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Cheap flights from Toronto Region of Waterloo Intl Airport to Chicago O'Hare Intl Airport from C$ 411

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 10/9. Fares are subject to change and may not be available on all flights or dates of travel.
YKF — ORD
8 Jul — 15 Jul1
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 8 June 2026.

Fri 4/96:05 a.m.
YKF
-
ORD
1 stop11h 35m
Multiple Airlines
Sun 6/95:30 p.m.
ORD
-
YKF
1 stop10h 50m
Multiple Airlines
Deal found 7/6C$ 850
Thu 13/86:05 a.m.
YKF
-
ORD
1 stop11h 35m
Multiple Airlines
Sun 16/85:30 p.m.
ORD
-
YKF
1 stop10h 50m
Multiple Airlines
Deal found 4/6C$ 852
Fri 14/86:05 a.m.
YKF
-
ORD
1 stop11h 35m
Multiple Airlines
Sun 16/85:30 p.m.
ORD
-
YKF
1 stop10h 50m
Multiple Airlines
Deal found 6/6C$ 881
Thu 16/76:05 a.m.
YKF
-
ORD
2 stops12h 24m
Multiple Airlines
Sun 19/75:30 p.m.
ORD
-
YKF
1 stop10h 50m
Multiple Airlines
Deal found 7/6C$ 1,055
Fri 3/76:05 a.m.
YKF
-
ORD
1 stop11h 35m
Multiple Airlines
Fri 10/75:30 p.m.
ORD
-
YKF
1 stop10h 50m
Multiple Airlines
Deal found 5/6C$ 1,070
Thu 25/66:05 a.m.
YKF
-
ORD
1 stop11h 35m
Multiple Airlines
Sun 28/65:30 p.m.
ORD
-
YKF
1 stop10h 50m
Multiple Airlines
Deal found 4/6C$ 1,079
Wed 1/78:40 p.m.
YKF
-
ORD
2 stops25h 03m
Multiple Airlines
Fri 3/75:30 p.m.
ORD
-
YKF
1 stop10h 50m
Multiple Airlines
Deal found 7/6C$ 1,102
Fri 10/78:40 p.m.
YKF
-
ORD
2 stops33h 57m
Multiple Airlines
Mon 13/75:30 p.m.
ORD
-
YKF
1 stop20h 30m
Multiple Airlines
Deal found 4/6C$ 1,151
Mon 29/66:05 a.m.
YKF
-
ORD
1 stop11h 35m
Multiple Airlines
Fri 3/75:30 p.m.
ORD
-
YKF
1 stop10h 50m
Multiple Airlines
Deal found 6/6C$ 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 8 June 2026.

Round-trip from

C$ 850

One-way from

C$ 411

Popular in

May

Cheapest in

September

Average price

C$ 390
4/9-6/9
  • 4/9-6/9
  • 2 total stops
  • 22h 25m total
  • Toronto to Chicago
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WestJet
  • WestJet
  • 10/9
  • 1 total stop
  • 21h 00m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 5% potential increase in price (C$ 32 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease (C$ 4 potential savings vs. average RT price).
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Average for round-trip flights in June 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 8 June 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
Quickest round-trip

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Fri 4/9

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

1 stop11h 35m

Chicago O'Hare Intl

Sun 6/9

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

1 stop10h 50m

C$ 850

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Fri 3/7

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

1 stop11h 35m

Chicago O'Hare Intl

Fri 10/7

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

1 stop10h 50m

C$ 1,070

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Thu 16/7

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

1 stop11h 35m

Chicago O'Hare Intl

Sun 19/7

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

1 stop10h 50m

C$ 1,073

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Fri 10/7

8:40 p.m.-5:37 a.m.

2 stops33h 57m

Chicago O'Hare Intl

Mon 13/7

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

1 stop20h 30m

C$ 1,151

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Mon 29/6

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

1 stop11h 35m

Chicago O'Hare Intl

Fri 3/7

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

1 stop10h 50m

C$ 1,182

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Thu 2/7

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

1 stop11h 35m

Chicago O'Hare Intl

Fri 3/7

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

1 stop10h 50m

C$ 1,193

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Fri 26/6

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

1 stop11h 35m

Chicago O'Hare Intl

Sun 5/7

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

1 stop10h 50m

C$ 1,257

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Fri 7/8

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

2 stops35h 30m

Chicago O'Hare Intl

Mon 10/8

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

2 stops34h 55m

C$ 1,314

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Wed 1/7

8:40 p.m.-5:52 a.m.

3 stops34h 12m

Chicago O'Hare Intl

Fri 3/7

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

1 stop10h 50m

C$ 1,344

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Sun 28/6

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

2 stops22h 35m

Chicago O'Hare Intl

Sun 12/7

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

1 stop10h 50m

C$ 1,365

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/6

Showing 1-10 of 21 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.

  • 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.

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
Skokie
Downers Grove
Elk Grove Village
Racine
Bolingbrook
Naperville
Romeoville
Schaumburg

Browse thousands of different options on Cheapflights for your next trip

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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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Pearson Intl to Midway flights
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Hamilton to O'Hare Intl flights

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