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Cheap flights from Toronto Region of Waterloo Intl Airport to Chicago from C$ 193

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 22/3. 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.
Air Canada Logo
8:25 p.m. - 9:13 a.m.
YKF
-
ORD
13h 48m
1 stop
Air Canada Logo
9:50 a.m. - 6:35 p.m.
ORD
-
YKF
7h 45m
1 stop
C$ 309Air Canada
Tue, 24 Mar - Tue, 31 Mar
Air Canada Logo
2:10 p.m. - 7:45 p.m.
YKF
-
ORD
6h 35m
1 stop
Air Canada Logo
4:15 p.m. - 11:20 p.m.
ORD
-
YKF
6h 05m
1 stop
C$ 313Air Canada
Tue, 24 Mar - Tue, 31 Mar
Multiple Airlines Logo
7:05 a.m. - 1:35 p.m.
YKF
-
ORD
31h 30m
1 stop
Multiple Airlines Logo
2:20 p.m. - 5:29 a.m.
ORD
-
YKF
14h 09m
1 stop
C$ 790Multiple Airlines
Sun, 22 Mar - Fri, 27 Mar
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$ 812WestJet
Fri, 22 May - Sat, 30 May
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$ 868WestJet
Mon, 1 Jun - Mon, 8 Jun
Multiple Airlines Logo
4:25 p.m. - 11:38 p.m.
YKF
-
ORD
32h 13m
2 stops
Multiple Airlines Logo
2:20 p.m. - 5:29 a.m.
ORD
-
YKF
14h 09m
1 stop
C$ 958Multiple Airlines
Sun, 22 Mar - Fri, 27 Mar
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$ 962WestJet
Sat, 13 Jun - Mon, 15 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$ 1,022WestJet
Sat, 13 Jun - Mon, 15 Jun
Multiple Airlines Logo
7:05 a.m. - 7:54 a.m.
YKF
-
ORD
25h 49m
2 stops
Multiple Airlines Logo
8:16 p.m. - 5:29 a.m.
ORD
-
YKF
32h 13m
3 stops
C$ 1,223Multiple Airlines
Fri, 27 Feb - Sun, 1 Mar
WestJet Logo
7:45 p.m. - 4:43 p.m.
YKF
-
ORD
21h 58m
1 stop
WestJet Logo
5:30 p.m. - 6:55 p.m.
ORD
-
YKF
24h 25m
1 stop
C$ 1,408WestJet
Fri, 3 Jul - Sun, 5 Jul

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

Our best Air Canada deals on Toronto Region of Waterloo Intl Airport to Chicago O'Hare Intl Airport flight tickets
Air Canada
24 Mar
YKF8:25 p.m.Toronto Region of Waterloo Intl
13h 48m
1 stop
ORD9:13 a.m.Chicago O'Hare Intl
31 Mar
ORD9:50 a.m.Chicago O'Hare Intl
7h 45m
1 stop
YKF6:35 p.m.Toronto Region of Waterloo Intl
C$ 309
Air Canada
24 Mar
YKF2:10 p.m.Toronto Region of Waterloo Intl
6h 35m
1 stop
ORD7:45 p.m.Chicago O'Hare Intl
31 Mar
ORD4:15 p.m.Chicago O'Hare Intl
6h 05m
1 stop
YKF11:20 p.m.Toronto Region of Waterloo Intl
C$ 313

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
22 May
YKF8:40 p.m.Toronto Region of Waterloo Intl
21h 00m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
30 May
ORD5:30 p.m.Chicago O'Hare Intl
25h 20m
1 stop
YKF7:50 p.m.Toronto Region of Waterloo Intl
C$ 812
WestJet
1 Jun
YKF8:40 p.m.Toronto Region of Waterloo Intl
21h 00m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
8 Jun
ORD5:30 p.m.Chicago O'Hare Intl
25h 20m
1 stop
YKF7:50 p.m.Toronto Region of Waterloo Intl
C$ 868
WestJet
13 Jun
YKF8:40 p.m.Toronto Region of Waterloo Intl
21h 00m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
15 Jun
ORD5:30 p.m.Chicago O'Hare Intl
25h 20m
1 stop
YKF7:50 p.m.Toronto Region of Waterloo Intl
C$ 962

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 8 February 2026.
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

Tue 24/3

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

1 stop13h 48m

Chicago O'Hare Intl

Tue 31/3

9:50 a.m.-6:35 p.m.

1 stop7h 45m

C$ 309

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Tue 24/3

2:10 p.m.-7:45 p.m.

1 stop6h 35m

Chicago O'Hare Intl

Tue 31/3

4:15 p.m.-11:20 p.m.

1 stop6h 05m

C$ 313

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Sun 22/3

7:05 a.m.-1:35 p.m.

1 stop31h 30m

Chicago O'Hare Intl

Fri 27/3

2:20 p.m.-5:29 a.m.

1 stop14h 09m

C$ 790

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Fri 22/5

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

1 stop21h 00m

Chicago O'Hare Intl

Sat 30/5

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

1 stop25h 20m

C$ 812

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

Mon 8/6

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

1 stop25h 20m

C$ 868

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Sun 22/3

4:25 p.m.-11:38 p.m.

2 stops32h 13m

Chicago O'Hare Intl

Fri 27/3

2:20 p.m.-5:29 a.m.

1 stop14h 09m

C$ 958

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Sat 13/6

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

1 stop21h 00m

Chicago O'Hare Intl

Mon 15/6

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

1 stop25h 20m

C$ 962

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Sat 13/6

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

1 stop21h 00m

Chicago O'Hare Intl

Mon 15/6

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

1 stop25h 20m

C$ 1,022

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Fri 27/2

7:05 a.m.-7:54 a.m.

2 stops25h 49m

Chicago O'Hare Intl

Sun 1/3

8:16 p.m.-5:29 a.m.

3 stops32h 13m

C$ 1,223

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Fri 3/7

7:45 p.m.-4:43 p.m.

1 stop21h 58m

Chicago O'Hare Intl

Sun 5/7

5:30 p.m.-6:55 p.m.

1 stop24h 25m

C$ 1,408

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$ 664. 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$ 1,061.

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$ 651. 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$ 1,123 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

21h 00m

Direct flights

None
The fastest flight from Toronto Region of Waterloo Intl Airport to Chicago O'Hare Intl Airport takes 21h 00m
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.
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 21h 00m 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
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Rosemont
Hoffman Estates
Northbrook
Tinley Park
Munster
Skokie
Great Lakes
Hammond
Harvey
Wheeling
Naperville
Glenview
Des Plaines
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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