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Cheap flights from Toronto Region of Waterloo Intl Airport to Chicago O'Hare Intl Airport from C$ 191

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 30/5. Fares are subject to change and may not be available on all flights or dates of travel.
YKF — ORD
27 May — 3 Jun1
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 27 April 2026.

Tue 9/68:40 p.m.
YKF
-
ORD
2 stops33h 52m
Multiple Airlines
Tue 16/65:30 p.m.
ORD
-
YKF
1 stop25h 20m
Multiple Airlines
Deal found 25/4C$ 730
Fri 5/68:40 p.m.
YKF
-
ORD
2 stops34h 19m
Multiple Airlines
Tue 16/64:06 p.m.
ORD
-
YKF
3 stops26h 44m
Multiple Airlines
Deal found 22/4C$ 875
Mon 8/68:40 p.m.
YKF
-
ORD
1 stop21h 00m
Multiple Airlines
Mon 15/65:35 p.m.
ORD
-
YKF
2 stops25h 15m
Multiple Airlines
Deal found 23/4C$ 905
Sat 27/68:40 p.m.
YKF
-
ORD
3 stops23h 44m
Multiple Airlines
Sun 12/75:30 p.m.
ORD
-
YKF
1 stop10h 50m
Multiple Airlines
Deal found 24/4C$ 910
Tue 9/68:40 p.m.
YKF
-
ORD
1 stop21h 00m
WestJet
Tue 16/65:30 p.m.
ORD
-
YKF
1 stop25h 20m
WestJet
Deal found 25/4C$ 933
Fri 19/68:40 p.m.
YKF
-
ORD
2 stops34h 22m
Multiple Airlines
Sun 21/68:34 p.m.
ORD
-
YKF
2 stops22h 16m
Multiple Airlines
Deal found 24/4C$ 950
Mon 8/68:40 p.m.
YKF
-
ORD
1 stop21h 00m
WestJet
Mon 15/65:30 p.m.
ORD
-
YKF
1 stop25h 20m
WestJet
Deal found 23/4C$ 1,024
Mon 1/68:40 p.m.
YKF
-
ORD
1 stop21h 00m
Multiple Airlines
Sun 7/68:59 p.m.
ORD
-
YKF
2 stops41h 01m
Multiple Airlines
Deal found 22/4C$ 1,065
Thu 20/86:05 a.m.
YKF
-
ORD
1 stop11h 35m
Multiple Airlines
Sun 23/85:30 p.m.
ORD
-
YKF
1 stop10h 50m
Multiple Airlines
Deal found 22/4C$ 1,081
Sun 30/87:05 p.m.
YKF
-
ORD
2 stops22h 35m
Multiple Airlines
Fri 4/95:30 p.m.
ORD
-
YKF
1 stop10h 50m
Multiple Airlines
Deal found 23/4C$ 1,103

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 27 April 2026.

Round-trip from

C$ 730

One-way from

C$ 191

Popular in

April

Cheapest in

July

Average price

C$ 433
WestJet
  • WestJet
  • 9/6-16/6
  • 3 total stops
  • 59h 12m total
  • Toronto to Chicago
Search Deals
Air Canada
  • Air Canada
  • 30/5
  • 1 total stop
  • 8h 55m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 8% potential increase in price (C$ 43 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 27 April 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

Tue 9/6

8:40 p.m.-5:32 a.m.

2 stops33h 52m

Chicago O'Hare Intl

Tue 16/6

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

1 stop25h 20m

C$ 730

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Tue 9/6

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

1 stop21h 00m

Chicago O'Hare Intl

Tue 16/6

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

1 stop25h 20m

C$ 933
Quickest round-trip

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Thu 20/8

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

1 stop11h 35m

Chicago O'Hare Intl

Sun 23/8

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

1 stop10h 50m

C$ 1,081

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Sun 30/8

7:05 p.m.-4:40 p.m.

2 stops22h 35m

Chicago O'Hare Intl

Fri 4/9

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

1 stop10h 50m

C$ 1,103

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Fri 10/7

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

1 stop11h 35m

Chicago O'Hare Intl

Sun 12/7

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

1 stop10h 50m

C$ 1,137

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Fri 12/6

8:40 p.m.-5:59 a.m.

2 stops34h 19m

Chicago O'Hare Intl

Sun 14/6

12:59 p.m.-7:50 p.m.

3 stops29h 51m

C$ 1,235

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Mon 1/6

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

1 stop21h 00m

Chicago O'Hare Intl

Sun 7/6

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

1 stop25h 20m

C$ 1,308
Cheapest one-way
Quickest one-way

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Thu 2/7

5:30 a.m.-9:00 a.m.

1 stop4h 30m

C$ 209

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Tue 6/10

2:10 p.m.-7:48 p.m.

1 stop6h 38m

C$ 232

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Tue 12/5

4:00 p.m.-10:01 p.m.

1 stop7h 01m

C$ 235

Flights are sorted by cheapest round-trip flights first.

Deals found on 23/4

Showing 1-10 of 16 resultsSorted by cheapest first
1
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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$ 933. 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
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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Hamilton to O'Hare Intl 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?

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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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