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.

$104 CHEAP FLIGHTS from New York State to Chicago

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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

Sat, Nov 21 - Tue, Nov 24

1:03 pm - 12:43 amBUF Buffalo-ORD Chicago O'Hare Intl

12h 40m1 stop Orlando

5:40 am - 8:24 pmORD Chicago O'Hare Intl-BUF Buffalo

13h 44m1 stop Orlando

$198Frontier

Mon, Jan 25 - Wed, Jan 27

9:38 pm - 3:56 pmBUF Buffalo-ORD Chicago O'Hare Intl

19h 18m1 stop Orlando

5:01 am - 8:43 pmORD Chicago O'Hare Intl-BUF Buffalo

14h 42m1 stop Orlando

$217Frontier

Tue, Feb 2 - Tue, Feb 2

10:26 am - 2:00 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

4h 34m1 stop Detroit Metropolitan Wayne County

3:44 pm - 7:00 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 16mnonstop

$251American Airlines

Mon, Nov 23 - Mon, Nov 23

10:12 am - 12:11 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 59mnonstop

1:55 pm - 8:00 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

5h 05m1 stop Cleveland Hopkins Intl

$259American Airlines

Sat, Feb 6 - Thu, Feb 11

5:30 am - 2:50 pmALB Albany Intl-MDW Chicago Midway

10h 20m2 stops Baltimore/Washington Atlanta Hartsfield-Jackson

7:45 am - 2:00 pmMDW Chicago Midway-ALB Albany Intl

5h 15m2 stops Pittsburgh Baltimore/Washington

$267Southwest

Mon, Nov 23 - Thu, Nov 26

6:45 am - 8:15 pmALB Albany Intl-MDW Chicago Midway

14h 30m2 stops Tampa Birmingham

7:40 am - 5:00 pmMDW Chicago Midway-ALB Albany Intl

8h 20m2 stops Hartford Bradley Intl Baltimore/Washington

$273Southwest

Mon, Dec 21 - Tue, Dec 29

10:50 am - 12:50 pmALB Albany Intl-ORD Chicago O'Hare Intl

3h 00mnonstop

6:50 am - 10:09 amORD Chicago O'Hare Intl-ALB Albany Intl

2h 19mnonstop

$273United Airlines

Mon, Feb 15 - Thu, Feb 18

4:45 pm - 6:35 pmALB Albany Intl-ORD Chicago O'Hare Intl

2h 50mnonstop

11:59 am - 3:05 pmORD Chicago O'Hare Intl-ALB Albany Intl

2h 06mnonstop

$276United Airlines

Wed, Dec 16 - Mon, Jan 11

9:30 am - 4:42 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

8h 12m1 stop Boston Logan Intl

2:55 pm - 9:48 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

5h 53m1 stop Boston Logan Intl

$278JetBlue

Thu, Jan 28 - Sat, Jan 30

9:30 am - 1:49 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

5h 19m1 stop Boston Logan Intl

2:55 pm - 9:48 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

5h 53m1 stop Boston Logan Intl

$297JetBlue

Recent last minute flight deals from New York to Chicago

Tue, Nov 10 - Tue, Nov 17

9:29 am - 5:47 pmLGA New York LaGuardia-MDW Chicago Midway

9h 18m1 stop Atlanta Hartsfield-Jackson

6:08 am - 7:35 pmMDW Chicago Midway-LGA New York LaGuardia

12h 27m1 stop Atlanta Hartsfield-Jackson

$258Frontier

Tue, Nov 10 - Tue, Nov 17

6:30 am - 6:30 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

13h 00m1 stop Atlanta Hartsfield-Jackson

7:35 pm - 8:34 amORD Chicago O'Hare Intl-LGA New York LaGuardia

11h 59m1 stop Atlanta Hartsfield-Jackson

$258Frontier

Thu, Nov 5 - Mon, Dec 7

3:05 pm - 4:45 pmLGA New York LaGuardia-MDW Chicago Midway

2h 40mnonstop

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

2h 05mnonstop

$397Southwest

Sun, Nov 8 - Mon, Dec 7

8:55 pm - 10:30 pmLGA New York LaGuardia-MDW Chicago Midway

2h 35mnonstop

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

2h 05mnonstop

$397Southwest

Mon, Nov 9 - Sat, Dec 12

12:22 pm - 2:14 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 52mnonstop

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

2h 18mnonstop

$397American Airlines

Mon, Nov 9 - Mon, Nov 23

7:50 pm - 9:39 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 49mnonstop

8:05 am - 11:24 amORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 19mnonstop

