Find flights
When to book
FAQs

Cheap flights from Toronto Region of Waterloo Intl Airport to Chicago O'Hare Intl Airport from C$ 186

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/6. Fares are subject to change and may not be available on all flights or dates of travel.
YKF — ORD
25 Feb — 4 Mar1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Region of Waterloo Intl to O'Hare Intl

Enter your travel dates to find the best prices.

Cheapest flights from Region of Waterloo Intl to O'Hare Intl
Explore the most affordable flight options available from Region of Waterloo Intl to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 26 January 2026.

Fri 22/56:00 a.m.
YKF
-
ORD
1 stop11h 43m
WestJet
Sun 31/55:30 p.m.
ORD
-
YKF
1 stop30h 15m
WestJet
Deal found 24/1C$ 486
Fri 22/56:00 a.m.
YKF
-
ORD
1 stop11h 43m
Multiple Airlines
Sun 31/58:53 p.m.
ORD
-
YKF
2 stops26h 52m
Multiple Airlines
Deal found 24/1C$ 734
Mon 11/56:00 a.m.
YKF
-
ORD
1 stop11h 43m
WestJet
Mon 18/55:30 p.m.
ORD
-
YKF
1 stop30h 15m
WestJet
Deal found 24/1C$ 933
Fri 22/58:40 p.m.
YKF
-
ORD
1 stop21h 00m
WestJet
Sun 24/55:30 p.m.
ORD
-
YKF
1 stop25h 20m
WestJet
Deal found 26/1C$ 1,060
Fri 21/87:45 p.m.
YKF
-
ORD
1 stop21h 58m
WestJet
Wed 26/85:30 p.m.
ORD
-
YKF
1 stop24h 25m
WestJet
Deal found 25/1C$ 1,205
Thu 27/87:45 p.m.
YKF
-
ORD
1 stop21h 58m
WestJet
Fri 28/87:55 p.m.
ORD
-
YKF
2 stops22h 00m
WestJet
Deal found 24/1C$ 1,339
Sat 14/37:00 p.m.
YKF
-
ORD
2 stops16h 00m
WestJet
Wed 18/36:15 a.m.
ORD
-
YKF
2 stops22h 14m
WestJet
Deal found 25/1C$ 2,068

Find flight deals from Region of Waterloo Intl to O'Hare Intl

Discover tips and strategies to find the most affordable flight options for your journey from Region of Waterloo Intl (YKF) to O'Hare Intl (ORD). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 26 January 2026.

Round-trip from

C$ 1,060

One-way from

C$ 186

Popular in

January

Cheapest in

July

Average price

C$ 401
WestJet
  • WestJet
  • 22/5-24/5
  • 2 total stops
  • 46h 20m total
  • Toronto to Chicago
Search Deals
Air Canada
  • Air Canada
  • 2/6
  • 1 total stop
  • 5h 00m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 10% potential increase in price (C$ 57 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Region of Waterloo Intl to O'Hare Intl 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, Cheapflights users made 629,999 searches. Data last updated 26 January 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

Region of Waterloo Intl

Fly to

O'Hare Intl

Route

Depart

Return

Price

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Fri 22/5

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

1 stop11h 43m

Chicago O'Hare Intl

Sun 31/5

5:30 p.m.-12:45 a.m.

1 stop30h 15m

C$ 486

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Fri 22/5

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

1 stop11h 43m

Chicago O'Hare Intl

Sun 31/5

8:53 p.m.-12:45 a.m.

2 stops26h 52m

C$ 734

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Mon 11/5

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

1 stop11h 43m

Chicago O'Hare Intl

Mon 18/5

5:30 p.m.-12:45 a.m.

1 stop30h 15m

C$ 933

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

Sun 24/5

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

1 stop25h 20m

C$ 1,060

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Sat 14/3

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

2 stops16h 00m

Chicago O'Hare Intl

Wed 18/3

6:15 a.m.-5:29 a.m.

2 stops22h 14m

C$ 2,068

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Wed 6/5

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

1 stop21h 00m

C$ 241

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Mon 4/5

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

1 stop11h 43m

C$ 322

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Tue 2/6

4:00 p.m.-11:21 p.m.

2 stops8h 21m

C$ 342

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Sun 26/4

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

1 stop21h 00m

C$ 349

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Tue 16/6

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

1 stop21h 00m

C$ 384

Flights are sorted by cheapest round-trip flights first.

Deals found on 26/1

Showing 1-10 of 16 results
1
2

Best time to book a flight from Region of Waterloo Intl to O'Hare Intl

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from Region of Waterloo Intl with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Related info for your journey

Find useful and relevant information for your journey from Region of Waterloo Intl to O'Hare Intl. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Toronto Region of Waterloo Intl Airport to Chicago O'Hare Intl Airport?

    A quick flight from Toronto Region of Waterloo Intl Airport to Chicago O'Hare Intl Airport can take about 11h 43m. WestJet provides one of the quickest options available for as low as C$ 486. Toronto Region of Waterloo Intl Airport and Chicago O'Hare Intl Airport are separated by a distance of 636 km.

  • Can I find deals for flights from Region of Waterloo Intl to O'Hare Intl that include hotel bookings?

    Yes. In addition to deals on Region of Waterloo Intl to O'Hare Intl flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Region of Waterloo Intl to O'Hare Intl?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Region of Waterloo Intl to O'Hare Intl.

  • Can I find deals for business class flights from Region of Waterloo Intl to O'Hare Intl?

    Yes. Cheapflights offers flight deals from Region of Waterloo Intl to O'Hare Intl by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Travelling to a place near Chicago O'Hare Intl Airport?

Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locations
Evanston
Des Plaines
Skokie
Downers Grove
Elk Grove Village
Racine
Naperville
Bolingbrook
Romeoville

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Region of Waterloo Intl to O'Hare Intl

See prices for flight routes from nearby airports that may be better suited for you.
Pearson Intl to O'Hare Intl flights
Pearson Intl to Midway flights
Toronto Island to Midway flights
Toronto Island to O'Hare Intl flights
Hamilton to O'Hare Intl flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Region of Waterloo Intl to O'Hare Intl?

When you search for this flight from Region of Waterloo Intl to O'Hare Intl, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.

Why should you use Cheapflights to find cheap flight tickets from Region of Waterloo Intl to O'Hare Intl?

Cheapflights helps you find that perfect flight to O'Hare Intl from Region of Waterloo Intl by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Can Cheapflights find flights from Region of Waterloo Intl to O'Hare Intl with no change fees?

Users can book flights with no change fees policies with our dedicated filters. Book flights from Region of Waterloo Intl to O'Hare Intl flexibly with Cheapflights today.

Can Cheapflights notify me if prices for flights from Region of Waterloo Intl to O'Hare Intl become cheaper?

Yes, Cheapflights offers price alerts on Region of Waterloo Intl to O'Hare Intl flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.