Cheap First Class Flights to Chicago

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

YYZ — CHI
11 Oct — 18 Oct1
Return
1 adult
First
From?
To?
Tue 11/10
Tue 18/10
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Cheap First Class Flights to Chicago in 2022

Quick information regarding your upcoming first class trip to Chicago
Top Rated AirlineUnited AirlinesMost popular airline to fly first class with to Chicago in the past 7 days
No. of Airlines7Airlines 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
24 Jan. - 7 Feb.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

1 stop

6h 29m

1:00 a.m.-7:29 a.m.
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

1 stop

3h 18m

2:05 a.m.-5:23 a.m.
C$ 272

Delta

Pick Dates

Deal found 4/10/22

25 Oct. - 29 Oct.
YVR

Vancouver Intl

ORD

Chicago O'Hare Intl

Nonstop

4h 12m

2:30 a.m.-6:42 a.m.
ORD

Chicago O'Hare Intl

YVR

Vancouver Intl

Nonstop

4h 44m

3:40 p.m.-8:24 p.m.
C$ 448

United Airlines

Pick Dates

Deal found 5/10/22

23 Oct. - 26 Oct.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

1 stop

3h 40m

2:14 a.m.-5:54 a.m.
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

1 stop

6h 20m

2:00 a.m.-8:20 a.m.
C$ 273

Delta

Pick Dates

Deal found 5/10/22

24 Oct. - 29 Oct.
YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

7h 36m

2:14 a.m.-9:50 a.m.
MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

4h 34m

1:00 p.m.-5:34 p.m.
C$ 332

Delta

Pick Dates

Deal found 6/10/22

18 Nov. - 21 Nov.
YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

3h 42m

1:10 a.m.-4:52 a.m.
MDW

Chicago Midway

YYZ

Toronto Pearson Intl

1 stop

6h 35m

4:30 a.m.-11:05 a.m.
C$ 337

Delta

Pick Dates

Deal found 3/10/22

29 Dec. - 4 Jan.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

1 stop

7h 36m

1:13 a.m.-8:49 a.m.
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

1 stop

4h 40m

1:25 a.m.-6:05 a.m.
C$ 340

Delta

Pick Dates

Deal found 3/10/22

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
27 Oct.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

1 stop

3h 40m

2:14 a.m.-5:54 a.m.
C$ 168

Delta

Pick Dates

Deal found 4/10/22

27 Oct.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 00m

7:05 a.m.-9:05 a.m.
C$ 258

United Airlines

Pick Dates

Deal found 5/10/22

23 Oct.
YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

3h 28m

2:14 a.m.-5:42 a.m.
C$ 168

Delta

Pick Dates

Deal found 4/10/22

11 Nov.
YVR

Vancouver Intl

ORD

Chicago O'Hare Intl

Nonstop

4h 01m

1:45 a.m.-5:46 a.m.
C$ 371

United Airlines

Pick Dates

Deal found 4/10/22

4 Nov.
YVR

Vancouver Intl

ORD

Chicago O'Hare Intl

Nonstop

4h 01m

2:45 a.m.-6:46 a.m.
C$ 374

United Airlines

Pick Dates

Deal found 5/10/22

22 Oct.
YYZ

Toronto Pearson Intl

MDW

Chicago Midway

1 stop

3h 28m

2:14 a.m.-5:42 a.m.
C$ 386

Delta

Pick Dates

Deal found 4/10/22

Top First Class Airline Flying to Chicago

Search and compare the best first class tickets to Chicago with popular airlines
AirlineRatingFirst ClassPrice
Air New ZealandPriceFrom C$ 307First ClassRating
8.2
Search Air New Zealand flights

Frequently asked questions about Chicago First Class tickets

What airlines can I book First Class flights to Chicago with?

United Airlines, Delta, Aer Lingus, Air New Zealand, Copa Airlines, Egypt Air and ANA have First Class flights to Chicago. Try booking in advance to lower your costs and travel worry-free.

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 2 premium cabins provided right now: Business Class and First Class.

Search flights to Chicago by cabin class

Business Classfrom C$ 581/person
Prem Economyfrom C$ 422/person
Economyfrom C$ 129/person