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Cheap flights from Toronto Region of Waterloo Intl Airport to Chicago from C$ 300

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
8:40 p.m. - 6:34 a.m.YKF  Toronto Region of Waterloo Intl-ORD Chicago O'Hare Intl
34h 54m3 stops Calgary San Francisco Los Angeles
Multiple Airlines Logo
12:26 p.m. - 7:50 p.m.ORD  Chicago O'Hare Intl-YKF Toronto Region of Waterloo Intl
30h 24m3 stops Dallas/Fort Worth San Francisco Calgary
C$ 1,375Multiple Airlines
Mon, 12 Oct - Thu, 15 Oct
Multiple Airlines Logo
8:40 p.m. - 12:29 a.m.YKF  Toronto Region of Waterloo Intl-ORD Chicago O'Hare Intl
28h 49m3 stops Calgary Phoenix Sky Harbor Intl Dallas/Fort Worth
Multiple Airlines Logo
3:30 p.m. - 7:50 p.m.ORD  Chicago O'Hare Intl-YKF Toronto Region of Waterloo Intl
27h 20m3 stops Las Vegas Harry Reid Intl Phoenix Sky Harbor Intl Calgary
C$ 1,380Multiple Airlines
Fri, 16 Oct - Sun, 18 Oct
Multiple Airlines Logo
8:40 p.m. - 12:29 a.m.YKF  Toronto Region of Waterloo Intl-ORD Chicago O'Hare Intl
28h 49m3 stops Calgary Los Angeles Dallas/Fort Worth
Multiple Airlines Logo
8:01 p.m. - 7:50 p.m.ORD  Chicago O'Hare Intl-YKF Toronto Region of Waterloo Intl
22h 49m2 stops Los Angeles Calgary
C$ 1,399Multiple Airlines
Fri, 16 Oct - Sun, 18 Oct
Multiple Airlines Logo
8:40 p.m. - 12:29 a.m.YKF  Toronto Region of Waterloo Intl-ORD Chicago O'Hare Intl
28h 49m3 stops Calgary Phoenix Sky Harbor Intl Dallas/Fort Worth
Multiple Airlines Logo
3:30 p.m. - 7:50 p.m.ORD  Chicago O'Hare Intl-YKF Toronto Region of Waterloo Intl
27h 20m3 stops Las Vegas Harry Reid Intl Phoenix Sky Harbor Intl Calgary
C$ 1,412Multiple Airlines
Fri, 16 Oct - Sun, 18 Oct
Multiple Airlines Logo
8:40 p.m. - 5:16 a.m.YKF  Toronto Region of Waterloo Intl-ORD Chicago O'Hare Intl
33h 36m3 stops Calgary Los Angeles Las Vegas Harry Reid Intl
Multiple Airlines Logo
8:01 p.m. - 7:50 p.m.ORD  Chicago O'Hare Intl-YKF Toronto Region of Waterloo Intl
22h 49m2 stops Los Angeles Calgary
C$ 1,468Multiple Airlines
Sun, 11 Oct - Sun, 18 Oct
Multiple Airlines Logo
8:40 p.m. - 12:29 a.m.YKF  Toronto Region of Waterloo Intl-ORD Chicago O'Hare Intl
28h 49m3 stops Calgary Los Angeles Dallas/Fort Worth
Multiple Airlines Logo
8:01 p.m. - 7:50 p.m.ORD  Chicago O'Hare Intl-YKF Toronto Region of Waterloo Intl
22h 49m2 stops Los Angeles Calgary
C$ 1,520Multiple Airlines
Fri, 16 Oct - Sun, 18 Oct
Multiple Airlines Logo
8:40 p.m. - 12:29 a.m.YKF  Toronto Region of Waterloo Intl-ORD Chicago O'Hare Intl
28h 49m3 stops Calgary Los Angeles Dallas/Fort Worth
Multiple Airlines Logo
8:01 p.m. - 7:50 p.m.ORD  Chicago O'Hare Intl-YKF Toronto Region of Waterloo Intl
22h 49m2 stops Los Angeles Calgary
C$ 1,525Multiple Airlines
Fri, 9 Oct - Tue, 13 Oct
Multiple Airlines Logo
8:40 p.m. - 12:29 a.m.YKF  Toronto Region of Waterloo Intl-ORD Chicago O'Hare Intl
28h 49m3 stops Calgary Los Angeles Dallas/Fort Worth
Multiple Airlines Logo
8:01 p.m. - 7:50 p.m.ORD  Chicago O'Hare Intl-YKF Toronto Region of Waterloo Intl
22h 49m2 stops Los Angeles Calgary
C$ 1,571Multiple Airlines
Fri, 9 Oct - Tue, 13 Oct
Multiple Airlines Logo
8:40 p.m. - 12:24 a.m.YKF  Toronto Region of Waterloo Intl-ORD Chicago O'Hare Intl
28h 44m3 stops Calgary Los Angeles Denver Intl
Multiple Airlines Logo
7:40 a.m. - 7:50 p.m.ORD  Chicago O'Hare Intl-YKF Toronto Region of Waterloo Intl
35h 10m3 stops Houston George Bush Intcntl Los Angeles Calgary
C$ 1,641Multiple Airlines
Fri, 9 Oct - Tue, 13 Oct
Multiple Airlines Logo
8:40 p.m. - 12:24 a.m.YKF  Toronto Region of Waterloo Intl-ORD Chicago O'Hare Intl
28h 44m3 stops Calgary Los Angeles Denver Intl
Multiple Airlines Logo
8:01 p.m. - 7:50 p.m.ORD  Chicago O'Hare Intl-YKF Toronto Region of Waterloo Intl
22h 49m2 stops Los Angeles Calgary
C$ 1,666Multiple Airlines
Fri, 9 Oct - Sun, 18 Oct

