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Cheap flights from Toronto Region of Waterloo Intl Airport to Chicago O'Hare Intl Airport from C$ 211

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 24/2. Fares are subject to change and may not be available on all flights or dates of travel.
YKF — ORD
26 Nov — 3 Dec1
1 adult
1 adult, Economy, 0 bags

Find flight deals from Region of Waterloo Intl to O'Hare Intl

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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 October 2025.

Thu 13/117:05 a.m.YKF - ORD
3 stops27h 42mMultiple Airlines
Sun 16/119:22 p.m.ORD - YKF
3 stops31h 06mMultiple Airlines
Deal found 27/10C$ 859
Thu 11/127:05 a.m.YKF - ORD
1 stop31h 30mMultiple Airlines
Thu 18/129:33 p.m.ORD - YKF
2 stops41h 27mMultiple Airlines
Deal found 27/10C$ 908
Sat 15/116:20 a.m.YKF - ORD
2 stops24h 12mMultiple Airlines
Mon 24/112:20 p.m.ORD - YKF
1 stop24h 40mMultiple Airlines
Deal found 26/10C$ 949
Sat 8/116:20 a.m.YKF - ORD
2 stops24h 12mMultiple Airlines
Sat 15/114:38 p.m.ORD - YKF
3 stops35h 50mMultiple Airlines
Deal found 25/10C$ 1,216
Thu 30/107:05 a.m.YKF - ORD
2 stops28h 15mMultiple Airlines
Fri 31/102:20 p.m.ORD - YKF
1 stop24h 40mMultiple Airlines
Deal found 27/10C$ 1,763

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 27 October 2025.

Round-trip from

C$ 859

One-way from

C$ 211

Popular in

October

Cheapest in

July

Average price

C$ 414
13/11-16/11
  • 13/11-16/11
  • 6 total stops
  • 58h 48m total
  • Toronto to Chicago
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Air Canada
  • Air Canada
  • 24/2
  • 1 total stop
  • 4h 32m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 5% potential increase in price (C$ 28 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 8 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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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 27 October 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 13/11

7:05 a.m.-9:47 a.m.

3 stops27h 42m

Chicago O'Hare Intl

Sun 16/11

9:22 p.m.-5:28 a.m.

3 stops31h 06m

C$ 859

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Thu 11/12

7:05 a.m.-1:35 p.m.

1 stop31h 30m

Chicago O'Hare Intl

Thu 18/12

9:33 p.m.-4:00 p.m.

2 stops41h 27m

C$ 908

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Sat 15/11

6:20 a.m.-5:32 a.m.

2 stops24h 12m

Chicago O'Hare Intl

Mon 24/11

2:20 p.m.-4:00 p.m.

1 stop24h 40m

C$ 949

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Sat 8/11

6:20 a.m.-5:32 a.m.

2 stops24h 12m

Chicago O'Hare Intl

Sat 15/11

4:38 p.m.-5:28 a.m.

3 stops35h 50m

C$ 1,216

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Tue 24/2

6:30 a.m.-10:02 a.m.

1 stop4h 32m

C$ 211

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Sun 15/3

5:35 p.m.-9:59 p.m.

1 stop5h 24m

C$ 355

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Wed 10/12

4:25 p.m.-2:21 p.m.

2 stops46h 56m

C$ 375

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Thu 27/11

6:20 a.m.-5:32 a.m.

3 stops24h 12m

C$ 400

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Sat 1/11

6:20 a.m.-6:52 a.m.

3 stops25h 32m

C$ 1,079

Flights are sorted by cheapest round-trip flights first.

Deals found on 26/10

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
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.
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