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

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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

Wed, Oct 28 - Thu, Oct 29

10:29 am - 12:16 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 47mnonstop

1:31 pm - 5:00 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 29mnonstop

$246American Airlines

Tue, Nov 24 - Tue, Nov 24

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

3h 02mnonstop

4:17 pm - 7:45 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 28mnonstop

$246American Airlines

Sat, Nov 21 - Wed, Nov 25

7:35 pm - 9:42 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

3h 07mnonstop

6:00 am - 9:24 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 24mnonstop

$246Delta

Sat, Dec 12 - Mon, Dec 21

7:30 am - 9:32 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

3h 02mnonstop

6:25 pm - 10:00 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 35mnonstop

$246Delta

Sat, Nov 7 - Sat, Nov 14

3:30 pm - 5:10 pmLGA New York LaGuardia-MDW Chicago Midway

2h 40mnonstop

11:50 am - 2:50 pmMDW Chicago Midway-LGA New York LaGuardia

2h 00mnonstop

$246Southwest

Sat, Oct 31 - Sat, Nov 7

10:05 am - 11:25 amLGA New York LaGuardia-MDW Chicago Midway

2h 20mnonstop

3:35 pm - 6:40 pmMDW Chicago Midway-LGA New York LaGuardia

2h 05mnonstop

$246Southwest

Wed, Nov 11 - Sat, Nov 14

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

$247JetBlue

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

$247JetBlue

Recent last minute flight deals from New York to Chicago

Wed, Oct 14 - Wed, Oct 28

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

2h 54mnonstop

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

7h 29m1 stop Boston Logan Intl

$257JetBlue

Wed, Oct 14 - Thu, Dec 3

3:25 pm - 4:45 pmLGA New York LaGuardia-MDW Chicago Midway

2h 20mnonstop

5:00 am - 8:05 amMDW Chicago Midway-LGA New York LaGuardia

2h 05mnonstop

$270Southwest

Sun, Oct 11 - Tue, Oct 27

7:14 am - 9:05 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 51mnonstop

4:25 pm - 7:59 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 34mnonstop

$270American Airlines

Wed, Oct 14 - Tue, Oct 27

3:00 pm - 4:50 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 50mnonstop

8:02 am - 11:40 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 38mnonstop

$270American Airlines

Mon, Oct 12 - Mon, Oct 26

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

2h 57mnonstop

6:10 am - 9:27 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 17mnonstop

$270Delta

Wed, Oct 14 - Thu, Oct 29

7:35 pm - 9:43 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

3h 08mnonstop

1:50 pm - 5:20 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 30mnonstop

$270Delta

Wed, Oct 14 - Wed, Oct 28

5:21 pm - 7:05 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 44mnonstop

6:26 pm - 9:59 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 33mnonstop

$270United Airlines

Wed, Oct 14 - Tue, Oct 27

3:28 pm - 5:12 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

$270United Airlines

Wed, Oct 14 - 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 - 9:29 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

7h 29m1 stop Boston Logan Intl

$270JetBlue

Thu, Oct 15 - Mon, Nov 9

8:55 am - 10:25 amLGA New York LaGuardia-MDW Chicago Midway

2h 30mnonstop

5:00 am - 8:05 amMDW Chicago Midway-LGA New York LaGuardia

2h 05mnonstop

$271Southwest

Recent direct flight deals from New York to Chicago

Sat, Nov 7 - Sat, Nov 14

3:30 pm - 5:10 pmLGA New York LaGuardia-MDW Chicago Midway

2h 40mnonstop

11:50 am - 2:50 pmMDW Chicago Midway-LGA New York LaGuardia

2h 00mnonstop

$246Southwest

Sat, Oct 31 - Sat, Nov 7

10:05 am - 11:25 amLGA New York LaGuardia-MDW Chicago Midway

2h 20mnonstop

3:35 pm - 6:40 pmMDW Chicago Midway-LGA New York LaGuardia

2h 05mnonstop

$246Southwest

Wed, Oct 28 - Thu, Oct 29

10:29 am - 12:16 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 47mnonstop

1:31 pm - 5:00 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 29mnonstop

$246American Airlines

Tue, Nov 24 - Tue, Nov 24

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

3h 02mnonstop

4:17 pm - 7:45 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 28mnonstop

$246American Airlines

Sat, Nov 21 - Wed, Nov 25

7:35 pm - 9:42 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

3h 07mnonstop

6:00 am - 9:24 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 24mnonstop

$246Delta

Sat, Dec 12 - Mon, Dec 21

7:30 am - 9:32 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

3h 02mnonstop

6:25 pm - 10:00 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 35mnonstop

$246Delta

Mon, Feb 15 - Fri, Feb 19

8:15 am - 10:04 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 49mnonstop

3:00 pm - 6:11 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 11mnonstop

$247United Airlines

Mon, Oct 26 - Thu, Oct 29

8:25 pm - 10:16 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 51mnonstop

8:00 am - 11:12 amORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 12mnonstop

$248United Airlines

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

$335JetBlue

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

$336JetBlue

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

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$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

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

FAQs for booking flights from New York State to Chicago

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

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