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, 2% potential price drop
Average priceC$ 335Average for round-trip flights in November 2021
Round-trip fromC$ 268From Toronto to Chicago
One-way fromC$ 13One-way flight from Toronto to Chicago

Cheap flights to Chicago in November, December 2021

The best prices found for MDW flights for November, December
19 Dec - 25 Dec
C$ 251pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
16 Dec - 19 Dec
C$ 272pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
30 Dec - 4 Jan
C$ 273pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island

Chicago 2021 flight deals

Cheap flights to Chicago found for this year
19 Dec - 25 Dec
C$ 251pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
16 Dec - 19 Dec
C$ 272pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
30 Dec - 4 Jan
C$ 273pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island

Last minute flights to Chicago

Late deals on round-trip flights to Chicago, departing today and this week
8 Dec - 15 Dec
C$ 287pp
YYZ
Toronto Pearson Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
YYZ
Toronto Pearson Intl
6 Dec - 11 Dec
C$ 291pp
YYZ
Toronto Pearson Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
YYZ
Toronto Pearson Intl
8 Dec - 9 Dec
C$ 314pp
YYZ
Toronto Pearson Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
YYZ
Toronto Pearson Intl

COVID Restrictions

View COVID Travel Restrictions for Chicago

Can I fly to Chicago from USA right now?

Information is based on travel restrictions for travel to Chicago within the United States

Most visitors from USA need to provide a negative COVID-19 test result and/or quarantine to enter Chicago.

COVID-19 testing requirements
Visitors from USA must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours before departing to Chicago.

Quarantine requirements
Visitors from USA are not required to quarantine after entering Chicago.

Can I fly back to USA from Chicago?

Returning to USA from Chicago

COVID-19 testing requirements
Visitors from Chicago must present a negative RT-PCR (NAAT) test taken 72 hours before departing to USA.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering USA.

Hide COVID Travel Restrictions for 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$ 382
February
C$ 316
March
C$ 353
April
C$ 357
May
C$ 385
June
C$ 431
July
C$ 473
August
C$ 467
September
C$ 446
October
C$ 417
November
C$ 407
December
C$ 409

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$ 307 - C$ 466
CHI
Temperature
1 - 29 °C
CHI
Precipitation
17 - 109 mm
Whilst there are several times of the year to choose from, October is seen as the time to fly to Chicago, however, it is possible to get good deals throughout the year. If weather is an important factor for you when considering when to fly to Chicago, the warmest period tends to be July, with the wettest being May.

When is the best time to book a flight to Chicago?

To ensure you get the cheapest price possible for a flight to Chicago, you should look to book at least 34 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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?

Flights at noon are typically the cheapest time of the day to fly to Chicago. Flights in the evening are usually the most expensive.

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.

How popular are flights to Chicago this year?

There has been a 87% increase in demand for Chicago flights over the last year.

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 November 30, 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 November 30, 2021.
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