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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 8 August 2026.
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 8 August 2026.
Tue 1/94:10 p.m. -
1 stop5h 20m
Tue 8/91:55 p.m. -
1 stop8h 04m
Deal found 4/8C$ 601
Fri 25/92:24 p.m. -
1 stop7h 06m
Mon 28/97:05 a.m. -
1 stop5h 29m
Deal found 5/8C$ 603
Wed 16/96:00 a.m. -
1 stop7h 59m
Mon 21/95:10 p.m. -
1 stop4h 49m
Deal found 8/8C$ 604
Tue 12/17:45 a.m. -
1 stop5h 52m
Wed 13/11:35 p.m. -
1 stop4h 32m
Deal found 7/8C$ 674
Sat 5/99:45 a.m. -
Nonstop2h 36m
Sun 6/92:01 p.m. -
Nonstop2h 29m
Deal found 8/8C$ 685
Fri 21/89:45 a.m. -
Nonstop2h 36m
Mon 24/87:11 a.m. -
Nonstop2h 29m
Deal found 6/8C$ 699
Best first class flights to Chicago
Discover carefully curated first class flight deals to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 8 August 2026.
Tue 1/94:10 p.m. -
1 stop5h 20m
Tue 8/91:55 p.m. -
1 stop8h 04m
Deal found 4/8C$ 601
Sat 5/99:45 a.m. -
Nonstop2h 36m
Sun 6/92:01 p.m. -
Nonstop2h 29m
Deal found 8/8C$ 685
Fri 25/92:24 p.m. -
1 stop7h 06m
Mon 28/97:05 a.m. -
1 stop5h 29m
Deal found 5/8C$ 603
Wed 16/96:00 a.m. -
1 stop7h 59m
Mon 21/95:10 p.m. -
1 stop4h 49m
Deal found 8/8C$ 604
Sat 5/96:25 a.m. -
Nonstop2h 19m
Sat 12/91:55 p.m. -
Nonstop2h 21m
Deal found 5/8C$ 1,336
Tue 12/17:45 a.m. -
1 stop5h 52m
Wed 13/11:35 p.m. -
1 stop4h 32m
Deal found 7/8C$ 674
Sat 29/81:15 p.m. -
Nonstop2h 40m
Deal found 4/8C$ 358
Fri 30/107:00 a.m. -
1 stop11h 03m
Deal found 7/8C$ 442
Fri 30/106:00 a.m. -
Nonstop3h 00m
Deal found 6/8C$ 468
Tue 8/97:00 a.m. -
1 stop9h 24m
Deal found 5/8C$ 474
Fri 30/101:05 p.m. -
2 stops11h 34m
Deal found 5/8C$ 1,138
Wed 19/88:30 a.m. -
2 stops13h 29m
Deal found 4/8C$ 1,499
One-way first class flights to Chicago
Search for one-way first class flight options to Chicago. Find affordable one-way fares based on user searches. Data last updated 8 August 2026.
Sat 29/81:15 p.m. -
Nonstop2h 40m
Deal found 4/8C$ 358
Fri 30/107:00 a.m. -
1 stop11h 03m
Deal found 7/8C$ 442
Fri 30/106:00 a.m. -
Nonstop3h 00m
Deal found 6/8C$ 468
Tue 8/97:00 a.m. -
1 stop9h 24m
Deal found 5/8C$ 474
Tue 15/96:15 a.m. -
2 stops13h 40m
Deal found 5/8C$ 745
Wed 23/911:07 a.m. -
1 stop10h 50m
Deal found 4/8C$ 747
Quickest first class flights to Chicago
Explore quickest first class flight options to Chicago based on user searches, and compare prices and availability for your desired travel dates. Data last updated 8 August 2026.
Mon 14/99:00 p.m. -
Nonstop2h 05m
Sat 19/99:18 p.m. -
Nonstop1h 41m
Deal found 8/8C$ 956
Sat 3/106:25 a.m. -
Nonstop2h 19m
Mon 5/106:21 p.m. -
Nonstop2h 14m
Deal found 5/8C$ 1,306
Sat 5/96:25 a.m. -
Nonstop2h 19m
Sat 12/91:55 p.m. -
Nonstop2h 21m
Deal found 5/8C$ 1,336
Fri 28/86:25 a.m. -
Nonstop2h 19m
Sun 30/810:40 a.m. -
Nonstop2h 19m
Deal found 6/8C$ 1,391
Sat 5/99:45 a.m. -
Nonstop2h 36m
Sun 6/92:01 p.m. -
Nonstop2h 29m
Deal found 8/8C$ 685
Fri 21/89:45 a.m. -
Nonstop2h 36m
Mon 24/87:11 a.m. -
Nonstop2h 29m
Deal found 6/8C$ 699
Sun 6/95:27 p.m. -
Nonstop2h 03m
Deal found 3/8C$ 1,390
Sat 29/81:15 p.m. -
Nonstop2h 40m
Deal found 4/8C$ 358
Fri 30/106:00 a.m. -
Nonstop3h 00m
Deal found 6/8C$ 468
Wed 26/87:30 a.m. -
1 stop7h 10m
Deal found 5/8C$ 780
Wed 19/87:30 a.m. -
1 stop7h 10m
Deal found 6/8C$ 832
Fri 14/86:00 a.m. -
1 stop8h 40m
Deal found 5/8C$ 881
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.
CA0-CHI
YYZ-ORD
YOW-ORD
YUL-ORD
YVR-ORD
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 8 August 2026.
What is the cheapest price for a First Class ticket to Chicago?
It would cost one person about C$ 15,871 to fly First Class to Chicago, usually. The lowest price a user reported recently is C$ 1,352 (for a First Class class ticket flying from Montreal Pierre Elliott Trudeau Intl Airport to Chicago).
How much do Business Class flight tickets to Chicago cost?
Business flights to Chicago should cost around C$ 3,959 a person. It is worth noting that many users save, on average, 76% 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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