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.

$115 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

Wed, Oct 21 - Thu, Oct 22

6:30 am - 10:07 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

4h 37m1 stop Washington, D.C. Reagan-National

4:26 pm - 8:00 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 34mnonstop

$232American Airlines

Fri, Dec 4 - Mon, Dec 7

5:35 pm - 7:15 pmLGA New York LaGuardia-MDW Chicago Midway

2h 40mnonstop

11:30 am - 5:55 pmMDW Chicago Midway-LGA New York LaGuardia

5h 25m1 stop Lambert-St Louis

$233Southwest

Fri, Oct 23 - Mon, Nov 2

4:20 pm - 10:00 pmLGA New York LaGuardia-MDW Chicago Midway

6h 40m1 stop Kansas City

9:35 am - 12:40 pmMDW Chicago Midway-LGA New York LaGuardia

2h 05mnonstop

$233Southwest

Thu, Nov 12 - Sat, Nov 14

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

10h 16m1 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

Wed, Oct 14 - Tue, Oct 20

6:10 am - 11:32 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

6h 22m1 stop Atlanta Hartsfield-Jackson

6:00 am - 4:14 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

9h 14m1 stop Atlanta Hartsfield-Jackson

$234Frontier

Mon, Nov 23 - Sat, Dec 12

6:00 am - 9:45 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

4h 45m1 stop Washington, D.C. Dulles Intl

2:00 pm - 5:15 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 15mnonstop

$234United Airlines

Sat, Oct 3 - Wed, Oct 7

8:15 pm - 10:08 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

$234JetBlue

Sat, Oct 3 - Sat, Oct 10

8:15 pm - 10:08 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 53mnonstop

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

2h 22mnonstop

$234JetBlue

Sun, Nov 8 - Tue, Nov 10

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

2h 51mnonstop

1:00 pm - 4:15 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 15mnonstop

$235United Airlines

Sat, Oct 10 - Tue, Oct 13

8:07 pm - 10:00 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 53mnonstop

6:29 pm - 9:57 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 28mnonstop

$235American Airlines

Recent last minute flight deals from New York to Chicago

Tue, Sep 22 - Wed, Sep 23

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

$244Frontier

Wed, Sep 23 - Wed, Sep 30

5:55 am - 10:20 amEWR Newark-ORD Chicago O'Hare Intl

29h 25m1 stop Orlando

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

8h 11m1 stop Orlando

$244Frontier

Sun, Sep 20 - Wed, Oct 7

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

2h 48mnonstop

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

2h 21mnonstop

$245JetBlue

Wed, Sep 23 - Wed, Oct 21

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

$245JetBlue

Wed, Sep 23 - Wed, Oct 28

3:01 pm - 4:59 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 58mnonstop

6:00 pm - 9:40 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 40mnonstop

$254Delta

Wed, Sep 23 - Wed, Oct 28

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

2h 33mnonstop

10:05 am - 1:26 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 21mnonstop

$254Delta

Wed, Sep 23 - Wed, Oct 21

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

2h 15mnonstop

5:10 pm - 8:15 pmMDW Chicago Midway-LGA New York LaGuardia

2h 05mnonstop

$254Southwest

Wed, Sep 23 - Wed, Oct 28

1:25 pm - 2:45 pmLGA New York LaGuardia-MDW Chicago Midway

2h 20mnonstop

7:25 pm - 10:35 pmMDW Chicago Midway-LGA New York LaGuardia

2h 10mnonstop

$254Southwest

Thu, Sep 24 - Tue, Oct 6

2:16 pm - 4:05 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 49mnonstop

10:10 am - 1:31 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 21mnonstop

$254American Airlines

Thu, Sep 24 - Tue, Oct 6

9:17 am - 11:05 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 48mnonstop

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

2h 18mnonstop

$254American Airlines

Recent direct flight deals from New York to Chicago

Sat, Oct 3 - Wed, Oct 7

8:15 pm - 10:08 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

$234JetBlue

Sat, Oct 3 - Sat, Oct 10

8:15 pm - 10:08 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 53mnonstop

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

2h 22mnonstop

$234JetBlue

Wed, Nov 4 - Sun, Nov 8

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

2h 52mnonstop

8:00 am - 11:22 amORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 22mnonstop

$235American Airlines

Fri, Oct 30 - Fri, Nov 6

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

2h 44mnonstop

1:35 pm - 5:04 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 29mnonstop

$235American Airlines

Sun, Dec 13 - Wed, Dec 16

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

2h 43mnonstop

7:22 pm - 10:47 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 25mnonstop

$235Delta

Wed, Nov 25 - Tue, Dec 1

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

2h 51mnonstop

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

2h 18mnonstop

$235Delta

Sat, Oct 17 - Sun, Oct 18

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

2h 44mnonstop

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

2h 17mnonstop

$235United Airlines

Wed, Dec 16 - Sun, Jan 3

8:21 am - 10:07 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 46mnonstop

6:30 pm - 9:50 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 20mnonstop

$235United Airlines

Wed, Dec 9 - Sun, Dec 13

8:30 am - 10:05 amLGA New York LaGuardia-MDW Chicago Midway

2h 35mnonstop

5:15 pm - 8:20 pmMDW Chicago Midway-LGA New York LaGuardia

2h 05mnonstop

$235Southwest

Wed, Oct 21 - Sun, Oct 25

6:00 am - 7:30 amLGA New York LaGuardia-MDW Chicago Midway

2h 30mnonstop

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

2h 05mnonstop

$235Southwest

Useful Info

Low season	January
High season	July
Cheapest flight	$115

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 Newark Liberty Airport to Chicago Midway 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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$115 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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