Cheap flights from Toronto to Chicago

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How far in advance should I book a flight from Toronto Kitchener-Waterloo Airport to Chicago?

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 34 days in advance, which can save you up to 86% on flights from Toronto Kitchener-Waterloo Airport to Chicago compared to booking the week you need them. Waiting 34 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at C$ 437. For sooner than that we have options available in the next 3 days from C$ 593.

What is the cheapest month to fly from Toronto Kitchener-Waterloo Airport to Chicago?

The best pricing can be found in the month of April. Prices to Chicago from Toronto Kitchener-Waterloo Airport average C$ 319. You can even find prices in April for less than C$ 319, as users have found deals to Chicago from as low as C$ 241. The month of January appears to be one of the more expensive times to travel to Chicago from Toronto Kitchener-Waterloo Airport. Flying in the targeted month can save you up to 10%.

When is the cheapest time to fly from Toronto Kitchener-Waterloo Airport to Chicago (YKF - CHI)?

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

Cheap flights from Kitchener-Waterloo to Chicago in January, February 2022

The best prices found for YKF to CHI flights for January, February
25 Feb. - 27 Feb.
YKF

Toronto Kitchener-Waterloo

ORD

Chicago O'Hare Intl

1 stop

27h 28m
ORD

Chicago O'Hare Intl

YKF

Toronto Kitchener-Waterloo

1 stop

28h 43m
C$ 298

Multiple Airlines

View Deal

Deal found 26/1/22

25 Feb. - 27 Feb.
YKF

Toronto Kitchener-Waterloo

ORD

Chicago O'Hare Intl

2 stops

32h 31m
ORD

Chicago O'Hare Intl

YKF

Toronto Kitchener-Waterloo

1 stop

28h 43m
C$ 327

Multiple Airlines

View Deal

Deal found 26/1/22

26 Feb. - 5 Mar.
YKF

Toronto Kitchener-Waterloo

ORD

Chicago O'Hare Intl

2 stops

23h 35m
ORD

Chicago O'Hare Intl

YKF

Toronto Kitchener-Waterloo

2 stops

24h 50m
C$ 584

WestJet

View Deal

Deal found 27/1/22

Kitchener-Waterloo to Chicago 2022 flight deals

Cheap flights to Chicago from Kitchener-Waterloo found for this year
1 May - 4 May
YKF

Toronto Kitchener-Waterloo

ORD

Chicago O'Hare Intl

1 stop

28h 34m
ORD

Chicago O'Hare Intl

YKF

Toronto Kitchener-Waterloo

1 stop

30h 00m
C$ 284

Multiple Airlines

View Deal

Deal found 26/1/22

1 May - 4 May
YKF

Toronto Kitchener-Waterloo

ORD

Chicago O'Hare Intl

1 stop

28h 34m
ORD

Chicago O'Hare Intl

YKF

Toronto Kitchener-Waterloo

1 stop

30h 00m
C$ 285

Multiple Airlines

View Deal

Deal found 25/1/22

25 Feb. - 27 Feb.
YKF

Toronto Kitchener-Waterloo

ORD

Chicago O'Hare Intl

1 stop

27h 28m
ORD

Chicago O'Hare Intl

YKF

Toronto Kitchener-Waterloo

1 stop

28h 43m
C$ 298

Multiple Airlines

View Deal

Deal found 26/1/22

Last minute flights from Kitchener-Waterloo to Chicago

Late deals on round-trip flights to Chicago from Kitchener-Waterloo, departing today and this week
1 Feb. - 8 Feb.
YKF

Toronto Kitchener-Waterloo

ORD

Chicago O'Hare Intl

2 stops

23h 33m
ORD

Chicago O'Hare Intl

YKF

Toronto Kitchener-Waterloo

2 stops

24h 50m
C$ 598

WestJet

View Deal

Deal found 25/1/22

One-way flights to Chicago All airports from Kitchener-Waterloo

The cheapest one-way flights from Kitchener-Waterloo to Chicago
17 Apr.
YKF

Toronto Kitchener-Waterloo

ORD

Chicago O'Hare Intl

1 stop

28h 28m
C$ 245

Multiple Airlines

View Deal

Deal found 24/1/22

13 Feb.
YKF

Toronto Kitchener-Waterloo

ORD

Chicago O'Hare Intl

1 stop

25h 05m
C$ 289

Multiple Airlines

View Deal

Deal found 26/1/22

28 May
YKF

Toronto Kitchener-Waterloo

ORD

Chicago O'Hare Intl

1 stop

26h 38m
C$ 291

Multiple Airlines

View Deal

Deal found 25/1/22

Related info for your journey

Useful info, stats and facts about Kitchener-Waterloo to Chicago flights.

Can I find flights from Toronto Kitchener-Waterloo Airport to Chicago for under C$ 300 on Cheapflights?

Yes, there are multiple flights from Toronto Kitchener-Waterloo Airport to Chicago for under C$ 300. The cheapest flight booked recently is on Multiple Airlines for just C$ 284, but on average you can expect to pay C$ 425.

Are there last-minute flights available from Toronto Kitchener-Waterloo Airport to Chicago for under C$ 600?

There are currently 1+ open flights from Toronto Kitchener-Waterloo Airport to Chicago within the next 7 days for less than C$ 600.

Can I fly to Chicago from Toronto Kitchener-Waterloo right now?

Information is based on travel restrictions from Toronto Kitchener-Waterloo to Chicago

Most visitors from Toronto Kitchener-Waterloo need to provide a negative COVID-19 test result and/or quarantine to enter Chicago.

COVID-19 testing requirements
Visitors from Toronto Kitchener-Waterloo must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 24 hours before departing to Chicago.

Quarantine requirements
Visitors from Toronto Kitchener-Waterloo are not required to quarantine after entering Chicago.

Can I fly back to Toronto Kitchener-Waterloo from Chicago?

Returning to Toronto Kitchener-Waterloo from Chicago

COVID-19 testing requirements
Visitors from Chicago must present a negative RT-PCR (NAAT) test taken 72 hours before departing to Toronto Kitchener-Waterloo.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering Toronto Kitchener-Waterloo.

Alternative routes for Kitchener-Waterloo to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Pearson Intl to Peoriafrom C$ 214 pp
Pearson Intl to Molinefrom C$ 315 pp