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Cheap Business Class flights to Chicago

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

YYZ — CHI
22 Jun — 29 Jun1
1 adult
Sat 22/6
Sat 29/6
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Cheap business 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 437,191 searches and data were last updated on 17 June 2024.

Average Price

C$ 2,235

Cheapest Price

C$ 745

Top Rated Airline

Air Canada

No. of Airlines

35
Average for round-trip business class flights in June 2024
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The lowest price for a business class flight ticket to Chicago
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Most popular airline to fly business class with to Chicago in the past 7 days
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Airlines that offer business class options for this route
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Chicago round-trip business class flight deals

Discover return business class flight deals to Chicago. Fares were last updated on 17 June 2024. In the last 7 days, Cheapflights users made a total of 437,191 searches.
6 Sep.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

1h 55m

1:25 p.m.-2:20 p.m.
C$ 299

American Airlines

Pick Dates

Deal found 17/6

5 Sep.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

1 stop

8h 28m

12:30 a.m.-7:58 a.m.
C$ 446

Air Canada

Pick Dates

Deal found 17/6

16 Aug.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

1 stop

8h 22m

12:30 a.m.-7:52 a.m.
C$ 449

Air Canada

Pick Dates

Deal found 17/6

23 Jun.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

1h 57m

7:00 a.m.-7:57 a.m.
C$ 487

Air Canada

Pick Dates

Deal found 16/6

27 Sep.
YYC

Calgary

ORD

Chicago O'Hare Intl

1 stop

8h 43m

12:10 a.m.-9:53 a.m.
C$ 580

Air Canada

Pick Dates

Deal found 16/6

25 Aug.
YYC

Calgary

ORD

Chicago O'Hare Intl

1 stop

7h 26m

12:10 a.m.-8:36 a.m.
C$ 585

Air Canada

Pick Dates

Deal found 17/6

Chicago one-way business class flight deals

Discover one-way business class flight deals to Chicago. Fares were last updated on 17 June 2024. In the last 7 days, Cheapflights users made a total of 437,191 searches.
2 Oct. - 13 Oct.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

1h 54m

6:30 a.m.-7:24 a.m.
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

Nonstop

1h 39m

11:45 a.m.-2:24 p.m.
C$ 534

American Airlines

Pick Dates

Deal found 17/6

22 Sep. - 22 Sep.
YUL

Montreal Pierre Elliott Trudeau Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 30m

8:20 a.m.-9:50 a.m.
ORD

Chicago O'Hare Intl

YUL

Montreal Pierre Elliott Trudeau Intl

Nonstop

2h 10m

3:35 p.m.-6:45 p.m.
C$ 623

United Airlines

Pick Dates

Deal found 16/6

29 Sep. - 13 Oct.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

1h 56m

7:00 a.m.-7:56 a.m.
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

1 stop

5h 59m

3:35 p.m.-10:34 p.m.
C$ 731

Air Canada

Pick Dates

Deal found 17/6

29 Sep. - 13 Oct.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

1h 55m

11:55 a.m.-12:50 p.m.
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

Nonstop

1h 39m

11:45 a.m.-2:24 p.m.
C$ 595

American Airlines

Pick Dates

Deal found 17/6

17 Oct. - 22 Oct.
YUL

Montreal Pierre Elliott Trudeau Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 30m

6:40 p.m.-8:10 p.m.
ORD

Chicago O'Hare Intl

YUL

Montreal Pierre Elliott Trudeau Intl

Nonstop

2h 10m

10:55 a.m.-2:05 p.m.
C$ 696

United Airlines

Pick Dates

Deal found 16/6

2 Oct. - 13 Oct.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

1 stop

6h 07m

7:30 a.m.-12:37 p.m.
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

1 stop

5h 59m

3:35 p.m.-10:34 p.m.
C$ 737

Air Canada

Pick Dates

Deal found 17/6

Frequently asked questions about Chicago business class tickets

Find answers to common questions related to business class tickets for flights to Chicago. Get information on booking, amenities, upgrade options, and more. This FAQ section was last updated on 17 June 2024.

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

    Looking for cheap deals? The cheapest price last booked, C$ 737/person, was for a Business Class flight ticket going from Toronto Pearson Intl Airport to Chicago. Business Class flights usually cost C$ 2,264 per person.

  • How much do Prem Economy Class flight tickets to Chicago cost?

    Try Prem Economy Class for your flight to Chicago instead of Business Class to save up to 7%. The average price a user would pay for Prem Economy Class tickets to Chicago is C$ 2,125.

  • How many premium cabins does Air Canada have for flights to Chicago?

    Air Canada currently offers a couple premium cabin classes on flights to Chicago: Business Class and Prem Economy Class. Still not enough? Try taking a look at other airlines or choosing a new departing point for more cabin options.

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

    Air Canada, Cathay Pacific, Philippine Airlines, Air India, United Airlines, EVA Air, American Airlines, British Airways, Emirates, Lufthansa, Jazz, Finnair, ANA, Air France, Condor, Delta, AeroMexico Connect, Caribbean Airlines, Aer Lingus, Icelandair, SWISS, Austrian Airlines, Azul, Aeromexico, Royal Jordanian, TAP AIR PORTUGAL, Air Transat, WestJet Encore, WestJet, KLM, Copa Airlines, Etihad Airways, Korean Air, Egypt Air and Brussels Airlines have Business Class flights to Chicago. Try booking in advance to lower your costs and travel worry-free.

See more FAQs

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First Classfrom C$ 755/person
Prem Econ Classfrom C$ 1,074/person
Economy Classfrom C$ 169/person
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