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Cheap First Class flights to Chicago

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YYZ — CHI
4 Jun — 11 Jun1
1 adult
Tue 4/6
Tue 11/6
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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 426,053 searches and data were last updated on 30 May 2024.

Average Price

C$ 5,586

Cheapest Price

C$ 1,009

Top Rated Airline

United Airlines

No. of Airlines

6
Average for round-trip first class flights in May 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 30 May 2024. In the last 7 days, Cheapflights users made a total of 426,053 searches.
28 Jul. - 6 Aug.
YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

8h 19m

9:45 a.m.-5:04 p.m.
MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

8h 29m

1:24 p.m.-10:53 p.m.
C$ 731

Delta

Pick Dates

Deal found 29/5

1 Jul. - 5 Jul.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

1 stop

7h 55m

6:15 a.m.-1:10 p.m.
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

Nonstop

1h 52m

12:00 p.m.-2:52 p.m.
C$ 761

United Airlines

Pick Dates

Deal found 29/5

28 Sep. - 11 Oct.
YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

6h 35m

12:30 p.m.-6:05 p.m.
MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

8h 17m

2:00 p.m.-11:17 p.m.
C$ 743

Delta

Pick Dates

Deal found 29/5

5 Oct. - 13 Oct.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

1 stop

4h 31m

7:43 p.m.-11:14 p.m.
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

Nonstop

1h 32m

7:26 a.m.-9:58 a.m.
C$ 769

United Airlines

Pick Dates

Deal found 29/5

2 Oct. - 11 Oct.
YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

5h 33m

12:30 p.m.-5:03 p.m.
MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

8h 17m

2:00 p.m.-11:17 p.m.
C$ 748

Delta

Pick Dates

Deal found 29/5

29 Aug. - 2 Sep.
YUL

Montreal Pierre Elliott Trudeau Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 43m

6:15 a.m.-7:58 a.m.
ORD

Chicago O'Hare Intl

YUL

Montreal Pierre Elliott Trudeau Intl

Nonstop

2h 23m

7:21 a.m.-10:44 a.m.
C$ 774

United Airlines

Pick Dates

Deal found 29/5

Chicago one-way first class flight deals

Discover one-way first class flight deals to Chicago. Fares were last updated on 30 May 2024. In the last 7 days, Cheapflights users made a total of 426,053 searches.
10 Jul.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

1 stop

8h 07m

12:30 p.m.-7:37 p.m.
C$ 404

Delta

Pick Dates

Deal found 29/5

7 Jul.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

1h 56m

7:00 a.m.-7:56 a.m.
C$ 409

United Airlines

Pick Dates

Deal found 30/5

10 Jul.
YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

7h 09m

12:30 p.m.-6:39 p.m.
C$ 404

Delta

Pick Dates

Deal found 29/5

28 Sep.
YYC

Calgary

ORD

Chicago O'Hare Intl

Nonstop

3h 39m

12:30 p.m.-5:09 p.m.
C$ 525

Delta

Pick Dates

Deal found 29/5

27 Sep.
YYC

Calgary

ORD

Chicago O'Hare Intl

1 stop

10h 34m

12:30 a.m.-12:04 p.m.
C$ 534

Delta

Pick Dates

Deal found 29/5

17 Jun.
YVR

Vancouver Intl

ORD

Chicago O'Hare Intl

Nonstop

4h 01m

11:35 p.m.-5:36 a.m.
C$ 791

United Airlines

Pick Dates

Deal found 29/5

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 May 2024.

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

    It would cost one person about C$ 5,586 to fly First Class to Chicago, usually. The lowest price a user reported recently is C$ 1,009 (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$ 4,010 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.

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Business Classfrom C$ 472/person
Prem Econ Classfrom C$ 1,071/person
Economy Classfrom C$ 160/person
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