In terms of precipitation, rainfall in Chicago O'Hare Intl Airport ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago O'Hare Intl Airport when rainfall is around 43.0 mm.

If weather is an important factor for your trip to Chicago O'Hare Intl Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

What is the cheapest time of day to fly from YKF to ORD?

When flying from Toronto Region of Waterloo Intl Airport to Chicago O'Hare Intl Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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.

C$ 346+ Cheap Flights from Toronto Region of Waterloo Intl Airport to Chicago O'Hare Intl Airport

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

Enter your travel dates to find the best prices.

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Best

Last-minute

One-way

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 7 September 2026.

Sun 18/108:40 p.m. -

1 stop21h 00m

Tue 20/108:01 p.m. -

2 stops22h 49m

Deal found 5/9C$ 718

Thu 15/106:05 a.m. -

1 stop11h 35m

Mon 19/105:30 p.m. -

1 stop20h 30m

Deal found 5/9C$ 739

Thu 15/106:05 a.m. -

1 stop11h 35m

Tue 20/108:01 p.m. -

2 stops22h 49m

Deal found 5/9C$ 744

Sun 18/106:05 a.m. -

1 stop11h 35m

Mon 19/105:30 p.m. -

1 stop20h 30m

Deal found 5/9C$ 751

Thu 15/106:05 a.m. -

1 stop11h 35m

Fri 16/105:30 p.m. -

1 stop20h 30m

Deal found 5/9C$ 758

Wed 14/106:10 a.m. -

2 stops35h 30m

Mon 19/105:30 p.m. -

1 stop20h 30m

Deal found 5/9C$ 762

Wed 14/108:40 p.m. -

1 stop21h 00m

Tue 20/108:01 p.m. -

2 stops22h 49m

Deal found 5/9C$ 769

Fri 16/108:40 p.m. -

2 stops15h 52m

Mon 19/105:30 p.m. -

1 stop20h 30m

Deal found 5/9C$ 831

Thu 15/106:05 a.m. -

1 stop11h 35m

Sun 18/106:00 a.m. -

2 stops36h 50m

Deal found 5/9C$ 863

Fri 16/106:05 a.m. -

1 stop11h 35m

Tue 20/108:01 p.m. -

2 stops22h 49m

Deal found 5/9C$ 955

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

Round-trip from	C$ 718
One-way from	C$ 346
Popular in	October
Cheapest in	February
Average price	C$ 365

18/10-20/10
3 total stops
43h 49m total
Toronto to Chicago

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WestJet
21/10-31/12
1 total stop
21h 00m total
Toronto to Chicago

Search Deals

Highest demand for flights based on searches. 1% potential increase in price (C$ 8 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 September 2026

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Cheapflights Fare Finder

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 Toronto Region of Waterloo Intl - ORD Chicago O'Hare Intl

YKFORD

Toronto Region of Waterloo Intl

Wed 21/10

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

1 stop21h 00m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 410

TorontoChicago

YKF Toronto Region of Waterloo Intl - ORD Chicago O'Hare Intl

YKFORD

Toronto Region of Waterloo Intl

Sun 4/10

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

1 stop21h 00m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 439

TorontoChicago

YKF Toronto Region of Waterloo Intl - ORD Chicago O'Hare Intl

YKFORD

Toronto Region of Waterloo Intl

Wed 14/10

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

1 stop21h 00m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 455

TorontoChicago

YKF Toronto Region of Waterloo Intl - ORD Chicago O'Hare Intl

YKFORD

Toronto Region of Waterloo Intl

Mon 5/10

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

1 stop21h 00m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 458

TorontoChicago

YKF Toronto Region of Waterloo Intl - ORD Chicago O'Hare Intl

YKFORD

Toronto Region of Waterloo Intl

Wed 14/10

8:40 p.m.-10:12 a.m.

