YQG to CHI, Windsor International Airport to Cheap Flights

Based on HopeGoo data, Porter Airlines offers one-way fares as low as US$170 on Cheapest nonstop routes (e.g. YQG to MDW on Sat, Feb 21), while Air Canada offers Cheapest nonstop round-trips from US$345 departing on Sat, Mar 28 and returning on Sat, Apr 4.

By analyzing data from all airlines on the HopeGoo flight calendar, it looks like the best time to book a flight from Windsor to Chicago is around 40 days (6 weeks) in advance, and the best time to fly is usually on Tuesday, Wednesday, and Saturday. Tuesday typically offers the cheapest flights for departure, while Saturday offers the best return deals.

To find best deals on flights from Windsor to Chicago, you can use various tools on HopeGoo: · Be flexible with your travel dates to get the cheapest flight deal. Now the cheapest flight deal is on Sat, Feb 21, with one-way flights priced at just US$170. · Compare airlines strategically. Budget carriers often provide the lowest base fares, while we found the most affordable airline currently operating on this route is Porter Airlines. · Set up price alerts to easily monitor ticket prices without having to check every day. · Check HopeGoo flight deals and promo codes frequently. · Avoid peak season unless you book very early. It seems the peak season for Chicago travel is around July. · Get exclusive promo codes for HopeGoo app users.

The cheapest months to fly from Windsor to Chicago is October, when demand for travel is lower.

After crunching the numbers on our February flight calendar, it's currently cheapest to fly from Windsor to Chicago on February 24, 2026 with Porter Airlines, with prices starting at US$376.

The time difference between Chicago and Windsor is 1h.

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