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.

$111 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

Tue, Nov 3 - Sat, Nov 7

9:29 am - 6:16 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

9h 47m1 stop Atlanta Hartsfield-Jackson

7:20 pm - 8:34 amORD Chicago O'Hare Intl-LGA New York LaGuardia

12h 14m1 stop Atlanta Hartsfield-Jackson

$234Frontier

Thu, Nov 12 - Tue, Nov 17

9:29 am - 6:45 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

10h 16m1 stop Atlanta Hartsfield-Jackson

10:40 am - 7:35 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

7h 55m1 stop Dallas/Fort Worth

$234Frontier

Sat, Oct 17 - Fri, Oct 23

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

$269JetBlue

Sat, Oct 17 - Tue, Oct 20

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

2h 55mnonstop

6:10 am - 9:30 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 20mnonstop

$269JetBlue

Mon, Oct 26 - Tue, Oct 27

7:20 am - 9:02 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 42mnonstop

8:20 pm - 11:44 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 24mnonstop

$280Delta

Mon, Oct 12 - Wed, Oct 14

6:00 am - 7:36 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 36mnonstop

6:00 am - 9:12 amORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 12mnonstop

$280Delta

Tue, Jan 5 - Tue, Jan 5

11:34 am - 1:30 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 56mnonstop

3:46 pm - 7:04 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 18mnonstop

$281American Airlines

Fri, Nov 6 - Fri, Nov 6

10:40 am - 12:35 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 55mnonstop

4:31 pm - 8:03 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 32mnonstop

$282American Airlines

Thu, Oct 29 - Mon, Nov 2

6:00 am - 11:38 amROC Greater Rochester Intl-ORD Chicago O'Hare Intl

6h 38m1 stop Washington, D.C. Dulles Intl

1:55 pm - 4:36 pmORD Chicago O'Hare Intl-ROC Greater Rochester Intl

1h 41mnonstop

$287United Airlines

Wed, Oct 21 - Mon, Oct 26

7:55 pm - 11:32 pmROC Greater Rochester Intl-ORD Chicago O'Hare Intl

4h 37m1 stop Washington, D.C. Dulles Intl

7:07 am - 10:02 amORD Chicago O'Hare Intl-ROC Greater Rochester Intl

1h 55mnonstop

$287United Airlines

Recent last minute flight deals from New York to Chicago

Tue, Sep 29 - Wed, Oct 28

6:15 am - 11:51 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

6h 36m1 stop Atlanta Hartsfield-Jackson

7:15 am - 4:01 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

7h 46m1 stop Atlanta Hartsfield-Jackson

$239Frontier

Tue, Sep 29 - Wed, Oct 28

6:15 am - 5:46 pmLGA New York LaGuardia-MDW Chicago Midway

12h 31m1 stop Atlanta Hartsfield-Jackson

6:16 am - 4:01 pmMDW Chicago Midway-LGA New York LaGuardia

8h 45m1 stop Atlanta Hartsfield-Jackson

$240Frontier

Wed, Sep 30 - Sat, Oct 10

1:00 pm - 6:23 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

6h 23m1 stop Atlanta Hartsfield-Jackson

6:10 am - 9:30 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 20mnonstop

$277Multiple Airlines

Wed, Sep 30 - Fri, Oct 2

1:00 pm - 6:23 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

6h 23m1 stop Atlanta Hartsfield-Jackson

7:00 am - 10:27 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 27mnonstop

$285Multiple Airlines

Tue, Sep 29 - Sat, Oct 10

8:10 am - 9:58 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 48mnonstop

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

2h 22mnonstop

$302JetBlue

Mon, Sep 28 - Wed, Oct 7

8:05 pm - 9:58 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 53mnonstop

10:59 am - 2:20 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 21mnonstop

$302JetBlue

Sat, Sep 26 - Tue, Oct 27

8:44 pm - 10:30 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 46mnonstop

12:52 pm - 4:17 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 25mnonstop

$306American Airlines

Tue, Sep 29 - Wed, Oct 28

5:57 pm - 8:00 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

3h 03mnonstop

6:50 am - 10:05 amORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 15mnonstop

$306American Airlines

Wed, Sep 30 - Tue, Oct 13

5:30 pm - 7:15 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 45mnonstop

5:55 pm - 9:16 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 21mnonstop

$306Delta

Wed, Sep 30 - Tue, Oct 13

4:15 pm - 6:04 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 49mnonstop

5:55 pm - 9:16 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 21mnonstop

$306Delta

Recent direct flight deals from New York to Chicago

Sat, Oct 17 - Fri, Oct 23

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

$269JetBlue

Sat, Oct 17 - Tue, Oct 20

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

2h 55mnonstop

6:10 am - 9:30 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 20mnonstop

$269JetBlue

Mon, Oct 26 - Tue, Oct 27

7:20 am - 9:02 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 42mnonstop

8:20 pm - 11:44 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 24mnonstop

$280Delta

Mon, Oct 12 - Wed, Oct 14

6:00 am - 7:36 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 36mnonstop

6:00 am - 9:12 amORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 12mnonstop

$280Delta

Tue, Jan 5 - Tue, Jan 5

11:34 am - 1:30 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 56mnonstop

3:46 pm - 7:04 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 18mnonstop

$281American Airlines

Fri, Nov 6 - Fri, Nov 6

2:10 pm - 4:05 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 55mnonstop

8:00 pm - 11:25 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 25mnonstop

$282American Airlines

Sat, Oct 10 - Sun, Oct 11

7:29 pm - 9:13 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 44mnonstop

6:00 am - 9:15 amORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 15mnonstop

$287United Airlines

Thu, Oct 15 - Sun, Oct 18

8:10 am - 9:47 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 37mnonstop

7:00 am - 10:17 amORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 17mnonstop

$287United Airlines

Fri, Nov 6 - Sun, Nov 8

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

2h 25mnonstop

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

2h 05mnonstop

$287Southwest

Tue, Oct 20 - Mon, Oct 26

5:55 pm - 7:25 pmLGA New York LaGuardia-MDW Chicago Midway

2h 30mnonstop

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

2h 05mnonstop

$287Southwest

Useful Info

Low season	January
High season	July
Cheapest flight	$111

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

Most popular time to fly with an average 6% 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

Schererville

Chesterton

Munster

Porter

Monticello

Saint John

Griffith

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$111 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

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