background

Business Class Flight Deals from New York to Chicago from $411

Bundle + Save

Bundle + Save

Top flight deals from leading airlines:

QR LogoSQ LogoNH LogoEK LogoJL LogoTK LogoAF Logo

... and +100s more

Customer-First Commitment

Free cancellation for many rates

Best Price Guarantee

If a VIP member finds a better price elsewhere, we'll refund up to 200% of the difference

Priority Customer Service

VIP member priority support for seamless bookings and exclusive travel benefits

Help 24/7

We’re always here for you - reach us 24 hours a day, 7 days a week

Top Deals on Business Class Flights from New York City to Chicago

New York City, US (NYC) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 29

LGA
2h 33m
Direct

May 29

ORD
American Airlines Logo
American Airlines

Jun 5

ORD
4h 50m
CLT

Jun 5

EWR

as low as

$513

New York City, US (NYC) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 29

LGA
2h 46m
Direct

May 29

ORD
American Airlines Logo
American Airlines

Jun 5

ORD
2h 29m
Direct

Jun 5

EWR

as low as

$520

New York City, US (NYC) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 29

LGA
2h 33m
Direct

May 29

ORD
American Airlines Logo
American Airlines

Jun 5

ORD
2h 29m
Direct

Jun 5

EWR

as low as

$520

New York City, US (NYC) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 29

LGA
2h 33m
Direct

May 29

ORD
American Airlines Logo
American Airlines

Jun 5

ORD
2h 7m
Direct

Jun 5

EWR

as low as

$546

New York City, US (NYC) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 29

LGA
2h 46m
Direct

May 29

ORD
American Airlines Logo
American Airlines

Jun 5

ORD
2h 7m
Direct

Jun 5

EWR

as low as

$546

New York City, US (NYC) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 29

LGA
2h 33m
Direct

May 29

ORD
American Airlines Logo
American Airlines

Jun 5

ORD
2h 2m
Direct

Jun 5

LGA

as low as

$570

New York City, US (NYC) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 29

LGA
2h 46m
Direct

May 29

ORD
American Airlines Logo
American Airlines

Jun 5

ORD
2h 2m
Direct

Jun 5

LGA

as low as

$570

New York City, US (NYC) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 29

LGA
2h 33m
Direct

May 29

ORD
American Airlines Logo
American Airlines

Jun 5

ORD
2h 11m
Direct

Jun 5

EWR

as low as

$576

New York City, US (NYC) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 29

JFK
3h 9m
Direct

May 29

ORD
American Airlines Logo
American Airlines

Jun 5

ORD
2h 29m
Direct

Jun 5

EWR

as low as

$602

New York City, US (NYC) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 29

JFK
3h 9m
Direct

May 29

ORD
American Airlines Logo
American Airlines

Jun 5

ORD
2h 7m
Direct

Jun 5

EWR

as low as

$628

New York City, US (NYC) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 29

JFK
3h 9m
Direct

May 29

ORD
American Airlines Logo
American Airlines

Jun 5

ORD
2h 2m
Direct

Jun 5

LGA

as low as

$652

New York City, US (NYC) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 29

JFK
3h 9m
Direct

May 29

ORD
American Airlines Logo
American Airlines

Jun 5

ORD
2h 11m
Direct

Jun 5

EWR

as low as

$658

Top Deals on Business Class Flights from Buffalo to Chicago

Buffalo, US (BUF) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

BUF
1h 55m
Direct

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
1h 44m
Direct

Jun 6

BUF

as low as

$472

Buffalo, US (BUF) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

BUF
1h 57m
Direct

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
1h 44m
Direct

Jun 6

BUF

as low as

$472

Buffalo, US (BUF) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

BUF
1h 53m
Direct

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
1h 44m
Direct

Jun 6

BUF

as low as

$472

Buffalo, US (BUF) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

BUF
1h 57m
Direct

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
1h 32m
Direct

Jun 6

BUF

as low as

$472

Buffalo, US (BUF) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

BUF
1h 55m
Direct

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
1h 32m
Direct

Jun 6

BUF

as low as

$472

Buffalo, US (BUF) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

BUF
1h 53m
Direct

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
1h 32m
Direct

Jun 6

BUF

as low as

$472

Buffalo, US (BUF) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

BUF
1h 54m
Direct

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
1h 44m
Direct

Jun 6

BUF

as low as

$498

Buffalo, US (BUF) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

BUF
1h 54m
Direct

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
1h 44m
Direct

Jun 6

BUF

as low as

$498

Buffalo, US (BUF) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

BUF
1h 54m
Direct

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
1h 32m
Direct

Jun 6

BUF

as low as

$498

Buffalo, US (BUF) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

BUF
1h 54m
