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Cheap flights from Toronto Region of Waterloo Intl Airport to Chicago O'Hare Intl Airport from C$ 296

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 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
YKF — ORD
25 Aug — 1 Sep1
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 July 2026.

Fri 4/98:40 p.m.
YKF
-
ORD
1 stop21h 00m
WestJet
Tue 8/95:30 p.m.
ORD
-
YKF
1 stop25h 20m
WestJet
Deal found 25/7C$ 755
Sun 6/98:40 p.m.
YKF
-
ORD
1 stop21h 00m
WestJet
Sun 13/95:30 p.m.
ORD
-
YKF
1 stop25h 20m
WestJet
Deal found 23/7C$ 831
Mon 7/98:40 p.m.
YKF
-
ORD
2 stops14h 35m
Multiple Airlines
Mon 14/97:54 p.m.
ORD
-
YKF
2 stops22h 56m
Multiple Airlines
Deal found 24/7C$ 838
Fri 21/88:40 p.m.
YKF
-
ORD
2 stops24h 28m
Multiple Airlines
Fri 28/85:30 p.m.
ORD
-
YKF
1 stop20h 30m
Multiple Airlines
Deal found 24/7C$ 858
Sat 22/86:05 a.m.
YKF
-
ORD
1 stop11h 35m
Multiple Airlines
Fri 28/85:30 p.m.
ORD
-
YKF
1 stop10h 50m
Multiple Airlines
Deal found 24/7C$ 860
Fri 4/98:40 p.m.
YKF
-
ORD
1 stop21h 00m
Multiple Airlines
Tue 8/95:30 p.m.
ORD
-
YKF
2 stops23h 50m
Multiple Airlines
Deal found 25/7C$ 865
Fri 18/98:40 p.m.
YKF
-
ORD
2 stops19h 12m
Multiple Airlines
Mon 21/97:54 p.m.
ORD
-
YKF
2 stops22h 56m
Multiple Airlines
Deal found 25/7C$ 875
Fri 4/98:40 p.m.
YKF
-
ORD
1 stop21h 00m
Multiple Airlines
Mon 7/95:30 p.m.
ORD
-
YKF
1 stop20h 30m
Multiple Airlines
Deal found 24/7C$ 900
Wed 9/98:40 p.m.
YKF
-
ORD
2 stops19h 03m
Multiple Airlines
Wed 16/93:40 p.m.
ORD
-
YKF
2 stops27h 10m
Multiple Airlines
Deal found 26/7C$ 902
Thu 3/96:05 a.m.
YKF
-
ORD
1 stop11h 35m
Multiple Airlines
Sun 6/98:40 a.m.
ORD
-
YKF
3 stops19h 40m
Multiple Airlines
Deal found 25/7C$ 916

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 July 2026.

Round-trip from

C$ 755

One-way from

C$ 296

Popular in

May

Cheapest in

September

Average price

C$ 399
WestJet
  • WestJet
  • 4/9-8/9
  • 2 total stops
  • 46h 20m total
  • Toronto to Chicago
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WestJet
  • WestJet
  • 1/10
  • 1 total stop
  • 21h 00m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 4% potential increase in price (C$ 23 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease (C$ 5 potential savings vs. average RT price).
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Average for round-trip flights in July 2026
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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 26 July 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

Fly to

Route

Depart

Return

Price

Cheapest round-trip

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Sun 6/9

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

1 stop21h 00m

Chicago O'Hare Intl

Sun 13/9

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

1 stop25h 20m

C$ 831

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Fri 21/8

8:40 p.m.-8:08 p.m.

2 stops24h 28m

Chicago O'Hare Intl

Fri 28/8

5:30 p.m.-3:00 p.m.

1 stop20h 30m

C$ 858

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Fri 4/9

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

1 stop21h 00m

Chicago O'Hare Intl

Tue 8/9

5:30 p.m.-6:20 p.m.

2 stops23h 50m

C$ 865
Quickest round-trip

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Thu 3/9

6:05 a.m.-4:40 p.m.

1 stop11h 35m

Chicago O'Hare Intl

Sun 6/9

8:40 a.m.-5:20 a.m.

3 stops19h 40m

C$ 992

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Tue 8/9

4:15 p.m.-10:15 a.m.

3 stops19h 00m

Chicago O'Hare Intl

Tue 15/9

3:40 p.m.-7:50 p.m.

3 stops27h 10m

C$ 1,029

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Fri 21/8

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

1 stop21h 00m

Chicago O'Hare Intl

Mon 24/8

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

1 stop25h 20m

C$ 1,055

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Thu 17/9

6:05 a.m.-4:40 p.m.

1 stop11h 35m

Chicago O'Hare Intl

Mon 21/9

12:30 p.m.-3:00 p.m.

3 stops25h 30m

C$ 1,108

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Thu 13/8

6:05 a.m.-4:40 p.m.

1 stop11h 35m

Chicago O'Hare Intl

Mon 17/8

5:30 p.m.-5:25 a.m.

2 stops34h 55m

C$ 1,136

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Sun 23/8

6:10 a.m.-4:40 p.m.

2 stops35h 30m

Chicago O'Hare Intl

Sun 30/8

5:30 p.m.-5:20 a.m.

1 stop10h 50m

C$ 1,161

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Fri 4/9

6:10 a.m.-4:40 p.m.

2 stops35h 30m

Chicago O'Hare Intl

Mon 7/9

5:30 p.m.-5:25 a.m.

2 stops34h 55m

C$ 1,195

Flights are sorted by cheapest round-trip flights first.

Deals found on 22/7

Showing 1-10 of 22 resultsSorted by cheapest first
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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.

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 21h. WestJet provides one of the quickest options available for as low as C$ 831. 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
Northbrook
Evanston
Des Plaines
Downers Grove
Elk Grove Village
Racine
Bolingbrook
Naperville
Schaumburg

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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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