:28 a.m.

3 stops31h 45m

C$ 1,427

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Mon 5/1

6:20 a.m.-1:10 p.m.

3 stops31h 50m

Chicago O'Hare Intl

Thu 8/1

8:43 p.m.-5:28 a.m.

3 stops31h 45m

C$ 1,623

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Fri 1/5

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

1 stop11h 43m

C$ 192

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Sat 13/6

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

1 stop11h 43m

C$ 227

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Mon 9/3

8:25 p.m.-9:13 p.m.

2 stops25h 48m

C$ 282

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Sat 31/1

7:00 p.m.-2:17 p.m.

3 stops20h 17m

C$ 300

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Sat 31/1

7:00 p.m.-11:50 p.m.

2 stops29h 50m

C$ 307

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Wed 3/6

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

1 stop11h 43m

C$ 313

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Wed 27/5

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

1 stop11h 43m

C$ 317

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 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$ 670. 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$ 1,088.

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$ 627. 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 at noon when prices are C$ 1,113 on average. Flights to Chicago O'Hare Intl Airport from Toronto Region of Waterloo Intl Airport at noon 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

Fastest flight time

19h 10m

Direct flights

None
The fastest flight from Toronto Region of Waterloo Intl Airport to Chicago O'Hare Intl Airport takes 19h 10m
There are no direct flights from Toronto Region of Waterloo Intl Airport to Chicago O'Hare Intl Airport. There are no popular flight routes from Toronto Region of Waterloo Intl Airport to Chicago O'Hare Intl Airport.
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  • 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 19h 10m 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 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.

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Schaumburg
Rosemont
Hoffman Estates
Northbrook
Tinley Park
Munster
Skokie
Hammond
Harvey
Naperville
Glenview
Great Lakes
Wheeling
Elmhurst
Harvard
Merrillville
Elk Grove Village
Oak Brook
Kenosha

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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