Direct

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
1h 32m
Direct

Jun 6

BUF

as low as

$498

Buffalo, US (BUF) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

BUF
1h 57m
Direct

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
1h 33m
Direct

Jun 6

BUF

as low as

$515

Buffalo, US (BUF) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

BUF
1h 55m
Direct

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
1h 33m
Direct

Jun 6

BUF

as low as

$515

Top Deals on Business Class Flights from Syracuse to Chicago

Syracuse, US (SYR) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

SYR
2h 11m
Direct

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
1h 48m
Direct

Jun 6

SYR

as low as

$411

Syracuse, US (SYR) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

SYR
2h 11m
Direct

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
1h 48m
Direct

Jun 6

SYR

as low as

$411

Syracuse, US (SYR) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

SYR
2h 11m
Direct

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
1h 48m
Direct

Jun 6

SYR

as low as

$411

Syracuse, US (SYR) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

SYR
2h 11m
Direct

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
2h 14m
Direct

Jun 6

SYR

as low as

$445

Syracuse, US (SYR) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

SYR
2h 11m
Direct

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
2h 14m
Direct

Jun 6

SYR

as low as

$445

Syracuse, US (SYR) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

SYR
5h 14m
CLT

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
1h 48m
Direct

Jun 6

SYR

as low as

$495

Syracuse, US (SYR) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

SYR
5h 26m
CLT

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
1h 48m
Direct

Jun 6

SYR

as low as

$495

Syracuse, US (SYR) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

SYR
7h 3m
CLT

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
1h 48m
Direct

Jun 6

SYR

as low as

$495

Syracuse, US (SYR) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

SYR
2h 11m
Direct

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
5h 6m
DCA

Jun 6

SYR

as low as

$495

Syracuse, US (SYR) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

SYR
7h 42m
CLT

May 31

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
1h 48m
Direct

Jun 6

SYR

as low as

$495

Syracuse, US (SYR) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

SYR
2h 11m
Direct

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
5h 6m
DCA

Jun 6

SYR

as low as

$495

Syracuse, US (SYR) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

SYR
2h 11m
Direct

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
3h 39m
DCA

Jun 6

SYR

as low as

$495

Top Deals on Business Class Flights from Albany to Chicago

Albany, US (ALB) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

ALB
2h 28m
Direct

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
2h 14m
Direct

Jun 6

ALB

as low as

$573

Albany, US (ALB) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

ALB
2h 28m
Direct

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
2h 14m
Direct

Jun 6

ALB

as low as

$592

Albany, US (ALB) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

ALB
2h 28m
Direct

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
2h 1m
Direct

Jun 6

ALB

as low as

$607

Albany, US (ALB) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

ALB
2h 28m
Direct

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
2h 1m
Direct

Jun 6

ALB

as low as

$626

Albany, US (ALB) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

ALB
7h 59m
CLT

May 31

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
2h 14m
Direct

Jun 6

ALB

as low as

$627

Albany, US (ALB) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

ALB
5h 31m
CLT

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
2h 14m
Direct

Jun 6

ALB

as low as

$627

Albany, US (ALB) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

ALB
2h 28m
Direct

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
2h 14m
Direct

Jun 6

ALB

as low as

$649

Albany, US (ALB) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

ALB
7h 59m
CLT

May 31

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
2h 1m
Direct

Jun 6

ALB

as low as

$661

Albany, US (ALB) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

ALB
5h 31m
CLT

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
2h 1m
Direct

Jun 6

ALB

as low as

$661

Albany, US (ALB) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

ALB
5h 22m
DCA

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
2h 14m
Direct

Jun 6

ALB

as low as

$677

Albany, US (ALB) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

ALB
2h 28m
Direct

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
2h 1m
Direct

Jun 6

ALB

as low as

$683

Albany, US (ALB) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

