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Cheap First Class flights to Chicago

Explore and compare the cheapest first class flights to Chicago from hundreds of sites

YYZ — CHI
6 Jun — 13 Jun1
1 adult
Thu 6/6
Thu 13/6
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Cheap first class flights to Chicago in 2024

Find the latest flights to Chicago in 2024, with up-to-date prices and availability. In the last 7 days, Cheapflights users made a total of 420,726 searches and data were last updated on 1 June 2024.

Average Price

C$ 5,563

Cheapest Price

C$ 1,005

Top Rated Airline

United Airlines

No. of Airlines

6
Average for round-trip first class flights in June 2024
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The lowest price for a first class flight ticket to Chicago
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Most popular airline to fly first class with to Chicago in the past 7 days
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Airlines that offer first class options for this route
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Chicago round-trip first class flight deals

Discover return first class flight deals to Chicago. Fares were last updated on 1 June 2024. In the last 7 days, Cheapflights users made a total of 420,726 searches.
2 Oct. - 13 Oct.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 05m

9:00 p.m.-10:05 p.m.
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

Nonstop

1h 43m

6:00 p.m.-8:43 p.m.
C$ 741

United Airlines

Pick Dates

Deal found 1/6

14 Jun. - 16 Jun.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

1 stop

8h 09m

12:31 p.m.-7:40 p.m.
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

1 stop

7h 38m

8:30 a.m.-5:08 p.m.
C$ 902

Delta

Pick Dates

Deal found 31/5

4 Jul. - 12 Jul.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

1 stop

4h 32m

7:43 p.m.-11:15 p.m.
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

Nonstop

1h 43m

9:15 p.m.-11:58 p.m.
C$ 762

United Airlines

Pick Dates

Deal found 1/6

25 Jun. - 1 Jul.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

1 stop

4h 37m

7:43 p.m.-11:20 p.m.
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

Nonstop

1h 43m

9:15 p.m.-11:58 p.m.
C$ 800

United Airlines

Pick Dates

Deal found 1/6

14 Jun. - 16 Jun.
YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

5h 34m

12:30 p.m.-5:04 p.m.
MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

6h 34m

9:34 a.m.-5:08 p.m.
C$ 902

Delta

Pick Dates

Deal found 31/5

25 Jun. - 28 Jun.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

1 stop

4h 37m

7:43 p.m.-11:20 p.m.
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

Nonstop

1h 43m

9:15 p.m.-11:58 p.m.
C$ 849

United Airlines

Pick Dates

Deal found 1/6

Chicago one-way first class flight deals

Discover one-way first class flight deals to Chicago. Fares were last updated on 1 June 2024. In the last 7 days, Cheapflights users made a total of 420,726 searches.
28 Sep.
YYC

Calgary

ORD

Chicago O'Hare Intl

Nonstop

3h 39m

12:30 p.m.-5:09 p.m.
C$ 523

Delta

Pick Dates

Deal found 1/6

27 Sep.
YYC

Calgary

ORD

Chicago O'Hare Intl

1 stop

11h 04m

12:30 a.m.-12:34 p.m.
C$ 530

Delta

Pick Dates

Deal found 1/6

1 Aug.
YVR

Vancouver Intl

ORD

Chicago O'Hare Intl

2 stops

9h 58m

7:32 p.m.-7:30 a.m.
C$ 992

Delta

Pick Dates

Deal found 1/6

22 Jun.
YVR

Vancouver Intl

ORD

Chicago O'Hare Intl

2 stops

12h 40m

6:23 a.m.-9:03 p.m.
C$ 1,195

Delta

Pick Dates

Deal found 1/6

10 Jun.
YUL

Montreal Pierre Elliott Trudeau Intl

MDW

Chicago Midway

1 stop

7h 14m

7:30 a.m.-1:44 p.m.
C$ 1,725

Delta

Pick Dates

Deal found 1/6

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 1 June 2024.

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

    It would cost one person about C$ 5,563 to fly First Class to Chicago, usually. The lowest price a user reported recently is C$ 1,005 (for a First Class class ticket flying from Toronto Pearson Intl Airport to Chicago).

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

    Business flights to Chicago should cost around C$ 3,993 a person. It is worth noting that many users save, on average, 29% choosing Business over First Class while still travelling with comfort.

  • How many premium cabins does United Airlines have for flights to Chicago?

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

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

    United Airlines, Delta, American Airlines, Lufthansa, Emirates and China Eastern have First Class flights to Chicago. Try booking in advance to lower your costs and travel worry-free.

See more FAQs

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Business Classfrom C$ 470/person
Prem Econ Classfrom C$ 1,066/person
Economy Classfrom C$ 159/person
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