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.

$74 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

Fri, Sep 4 - Tue, Sep 8

4:25 pm - 9:35 pmLGA New York LaGuardia-MDW Chicago Midway

6h 10m1 stop Kansas City

4:40 pm - 11:15 pmMDW Chicago Midway-LGA New York LaGuardia

5h 35m1 stop Lambert-St Louis

$208Southwest

Fri, Oct 16 - Mon, Oct 19

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

6h 40m1 stop Kansas City

5:15 am - 12:45 pmMDW Chicago Midway-LGA New York LaGuardia

6h 30m1 stop Dallas Love Field

$208Southwest

Thu, Sep 24 - Wed, Sep 30

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

13h 08m1 stop Atlanta Hartsfield-Jackson

6:20 am - 4:00 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

8h 40m1 stop Atlanta Hartsfield-Jackson

$208Frontier

Wed, Sep 30 - Thu, Oct 1

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

6h 36m1 stop Atlanta Hartsfield-Jackson

10:26 am - 8:59 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

9h 33m1 stop Atlanta Hartsfield-Jackson

$208Frontier

Sat, Sep 5 - Tue, Sep 8

6:11 am - 8:00 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 49mnonstop

9:56 am - 3:30 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

4h 34m1 stop Washington, D.C. Reagan-National

$208American Airlines

Sat, Sep 5 - Tue, Sep 8

6:11 am - 8:00 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 49mnonstop

9:56 am - 3:30 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

4h 34m1 stop Washington, D.C. Reagan-National

$208American Airlines

Thu, Oct 29 - Sat, Oct 31

10:38 am - 3:24 pmSWF New Windsor Stewart-ORD Chicago O'Hare Intl

29h 46m1 stop Fort Lauderdale

4:44 pm - 11:16 amORD Chicago O'Hare Intl-SWF New Windsor Stewart

17h 32m1 stop Orlando

$210Multiple Airlines

Sat, Sep 12 - Sat, Sep 19

12:59 pm - 7:01 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

7h 02m1 stop Boston Logan Intl

6:30 am - 9:48 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 18mnonstop

$211JetBlue

Thu, Sep 10 - Mon, Sep 14

6:50 am - 1:45 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

7h 55m1 stop Fort Lauderdale

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

2h 27mnonstop

$211JetBlue

Fri, Sep 18 - Tue, Sep 22

4:00 pm - 11:08 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

8h 08m1 stop Fort Lauderdale

6:20 am - 4:00 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

8h 40m1 stop Atlanta Hartsfield-Jackson

$212Multiple Airlines

Recent last minute flight deals from New York to Chicago

Sat, Aug 22 - Tue, Sep 1

5:55 am - 10:50 amEWR Newark-MDW Chicago Midway

5h 55m1 stop Atlanta Hartsfield-Jackson

11:50 am - 1:03 amMDW Chicago Midway-EWR Newark

12h 13m1 stop Atlanta Hartsfield-Jackson

$217Frontier

Sat, Aug 22 - Mon, Aug 31

10:29 pm - 7:53 amEWR Newark-ORD Chicago O'Hare Intl

10h 24m1 stop Atlanta Hartsfield-Jackson

1:59 pm - 1:03 amORD Chicago O'Hare Intl-EWR Newark

10h 04m1 stop Atlanta Hartsfield-Jackson

$222Frontier

Sat, Aug 22 - Tue, Sep 1

9:46 pm - 11:42 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 56mnonstop

11:10 am - 2:26 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 16mnonstop

$223American Airlines

Sat, Aug 22 - Tue, Sep 1

7:49 am - 11:38 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

4h 49m1 stop Washington, D.C. Reagan-National

11:10 am - 2:26 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 16mnonstop

$233American Airlines

Wed, Aug 19 - Wed, Sep 23

10:29 pm - 7:53 amEWR Newark-ORD Chicago O'Hare Intl

10h 24m1 stop Atlanta Hartsfield-Jackson

3:00 pm - 11:06 pmORD Chicago O'Hare Intl-EWR Newark

7h 06m1 stop Fort Lauderdale

$235Multiple Airlines

Fri, Aug 21 - Mon, Aug 31

6:00 am - 7:40 amEWR Newark-ORD Chicago O'Hare Intl

2h 40mnonstop

6:00 am - 9:07 amORD Chicago O'Hare Intl-EWR Newark

2h 07mnonstop

$255United Airlines

