Top flight deals from leading airlines:

... and +100s more

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Free cancellation for many rates

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Help 24/7

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Stops

Up to nonstop

$432

Up to 1 stop

$4275

Airlines

American Airlines
$432
United Airlines
$4275

Cabin Class

First

$432

Business

$4275

Departure Airports

New York John F Kennedy Airport
$454
New York LaGuardia Airport
$468
Newark Liberty Airport
$432

Arrival Airports

Chicago O Hare Airport
$432

Layover Airports

Cleveland Hopkins International Airport
$4275
Reagan Washington National Airport
$4275

Best Price. GUARANTEED.

Exclusively for Priceline Members
Tired of searching? Book now!
We'll refund the difference if you find a lower price.

American Airlines

05/16/26

6:35am

EWR

2h 50m

Direct

05/16/26

8:25am

ORD

American Airlines

05/23/26

8:15pm

ORD

2h 15m

Direct

05/23/26

11:30pm

EWR

^$432

American Airlines

05/16/26

7:10am

EWR

2h 52m

Direct

05/16/26

9:02am

ORD

American Airlines

05/23/26

6:47am

ORD

2h 15m

Direct

05/23/26

10:02am

EWR

^$450

American Airlines

05/16/26

6:35am

EWR

2h 50m

Direct

05/16/26

8:25am

ORD

American Airlines

05/23/26

6:47am

ORD

2h 15m

Direct

05/23/26

10:02am

EWR

^$450

Bundle + Save

Book a flight & hotel together for extra savings.

On average save $240 per traveler

American Airlines

05/16/26

6:35am

EWR

2h 50m

Direct

05/16/26

8:25am

ORD

American Airlines

05/23/26

1:12pm

ORD

2h 19m

Direct

05/23/26

4:31pm

EWR

^$454

American Airlines

05/16/26

7:10am

EWR

2h 52m

Direct

05/16/26

9:02am

ORD

American Airlines

05/23/26

8:15pm

ORD

2h 15m

Direct

05/23/26

11:30pm

EWR

^$454

American Airlines

05/16/26

9:03am

JFK

2h 55m

Direct

05/16/26

10:58am

ORD

American Airlines

05/23/26

8:15pm

ORD

2h 15m

Direct

05/23/26

11:30pm

EWR

^$454

American Airlines

05/16/26

6:35am

EWR

2h 50m

Direct

05/16/26

8:25am

ORD

American Airlines

05/23/26

3:24pm

ORD

2h 35m

Direct

05/23/26

6:59pm

JFK

^$454

American Airlines

05/16/26

6:35am

EWR

2h 50m

Direct

05/16/26

8:25am

ORD

American Airlines

05/23/26

5:39pm

ORD

2h 21m

Direct

05/23/26

9:00pm

EWR

^$454

American Airlines

05/16/26

6:38am

LGA

2h 53m

Direct

05/16/26

8:31am

ORD

American Airlines

05/23/26

8:15pm

ORD

2h 15m

Direct

05/23/26

11:30pm

EWR

^$468

American Airlines

05/16/26

6:35am

EWR

2h 50m

Direct

05/16/26

8:25am

ORD

American Airlines

05/23/26

8:23pm

ORD

2h 14m

Direct

05/23/26

11:37pm

LGA

^$468

American Airlines

05/16/26

8:59pm

LGA

2h 48m

Direct

05/16/26

10:47pm

ORD

American Airlines

05/23/26

8:15pm

ORD

2h 15m

Direct

05/23/26

11:30pm

EWR

^$468

American Airlines

05/16/26

9:03am

JFK

2h 55m

Direct

05/16/26

10:58am

ORD

American Airlines

05/23/26

6:47am

ORD

2h 15m

Direct

05/23/26

10:02am

EWR

^$472

American Airlines

05/16/26

5:20pm

EWR

Direct

05/16/26

7:20pm

ORD

American Airlines

05/23/26

8:15pm

ORD

2h 15m

Direct

05/23/26

11:30pm

EWR

^$474

Bundle + Save

Book a flight & hotel together for extra savings.

