Cheap First Class flights to Chicago

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

YYZ — CHI
26 Sep — 3 Oct1
1 adult
First
From?
To?
Tue 26/9
Tue 3/10
Best travel deals
Find the best flight deals available from hundreds of sites within seconds
Trusted and free
Cheapflights is 100% free to use. No hidden charges!
Book with flexibility
Easily find flight tickets with no change fees

Cheap first class flights to Chicago in 2023

Quick information regarding your upcoming first class trip to Chicago

Average Price

C$ 2,379

Cheapest Price

C$ 1,015

Top Rated Airline

United Airlines

No. of Airlines

5
Average for round-trip first class flights in September 2023
The lowest price for a first class flight ticket to Chicago
Most popular airline to fly first class with to Chicago in the past 7 days
Airlines that offer first class options for this route

Chicago round-trip first class flight deals

Explore the best, cheapest, and fastest round-trip first class flight tickets going to Chicago found most recently
25 Nov. - 26 Nov.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 00m

4:00 a.m.-5:00 a.m.
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

Nonstop

1h 47m

1:38 p.m.-3:25 p.m.
C$ 750

United Airlines

Pick Dates

Deal found 20/9

30 Dec. - 5 Jan.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

1 stop

4h 07m

8:50 a.m.-11:57 a.m.
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

1 stop

4h 39m

5:35 a.m.-10:14 a.m.
C$ 800

Delta

Pick Dates

Deal found 20/9

22 Nov. - 25 Nov.
YUL

Montreal Pierre Elliott Trudeau Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 56m

1:05 a.m.-3:01 a.m.
ORD

Chicago O'Hare Intl

YUL

Montreal Pierre Elliott Trudeau Intl

Nonstop

2h 17m

1:00 p.m.-3:17 p.m.
C$ 758

United Airlines

Pick Dates

Deal found 19/9

22 Nov. - 25 Nov.
YUL

Montreal Pierre Elliott Trudeau Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 56m

1:05 a.m.-3:01 a.m.
ORD

Chicago O'Hare Intl

YUL

Montreal Pierre Elliott Trudeau Intl

Nonstop

2h 17m

1:00 p.m.-3:17 p.m.
C$ 759

United Airlines

Pick Dates

Deal found 20/9

23 Dec. - 6 Jan.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

1 stop

7h 42m

8:50 a.m.-3:32 p.m.
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

1 stop

8h 04m

2:10 a.m.-10:14 a.m.
C$ 844

Delta

Pick Dates

Deal found 20/9

30 Dec. - 5 Jan.
YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

3h 40m

8:50 a.m.-11:30 a.m.
MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

5h 39m

4:35 a.m.-10:14 a.m.
C$ 844

Delta

Pick Dates

Deal found 20/9

Chicago one-way first class flight deals

Explore the best, cheapest, and fastest one-way first class flight tickets going to Chicago found most recently
19 Oct.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

1 stop

4h 31m

3:44 p.m.-7:15 p.m.
C$ 442

United Airlines

Pick Dates

Deal found 20/9

12 Oct.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

1 stop

7h 27m

8:02 a.m.-2:29 p.m.
C$ 454

Delta

Pick Dates

Deal found 20/9

7 Oct.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 04m

1:30 p.m.-2:34 p.m.
C$ 499

United Airlines

Pick Dates

Deal found 20/9

12 Oct.
YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

6h 11m

8:02 a.m.-1:13 p.m.
C$ 570

Delta

Pick Dates

Deal found 20/9

6 Oct.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

1 stop

9h 30m

10:45 a.m.-7:15 p.m.
C$ 519

United Airlines

Pick Dates

Deal found 20/9

29 Sep.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 04m

5:15 p.m.-6:19 p.m.
C$ 535

United Airlines

Pick Dates

Deal found 20/9

Top first class airline flying to Chicago

Search and compare the best first class tickets to Chicago with popular airlines
AirlineRatingFirst ClassPrice
United AirlinesPriceFrom C$ 275First ClassRating
7.4
Search United Airlines flights

Frequently asked questions about Chicago first class tickets

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

It would cost one person about C$ 2,379 to fly First Class to Chicago, usually. The lowest price a user reported recently is C$ 1,015 (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, Lufthansa and China Eastern have First Class flights to Chicago. Try booking in advance to lower your costs and travel worry-free.

How much do Business Class flight tickets to Chicago cost?

Business flights to Chicago should cost around C$ 2,022 a person. It is worth noting that many users save, on average, 16% choosing Business over First Class while still travelling with comfort.

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: Business Class, First Class and Prem Economy Class.

Search flights to Chicago by cabin class

Business Classfrom C$ 370/person
Prem Economyfrom C$ 638/person
Economyfrom C$ 187/person

Search first class flights to other cities in USA

Browse 2023 first class flight tickets for locations just as great as USA

Expand your first class flight ticket search

Look further for the perfect first class travel experience if you are not set on Chicago
First class flights to USAfrom C$ 1,156/person

Search first class flights to airports around the USA area

Changing airports may help save you money on first class tickets. Here are the closest airports near USA with premium cabin flights available.

Affordable deals for popular routes to Chicago

Want to maximise your travel cost savings even more? Check out these flight routes taken by travellers like you to get to Chicago for all available cabin classes
Toronto Island to Midway flightsfrom from C$ 342 pp/person
Calgary to O'Hare Intl flightsfrom from C$ 344 pp/person
Pearson Intl to O'Hare Intl flightsfrom from C$ 413 pp/person
Ottawa to O'Hare Intl flightsfrom from C$ 507 pp/person
Québec City to O'Hare Intl flightsfrom from C$ 657 pp/person