Cheap Flights to Chicago from C$ 182

Q: 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.

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$ 335	Average for round-trip flights in November 2021
Round-trip from	C$ 268	From Toronto to Chicago
One-way from	C$ 13	One-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.