Cheap Flights to Chicago

Popular in	August	High demand for flights, 3% potential price rise
Cheapest in	February	Best time to find cheap flights, 2% potential price drop
Average price	C$ 348	Average for round-trip flights in October 2020
Round-trip from	C$ 261	From Toronto to Chicago
One-way from	C$ 161	One-way flight from Toronto to Chicago

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.

Cheapest prices for Chicago flights by month

January

C$ 336

February

C$ 340

March

C$ 344

April

C$ 370

May

C$ 339

June

C$ 400

July

C$ 417

August

C$ 392

September

C$ 368

October

C$ 343

November

C$ 342

December

C$ 317

December is currently the cheapest month to fly to Chicago. At this moment in time July 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.

YTO - CHI Price	C$ 317 - C$ 482
CHI Temperature	1 - 29 °C
CHI Rainfall	17 - 109 mm

Flying to Chicago in December 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 book a flight 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 56 days in advance of your trip. Fares are likely to increase in the final two weeks or so before your departure date.

Which day is cheapest to fly to Chicago?

The cheapest day to fly to Chicago is usually Wednesday. At the moment, Monday is the most expensive.

What time of day is cheapest to fly to Chicago?

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.

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.