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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
4 May — 11 May1
1 adult
Sat 4/5
Sat 11/5
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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 494,117 searches and data were last updated on 29 April 2024.

Average Price

C$ 2,033

Cheapest Price

C$ 989

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 29 April 2024. In the last 7 days, Cheapflights users made a total of 494,117 searches.
19 May - 25 May
YUL

Montreal Pierre Elliott Trudeau Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 46m

6:15 a.m.-8:01 a.m.
ORD

Chicago O'Hare Intl

YUL

Montreal Pierre Elliott Trudeau Intl

Nonstop

2h 25m

6:04 p.m.-9:29 p.m.
C$ 790

United Airlines

Pick Dates

Deal found 28/4

3 Oct. - 13 Oct.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

1 stop

7h 10m

12:30 p.m.-6:40 p.m.
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

1 stop

7h 14m

8:55 a.m.-5:09 p.m.
C$ 804

Delta

Pick Dates

Deal found 29/4

11 May - 14 May
YUL

Montreal Pierre Elliott Trudeau Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 46m

6:15 a.m.-8:01 a.m.
ORD

Chicago O'Hare Intl

YUL

Montreal Pierre Elliott Trudeau Intl

Nonstop

2h 24m

7:20 a.m.-10:44 a.m.
C$ 820

United Airlines

Pick Dates

Deal found 28/4

29 Sep. - 13 Oct.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

1 stop

9h 11m

6:45 a.m.-2:56 p.m.
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

1 stop

7h 14m

8:55 a.m.-5:09 p.m.
C$ 841

Delta

Pick Dates

Deal found 29/4

3 Oct. - 13 Oct.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

1 stop

14h 14m

10:00 a.m.-11:14 p.m.
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

Nonstop

1h 40m

9:18 p.m.-11:58 p.m.
C$ 831

United Airlines

Pick Dates

Deal found 29/4

1 Jun. - 9 Jun.
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$ 860

United Airlines

Pick Dates

Deal found 28/4

Chicago one-way first class flight deals

Discover one-way first class flight deals to Chicago. Fares were last updated on 29 April 2024. In the last 7 days, Cheapflights users made a total of 494,117 searches.
9 Aug.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

1 stop

12h 57m

7:43 p.m.-7:40 a.m.
C$ 476

United Airlines

Pick Dates

Deal found 28/4

9 Aug.
YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

8h 18m

9:45 a.m.-5:03 p.m.
C$ 508

Delta

Pick Dates

Deal found 28/4

5 May
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

1 stop

9h 10m

6:45 a.m.-2:55 p.m.
C$ 530

Delta

Pick Dates

Deal found 29/4

10 May
YYC

Calgary

ORD

Chicago O'Hare Intl

1 stop

10h 59m

6:25 a.m.-6:24 p.m.
C$ 596

Delta

Pick Dates

Deal found 29/4

23 Sep.
YUL

Montreal Pierre Elliott Trudeau Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 43m

6:15 a.m.-7:58 a.m.
C$ 687

United Airlines

Pick Dates

Deal found 29/4

16 May
YVR

Vancouver Intl

ORD

Chicago O'Hare Intl

1 stop

6h 36m

3:29 p.m.-12:05 a.m.
C$ 601

Delta

Pick Dates

Deal found 29/4

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 494,117 searches and data was last updated on 29 April 2024.
AirlineRatingFirst ClassPrice
United AirlinesPriceFrom C$ 268First 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 29 April 2024.

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

    It would cost one person about C$ 2,033 to fly First Class to Chicago, usually. The lowest price a user reported recently is C$ 989 (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, American Airlines, 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$ 825/person
Economy Classfrom C$ 173/person
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