2 stops14h 32m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 530

TorontoChicago

YKF Toronto Region of Waterloo Intl - ORD Chicago O'Hare Intl

YKFORD

Toronto Region of Waterloo Intl

Wed 23/9

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

1 stop21h 00m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 595

Quickest round-trip

TorontoChicago

YKF Toronto Region of Waterloo Intl - ORD Chicago O'Hare Intl

YKFORD

Toronto Region of Waterloo Intl

Fri 16/10

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

1 stop11h 35m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 610

TorontoChicago

YKF Toronto Region of Waterloo Intl - ORD Chicago O'Hare Intl

YKFORD

Toronto Region of Waterloo Intl

Sat 12/9

8:40 p.m.-5:48 p.m.

3 stops22h 08m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 659

TorontoChicago

YKF Toronto Region of Waterloo Intl - ORD Chicago O'Hare Intl

YKFORD

Toronto Region of Waterloo Intl

Fri 2/10

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

1 stop11h 35m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 686

TorontoChicago

YKF Toronto Region of Waterloo Intl - ORD Chicago O'Hare Intl

YKFORD

Toronto Region of Waterloo Intl

Thu 8/10

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

1 stop11h 35m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 695

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/9

Showing 1-10 of 22 resultsSorted by cheapest first

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.

YKF-ORD

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

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.

Northbrook

Evanston

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Racine

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Schaumburg

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Skokie

Browse thousands of different options on Cheapflights for your next trip

Alternative routes

Complete your trip

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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.

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Cheap flights from Toronto Region of Waterloo Intl Airport to Chicago O'Hare Intl Airport from C$ 346

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 21/10. Fares are subject to change and may not be available on all flights or dates of travel.

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

Cheapest flights from Region of Waterloo Intl to O'Hare IntlExplore 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 7 September 2026.

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 7 September 2026.

Best flights from Region of Waterloo Intl to O'Hare IntlDiscover carefully curated flight deals from Region of Waterloo Intl to O'Hare Intl that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 7 September 2026.

Discover carefully curated flight deals from Region of Waterloo Intl to O'Hare Intl that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 7 September 2026.

Last-minute flights from Region of Waterloo Intl to O'Hare IntlDiscover last-minute flight deals from Region of Waterloo Intl to O'Hare Intl. Data last updated 7 September 2026 and is based on user searches.

Discover last-minute flight deals from Region of Waterloo Intl to O'Hare Intl. Data last updated 7 September 2026 and is based on user searches.

One-way flights from Region of Waterloo Intl to O'Hare IntlSearch for one-way flight options from Region of Waterloo Intl to O'Hare Intl. Find affordable one-way fares based on user searches. Data last updated 7 September 2026.

Search for one-way flight options from Region of Waterloo Intl to O'Hare Intl. Find affordable one-way fares based on user searches. Data last updated 7 September 2026.

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

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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.

Best time to book a flight from Region of Waterloo Intl to O'Hare Intl

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Related info for your journey

Can I find deals for flights from Region of Waterloo Intl to O'Hare Intl that include hotel bookings?

How can I 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?

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Alternative routes for Region of Waterloo Intl to O'Hare Intl

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Direct flights to Illinois

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Other flights to O'Hare Intl

Explore flights to O'Hare Intl departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on 7 September 2026.

Region of Waterloo Intl and O'Hare Intl flights

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Can Cheapflights notify me if prices for flights from Region of Waterloo Intl to O'Hare Intl become cheaper?

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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 7 September 2026.

Best flights from Region of Waterloo Intl to O'Hare Intl
Discover carefully curated flight deals from Region of Waterloo Intl to O'Hare Intl that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 7 September 2026.

Last-minute flights from Region of Waterloo Intl to O'Hare Intl
Discover last-minute flight deals from Region of Waterloo Intl to O'Hare Intl. Data last updated 7 September 2026 and is based on user searches.

One-way flights from Region of Waterloo Intl to O'Hare Intl
Search for one-way flight options from Region of Waterloo Intl to O'Hare Intl. Find affordable one-way fares based on user searches. Data last updated 7 September 2026.