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Cheap flights from Toronto Region of Waterloo Intl Airport to Chicago O'Hare Intl Airport from C$ 161

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 18/10. Fares are subject to change and may not be available on all flights or dates of travel.
YKF — ORD
11 Oct — 18 Oct1
1 adult
1 adult, Economy

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 11 September 2025.

Round-trip from

C$ 299

One-way from

C$ 161

Popular in

December

Cheapest in

July

Average price

C$ 346
WestJet
  • WestJet
  • 24/10-27/10
  • 2 total stops
  • 25h 51m total
  • Toronto to Chicago
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WestJet
  • WestJet
  • 18/10
  • 1 total stop
  • 11h 43m total
  • Toronto to Chicago
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Highest demand for flights based on searches. 6% potential increase in price (C$ 36 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 September 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 11 September 2025.

Fri 24/106:00 a.m.YKF - ORD
1 stop11h 43mWestJet
Mon 27/102:20 p.m.ORD - YKF
1 stop14h 08mWestJet
Deal found 9/9C$ 269
Thu 16/106:00 a.m.YKF - ORD
1 stop11h 43mWestJet
Sun 19/105:30 p.m.ORD - YKF
1 stop30h 15mWestJet
Deal found 8/9C$ 279
Fri 24/106:00 a.m.YKF - ORD
1 stop11h 43mWestJet
Sun 26/102:20 p.m.ORD - YKF
1 stop14h 08mWestJet
Deal found 9/9C$ 349
Fri 17/106:00 a.m.YKF - ORD
1 stop11h 43mWestJet
Sun 26/102:20 p.m.ORD - YKF
1 stop14h 08mWestJet
Deal found 11/9C$ 380
Sat 25/106:00 a.m.YKF - ORD
1 stop11h 43mMultiple Airlines
Sat 1/115:45 p.m.ORD - YKF
2 stops35h 43mMultiple Airlines
Deal found 9/9C$ 402
Thu 23/106:00 a.m.YKF - ORD
1 stop11h 43mWestJet
Sun 26/102:20 p.m.ORD - YKF
1 stop14h 08mWestJet
Deal found 11/9C$ 418
Fri 24/106:25 p.m.YKF - ORD
2 stops23h 18mMultiple Airlines
Fri 31/102:20 p.m.ORD - YKF
1 stop14h 08mMultiple Airlines
Deal found 9/9C$ 423
Mon 20/106:00 a.m.YKF - ORD
1 stop11h 43mWestJet
Fri 31/102:20 p.m.ORD - YKF
1 stop14h 08mWestJet
Deal found 10/9C$ 424
Fri 3/106:00 a.m.YKF - ORD
1 stop11h 43mMultiple Airlines
Sun 5/105:30 p.m.ORD - YKF
1 stop10h 45mMultiple Airlines
Deal found 10/9C$ 467
Thu 2/106:00 a.m.YKF - ORD
1 stop11h 43mMultiple Airlines
Sun 5/105:30 p.m.ORD - YKF
1 stop10h 45mMultiple Airlines
Deal found 9/9C$ 481

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 11 September 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

Fri 24/10

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

1 stop11h 43m

Chicago O'Hare Intl

Mon 27/10

2:20 p.m.-5:28 a.m.

1 stop14h 08m

C$ 269

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Fri 24/10

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

1 stop11h 43m

Chicago O'Hare Intl

Sun 26/10

2:20 p.m.-5:28 a.m.

1 stop14h 08m

C$ 279

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Thu 16/10

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

1 stop11h 43m

Chicago O'Hare Intl

Sun 19/10

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

1 stop30h 15m

C$ 279

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Fri 17/10

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

1 stop11h 43m

Chicago O'Hare Intl

Sun 26/10

2:20 p.m.-5:28 a.m.

1 stop14h 08m

C$ 380

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Thu 23/10

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

1 stop11h 43m

Chicago O'Hare Intl

Sun 26/10

2:20 p.m.-5:28 a.m.

1 stop14h 08m

C$ 418

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Fri 24/10

6:25 p.m.-4:43 p.m.

2 stops23h 18m

Chicago O'Hare Intl

Fri 31/10

2:20 p.m.-5:28 a.m.

1 stop14h 08m

C$ 423

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Mon 20/10

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

1 stop11h 43m

Chicago O'Hare Intl

Fri 31/10

2:20 p.m.-5:28 a.m.

1 stop14h 08m

C$ 424

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Fri 3/10

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

1 stop11h 43m

Chicago O'Hare Intl

Sun 5/10

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

1 stop10h 45m

C$ 467

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Thu 2/10

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

1 stop11h 43m

Chicago O'Hare Intl

Sun 5/10

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

1 stop10h 45m

C$ 481

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Sat 18/10

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

1 stop11h 43m

C$ 161

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 16 results
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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 11 September 2025.
See what other customers who have flown with Air Canada 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.
Air Canada
7.1
Good
10,000 reviews
Check prices

Entertainment

6.8

Crew

7.8

Boarding

7.3

Comfort

7.1

Overall

7.1

Food

6.3

Reviews

1 / 20
8.0
Excellent

Jadi-Ann,Jun 2025

YYZ - KIN

The flight was smooth with minor turbulence. The staff was courteous. Since I have an aeroplan account I was able to use the inflight wifi. I wanted extra space and the window seat and I had to pay for that. At first, I was okay with that, however, I felt that it was the same distance between for everyone. Maybe I could be wrong.
Air Canada
7.1
Good
10,000 reviews
Air Canada
7.1
Good
10,000 reviews
Check prices

Entertainment

6.8

Crew

7.8

Boarding

7.3

Comfort

7.1

Overall

7.1

Food

6.3

Reviews

1 / 20
8.0
Excellent

Jadi-Ann,Jun 2025

YYZ - KIN

The flight was smooth with minor turbulence. The staff was courteous. Since I have an aeroplan account I was able to use the inflight wifi. I wanted extra space and the window seat and I had to pay for that. At first, I was okay with that, however, I felt that it was the same distance between for everyone. Maybe I could be wrong.

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$ 269. Toronto Region of Waterloo Intl Airport and Chicago O'Hare Intl Airport are separated by a distance of 636 km.

  • 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$ 330.

  • 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$ 349). 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
Evanston
Des Plaines
Elk Grove Village
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 11 September 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 330AverageC$ 397FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

Fly with Cheapflights

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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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