Sun, Aug 23 - Thu, Sep 17

10:29 pm - 7:53 amEWR Newark-ORD Chicago O'Hare Intl

10h 24m1 stop Atlanta Hartsfield-Jackson

3:00 pm - 11:06 pmORD Chicago O'Hare Intl-EWR Newark

7h 06m1 stop Fort Lauderdale

$257Multiple Airlines

Sat, Aug 22 - Sat, Sep 19

9:45 pm - 11:22 pmEWR Newark-ORD Chicago O'Hare Intl

2h 37mnonstop

2:32 pm - 6:01 pmORD Chicago O'Hare Intl-EWR Newark

2h 29mnonstop

$267United Airlines

Sat, Aug 22 - Tue, Sep 1

5:55 pm - 7:57 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

3h 02mnonstop

5:40 pm - 9:07 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 27mnonstop

$267Delta

Sat, Aug 22 - Tue, Sep 1

7:35 pm - 9:52 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

3h 17mnonstop

6:00 am - 9:24 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 24mnonstop

$267Delta

Recent direct flight deals from New York to Chicago

Fri, Oct 2 - Sun, Oct 4

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

$212JetBlue

Fri, Sep 18 - Sat, Sep 19

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

2h 25mnonstop

12:10 pm - 3:20 pmMDW Chicago Midway-LGA New York LaGuardia

2h 10mnonstop

$213Southwest

Fri, Sep 18 - Mon, Sep 21

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

2h 25mnonstop

7:50 pm - 10:55 pmMDW Chicago Midway-LGA New York LaGuardia

2h 05mnonstop

$213Southwest

Fri, Sep 11 - Sun, Sep 13

7:35 pm - 9:37 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

3h 02mnonstop

6:00 am - 9:21 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 21mnonstop

$214JetBlue

Mon, Sep 7 - Thu, Sep 17

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

2h 40mnonstop

1:00 pm - 4:19 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 19mnonstop

$217United Airlines

Fri, Aug 28 - Mon, Aug 31

11:15 am - 12:59 pmEWR Newark-ORD Chicago O'Hare Intl

2h 44mnonstop

6:00 am - 9:07 amORD Chicago O'Hare Intl-EWR Newark

2h 07mnonstop

$218United Airlines

Sat, Aug 29 - Tue, Sep 1

6:50 am - 8:36 amEWR Newark-ORD Chicago O'Hare Intl

2h 46mnonstop

5:49 pm - 9:14 pmORD Chicago O'Hare Intl-EWR Newark

2h 25mnonstop

$218American Airlines

Fri, Aug 28 - Wed, Sep 2

2:20 pm - 4:12 pmEWR Newark-ORD Chicago O'Hare Intl

2h 52mnonstop

6:43 am - 10:02 amORD Chicago O'Hare Intl-EWR Newark

2h 19mnonstop

$218American Airlines

Tue, Sep 1 - Tue, Sep 1

7:33 am - 9:27 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 54mnonstop

6:00 pm - 9:37 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 37mnonstop

$237Delta

Tue, Sep 1 - Tue, Sep 1

10:30 am - 12:17 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 47mnonstop

6:00 pm - 9:37 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 37mnonstop

$237Delta

Useful Info

Low season	January
High season	July
Cheapest flight	$74

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

Most popular time to fly with an average 7% increase in price.

Flight from Stewart Intl. 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

Saint Joseph

Hammond

Portage

Lansing

Valparaiso

Chesterton

Munster

Schererville

Porter

Monticello

Saint John

Griffith

Everything you need to know for your flight to Chicago

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Return flight deals

Cabin class types available on flights to New York

First Class flights to Chicagofrom $434

Business Class flights to Chicagofrom $457

Premium Economy Class flights to Chicagofrom $246

Economy Class flights to Chicagofrom $174

$74 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?

Everything you need to know for your flight to Chicago

Cabin class types available on flights to New York

Complete your trip to Chicago with a hotel stay or car rental

Find direct flights for Chicago

Flights to other popular destinations

Flights from domestic origins to Chicago

Choose which airport to fly into in Chicago

Find deals for your return flight