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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
23 Apr — 30 Apr1
1 adult
Tue 23/4
Tue 30/4
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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 507,522 searches and data were last updated on 18 April 2024.

Average Price

C$ 2,492

Cheapest Price

C$ 802

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 18 April 2024. In the last 7 days, Cheapflights users made a total of 507,522 searches.
6 Oct.
YUL

Montreal Pierre Elliott Trudeau Intl

ORD

Chicago O'Hare Intl

1 stop

4h 53m

6:00 a.m.-9:53 a.m.
C$ 436

Air Canada

Pick Dates

Deal found 18/4

6 Oct.
YUL

Montreal Pierre Elliott Trudeau Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 42m

6:03 p.m.-7:45 p.m.
C$ 722

American Airlines

Pick Dates

Deal found 17/4

6 Oct.
YUL

Montreal Pierre Elliott Trudeau Intl

ORD

Chicago O'Hare Intl

1 stop

4h 53m

6:00 a.m.-9:53 a.m.
C$ 439

Air Canada

Pick Dates

Deal found 17/4

8 May
YUL

Montreal Pierre Elliott Trudeau Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 36m

8:30 a.m.-10:06 a.m.
C$ 453

Air Canada

Pick Dates

Deal found 18/4

8 May
YUL

Montreal Pierre Elliott Trudeau Intl

ORD

Chicago O'Hare Intl

1 stop

4h 54m

6:00 a.m.-9:54 a.m.
C$ 455

Air Canada

Pick Dates

Deal found 18/4

6 Oct.
YUL

Montreal Pierre Elliott Trudeau Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 30m

6:40 p.m.-8:10 p.m.
C$ 468

Air Canada

Pick Dates

Deal found 17/4

Chicago one-way business class flight deals

Discover one-way business class flight deals to Chicago. Fares were last updated on 18 April 2024. In the last 7 days, Cheapflights users made a total of 507,522 searches.
5 Oct. - 13 Oct.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

1h 53m

2:00 p.m.-2:53 p.m.
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

Nonstop

1h 53m

5:08 p.m.-8:01 p.m.
C$ 778

Air Canada

Pick Dates

Deal found 18/4

27 Jul. - 1 Aug.
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

10:55 a.m.-2:13 p.m.
C$ 1,317

United Airlines

Pick Dates

Deal found 16/4

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

Nonstop

1h 53m

5:08 p.m.-8:01 p.m.
C$ 785

Air Canada

Pick Dates

Deal found 18/4

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

1 stop

5h 59m

3:35 p.m.-10:34 p.m.
C$ 792

Air Canada

Pick Dates

Deal found 18/4

29 May - 30 May
YVR

Vancouver Intl

ORD

Chicago O'Hare Intl

1 stop

19h 42m

7:36 a.m.-5:18 a.m.
ORD

Chicago O'Hare Intl

YVR

Vancouver Intl

1 stop

21h 47m

2:01 a.m.-9:48 p.m.
C$ 2,581

Aeromexico

Pick Dates

Deal found 17/4

17 Aug. - 22 Aug.
YOW

Ottawa

ORD

Chicago O'Hare Intl

Nonstop

2h 25m

5:30 p.m.-6:55 p.m.
ORD

Chicago O'Hare Intl

YOW

Ottawa

Nonstop

2h 20m

6:29 p.m.-9:49 p.m.
C$ 1,307

Air Canada

Pick Dates

Deal found 17/4

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 18 April 2024.

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

    Looking for cheap deals? The cheapest price last booked, C$ 802/person, was for a Business Class flight ticket going from Toronto Pearson Intl Airport to Chicago. Business Class flights usually cost C$ 2,492 per person.

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

    Air Canada, Cathay Pacific, Air India, United Airlines, Philippine 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 5%. The average price a user would pay for Prem Economy Class tickets to Chicago is C$ 2,381.

  • 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$ 448/person
Prem Econ Classfrom C$ 943/person
Economy Classfrom C$ 172/person
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