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.

$99 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, Feb 27 - Tue, Mar 2

9:38 pm - 12:55 amBUF Buffalo-ORD Chicago O'Hare Intl

28h 17m1 stop Orlando

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

14h 42m1 stop Orlando

$198Frontier

Fri, Dec 11 - Tue, Dec 15

1:15 pm - 2:30 pmBUF Buffalo-ORD Chicago O'Hare Intl

26h 15m1 stop Atlanta Hartsfield-Jackson

4:00 pm - 12:20 pmORD Chicago O'Hare Intl-BUF Buffalo

19h 20m1 stop Atlanta Hartsfield-Jackson

$227Frontier

Tue, Feb 2 - Tue, Feb 2

6:03 am - 8:01 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 58mnonstop

10:05 am - 3:19 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

4h 14m1 stop Detroit Metropolitan Wayne County

$261American Airlines

Fri, Jan 15 - Mon, Jan 18

4:35 pm - 11:05 pmALB Albany Intl-MDW Chicago Midway

7h 30m2 stops Nashville Intl Lambert-St Louis

3:40 pm - 12:15 amMDW Chicago Midway-ALB Albany Intl

7h 35m1 stop Baltimore/Washington

$268Southwest

Sat, Dec 5 - Tue, Dec 8

7:06 am - 9:10 amALB Albany Intl-ORD Chicago O'Hare Intl

3h 04mnonstop

6:30 am - 2:21 pmORD Chicago O'Hare Intl-ALB Albany Intl

6h 51m1 stop Philadelphia

$269American Airlines

Sat, Dec 5 - Sat, Dec 5

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

2h 20mnonstop

4:25 pm - 9:40 pmMDW Chicago Midway-ALB Albany Intl

4h 15m1 stop Baltimore/Washington

$269Southwest

Mon, Dec 21 - Mon, Dec 21

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

3h 00mnonstop

6:10 pm - 9:26 pmORD Chicago O'Hare Intl-ALB Albany Intl

2h 16mnonstop

$273United Airlines

Tue, Jan 26 - Mon, Feb 1

9:00 am - 10:52 amALB Albany Intl-ORD Chicago O'Hare Intl

2h 52mnonstop

7:02 pm - 10:18 pmORD Chicago O'Hare Intl-ALB Albany Intl

2h 16mnonstop

$274United Airlines

Tue, Jan 5 - Wed, Jan 6

6:00 am - 9:53 amALB Albany Intl-ORD Chicago O'Hare Intl

4h 53m1 stop Detroit Metropolitan Wayne County

3:01 pm - 11:54 pmORD Chicago O'Hare Intl-ALB Albany Intl

7h 53m1 stop Atlanta Hartsfield-Jackson

$279Delta

Wed, Jan 6 - Wed, Jan 6

6:00 am - 9:53 amALB Albany Intl-ORD Chicago O'Hare Intl

4h 53m1 stop Detroit Metropolitan Wayne County

5:45 pm - 11:05 pmORD Chicago O'Hare Intl-ALB Albany Intl

4h 20m1 stop New York LaGuardia

$279Delta

Recent last minute flight deals from New York to Chicago

Sat, Nov 14 - Thu, Nov 26

8:30 pm - 9:24 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

13h 54m1 stop Dallas/Fort Worth

7:49 am - 8:00 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

11h 11m1 stop Atlanta Hartsfield-Jackson

$272Frontier

Sat, Nov 14 - Tue, Nov 17

8:30 pm - 9:24 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

13h 54m1 stop Dallas/Fort Worth

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

11h 59m1 stop Atlanta Hartsfield-Jackson

$278Frontier

Mon, Nov 16 - Fri, Dec 4

6:55 pm - 8:45 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 50mnonstop

8:25 pm - 11:44 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 19mnonstop

$381Delta

Thu, Nov 12 - Sat, Dec 12

6:30 am - 7:33 amBUF Buffalo-ORD Chicago O'Hare Intl

2h 03mnonstop

10:29 am - 1:17 pmORD Chicago O'Hare Intl-BUF Buffalo

1h 48mnonstop

$400United Airlines

Sat, Nov 14 - Thu, Nov 26

3:21 pm - 5:20 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 59mnonstop

10:45 am - 2:04 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 19mnonstop

$402Delta

Sat, Nov 14 - Thu, Nov 26

2:00 pm - 3:30 pmLGA New York LaGuardia-MDW Chicago Midway

