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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
2 May — 9 May1
1 adult
Thu 2/5
Thu 9/5
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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 504,135 searches and data were last updated on 27 April 2024.

Average Price

C$ 2,563

Cheapest Price

C$ 867

Top Rated Airline

Air Canada

No. of Airlines

32
Average for round-trip business class flights in April 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 27 April 2024. In the last 7 days, Cheapflights users made a total of 504,135 searches.
22 Jun.
YVR

Vancouver Intl

ORD

Chicago O'Hare Intl

1 stop

9h 59m

9:55 p.m.-9:54 a.m.
C$ 771

Air Canada

Pick Dates

Deal found 26/4

10 Jun.
YUL

Montreal Pierre Elliott Trudeau Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 36m

5:20 p.m.-6:56 p.m.
C$ 893

American Airlines

Pick Dates

Deal found 26/4

13 Sep.
YVR

Vancouver Intl

ORD

Chicago O'Hare Intl

Nonstop

4h 11m

8:15 a.m.-2:26 p.m.
C$ 797

Air Canada

Pick Dates

Deal found 26/4

22 Jun.
YVR

Vancouver Intl

ORD

Chicago O'Hare Intl

Nonstop

4h 13m

1:25 p.m.-7:38 p.m.
C$ 1,229

American Airlines

Pick Dates

Deal found 26/4

22 Jun.
YVR

Vancouver Intl

ORD

Chicago O'Hare Intl

Nonstop

4h 13m

1:25 p.m.-7:38 p.m.
C$ 1,230

American Airlines

Pick Dates

Deal found 27/4

17 May
YOW

Ottawa

ORD

Chicago O'Hare Intl

Nonstop

2h 25m

6:35 a.m.-8:00 a.m.
C$ 1,544

Air Canada

Pick Dates

Deal found 26/4

Chicago one-way business class flight deals

Discover one-way business class flight deals to Chicago. Fares were last updated on 27 April 2024. In the last 7 days, Cheapflights users made a total of 504,135 searches.
11 Jun. - 12 Jun.
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 35m

11:54 a.m.-2:29 p.m.
C$ 689

American Airlines

Pick Dates

Deal found 25/4

5 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 48m

12:04 p.m.-2:52 p.m.
C$ 741

Air Canada

Pick Dates

Deal found 27/4

26 Jun. - 10 Jul.
YUL

Montreal Pierre Elliott Trudeau Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 31m

8:30 a.m.-10:01 a.m.
ORD

Chicago O'Hare Intl

YUL

Montreal Pierre Elliott Trudeau Intl

Nonstop

2h 18m

3:35 p.m.-6:53 p.m.
C$ 943

United Airlines

Pick Dates

Deal found 26/4

5 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

Nonstop

1h 48m

12:04 p.m.-2:52 p.m.
C$ 748

Air Canada

Pick Dates

Deal found 27/4

8 Aug. - 19 Aug.
YYC

Calgary

ORD

Chicago O'Hare Intl

Nonstop

3h 21m

1:24 p.m.-5:45 p.m.
ORD

Chicago O'Hare Intl

YYC

Calgary

Nonstop

3h 37m

9:55 a.m.-12:32 p.m.
C$ 1,676

WestJet Encore

Pick Dates

Deal found 27/4

5 Oct. - 13 Oct.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

1 stop

5h 27m

8:10 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$ 962

Air Canada

Pick Dates

Deal found 27/4

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 27 April 2024.

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

    Looking for cheap deals? The cheapest price last booked, C$ 867/person, was for a Business Class flight ticket going from Toronto Pearson Intl Airport to Chicago. Business Class flights usually cost C$ 2,563 per person.

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

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

  • 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 8%. The average price a user would pay for Prem Economy Class tickets to Chicago is C$ 2,368.

  • 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.

See more FAQs

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First Classfrom C$ 444/person
Prem Econ Classfrom C$ 825/person
Economy Classfrom C$ 173/person
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