On average save $240 per traveler

American Airlines

05/16/26

7:10am

EWR

2h 52m

Direct

05/16/26

9:02am

ORD

American Airlines

05/23/26

5:39pm

ORD

2h 21m

Direct

05/23/26

9:00pm

EWR

^$476

American Airlines

05/16/26

7:10am

EWR

2h 52m

Direct

05/16/26

9:02am

ORD

American Airlines

05/23/26

3:24pm

ORD

2h 35m

Direct

05/23/26

6:59pm

JFK

^$476

American Airlines

05/16/26

7:10am

EWR

2h 52m

Direct

05/16/26

9:02am

ORD

American Airlines

05/23/26

1:12pm

ORD

2h 19m

Direct

05/23/26

4:31pm

EWR

^$476

American Airlines

05/16/26

9:03am

JFK

2h 55m

Direct

05/16/26

10:58am

ORD

American Airlines

05/23/26

5:39pm

ORD

2h 21m

Direct

05/23/26

9:00pm

EWR

^$476

American Airlines

05/16/26

9:03am

JFK

2h 55m

Direct

05/16/26

10:58am

ORD

American Airlines

05/23/26

3:24pm

ORD

2h 35m

Direct

05/23/26

6:59pm

JFK

^$476

American Airlines

05/16/26

9:03am

JFK

2h 55m

Direct

05/16/26

10:58am

ORD

American Airlines

05/23/26

1:12pm

ORD

2h 19m

Direct

05/23/26

4:31pm

EWR

^$476

American Airlines

05/16/26

7:29am

LGA

2h 53m

Direct

05/16/26

9:22am

ORD

American Airlines

05/23/26

6:47am

ORD

2h 15m

Direct

05/23/26

10:02am

EWR

^$486

American Airlines

05/16/26

6:38am

LGA

2h 53m

Direct

05/16/26

8:31am

ORD

American Airlines

05/23/26

6:47am

ORD

2h 15m

Direct

05/23/26

10:02am

EWR

^$486

American Airlines

05/16/26

8:59pm

LGA

2h 48m

Direct

05/16/26

10:47pm

ORD

American Airlines

05/23/26

6:47am

ORD

2h 15m

Direct

05/23/26

10:02am

EWR

^$486

American Airlines

05/16/26

7:10am

EWR

2h 52m

Direct

05/16/26

9:02am

ORD

American Airlines

05/23/26

8:23pm

ORD

2h 14m

Direct

05/23/26

11:37pm

LGA

^$490

Bundle + Save

Book a flight & hotel together for extra savings.

On average save $240 per traveler

American Airlines

05/16/26

6:38am

LGA

2h 53m

Direct

05/16/26

8:31am

ORD

American Airlines

05/23/26

1:12pm

ORD

2h 19m

Direct

05/23/26

4:31pm

EWR

^$490

American Airlines

05/16/26

9:03am

JFK

2h 55m

Direct

05/16/26

10:58am

ORD

American Airlines

05/23/26

8:23pm

ORD

2h 14m

Direct

05/23/26

11:37pm

LGA

^$490

American Airlines

05/16/26

8:59pm

LGA

2h 48m

Direct

05/16/26

10:47pm

ORD

American Airlines

05/23/26

1:12pm

ORD

2h 19m

Direct

05/23/26

4:31pm

EWR

^$490

American Airlines

05/16/26

8:59pm

LGA

2h 48m

Direct

05/16/26

10:47pm

ORD

American Airlines

05/23/26

5:39pm

ORD

2h 21m

Direct

05/23/26

9:00pm

EWR

^$490

American Airlines

05/16/26

10:42am

EWR

2h 46m

Direct

05/16/26

12:28pm

ORD

American Airlines

05/23/26

6:00am

ORD

2h 12m

Direct

05/23/26

9:12am

LGA

^$540

United Airlines

05/16/26

8:00am

EWR

4h 51m

DCA

05/16/26

11:51am

ORD

United Airlines

05/16/26

12:53pm

ORD

7h 17m

CLE

05/16/26

9:10pm

EWR

^$4275

Top Deals on flights Business Class from New York City to Chicago O Hare Airport

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

American Airlines

Jun 24

6:59am

EWR

2h 46m

Direct

Jun 24

8:45am

ORD

as low as

^$216

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

United Airlines

May 17

4:00pm

EWR

6h 41m

DCA

May 17

9:41pm

ORD

as low as

^$3358

Good to Know

Essential information to help you plan your flight Business Class from New York City to Chicago O Hare Airport

Cheapest Flight

$216

The lowest price we found in the last two weeks, departing Jun 24 and returning Jun 24

2h 46m ‧ business

Fastest Flights

$540

The fastest flight that we found in the last two weeks, departing May 16 and returning May 23

2h 46m ‧ first

Cheapest Flight Round-trip

$432

Cheapest price found in the last 14 days, departing May 16 and returning May 23

2h 50m ‧ first

Cheapest Flight One-way

$216

Cheapest price found in the last 14 days, departing Jun 24

2h 46m ‧ business

Cheapest Layover airport

$3358

The cheapest layover airport to Chicago is currently $3358

1 stop ‧ 6h 41m ‧ business

Best Arrival airport

$216

The best arrival airport to Chicago is currently $216

2h 46m ‧ business

Best Departure airport

$216

The best departure airport to Chicago is currently $216

2h 46m ‧ business

Cheapest Airline

$216

The cheapest airline to Chicago is currently $216

2h 46m ‧ business

Flights to Chicago

Flights
North America
United States
Illinois
Chicago
Chicago O Hare Airport

Top Destinations

Origins

Return flights

Cabin Class

Flights
North America
United States
New York
New York City

➔ Business Class Flights From Newark Liberty Airport To Chicago O Hare Airport ➔ Business Class Flights From New York Laguardia Airport To Chicago O Hare Airport

➔ Business Class Flights From Chicago O Hare Airport To New York City

➔ Flights From New York City To Chicago O Hare Airport

Business Class Flight Deals from New York City to Chicago O Hare Airport from $216

Stops

Airlines

Cabin Class

Departure Airports

Arrival Airports

Layover Airports

Best Price. GUARANTEED.

Top Deals on flights Business Class from New York City to Chicago O Hare Airport

Good to Know

Flights to Chicago