Cheap Flights to Chicago

Round-trip
Economy
Wichita (ICT)
Chicago (CHI)
Fri. 24/6
Fri. 1/7
Any month
Compare vs. Cheapflights |
Home North America USA Illinois Cheap flights to Chicago, Illinois

Flights to Chicago in 2022

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
Popular inAugustHigh demand for flights, 29% potential price rise
Cheapest inJuneBest time to find cheap flights, 4% potential price drop
Average priceC$ 282Average for round-trip flights in June 2022
Round-trip fromC$ 176From Toronto to Chicago
One-way fromC$ 13One-way flight from Toronto to Chicago

Cheap flights to Chicago in June, July 2022

The best prices found for ORD flights for June, July
21 Jul - 24 Jul
C$ 206pp
YYZ
Toronto Pearson Intl
Swoop
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Swoop
Direct
YYZ
Toronto Pearson Intl
21 Jul - 24 Jul
C$ 211pp
YYZ
Toronto Pearson Intl
Swoop
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Swoop
Direct
YYZ
Toronto Pearson Intl
21 Jul - 24 Jul
C$ 215pp
YYZ
Toronto Pearson Intl
Swoop
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Swoop
Direct
YYZ
Toronto Pearson Intl

Chicago 2022 flight deals

Cheap flights to Chicago found for this year
28 Aug - 4 Sep
C$ 176pp
YYZ
Toronto Pearson Intl
Swoop
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Swoop
Direct
YYZ
Toronto Pearson Intl
15 Sep - 18 Sep
C$ 178pp
YYZ
Toronto Pearson Intl
Swoop
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Swoop
Direct
YYZ
Toronto Pearson Intl
21 Aug - 25 Aug
C$ 185pp
YYZ
Toronto Pearson Intl
Swoop
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Swoop
Direct
YYZ
Toronto Pearson Intl

Last minute flights to Chicago

Late deals on round-trip flights to Chicago, departing today and this week
29 Jun - 3 Jul
C$ 246pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
3 Jul - 9 Jul
C$ 249pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
28 Jun - 6 Sep
C$ 253pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island

COVID Restrictions

View COVID Travel Restrictions for Chicago

Can I fly to Chicago from Canada right now?

Information is based on travel restrictions from Canada to Chicago

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

COVID-19 testing requirements
Visitors from Canada are not required to present a negative COVID-19 PCR test or antigen result upon entering Chicago.

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

Can I fly back to Canada from Chicago?

Returning to Canada from Chicago

COVID-19 testing requirements
Visitors from Chicago must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours for RT-PCR (NAAT) and 1 day for Antigen (quick-test) before departing to Canada.

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

Hide COVID Travel Restrictions for Chicago

What is the cheapest month to fly to Chicago?

The cheapest ticket to Chicago found for each month in 2022 based on historical flight searches by Cheapflights users.
January
C$ 434
February
C$ 430
March
C$ 451
April
C$ 416
May
C$ 364
June
C$ 380
July
C$ 422
August
C$ 534
September
C$ 520
October
C$ 483
November
C$ 452
December
C$ 518
Currently, May is the cheapest month in which you can book a flight to Chicago. Flying to Chicago in August will prove the most costly. There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

When is the best time to fly to Chicago?

Average Chicago flight ticket prices and weather conditions for 2022 and 2023 by month.
YTO - CHI
Price
C$ 315 - C$ 584
CHI
Temperature
1 - 29 °C
CHI
Rainfall
17 - 109 mm

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 48 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 Thursday. At the moment, Sunday is the most expensive.

What time of day is cheapest to fly to Chicago?

Flights in the evening are typically the cheapest time of the day to fly to Chicago. Flights in the afternoon 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 324% 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 June 23, 2022.

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 June 23, 2022.
Home North America USA Illinois Cheap flights to Chicago, Illinois
  • Round-trip
  • One-way
  • Multi-city
  • Economy
  • Premium Economy
  • Business
  • First
  • Multiple
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First