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Cheap Business Class flights to Chicago

YYZ — CHI
6 Mar — 13 Mar1
1 adult
1 adult, Business, 0 bags

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Cheap business class flights to Chicago in 2026

Find the latest flights to Chicago in 2026, with up-to-date prices and availability. In the last 7 days, Cheapflights users made a total of 629,999 searches and data were last updated on 4 February 2026.

Average Price

C$ 3,174

Cheapest Price

C$ 511

Top Rated Airline

Air Canada

No. of Airlines

1

Arrival Airport

Chicago O'Hare Intl Airport
Average for round-trip business class flights in February 2026
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The lowest price for a business class flight ticket to Chicago
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Most popular airline to fly business class with to Chicago in the past 7 days
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Airline that offers business class options for this route
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Closest airport for this route
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Find business class flight deals to Chicago

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Cheapest business class flights to Chicago
Explore the most affordable business class flight options available to Chicago. Find the lowest fares based on data from user searches, with prices last updated on 4 February 2026.

Sat 11/49:15 a.m.
YUL
-
ORD
Nonstop2h 38m
United Airlines
Sun 19/412:50 p.m.
ORD
-
YUL
Nonstop2h 15m
United Airlines
Deal found 3/2C$ 470
Fri 17/41:20 p.m.
YUL
-
ORD
Nonstop2h 35m
United Airlines
Thu 23/48:40 a.m.
ORD
-
YUL
Nonstop2h 11m
United Airlines
Deal found 3/2C$ 661
Fri 13/31:10 p.m.
YUL
-
ORD
Nonstop2h 45m
United Airlines
Sun 15/37:15 a.m.
ORD
-
YUL
Nonstop2h 05m
United Airlines
Deal found 31/1C$ 686
Thu 14/512:30 p.m.
YUL
-
ORD
Nonstop2h 40m
American Airlines
Mon 18/58:18 a.m.
ORD
-
YUL
Nonstop2h 26m
American Airlines
Deal found 31/1C$ 785
Fri 13/39:00 p.m.
YYZ
-
ORD
Nonstop2h 04m
Air Canada
Sun 22/38:40 p.m.
ORD
-
YYZ
Nonstop1h 39m
Air Canada
Deal found 2/2C$ 923
Mon 23/26:45 a.m.
YYZ
-
ORD
Nonstop2h 15m
United Airlines
Wed 25/28:40 p.m.
ORD
-
YYZ
Nonstop1h 39m
United Airlines
Deal found 2/2C$ 938

Travel insights for business class flights from Canada to Chicago

Get recent, data-driven insights about business class flights from Canada to Chicago including ideal travel times, pricing trends, and more.

What airlines can I book Business Class flights to Chicago with?

American Airlines and Air Canada have Business Class flights to Chicago. Try booking in advance to lower your costs and travel worry-free.

American Airlines
American Airlines
From C$ 511
Air Canada
Air Canada
From C$ 507

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago when rainfall is around 43.0 mm.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

Top 2 business class airlines flying to Chicago

Explore the top four business class airlines operating flights to Chicago. Find out more about these airlines and their offerings, including amenities, in-flight services, and customer reviews. In the last 7 days, Cheapflights users made a total of 629,999 searches and data was last updated on 4 February 2026.
AirlineRatingFirst ClassPrice
American AirlinesPriceFrom C$ 169First ClassRating
7.2
Search American Airlines flights
Air CanadaPriceFrom C$ 121First ClassRating
7.1
Search Air Canada flights

Frequently asked questions about Chicago business class tickets

Find answers to common questions related to business class tickets for flights to Chicago. Get information on booking, amenities, upgrade options, and more. This FAQ section was last updated on 4 February 2026.

  • What is the cheapest price for a Business Class ticket to Chicago?

    Looking for cheap deals? The cheapest price last booked, C$ 511/person, was for a Business Class flight ticket going from Toronto Pearson Intl Airport to Chicago. Business Class flights usually cost C$ 3,174 per person.

  • How much do Prem Economy Class flight tickets to Chicago cost?

    Try Prem Economy Class for your flight to Chicago instead of Business Class to save up to 27%. The average price a user would pay for Prem Economy Class tickets to Chicago is C$ 2,319.

  • How many premium cabins does Air Canada have for flights to Chicago?

    Air Canada currently offers a couple premium cabin classes on flights to Chicago: Prem Economy Class, Business Class and First Class. Still not enough? Try taking a look at other airlines or choosing a new departing point for more cabin options.

  • What airlines can I book Business Class flights to Chicago with?

    American Airlines and Air Canada have Business Class flights to Chicago. Try booking in advance to lower your costs and travel worry-free.

See more FAQs

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Airlines operating business class flights to Chicago

Take a look at the available airlines operating business class flights to Chicago at this time.
Air Canada flights to Chicago O'Hare Intl
American Airlines flights to Chicago O'Hare Intl