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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
3 Oct
YKF8:40 p.m.Toronto Region of Waterloo Intl
18h 49m
2 stops
ORD2:29 p.m.Chicago O'Hare Intl
4 Oct
ORD6:25 p.m.Chicago O'Hare Intl
24h 25m
2 stops
YKF7:50 p.m.Toronto Region of Waterloo Intl
C$ 1,963
WestJet
2 Oct
YKF8:40 p.m.Toronto Region of Waterloo Intl
20h 57m
2 stops
ORD4:37 p.m.Chicago O'Hare Intl
4 Oct
ORD6:25 p.m.Chicago O'Hare Intl
24h 25m
2 stops
YKF7:50 p.m.Toronto Region of Waterloo Intl
C$ 1,970
WestJet
3 Oct
YKF8:40 p.m.Toronto Region of Waterloo Intl
21h 00m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
6 Oct
ORD5:30 p.m.Chicago O'Hare Intl
25h 20m
1 stop
YKF7:50 p.m.Toronto Region of Waterloo Intl
C$ 2,148

momondo Fare Finder

 
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

Cheapest round-trip

TorontoChicago

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

YKFORD

Toronto Region of Waterloo Intl

Mon 12/10

8:40 p.m.-6:34 a.m.

3 stops34h 54m

Chicago O'Hare Intl

Thu 15/10

12:26 p.m.-7:50 p.m.

3 stops30h 24m

C$ 1,375

TorontoChicago

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

YKFORD

Toronto Region of Waterloo Intl

Fri 16/10

8:40 p.m.-12:29 a.m.

3 stops28h 49m

Chicago O'Hare Intl

Sun 18/10

3:30 p.m.-7:50 p.m.

3 stops27h 20m

C$ 1,380

TorontoChicago

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

YKFORD

Toronto Region of Waterloo Intl

Fri 16/10

8:40 p.m.-12:29 a.m.

3 stops28h 49m

Chicago O'Hare Intl

Sun 18/10

8:01 p.m.-7:50 p.m.

2 stops22h 49m

C$ 1,399

TorontoChicago

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

YKFORD

Toronto Region of Waterloo Intl

Fri 16/10

8:40 p.m.-12:29 a.m.

3 stops28h 49m

Chicago O'Hare Intl

Sun 18/10

3:30 p.m.-7:50 p.m.

3 stops27h 20m

C$ 1,412

TorontoChicago

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

YKFORD

Toronto Region of Waterloo Intl

Sun 11/10

8:40 p.m.-5:16 a.m.

3 stops33h 36m

Chicago O'Hare Intl

Sun 18/10

8:01 p.m.-7:50 p.m.

2 stops22h 49m

C$ 1,468

TorontoChicago

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

YKFORD

Toronto Region of Waterloo Intl

Fri 16/10

8:40 p.m.-12:29 a.m.

3 stops28h 49m

Chicago O'Hare Intl

Sun 18/10

8:01 p.m.-7:50 p.m.

2 stops22h 49m

C$ 1,520

TorontoChicago

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

YKFORD

Toronto Region of Waterloo Intl

Fri 9/10

8:40 p.m.-12:29 a.m.

3 stops28h 49m

Chicago O'Hare Intl

Tue 13/10

8:01 p.m.-7:50 p.m.

2 stops22h 49m

C$ 1,525

TorontoChicago

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

YKFORD

Toronto Region of Waterloo Intl

Fri 9/10

8:40 p.m.-12:29 a.m.

3 stops28h 49m

Chicago O'Hare Intl

Tue 13/10

8:01 p.m.-7:50 p.m.

2 stops22h 49m

C$ 1,571

TorontoChicago

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

YKFORD

Toronto Region of Waterloo Intl

Fri 9/10

8:40 p.m.-12:24 a.m.

3 stops28h 44m

Chicago O'Hare Intl

Tue 13/10

7:40 a.m.-7:50 p.m.

3 stops35h 10m

C$ 1,641
Quickest round-trip

TorontoChicago

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

YKFORD

Toronto Region of Waterloo Intl

Fri 9/10

8:40 p.m.-12:24 a.m.

3 stops28h 44m

Chicago O'Hare Intl

Sun 18/10

8:01 p.m.-7:50 p.m.

2 stops22h 49m

C$ 1,666

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$ 684. 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$ 973.

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$ 707. 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$ 1,110 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$ 300

Fastest flight time

17h 30m

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$ 300. 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$ 1,375.
The fastest flight from Toronto Region of Waterloo Intl Airport to Chicago O'Hare Intl Airport takes 17h 30m
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

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 17h 30m 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
Crystal Lake
Schaumburg
Waukegan
Glenview
Rosemont
Des Plaines
Merrillville
Kenosha
Tinley Park
Northbrook
Skokie
Evanston
Benton Harbor
Hammond
Downers Grove
Naperville
Munster
Harvey
Monroe
Hoffman Estates

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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