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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
2 May — 9 May1
1 adult
Thu 2/5
Thu 9/5
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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 508,915 searches and data were last updated on 27 April 2024.

Average Price

C$ 1,986

Cheapest Price

C$ 1,003

Top Rated Airline

United Airlines

No. of Airlines

5
Average for round-trip first class flights in April 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 27 April 2024. In the last 7 days, Cheapflights users made a total of 508,915 searches.
25 May - 29 May
YUL

Montreal Pierre Elliott Trudeau Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 43m

4:50 p.m.-6:33 p.m.
ORD

Chicago O'Hare Intl

YUL

Montreal Pierre Elliott Trudeau Intl

Nonstop

2h 23m

7:21 a.m.-10:44 a.m.
C$ 777

United Airlines

Pick Dates

Deal found 26/4

27 May - 3 Jun.
YUL

Montreal Pierre Elliott Trudeau Intl

ORD

Chicago O'Hare Intl

1 stop

5h 17m

6:00 a.m.-10:17 a.m.
ORD

Chicago O'Hare Intl

YUL

Montreal Pierre Elliott Trudeau Intl

2 stops

11h 30m

8:45 a.m.-9:15 p.m.
C$ 1,279

Delta

Pick Dates

Deal found 25/4

28 Aug. - 7 Sep.
YUL

Montreal Pierre Elliott Trudeau Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 43m

11:30 a.m.-1:13 p.m.
ORD

Chicago O'Hare Intl

YUL

Montreal Pierre Elliott Trudeau Intl

Nonstop

2h 23m

7:21 a.m.-10:44 a.m.
C$ 811

United Airlines

Pick Dates

Deal found 26/4

25 May - 30 May
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$ 818

United Airlines

Pick Dates

Deal found 26/4

11 May - 11 May
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

1h 59m

7:59 a.m.-8:58 a.m.
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

Nonstop

1h 42m

6:01 p.m.-8:43 p.m.
C$ 825

United Airlines

Pick Dates

Deal found 25/4

25 May - 28 May
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 25m

1:55 p.m.-5:20 p.m.
C$ 859

United Airlines

Pick Dates

Deal found 26/4

Chicago one-way first class flight deals

Discover one-way first class flight deals to Chicago. Fares were last updated on 27 April 2024. In the last 7 days, Cheapflights users made a total of 508,915 searches.
3 May
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

1 stop

5h 51m

4:43 p.m.-9:34 p.m.
C$ 466

Delta

Pick Dates

Deal found 26/4

26 May
YOW

Ottawa

ORD

Chicago O'Hare Intl

Nonstop

2h 25m

5:26 p.m.-6:51 p.m.
C$ 590

United Airlines

Pick Dates

Deal found 25/4

6 May
YUL

Montreal Pierre Elliott Trudeau Intl

ORD

Chicago O'Hare Intl

1 stop

6h 07m

6:45 p.m.-11:52 p.m.
C$ 510

Delta

Pick Dates

Deal found 26/4

8 Jun.
YOW

Ottawa

ORD

Chicago O'Hare Intl

Nonstop

2h 25m

5:26 p.m.-6:51 p.m.
C$ 600

United Airlines

Pick Dates

Deal found 25/4

5 May
YUL

Montreal Pierre Elliott Trudeau Intl

ORD

Chicago O'Hare Intl

1 stop

6h 25m

6:00 a.m.-11:25 a.m.
C$ 557

Delta

Pick Dates

Deal found 26/4

8 May
YUL

Montreal Pierre Elliott Trudeau Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 46m

6:15 a.m.-8:01 a.m.
C$ 631

United Airlines

Pick Dates

Deal found 26/4

Top first class airline flying to Chicago

Explore the top four first 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 508,915 searches and data was last updated on 27 April 2024.
AirlineRatingFirst ClassPrice
United AirlinesPriceFrom C$ 272First ClassRating
7.4
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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 27 April 2024.

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

    It would cost one person about C$ 1,986 to fly First Class to Chicago, usually. The lowest price a user reported recently is C$ 1,003 (for a First Class class ticket flying from Toronto Pearson Intl Airport to Chicago).

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

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

  • 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.

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Airlines operating first class flights to Chicago
Take a look at the available airlines operating first class flights to Chicago at this time.

United Airlines flights to Chicago O'Hare Intl

Search flights to Chicago by cabin class

Business Classfrom C$ 410/person
Prem Econ Classfrom C$ 824/person
Economy Classfrom C$ 173/person
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