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Cheap flights from Toronto Region of Waterloo Intl Airport to Chicago from C$ 546

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
7:00 p.m. - 11:07 a.m.YKF  Toronto Region of Waterloo Intl-ORD Chicago O'Hare Intl
17h 07m2 stops Calgary Montreal Pierre Elliott Trudeau Intl
Multiple Airlines Logo
3:45 p.m. - 3:45 p.m.ORD  Chicago O'Hare Intl-YKF Toronto Region of Waterloo Intl
23h 00m2 stops Montreal Pierre Elliott Trudeau Intl Calgary
C$ 1,135Multiple Airlines
Thu, 3 Dec - Sun, 6 Dec
Multiple Airlines Logo
5:30 p.m. - 6:54 p.m.YKF  Toronto Region of Waterloo Intl-ORD Chicago O'Hare Intl
26h 24m3 stops Toronto Pearson Intl Calgary Phoenix Sky Harbor Intl
Multiple Airlines Logo
5:01 a.m. - 10:00 p.m.ORD  Chicago O'Hare Intl-YKF Toronto Region of Waterloo Intl
15h 59m2 stops Orlando Halifax Intl
C$ 2,053Multiple Airlines
Tue, 29 Dec - Fri, 1 Jan
Multiple Airlines Logo
7:00 p.m. - 11:07 a.m.YKF  Toronto Region of Waterloo Intl-ORD Chicago O'Hare Intl
17h 07m3 stops Toronto Pearson Intl Halifax Intl Montreal Pierre Elliott Trudeau Intl
Multiple Airlines Logo
5:01 a.m. - 10:00 p.m.ORD  Chicago O'Hare Intl-YKF Toronto Region of Waterloo Intl
15h 59m2 stops Orlando Halifax Intl
C$ 2,186Multiple Airlines
Mon, 28 Dec - Fri, 1 Jan
Multiple Airlines Logo
7:00 p.m. - 2:37 p.m.YKF  Toronto Region of Waterloo Intl-ORD Chicago O'Hare Intl
20h 37m2 stops Calgary Vancouver Intl
Multiple Airlines Logo
5:01 a.m. - 10:00 p.m.ORD  Chicago O'Hare Intl-YKF Toronto Region of Waterloo Intl
15h 59m2 stops Orlando Halifax Intl
C$ 2,375Multiple Airlines
Sat, 26 Dec - Fri, 1 Jan
Multiple Airlines Logo
8:30 p.m. - 1:08 a.m.YKF  Toronto Region of Waterloo Intl-ORD Chicago O'Hare Intl
29h 38m3 stops Toronto Pearson Intl Halifax Intl Orlando
Multiple Airlines Logo
5:01 a.m. - 10:00 p.m.ORD  Chicago O'Hare Intl-YKF Toronto Region of Waterloo Intl
15h 59m2 stops Orlando Halifax Intl
C$ 2,414Multiple Airlines
Mon, 28 Dec - Fri, 1 Jan
Multiple Airlines Logo
5:30 p.m. - 11:07 a.m.YKF  Toronto Region of Waterloo Intl-ORD Chicago O'Hare Intl
18h 37m3 stops Toronto Pearson Intl Calgary Montreal Pierre Elliott Trudeau Intl
Multiple Airlines Logo
7:05 a.m. - 10:00 p.m.ORD  Chicago O'Hare Intl-YKF Toronto Region of Waterloo Intl
13h 55m2 stops Montreal Pierre Elliott Trudeau Intl Halifax Intl
C$ 2,493Multiple Airlines
Fri, 25 Dec - Fri, 1 Jan
Multiple Airlines Logo
7:00 p.m. - 2:37 p.m.YKF  Toronto Region of Waterloo Intl-ORD Chicago O'Hare Intl
20h 37m2 stops Toronto Pearson Intl Vancouver Intl
Multiple Airlines Logo
5:01 a.m. - 10:00 p.m.ORD  Chicago O'Hare Intl-YKF Toronto Region of Waterloo Intl
15h 59m2 stops Orlando Halifax Intl
C$ 2,498Multiple Airlines
Tue, 29 Dec - Fri, 1 Jan
Multiple Airlines Logo
8:30 p.m. - 2:37 p.m.YKF  Toronto Region of Waterloo Intl-ORD Chicago O'Hare Intl
19h 07m2 stops Toronto Pearson Intl Vancouver Intl
Multiple Airlines Logo
5:01 a.m. - 10:00 p.m.ORD  Chicago O'Hare Intl-YKF Toronto Region of Waterloo Intl
15h 59m2 stops Orlando Halifax Intl
C$ 2,566Multiple Airlines
Mon, 28 Dec - Fri, 1 Jan
Multiple Airlines Logo
5:30 p.m. - 2:37 p.m.YKF  Toronto Region of Waterloo Intl-ORD Chicago O'Hare Intl
22h 07m2 stops Toronto Pearson Intl Vancouver Intl
Multiple Airlines Logo
5:01 a.m. - 10:00 p.m.ORD  Chicago O'Hare Intl-YKF Toronto Region of Waterloo Intl
15h 59m2 stops Orlando Halifax Intl
C$ 2,568Multiple Airlines
Mon, 28 Dec - Fri, 1 Jan
Multiple Airlines Logo
8:30 p.m. - 11:07 a.m.YKF  Toronto Region of Waterloo Intl-ORD Chicago O'Hare Intl
15h 37m3 stops Toronto Pearson Intl Halifax Intl Montreal Pierre Elliott Trudeau Intl
Multiple Airlines Logo
5:01 a.m. - 10:00 p.m.ORD  Chicago O'Hare Intl-YKF Toronto Region of Waterloo Intl
15h 59m2 stops Orlando Halifax Intl
C$ 2,585Multiple Airlines
Sat, 26 Dec - Fri, 1 Jan

