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Cheap flights from Toronto Region of Waterloo Intl Airport to Chicago O'Hare Intl Airport from C$ 187

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 6/10. Fares are subject to change and may not be available on all flights or dates of travel.
YKF — ORD
3 Aug — 10 Aug1
1 adult

Cheap 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 29 July 2025.

Round-trip from

C$ 447

One-way from

C$ 187

Popular in

December

Cheapest in

June

Average price

C$ 370
WestJet
  • WestJet
  • 11/9-18/9
  • 2 total stops
  • 41h 58m total
  • Toronto to Chicago
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6/10
  • 6/10
  • 1 total stop
  • 11h 43m total
  • Toronto to Chicago
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Highest demand for flights based on searches. 7% potential increase in price (C$ 40 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease (C$ 7 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Find flight deals from Region of Waterloo Intl to O'Hare Intl

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 29 July 2025.

Thu 11/96:00 a.m.YKF - ORD
1 stop11h 43mWestJet
Thu 18/95:30 p.m.ORD - YKF
1 stop30h 15mWestJet
Deal found 28/7C$ 447
Sun 12/106:00 a.m.YKF - ORD
1 stop11h 43mMultiple Airlines
Sun 19/105:30 p.m.ORD - YKF
1 stop10h 45mMultiple Airlines
Deal found 27/7C$ 502

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 29 July 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

Thu 11/9

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

1 stop11h 43m

Chicago O'Hare Intl

Thu 18/9

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

1 stop30h 15m

C$ 447

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Sun 12/10

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

1 stop11h 43m

Chicago O'Hare Intl

Sun 19/10

5:30 p.m.-5:15 a.m.

1 stop10h 45m

C$ 502

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Mon 6/10

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

1 stop11h 43m

C$ 187

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Tue 30/9

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

1 stop11h 43m

C$ 221

Flights are sorted by cheapest round-trip flights first.

Deals found on 29/7

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.

Reviews of airlines servicing O'Hare Intl

Get insights into the airlines that provide service to O'Hare Intl. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to O'Hare Intl. Reviews last updated 29 July 2025.
See what other customers who have flown with WestJet from Toronto Region of Waterloo Intl Airport to Chicago O'Hare Intl Airport have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
WestJet
7.2
Good
2,973 reviews
Check prices

Food

6.2

Crew

7.9

Boarding

7.4

Overall

7.2

Entertainment

6.1

Comfort

7.0

Reviews

1 / 20
6.0
Good

Deb,Jan 2025

YYZ - YYC

Boarding went smoothly, you didn't accept debit card for food on flight
WestJet
7.2
Good
2,973 reviews
WestJet
7.2
Good
2,973 reviews
Check prices

Food

6.2

Crew

7.9

Boarding

7.4

Overall

7.2

Entertainment

6.1

Comfort

7.0

Reviews

1 / 20
6.0
Good

Deb,Jan 2025

YYZ - YYC

Boarding went smoothly, you didn't accept debit card for food on flight

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.

  • What is the cheapest airline to fly from Toronto Region of Waterloo Intl Airport to Chicago O'Hare Intl Airport round-trip?

    Cheapflights users have booked flights from Toronto Region of Waterloo Intl Airport to Chicago O'Hare Intl Airport round-trip from C$ 447.

  • 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.

  • What is the cheapest month to book a flight from Toronto Region of Waterloo Intl Airport to Chicago O'Hare Intl Airport?

    Currently, January is the cheapest month in which you can book a flight from Toronto Region of Waterloo Intl Airport to Chicago O'Hare Intl Airport (average of C$ 261). Flying from Toronto Region of Waterloo Intl Airport to Chicago O'Hare Intl Airport in March is currently the most expensive (average of C$ 352). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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
Elk Grove Village
Evanston
Des Plaines
Skokie
Downers Grove
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.
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

Top airline flying from Region of Waterloo Intl to O'Hare Intl

Discover the top airline that operate flights from Region of Waterloo Intl to O'Hare Intl. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 29 July 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 327AverageC$ 403FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

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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?

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.

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