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.

$90 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, Sep 22 - Sat, Sep 26

6:15 am - 6:23 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

13h 08m1 stop Atlanta Hartsfield-Jackson

6:00 am - 7:44 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

12h 44m1 stop Dallas/Fort Worth

$221Frontier

Tue, Sep 22 - Sat, Sep 26

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

12h 31m1 stop Atlanta Hartsfield-Jackson

6:25 am - 4:00 pmMDW Chicago Midway-LGA New York LaGuardia

8h 35m1 stop Atlanta Hartsfield-Jackson

$221Frontier

Sat, Oct 17 - Tue, Oct 20

1:00 pm - 7:14 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

7h 14m1 stop Boston Logan Intl

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

6h 51m1 stop Boston Logan Intl

$235JetBlue

Tue, Oct 13 - Fri, Oct 16

10:20 am - 11:59 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 39mnonstop

2:00 pm - 5:25 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 25mnonstop

$243United Airlines

Fri, Oct 23 - Sun, Oct 25

4:25 pm - 6:09 pmLGA 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

$243United Airlines

Fri, Oct 23 - Mon, Oct 26

12:30 pm - 1:50 pmLGA New York LaGuardia-MDW Chicago Midway

2h 20mnonstop

12:55 pm - 4:00 pmMDW Chicago Midway-LGA New York LaGuardia

2h 05mnonstop

$243Southwest

Thu, Nov 12 - Fri, Nov 13

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

2h 40mnonstop

7:15 pm - 10:20 pmMDW Chicago Midway-LGA New York LaGuardia

2h 05mnonstop

$243Southwest

Tue, Sep 22 - Wed, Sep 30

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

6h 23m1 stop Atlanta Hartsfield-Jackson

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

2h 21mnonstop

$244Multiple Airlines

Wed, Sep 23 - Sat, Sep 26

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

$244Multiple Airlines

Tue, Sep 29 - Mon, Oct 5

1:00 pm - 7:01 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

7h 01m1 stop Boston Logan Intl

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

2h 27mnonstop

$245JetBlue

Recent last minute flight deals from New York to Chicago

Wed, Sep 9 - Mon, Oct 12

11:35 am - 6:23 pmEWR Newark-ORD Chicago O'Hare Intl

7h 48m1 stop Atlanta Hartsfield-Jackson

8:11 pm - 1:02 amORD Chicago O'Hare Intl-EWR Newark

27h 51m1 stop Orlando

$232Frontier

Wed, Sep 9 - Wed, Sep 16

11:35 am - 6:23 pmEWR Newark-ORD Chicago O'Hare Intl

7h 48m1 stop Atlanta Hartsfield-Jackson

3:50 pm - 1:01 amORD Chicago O'Hare Intl-EWR Newark

8h 11m1 stop Orlando

$236Frontier

Thu, Sep 10 - Mon, Sep 28

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

$251Multiple Airlines

Wed, Sep 9 - Wed, Sep 23

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

6h 23m1 stop Atlanta Hartsfield-Jackson

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

2h 21mnonstop

$251Multiple Airlines

Thu, Sep 10 - Mon, Sep 28

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

2h 48mnonstop

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

2h 27mnonstop

$277JetBlue

Sat, Sep 12 - 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

$277JetBlue

Thu, Sep 10 - Sun, Sep 13

7:20 am - 9:00 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 40mnonstop

6:00 am - 9:13 amORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 13mnonstop

$277United Airlines

Thu, Sep 10 - Wed, Sep 16

6:10 am - 7:50 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 40mnonstop

5:03 pm - 8:25 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 22mnonstop

$277United Airlines

Fri, Sep 11 - Sat, Sep 19

8:55 pm - 10:20 pmLGA New York LaGuardia-MDW Chicago Midway

2h 25mnonstop

7:50 am - 11:00 amMDW Chicago Midway-LGA New York LaGuardia

2h 10mnonstop

$277Southwest

Thu, Sep 10 - Mon, Sep 14

6:00 am - 7:15 amLGA New York LaGuardia-MDW Chicago Midway

2h 15mnonstop

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

2h 00mnonstop

$277Southwest

Recent direct flight deals from New York to Chicago

Sat, Sep 26 - Tue, Sep 29

3:15 pm - 4:45 pmLGA New York LaGuardia-MDW Chicago Midway

2h 30mnonstop

7:05 pm - 10:10 pmMDW Chicago Midway-LGA New York LaGuardia

2h 05mnonstop

$243Southwest

Thu, Nov 12 - Fri, Nov 13

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

2h 40mnonstop

7:15 pm - 10:20 pmMDW Chicago Midway-LGA New York LaGuardia

2h 05mnonstop

$243Southwest

Sat, Oct 17 - Sun, Oct 18

2:50 pm - 4:34 pmEWR Newark-ORD Chicago O'Hare Intl

2h 44mnonstop

5:00 am - 8:13 amORD Chicago O'Hare Intl-EWR Newark

2h 13mnonstop

$243United Airlines

Fri, Nov 6 - Sun, Nov 8

7:42 pm - 9:30 pmEWR Newark-ORD Chicago O'Hare Intl

2h 48mnonstop

5:55 am - 9:02 amORD Chicago O'Hare Intl-EWR Newark

2h 07mnonstop

$243United Airlines

Thu, Oct 15 - Thu, Oct 22

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

$247JetBlue

Thu, Sep 24 - Mon, Sep 28

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

2h 48mnonstop

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

2h 27mnonstop

$248JetBlue

Tue, Oct 13 - Thu, Oct 15

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

2h 44mnonstop

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

2h 12mnonstop

$265Delta

Tue, Sep 29 - Thu, Oct 1

8:45 pm - 10:18 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 33mnonstop

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

2h 15mnonstop

$265Delta

Sat, Oct 10 - Sat, Oct 17

7:02 pm - 9:05 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

3h 03mnonstop

10:34 am - 1:59 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 25mnonstop

$266American Airlines

Sat, Oct 10 - Sat, Oct 17

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

2h 44mnonstop

8:10 am - 11:29 amORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 19mnonstop

$266American Airlines

Useful Info

Low season	January
High season	July
Cheapest flight	$90

Best time to beat the crowds with an average 16% drop in price.

Most popular time to fly with an average 9% 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

Munster

Schererville

Chesterton

Porter

Monticello

Saint John

Griffith

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$90 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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Cheapest flight

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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