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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.

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Route

Depart

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Price

Cheapest round-trip

TorontoChicago

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

YKFORD

Toronto Region of Waterloo Intl

Thu 3/12

7:00 p.m.-11:07 a.m.

2 stops17h 07m

Chicago O'Hare Intl

Sun 6/12

3:45 p.m.-3:45 p.m.

2 stops23h 00m

C$ 1,135

TorontoChicago

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

YKFORD

Toronto Region of Waterloo Intl

Tue 29/12

5:30 p.m.-6:54 p.m.

3 stops26h 24m

Chicago O'Hare Intl

Fri 1/1

5:01 a.m.-10:00 p.m.

2 stops15h 59m

C$ 2,053

TorontoChicago

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

YKFORD

Toronto Region of Waterloo Intl

Mon 28/12

7:00 p.m.-11:07 a.m.

3 stops17h 07m

Chicago O'Hare Intl

Fri 1/1

5:01 a.m.-10:00 p.m.

2 stops15h 59m

C$ 2,186

TorontoChicago

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

YKFORD

Toronto Region of Waterloo Intl

Sat 26/12

7:00 p.m.-2:37 p.m.

2 stops20h 37m

Chicago O'Hare Intl

Fri 1/1

5:01 a.m.-10:00 p.m.

2 stops15h 59m

C$ 2,375

TorontoChicago

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

YKFORD

Toronto Region of Waterloo Intl

Mon 28/12

8:30 p.m.-1:08 a.m.

3 stops29h 38m

Chicago O'Hare Intl

Fri 1/1

5:01 a.m.-10:00 p.m.

2 stops15h 59m

C$ 2,414

TorontoChicago

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

YKFORD

Toronto Region of Waterloo Intl

Fri 25/12

5:30 p.m.-11:07 a.m.

3 stops18h 37m

Chicago O'Hare Intl

Fri 1/1

7:05 a.m.-10:00 p.m.

2 stops13h 55m

C$ 2,493

TorontoChicago

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

YKFORD

Toronto Region of Waterloo Intl

Tue 29/12

7:00 p.m.-2:37 p.m.

2 stops20h 37m

Chicago O'Hare Intl

Fri 1/1

5:01 a.m.-10:00 p.m.

2 stops15h 59m

C$ 2,498

TorontoChicago

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

YKFORD

Toronto Region of Waterloo Intl

Mon 28/12

8:30 p.m.-2:37 p.m.

2 stops19h 07m

Chicago O'Hare Intl

Fri 1/1

5:01 a.m.-10:00 p.m.

2 stops15h 59m

C$ 2,566

TorontoChicago

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

YKFORD

Toronto Region of Waterloo Intl

Mon 28/12

5:30 p.m.-2:37 p.m.

2 stops22h 07m

Chicago O'Hare Intl

Fri 1/1

5:01 a.m.-10:00 p.m.

2 stops15h 59m

C$ 2,568
Quickest round-trip

TorontoChicago

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

YKFORD

Toronto Region of Waterloo Intl

Sat 26/12

8:30 p.m.-11:07 a.m.

3 stops15h 37m

Chicago O'Hare Intl

Fri 1/1

5:01 a.m.-10:00 p.m.

2 stops15h 59m

C$ 2,585

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 14 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$ 691. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, 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$ 946.

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$ 711. 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$ 1,132 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$ 546

Fastest flight time

18h 37m

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$ 546. 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$ 1,135.
The fastest flight from Toronto Region of Waterloo Intl Airport to Chicago O'Hare Intl Airport takes 18h 37m
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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Frequently asked questions about flying from Toronto Region of Waterloo Intl Airport to Chicago O'Hare Intl Airport

  • 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 18h 37m 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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Schaumburg
Waukegan
Glenview
Des Plaines
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Kenosha
Tinley Park
Northbrook
Skokie
Rosemont
Hammond
Evanston
Benton Harbor
Naperville
Elgin
Downers Grove
Munster
Harvey
Monroe

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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