Cheap Flights to Chicago

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Home North America USA Illinois Cheap flights to Chicago, Illinois

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 inJanuaryHigh demand for flights, 5% potential price rise
Cheapest inAprilBest time to find cheap flights, 1% potential price drop
Average priceC$ 281Average for round-trip flights in April 2021
Round-trip fromC$ 356From Toronto to Chicago
One-way fromC$ 235One-way flight from Toronto to Chicago

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$ 353
May
C$ 324
June
C$ 381
July
C$ 397
August
C$ 374
September
C$ 351
October
C$ 327
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.

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Cheap flights to Chicago in April, May 2021

The best prices found for ORD flights for April, May
27 May - 30 May
C$ 342pp
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
27 May - 30 May
C$ 346pp
YYZ
Toronto Pearson Intl
Air Canada
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
Direct
YYZ
Toronto Pearson Intl
27 May - 30 May
C$ 347pp
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

Chicago 2021 flight deals

Cheap flights to Chicago found for this year
27 May - 30 May
C$ 342pp
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 Sep - 26 Sep
C$ 343pp
YTZ
Toronto Island
Air Canada
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
 
1 STOP
YTZ
Toronto Island
27 May - 30 May
C$ 346pp
YYZ
Toronto Pearson Intl
Air Canada
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
Direct
YYZ
Toronto Pearson Intl

Last minute flights to Chicago

Late deals on round-trip flights to Chicago, departing today and this week
22 Apr - 30 Apr
C$ 411pp
YYZ
Toronto Pearson Intl
United Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Direct
YYZ
Toronto Pearson Intl
22 Apr - 30 Apr
C$ 417pp
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
22 Apr - 30 Apr
C$ 437pp
YYZ
Toronto Pearson Intl
Delta
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
 
1 STOP
YYZ
Toronto Pearson Intl

Alternative, similarly priced destinations

See alternative destinations where airfare is generally forecast to be close to Chicago flight prices.

Find the best prices for you!

Cheap tickets to Chicago found by our users in Canada as recently as April 14, 2021.

Chicago, Illinois airports

See all airports in Chicago, select one to find and compare flight prices.

Cheapest flights to USA

Not set on Chicago? See the cheapest flights to Canada. Airfare prices updated on April 14, 2021.
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