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Cheap flights from Toronto Region of Waterloo Intl Airport to Chicago O'Hare Intl Airport from C$ 262

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 6/1. Fares are subject to change and may not be available on all flights or dates of travel.
YKF — ORD
11 Jan — 18 Jan1
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.

Best flights from Region of Waterloo Intl to O'Hare Intl
Discover carefully curated flight deals from Region of Waterloo Intl to O'Hare Intl that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 12 December 2025.

Sun 7/66:00 a.m.YKF - ORD
1 stop11h 43mWestJet
Sun 21/65:30 p.m.ORD - YKF
1 stop30h 15mWestJet
Deal found 11/12C$ 1,182

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 12 December 2025.

Round-trip from

C$ 1,182

One-way from

C$ 262

Popular in

December

Cheapest in

July

Average price

C$ 441
WestJet
  • WestJet
  • 7/6-21/6
  • 2 total stops
  • 41h 58m total
  • Toronto to Chicago
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Air Canada
  • Air Canada
  • 6/1
  • 1 total stop
  • 5h 30m total
  • Toronto to Chicago
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Highest demand for flights based on searches. 9% potential increase in price (C$ 51 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 13 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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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 12 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

Region of Waterloo Intl

Fly to

O'Hare Intl

Route

Depart

Return

Price

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Sun 7/6

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

1 stop11h 43m

Chicago O'Hare Intl

Sun 21/6

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

1 stop30h 15m

C$ 1,182

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Tue 6/1

5:35 p.m.-10:05 p.m.

1 stop5h 30m

C$ 262

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Tue 2/6

1:15 p.m.-4:59 p.m.

1 stop4h 44m

C$ 270

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Sat 31/1

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

3 stops20h 17m

C$ 314

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Thu 18/12

6:20 a.m.-9:40 p.m.

2 stops16h 20m

C$ 1,500

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Fri 26/12

6:25 a.m.-9:34 p.m.

2 stops16h 09m

C$ 1,579

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/12

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$ 1,182. 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
Elk Grove Village
Downers Grove
Racine
Naperville
Bolingbrook
Romeoville

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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.
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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?

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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.

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