Cheap Flights to Chicago from C$ 150

Q: 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.

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 in	August	High demand for flights, 29% potential price rise
Cheapest in	June	Best time to find cheap flights, 4% potential price drop
Average price	C$ 282	Average for round-trip flights in June 2022
Round-trip from	C$ 176	From Toronto to Chicago
One-way from	C$ 13	One-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.