Cheap flights from Toronto to Chicago Midway Airport

from as little as £280

10 nights in Chicago, departing Toronto Lester B. Pearson International Airport on 29 / Jul / 2025 with West Jet (price found 83 hours ago)

Subject to availability, prices correct of the last 24 hours
Chicago Midway Airport

The Toronto / Chicago Midway Airport route

All 714 km of it

Cheap flight deals for this route

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Chicago Midway Airport flight facts

What you need to know

Alternative flights from the UK to Chicago Midway Airport

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Alternative flights from Toronto to Chicago Midway Airport

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Chicago Midway Airport

29 / Jul / 2025 is currently the lowest priced day of the year to fly the Toronto/Chicago Midway Airport route. There are around ten flights on any given week from the UK to Chicago Midway Airport and the cheapest month to fly right now is July.

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Min / Max Temperature (°C)
LOWEST

-8 °C

AVG

10 °C

HIGHEST

29 °C

Rainfall (mm)
LOWEST

44 mm

AVG

71.8 mm

HIGHEST

94 mm

Key facts about Chicago Midway Airport

How to get cheap flights from Toronto to Chicago Midway Airport

Tips and advice from our flight experts

West Jet tends to have the best prices on flights from Toronto to Chicago Midway Airport. But, remember that Chicago Midway Airport is only one of the airports in Chicago – searching for flights from ‘Toronto’ to ‘Chicago’ will give you more options, and possibly lower prices.

We compare every airline that flies from Toronto to Chicago, so that you can find the best value flights. The most popular airlines are West Jet. Between them, they cover ten flights every week from Toronto to or via Chicago. The 714 km journey usually takes around 7 hrs 35 mins.

29 / Jul / 2025 is currently the cheapest date to fly from Toronto to Chicago Midway Airport. Prices can change though, so it's best to check Netflights regularly – we recommend booking at least two months in advance to get a good deal.

We don't just compare flight prices. If you need to book accommodation for your trip, or you want to hire a car to explore the USA, we've got some options for you to compare. Plus, when you sort your flights and hotel in one booking, you could save even more.

Other popular destinations near Chicago Midway Airport

Where other people are flying to

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