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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
25 May — 1 Jun1
1 adult
Sat 25/5
Sat 1/6
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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 406,307 searches and data were last updated on 20 May 2024.

Average Price

C$ 3,299

Cheapest Price

C$ 1,051

Top Rated Airline

Air Canada

No. of Airlines

34
Average for round-trip business class flights in May 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 20 May 2024. In the last 7 days, Cheapflights users made a total of 406,307 searches.
5 Oct.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

1h 57m

6:48 a.m.-7:45 a.m.
C$ 309

American Airlines

Pick Dates

Deal found 19/5

12 Jun.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 02m

9:00 p.m.-10:02 p.m.
C$ 402

Air Canada

Pick Dates

Deal found 20/5

12 Jun.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

1 stop

4h 31m

6:30 a.m.-10:01 a.m.
C$ 408

Air Canada

Pick Dates

Deal found 20/5

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$ 425

American Airlines

Pick Dates

Deal found 20/5

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$ 440

Air Canada

Pick Dates

Deal found 20/5

25 Aug.
YYC

Calgary

ORD

Chicago O'Hare Intl

1 stop

8h 44m

12:10 a.m.-9:54 a.m.
C$ 581

Air Canada

Pick Dates

Deal found 20/5

Chicago one-way business class flight deals

Discover one-way business class flight deals to Chicago. Fares were last updated on 20 May 2024. In the last 7 days, Cheapflights users made a total of 406,307 searches.
2 Oct. - 13 Oct.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

1h 56m

6:24 p.m.-7:20 p.m.
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

Nonstop

1h 39m

9:50 a.m.-12:29 p.m.
C$ 535

American Airlines

Pick Dates

Deal found 20/5

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

Nonstop

1h 32m

7:26 a.m.-9:58 a.m.
C$ 753

Air Canada

Pick Dates

Deal found 20/5

29 Sep. - 13 Oct.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

1h 57m

11:48 a.m.-12:45 p.m.
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

Nonstop

1h 39m

9:50 a.m.-12:29 p.m.
C$ 551

American Airlines

Pick Dates

Deal found 20/5

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$ 968

Air Canada

Pick Dates

Deal found 20/5

19 Sep. - 22 Sep.
YUL

Montreal Pierre Elliott Trudeau Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 40m

12:45 p.m.-2:25 p.m.
ORD

Chicago O'Hare Intl

YUL

Montreal Pierre Elliott Trudeau Intl

Nonstop

2h 19m

8:15 a.m.-11:34 a.m.
C$ 1,383

American Airlines

Pick Dates

Deal found 19/5

27 Jun. - 1 Jul.
YVR

Vancouver Intl

ORD

Chicago O'Hare Intl

Nonstop

4h 13m

1:25 p.m.-7:38 p.m.
ORD

Chicago O'Hare Intl

YVR

Vancouver Intl

Nonstop

4h 40m

9:50 a.m.-12:30 p.m.
C$ 2,674

American Airlines

Pick Dates

Deal found 20/5

Top business class airline flying to Chicago

Explore the top four business 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 406,307 searches and data was last updated on 20 May 2024.
AirlineRatingFirst ClassPrice
Air CanadaPriceFrom C$ 289First ClassRating
7.0
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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 20 May 2024.

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

    Looking for cheap deals? The cheapest price last booked, C$ 829/person, was for a Business Class flight ticket going from Montreal Pierre Elliott Trudeau Intl Airport to Chicago. Business Class flights usually cost C$ 3,673 per person.

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

    Air Canada, Cathay Pacific, Philippine Airlines, Air India, United Airlines, Emirates, EVA Air, American Airlines, British Airways, WestJet, Finnair, Lufthansa, Jazz, Korean Air, ANA, Air France, Condor, Delta, AeroMexico Connect, Aer Lingus, Icelandair, SWISS, Air Transat, Azul, Aeromexico, Royal Jordanian, TAP AIR PORTUGAL, WestJet Encore, KLM, Caribbean Airlines, 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 26%. The average price a user would pay for Prem Economy Class tickets to Chicago is C$ 2,745.

  • 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

Browse thousands of different options on Cheapflights for your next trip

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

Air Canada flights to Chicago O'Hare Intl

Search flights to Chicago by cabin class

First Classfrom C$ 609/person
Prem Econ Classfrom C$ 798/person
Economy Classfrom C$ 160/person
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