$397American Airlines

Fri, Nov 6 - Mon, Dec 7

6:59 pm - 8:43 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 44mnonstop

6:00 am - 9:18 amORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 18mnonstop

$397Delta

Mon, Nov 9 - Sat, Dec 12

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

2h 51mnonstop

6:10 pm - 9:31 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 21mnonstop

$397Delta

Fri, Nov 6 - Mon, Nov 16

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

2h 51mnonstop

8:45 am - 12:03 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 18mnonstop

$422United Airlines

Mon, Nov 9 - Sun, Nov 15

6:05 am - 7:51 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 46mnonstop

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

2h 12mnonstop

$422United Airlines

Recent direct flight deals from New York to Chicago

Mon, Dec 21 - Tue, Dec 29

10:50 am - 12:50 pmALB Albany Intl-ORD Chicago O'Hare Intl

3h 00mnonstop

6:50 am - 10:09 amORD Chicago O'Hare Intl-ALB Albany Intl

2h 19mnonstop

$273United Airlines

Mon, Nov 23 - Tue, Nov 24

7:20 pm - 9:24 pmALB Albany Intl-ORD Chicago O'Hare Intl

3h 04mnonstop

8:43 pm - 11:59 pmORD Chicago O'Hare Intl-ALB Albany Intl

2h 16mnonstop

$276American Airlines

Mon, Nov 23 - Tue, Nov 24

7:55 am - 9:15 amALB Albany Intl-MDW Chicago Midway

2h 20mnonstop

7:00 pm - 9:55 pmMDW Chicago Midway-ALB Albany Intl

1h 55mnonstop

$276Southwest

Thu, Dec 3 - Mon, Dec 7

7:50 am - 9:10 amALB Albany Intl-MDW Chicago Midway

2h 20mnonstop

6:25 pm - 9:25 pmMDW Chicago Midway-ALB Albany Intl

2h 00mnonstop

$276Southwest

Mon, Feb 15 - Thu, Feb 18

4:45 pm - 6:35 pmALB Albany Intl-ORD Chicago O'Hare Intl

2h 50mnonstop

11:59 am - 3:05 pmORD Chicago O'Hare Intl-ALB Albany Intl

2h 06mnonstop

$276United Airlines

Mon, Dec 28 - Fri, Jan 1

8:05 pm - 10:00 pmALB Albany Intl-ORD Chicago O'Hare Intl

2h 55mnonstop

8:26 am - 11:40 amORD Chicago O'Hare Intl-ALB Albany Intl

2h 14mnonstop

$276American Airlines

Wed, Jan 13 - Sat, Jan 16

7:50 pm - 9:52 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

3h 02mnonstop

1:25 pm - 4:45 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 20mnonstop

$297Delta

Tue, Jan 12 - Tue, Jan 19

7:56 am - 10:00 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

3h 04mnonstop

1:25 pm - 4:45 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 20mnonstop

$297Delta

Tue, Dec 8 - Sat, Dec 12

6:45 am - 8:10 amLGA New York LaGuardia-MDW Chicago Midway

2h 25mnonstop

3:50 pm - 6:55 pmMDW Chicago Midway-LGA New York LaGuardia

2h 05mnonstop

$367JetBlue

Wed, Nov 25 - Fri, Nov 27

6:35 am - 8:00 amLGA New York LaGuardia-MDW Chicago Midway

2h 25mnonstop

5:05 am - 8:10 amMDW Chicago Midway-LGA New York LaGuardia

2h 05mnonstop

$395JetBlue

Useful Info

Low season	January
High season	July
Cheapest flight	$104

Best time to beat the crowds with an average 22% drop in price.

Most popular time to fly with an average 2% increase in price.

Flight from Buffalo to Chicago O'Hare Airport

MidnightFlew with American Airlines-Oct 2026

get there a few hours early. after getting through checking find you gate an stay there.

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

Munster

Chesterton

Schererville

Porter

Monticello

Saint John

Griffith

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$104 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

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

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Flights from domestic origins to Chicago

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Flights to other popular destinations

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