Cheap Flights to Chicago from C$ 233

Cheapest Prices for Chicago flights by month

January

C$ 369

February

C$ 331

March

C$ 373

April

C$ 372

May

C$ 387

June

C$ 380

July

C$ 370

August

C$ 352

September

C$ 333

October

C$ 333

November

C$ 315

December

C$ 307

December is currently the cheapest month to fly to Chicago. At this moment in time May is the most expensive month. These prices are determined by multiple factors and booking in advance can help keep costs down if your schedule is not as flexible.

When is the best time to fly to Chicago?

Choose a month below to see average flight price and weather conditions.

+45.0%

+30.0%

+15.0%

Base

Price	343 - 494 CAD
Temperature	0.6 - 29 °C
Rainfall	17.4 - 108.9 mm

Flying to Chicago in November is usually considered the best time to fly. However, you will find other deals are always available year round. July sees the temperatures in Chicago peak to their warmest. May tends, on average, to see the most amount of rainfall.

When is the best time to fly?

Peak Season:

Summer runs from June through August and is a hugely popular time in the city, despite the heat and humidity from the Lake. This is also the Chicago’s peak festival season, which sees major events taking place in the parks and neighbourhoods every weekend. Prices for flights to Chicago and crowd numbers can see an increase when the city hosts its most popular festivals.

Foodies should book a flight to Chicago during mid-July for the Taste of Chicago festival. This outdoor food event takes place at the lakefront and showcases a variety of cuisines and local flavours accompanied by live music. August is host to another popular event – the Chicago Air and Water Show. With free admission and lakefront location, the show attracts huge numbers of fans of aviation and adventure seekers.

September can be the most enjoyable and mild month of the year but there’s less going on during this period.

Off-peak Season:

January to March is when Chicago is least busy, making cheap flights to Chicago and hotel deals more attainable. However, true to its reputation as the “Windy City”, cold temperatures and brisk winds will make you want to stay inside for most of your visit.

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Find the best prices for you!

Prices found by our users for local departures to Chicago

Toronto from C$ 233 pp

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Airport for Chicago

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Toronto to Chicago from C$ 233 pp

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Most popular in	May	High demand for flights, 7% potential price rise
Cheapest in	December	Best time to find cheap flights, 2% potential price drop
Average price	C$ 331	Price for this month
Cheapest price	C$ 233	From Toronto to Chicago

Cheap Flights to Chicago

Cheapest Prices for Chicago flights by month

When is the best time to fly to Chicago?

Choose a month below to see average flight price and weather conditions.

When is the best time to book flights to Chicago?

The price you pay for your flight to Chicago may vary depending on when you book.For the best chance of a lower fare, look to book 37 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

Which day is cheapest to fly to Chicago?

The cheapest day to fly to Chicago is usually Thursday. At the moment, Sunday is the most expensive.

What time of day is cheapest to fly?

At the moment, flights at Noon are likely to offer the best value for money for your Chicago trip. A flight in the Evening will more often than not be of higher cost.

Find the best prices for you!

Prices found by our users for local departures to Chicago

Airport for Chicago

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