How does KAYAK find such low prices on flights from New York State to Chicago?

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from New York State to Chicago.

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from New York State to Chicago?

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from New York State is likely to change within 7 days, so travelers know whether to wait or book now.

What is the Hacker Fare option on flights from New York State to Chicago?

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to New York State with another airline.

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from New York State to Chicago?

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from New York State up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

$88 CHEAP FLIGHTS from New York State to Chicago

Save 19% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals

Cheap Flights from New York to Chicago

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

Last minute

Direct

Recent round-trip flight deals from New York to Chicago

Fri, Nov 13 - Thu, Nov 19

1:48 pm - 6:45 pmBUF Buffalo-ORD Chicago O'Hare Intl

5h 57m1 stop Atlanta Hartsfield-Jackson

7:31 am - 1:49 pmORD Chicago O'Hare Intl-BUF Buffalo

5h 18m1 stop Atlanta Hartsfield-Jackson

$229Frontier

Fri, Nov 13 - Thu, Nov 19

1:48 pm - 11:47 pmBUF Buffalo-MDW Chicago Midway

10h 59m1 stop Atlanta Hartsfield-Jackson

6:08 am - 1:49 pmMDW Chicago Midway-BUF Buffalo

6h 41m1 stop Atlanta Hartsfield-Jackson

$229Frontier

Thu, Dec 31 - Tue, Jan 5

6:40 am - 8:05 amLGA New York LaGuardia-MDW Chicago Midway

2h 25mnonstop

12:30 pm - 3:35 pmMDW Chicago Midway-LGA New York LaGuardia

2h 05mnonstop

$247Southwest

Sat, Dec 5 - Mon, Dec 7

7:25 am - 9:00 amLGA New York LaGuardia-MDW Chicago Midway

2h 35mnonstop

4:55 pm - 8:00 pmMDW Chicago Midway-LGA New York LaGuardia

2h 05mnonstop

$247Southwest

Wed, Nov 11 - Wed, Nov 18

6:40 am - 12:00 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

6h 20m1 stop Boston Logan Intl

1:00 pm - 7:59 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

5h 59m1 stop Boston Logan Intl

$248JetBlue

Wed, Nov 11 - Tue, Nov 17

6:40 am - 12:00 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

6h 20m1 stop Boston Logan Intl

1:00 pm - 9:29 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

7h 29m1 stop Boston Logan Intl

$248JetBlue

Thu, Nov 5 - Sat, Nov 7

2:59 pm - 4:55 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 56mnonstop

6:44 am - 10:09 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 25mnonstop

$249American Airlines

Tue, Nov 24 - Thu, Nov 26

7:45 am - 9:47 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

3h 02mnonstop

6:03 am - 9:25 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 22mnonstop

$249American Airlines

Sun, Nov 22 - Tue, Nov 24

7:15 am - 9:06 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 51mnonstop

6:00 am - 9:07 amORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 07mnonstop

$250Delta

Fri, Dec 11 - Tue, Dec 15

7:36 pm - 9:36 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

3h 00mnonstop

6:00 am - 9:20 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 20mnonstop

$251Delta

Recent last minute flight deals from New York to Chicago

Thu, Oct 8 - Wed, Dec 9

7:30 am - 9:27 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 57mnonstop

1:35 pm - 5:05 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 30mnonstop

$270Delta

Thu, Oct 8 - Wed, Dec 9

7:59 am - 9:48 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 49mnonstop

3:42 pm - 7:00 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 18mnonstop

$270American Airlines

Thu, Oct 8 - Wed, Nov 11

9:10 am - 10:54 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 44mnonstop

7:00 am - 10:09 amORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 09mnonstop

$270United Airlines

Tue, Oct 13 - Tue, Oct 27

9:30 am - 11:24 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 54mnonstop

1:00 pm - 7:59 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

5h 59m1 stop Boston Logan Intl

$271JetBlue

Thu, Oct 8 - Wed, Dec 9

6:05 am - 12:00 pmLGA New York LaGuardia-MDW Chicago Midway

6h 55m1 stop Lambert-St Louis

12:30 pm - 3:35 pmMDW Chicago Midway-LGA New York LaGuardia

2h 05mnonstop

$280Southwest

Thu, Oct 8 - Wed, Nov 11

6:05 am - 12:00 pmLGA New York LaGuardia-MDW Chicago Midway

6h 55m1 stop Lambert-St Louis

1:55 pm - 5:00 pmMDW Chicago Midway-LGA New York LaGuardia

2h 05mnonstop

$280Southwest

Thu, Oct 8 - Wed, Dec 9

7:10 am - 10:29 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

4h 19m1 stop Detroit Metropolitan Wayne County

6:00 am - 9:20 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 20mnonstop

$280Delta

Thu, Oct 8 - Wed, Nov 11

11:30 am - 3:37 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

5h 07m1 stop Boston Logan Intl

6:59 am - 10:19 amORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 20mnonstop

