Cheap Flights to Chicago from C$ 226

Flights to Chicago in 2021

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

Popular in	January	High demand for flights, 5% potential price rise
Cheapest in	April	Best time to find cheap flights, 2% potential price drop
Average price	C$ 318	Average for round-trip flights in July 2021
Round-trip from	C$ 328	From Toronto to Chicago
One-way from	C$ 13	One-way flight from Toronto to Chicago

Cheap flights to Chicago in July, August 2021

The best prices found for ORD flights for July, August

26 Aug - 29 Aug

C$ 402pp

YYZ

Toronto Pearson Intl

Air Canada

Direct

ORD

Chicago O'Hare Intl

ORD

Chicago O'Hare Intl

Air Canada

Direct

YYZ

Toronto Pearson Intl

20 Aug - 20 Sep

C$ 416pp

YYZ

Toronto Pearson Intl

Air Canada

Direct

ORD

Chicago O'Hare Intl

ORD

Chicago O'Hare Intl

Air Canada

1 STOP

YYZ

Toronto Pearson Intl

24 Aug - 7 Sep

C$ 417pp

YYZ

Toronto Pearson Intl

Air Canada

1 STOP

ORD

Chicago O'Hare Intl

ORD

Chicago O'Hare Intl

Air Canada

1 STOP

YYZ

Toronto Pearson Intl

Chicago 2021 flight deals

Cheap flights to Chicago found for this year

2 Nov - 3 Nov

C$ 303pp

YTZ

Toronto Island

Air Canada

1 STOP

ORD

Chicago O'Hare Intl

ORD

Chicago O'Hare Intl

Air Canada

1 STOP

YTZ

Toronto Island

2 Nov - 3 Nov

C$ 319pp

YYZ

Toronto Pearson Intl

Air Canada

Direct

ORD

Chicago O'Hare Intl

ORD

Chicago O'Hare Intl

Air Canada

Direct

YYZ

Toronto Pearson Intl

6 Oct - 13 Oct

C$ 323pp

YYZ

Toronto Pearson Intl

Air Canada

2 STOPS

ORD

Chicago O'Hare Intl

ORD

Chicago O'Hare Intl

Air Canada

1 STOP

YYZ

Toronto Pearson Intl

Last minute flights to Chicago

Late deals on round-trip flights to Chicago, departing today and this week

2 Aug - 25 Aug

C$ 489pp

YYZ

Toronto Pearson Intl

Air Canada

Direct

ORD

Chicago O'Hare Intl

ORD

Chicago O'Hare Intl

Air Canada

1 STOP

YYZ

Toronto Pearson Intl

5 Aug - 17 Aug

C$ 501pp

YYZ

Toronto Pearson Intl

Air Canada

Direct

ORD

Chicago O'Hare Intl

ORD

Chicago O'Hare Intl

Air Canada

1 STOP

YYZ

Toronto Pearson Intl

5 Aug - 17 Aug

C$ 514pp

YYZ

Toronto Pearson Intl

Air Canada

Direct

ORD

Chicago O'Hare Intl

ORD

Chicago O'Hare Intl

Air Canada

Direct

YYZ

Toronto Pearson Intl

Cheapest prices for Chicago flights by month

The cheapest ticket to Chicago found for each month in 2021 based on historical flight searches by Cheapflights users.

January

C$ 320

February

C$ 324

March

C$ 328

April

C$ 352

May

C$ 323

June

C$ 381

July

C$ 397

August

C$ 373

September

C$ 350

October

C$ 326

November

C$ 326

December

C$ 302

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?

Average Chicago flight ticket prices and weather conditions for 2021 and 2022 by month.

YTO - CHI Price	C$ 302 - C$ 459
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 34 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.