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Cheap First Class flights to Chicago

YYZ — CHI
30 May — 6 Jun1
1 adult
1 adult, First, 0 bags

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Cheap first 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 30 April 2026.

Average Price

C$ 1,710

Cheapest Price

C$ 1,541

Arrival Airport

Chicago O'Hare Intl Airport
Average for round-trip first class flights in April 2026
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Cheapest first class flights to Chicago
Explore the most affordable first class flight options available to Chicago. Find the lowest fares based on data from user searches, with prices last updated on 30 April 2026.

Sat 18/76:30 a.m.
YYZ
-
ORD
1 stop6h 15m
Delta
Sat 25/75:18 p.m.
ORD
-
YYZ
1 stop4h 44m
Delta
Deal found 27/4C$ 687
Thu 10/92:15 p.m.
YYZ
-
ORD
1 stop7h 09m
Delta
Sun 13/98:55 a.m.
ORD
-
YYZ
1 stop3h 30m
Delta
Deal found 26/4C$ 729
Thu 10/912:15 p.m.
YYZ
-
MDW
1 stop7h 16m
Delta
Sun 13/99:30 a.m.
MDW
-
YYZ
1 stop6h 53m
Delta
Deal found 26/4C$ 729
Fri 22/52:20 p.m.
YYZ
-
ORD
1 stop6h 54m
Delta
Sun 24/57:00 a.m.
ORD
-
YYZ
1 stop5h 30m
Delta
Deal found 27/4C$ 751
Sat 30/59:45 a.m.
YUL
-
ORD
Nonstop2h 35m
United Airlines
Mon 1/66:04 p.m.
ORD
-
YUL
Nonstop2h 22m
United Airlines
Deal found 28/4C$ 780
Sat 18/76:30 a.m.
YYZ
-
MDW
1 stop7h 39m
Delta
Sat 25/76:35 p.m.
MDW
-
YYZ
1 stop3h 27m
Delta
Deal found 27/4C$ 809

Travel insights for first class flights from Canada to Chicago

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

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).

Frequently asked questions about Chicago first class tickets

Find answers to common questions related to first class tickets for flights to Chicago. Get information on booking, amenities, upgrade options, and more. This FAQ section was last updated on 30 April 2026.

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

    It would cost one person about C$ 1,710 to fly First Class to Chicago, usually. The lowest price a user reported recently is C$ 1,541 (for a First Class class ticket flying from Calgary Airport to Chicago).

  • How much do Business Class flight tickets to Chicago cost?

    Business flights to Chicago should cost around C$ 1,265 a person. It is worth noting that many users save, on average, 26% choosing Business over First Class while still travelling with comfort.

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

    Travellers who want to experience premium cabins usually book through Air Canada, the most popular airline with flights to Chicago. There are 3 premium cabins provided right now: Business Class, Prem Economy Class and First Class.

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