$280American Airlines

Tue, Oct 13 - Wed, Oct 14

9:30 am - 11:24 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 54mnonstop

9:38 am - 5:29 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

6h 51m1 stop Boston Logan Intl

$321JetBlue

Sat, Oct 10 - Mon, Oct 26

6:29 pm - 8:13 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 44mnonstop

2:00 pm - 5:15 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 15mnonstop

$326United Airlines

Recent direct flight deals from New York to Chicago

Thu, Dec 31 - Tue, Jan 5

6:40 am - 8:05 amLGA New York LaGuardia-MDW Chicago Midway

2h 25mnonstop

12:30 pm - 3:35 pmMDW Chicago Midway-LGA New York LaGuardia

2h 05mnonstop

$247Southwest

Sat, Dec 5 - Mon, Dec 7

7:25 am - 9:00 amLGA New York LaGuardia-MDW Chicago Midway

2h 35mnonstop

4:55 pm - 8:00 pmMDW Chicago Midway-LGA New York LaGuardia

2h 05mnonstop

$247Southwest

Mon, Oct 26 - Tue, Oct 27

9:16 pm - 11:00 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 44mnonstop

1:45 pm - 5:06 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 21mnonstop

$249American Airlines

Thu, Nov 5 - Sat, Nov 7

2:59 pm - 4:55 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 56mnonstop

6:44 am - 10:09 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 25mnonstop

$249American Airlines

Sun, Nov 22 - Tue, Nov 24

7:15 am - 9:06 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 51mnonstop

6:00 am - 9:07 amORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 07mnonstop

$250Delta

Wed, Nov 11 - Sun, Nov 15

11:20 am - 1:08 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 48mnonstop

7:00 am - 10:15 amORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 15mnonstop

$251Delta

Thu, Dec 31 - Sun, Jan 3

2:30 pm - 4:13 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 43mnonstop

10:05 am - 1:22 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 17mnonstop

$251United Airlines

Mon, Jan 25 - Sun, Jan 31

11:20 am - 1:08 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 48mnonstop

11:59 am - 3:14 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 15mnonstop

$251United Airlines

Fri, Oct 23 - Sat, Oct 24

8:15 pm - 10:10 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 55mnonstop

12:38 pm - 4:00 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 22mnonstop

$298JetBlue

Wed, Oct 21 - Sat, Oct 24

9:30 am - 11:24 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 54mnonstop

12:38 pm - 4:00 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 22mnonstop

$317JetBlue

Useful Info

Low season	January
High season	July
Cheapest flight	$88

Best time to beat the crowds with an average 19% drop in price.

Most popular time to fly with an average 4% increase in price.

Flight from Buffalo to Chicago O'Hare Airport

kelechiFlew with United Airlines-Jul 2026

Leave enough time for connecting in Chicago. It’s a very busy airport

SheenaFlew with Southwest-Jun 2024

Get to the airport early. NY airports are always busy, even when you have TSA pre check

How does KAYAK find such low prices on flights from New York State to Chicago?
KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from New York State to Chicago.
How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from New York State to Chicago?
KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from New York State is likely to change within 7 days, so travelers know whether to wait or book now.
What is the Hacker Fare option on flights from New York State to Chicago?
Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to New York State with another airline.
What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from New York State to Chicago?
Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from New York State up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Merrillville

Hammond

Saint Joseph

Portage

Lansing

Valparaiso

Chesterton

Schererville

Munster

Porter

Monticello

Saint John

Griffith

More options for your flight to Chicago

Add a hotel or car rental

Cabin class

Direct Flights

Origins

Other airports

Other destinations

Return flight

Complete your trip to Chicago with a hotel stay or car rental

Car rentals in Chicago

$88 Find Cheap Flights from New York State to Chicago - Compare and Save

Cheap Flights from New York to Chicago

Recent round-trip flight deals from New York to Chicago

Recent one-way flight deals from New York to Chicago

Recent last minute flight deals from New York to Chicago

Recent direct flight deals from New York to Chicago

Good to know

Low season

High season

Cheapest flight

Flights from New York to Chicago: the best tips from KAYAK users

FAQs for booking flights from New York State to Chicago

Traveling to a place near Chicago?

More options for your flight to Chicago

Complete your trip to Chicago with a hotel stay or car rental

Cabin class types available on flights to New York

Find direct flights for Chicago

Flights from domestic origins to Chicago

Choose which airport to fly into in Chicago

Flights to other popular destinations

Find deals for your return flight