ALB
11h 3m
CLT

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
2h 14m
Direct

Jun 6

ALB

as low as

$705

Top Deals on Business Class Flights from Rochester to Chicago

Rochester, US (ROC) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

ROC
2h
Direct

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
1h 37m
Direct

Jun 6

ROC

as low as

$655

Rochester, US (ROC) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

ROC
1h 59m
Direct

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
1h 37m
Direct

Jun 6

ROC

as low as

$655

Rochester, US (ROC) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

ROC
2h
Direct

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
1h 37m
Direct

Jun 6

ROC

as low as

$655

Rochester, US (ROC) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

ROC
2h
Direct

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
4h 9m
DCA

Jun 6

ROC

as low as

$680

Rochester, US (ROC) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

ROC
1h 59m
Direct

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
5h 7m
PHL

Jun 6

ROC

as low as

$680

Rochester, US (ROC) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

ROC
1h 59m
Direct

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
4h 19m
CLT

Jun 6

ROC

as low as

$680

Rochester, US (ROC) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

ROC
2h
Direct

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
4h 9m
DCA

Jun 6

ROC

as low as

$680

Rochester, US (ROC) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

ROC
2h
Direct

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
4h 19m
CLT

Jun 6

ROC

as low as

$680

Rochester, US (ROC) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

ROC
2h
Direct

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
4h 19m
CLT

Jun 6

ROC

as low as

$680

Rochester, US (ROC) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

ROC
2h
Direct

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
5h 7m
PHL

Jun 6

ROC

as low as

$680

Rochester, US (ROC) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

ROC
1h 59m
Direct

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
4h 9m
DCA

Jun 6

ROC

as low as

$680

Rochester, US (ROC) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 30

ROC
2h
Direct

May 30

ORD
American Airlines Logo
American Airlines

Jun 6

ORD
5h 7m
PHL

Jun 6

ROC

as low as

$680

Top Deals on Business Class Flights from White Plains to Chicago

White Plains, US (HPN) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 29

HPN
2h 30m
Direct

May 29

ORD
American Airlines Logo
American Airlines

Jun 5

ORD
2h 9m
Direct

Jun 5

HPN

as low as

$637

White Plains, US (HPN) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 29

HPN
2h 30m
Direct

May 29

ORD
American Airlines Logo
American Airlines

Jun 5

ORD
2h 26m
Direct

Jun 5

HPN

as low as

$637

White Plains, US (HPN) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 29

HPN
2h 30m
Direct

May 29

ORD
American Airlines Logo
American Airlines

Jun 5

ORD
2h 26m
Direct

Jun 5

HPN

as low as

$637

White Plains, US (HPN) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 29

HPN
2h 30m
Direct

May 29

ORD
American Airlines Logo
American Airlines

Jun 5

ORD
2h 9m
Direct

Jun 5

HPN

as low as

$637

White Plains, US (HPN) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 29

HPN
2h 30m
Direct

May 29

ORD
American Airlines Logo
American Airlines

Jun 5

ORD
2h 16m
Direct

Jun 5

HPN

as low as

$637

White Plains, US (HPN) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 29

HPN
2h 30m
Direct

May 29

ORD
American Airlines Logo
American Airlines

Jun 5

ORD
2h 16m
Direct

Jun 5

HPN

as low as

$637

White Plains, US (HPN) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 29

HPN
2h 30m
Direct

May 29

ORD
American Airlines Logo
American Airlines

Jun 5

ORD
2h 10m
Direct

Jun 5

HPN

as low as

$672

White Plains, US (HPN) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 29

HPN
2h 30m
Direct

May 29

ORD
American Airlines Logo
American Airlines

Jun 5

ORD
2h 10m
Direct

Jun 5

HPN

as low as

$672

White Plains, US (HPN) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 29

HPN
6h 39m
CLT

May 30

ORD
American Airlines Logo
American Airlines

Jun 5

ORD
2h 16m
Direct

Jun 5

HPN

as low as

$699

White Plains, US (HPN) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 29

HPN
6h 39m
CLT

May 30

ORD
American Airlines Logo
American Airlines

Jun 5

ORD
2h 9m
Direct

Jun 5

HPN

as low as

$699

White Plains, US (HPN) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 29

HPN
2h 34m
Direct

May 29

ORD
American Airlines Logo
American Airlines

Jun 5

ORD
2h 9m
Direct

Jun 5

HPN

as low as

$710

White Plains, US (HPN) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 29

HPN
2h 34m
Direct

May 29

ORD
American Airlines Logo
American Airlines

Jun 5

ORD
2h 16m
Direct

Jun 5

HPN

as low as

$710