2h 30mnonstop

5:10 am - 8:15 amMDW Chicago Midway-LGA New York LaGuardia

2h 05mnonstop

$402Southwest

Sat, Nov 14 - Thu, Nov 26

8:59 am - 10:53 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 54mnonstop

2:32 pm - 5:53 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 21mnonstop

$402American Airlines

Sun, Nov 15 - Thu, Nov 26

7:12 am - 8:59 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 47mnonstop

2:32 pm - 5:53 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 21mnonstop

$402American Airlines

Thu, Nov 12 - Sat, Dec 12

10:51 am - 3:13 pmBUF Buffalo-ORD Chicago O'Hare Intl

5h 22m1 stop Newark

10:29 am - 1:17 pmORD Chicago O'Hare Intl-BUF Buffalo

1h 48mnonstop

$410United Airlines

Sat, Nov 14 - Thu, Nov 26

6:35 am - 2:45 pmLGA New York LaGuardia-MDW Chicago Midway

9h 10m1 stop Dallas Love Field

5:10 am - 8:15 amMDW Chicago Midway-LGA New York LaGuardia

2h 05mnonstop

$412Southwest

Recent direct flight deals from New York to Chicago

Wed, Dec 16 - Sat, Dec 19

7:06 am - 9:10 amALB Albany Intl-ORD Chicago O'Hare Intl

3h 04mnonstop

7:15 pm - 10:37 pmORD Chicago O'Hare Intl-ALB Albany Intl

2h 22mnonstop

$269American Airlines

Wed, Dec 16 - Sat, Dec 19

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

2h 20mnonstop

6:45 pm - 9:45 pmMDW Chicago Midway-ALB Albany Intl

2h 00mnonstop

$269Southwest

Mon, Dec 21 - Mon, Dec 21

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

3h 00mnonstop

6:10 pm - 9:26 pmORD Chicago O'Hare Intl-ALB Albany Intl

2h 16mnonstop

$273United Airlines

Mon, Dec 21 - Fri, Jan 1

6:50 pm - 8:25 pmALB Albany Intl-MDW Chicago Midway

2h 35mnonstop

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

2h 00mnonstop

$273Southwest

Tue, Jan 26 - Mon, Feb 1

9:00 am - 10:52 amALB Albany Intl-ORD Chicago O'Hare Intl

2h 52mnonstop

7:02 pm - 10:18 pmORD Chicago O'Hare Intl-ALB Albany Intl

2h 16mnonstop

$274United Airlines

Tue, Dec 8 - Thu, Dec 10

12:09 pm - 2:00 pmALB Albany Intl-ORD Chicago O'Hare Intl

2h 51mnonstop

8:15 am - 11:30 amORD Chicago O'Hare Intl-ALB Albany Intl

2h 15mnonstop

$274American Airlines

Mon, Dec 7 - Tue, Dec 8

8:30 pm - 10:13 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 43mnonstop

2:39 pm - 6:00 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 21mnonstop

$297Delta

Thu, Dec 3 - Sat, Dec 5

7:10 am - 9:02 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 52mnonstop

10:06 am - 1:19 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 13mnonstop

$297Delta

Thu, Dec 24 - Fri, Jan 1

6:40 pm - 8:20 pmLGA New York LaGuardia-MDW Chicago Midway

2h 40mnonstop

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

2h 05mnonstop

$419JetBlue

Thu, Dec 24 - Thu, Dec 31

6:40 pm - 8:20 pmLGA New York LaGuardia-MDW Chicago Midway

2h 40mnonstop

5:00 pm - 8:05 pmMDW Chicago Midway-LGA New York LaGuardia

2h 05mnonstop

$429JetBlue

Useful Info

Low season	January
High season	July
Cheapest flight	$99

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

Most popular time to fly with an average 1% increase in price.

Flight from Syracuse 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

Chesterton

Munster

Schererville

Porter

Monticello

Saint John

Griffith

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$99 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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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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