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.

$89 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 15 - Tue, Sep 22

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

$222Frontier

Mon, Sep 28 - Wed, Sep 30

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

$222Frontier

Fri, Oct 16 - Mon, Oct 19

9:15 am - 2:32 pmEWR Newark-ORD Chicago O'Hare Intl

6h 17m1 stop Washington, D.C. Reagan-National

9:05 am - 5:17 pmORD Chicago O'Hare Intl-EWR Newark

7h 12m1 stop Boston Logan Intl

$229United Airlines

Sun, Oct 4 - Thu, Oct 8

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

$230JetBlue

Mon, Sep 21 - Wed, Sep 23

6:55 am - 7:55 amBUF Buffalo-ORD Chicago O'Hare Intl

2h 00mnonstop

6:29 am - 9:08 amORD Chicago O'Hare Intl-BUF Buffalo

1h 39mnonstop

$237United Airlines

Tue, Oct 27 - Tue, Nov 3

5:49 pm - 6:59 pmBUF Buffalo-ORD Chicago O'Hare Intl

2h 10mnonstop

3:19 pm - 6:05 pmORD Chicago O'Hare Intl-BUF Buffalo

1h 46mnonstop

$237American Airlines

Sat, Dec 5 - Mon, Dec 7

8:00 am - 9:05 amBUF Buffalo-ORD Chicago O'Hare Intl

2h 05mnonstop

3:19 pm - 6:05 pmORD Chicago O'Hare Intl-BUF Buffalo

1h 46mnonstop

$237American Airlines

Wed, Sep 30 - Sat, Oct 3

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 - Thu, Oct 1

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

Sat, Sep 19 - Sun, Sep 20

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

Recent last minute flight deals from New York to Chicago

Wed, Sep 2 - Wed, Sep 16

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

10h 24m1 stop Atlanta Hartsfield-Jackson

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

8h 11m1 stop Orlando

$230Frontier

Tue, Sep 1 - Wed, Sep 2

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

6h 00m1 stop Atlanta Hartsfield-Jackson

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

12h 13m1 stop Atlanta Hartsfield-Jackson

$238Frontier

Sat, Sep 5 - Mon, Sep 21

8:00 pm - 9:58 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 58mnonstop

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

2h 27mnonstop

$277JetBlue

Sat, Sep 5 - Sat, Sep 26

2:30 pm - 4:18 pmJFK 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 5 - Mon, Sep 21

1:00 pm - 8:08 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

8h 08m1 stop Atlanta Hartsfield-Jackson

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

2h 27mnonstop

$284Multiple Airlines

Sat, Sep 5 - Sat, Oct 3

5:19 pm - 7:20 pmEWR Newark-ORD Chicago O'Hare Intl

3h 01mnonstop

10:11 am - 1:30 pmORD Chicago O'Hare Intl-EWR Newark

2h 19mnonstop

$286American Airlines

Sun, Sep 6 - Mon, Sep 21

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

2h 46mnonstop

8:38 pm - 11:59 pmORD Chicago O'Hare Intl-EWR Newark

2h 21mnonstop

$286American Airlines

Sat, Sep 5 - Sat, Sep 26

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

2h 40mnonstop

5:07 pm - 8:37 pmORD Chicago O'Hare Intl-EWR Newark

2h 30mnonstop

$286United Airlines

Sun, Sep 6 - Mon, Sep 21

8:29 pm - 10:15 pmEWR Newark-ORD Chicago O'Hare Intl

2h 46mnonstop

5:00 am - 8:14 amORD Chicago O'Hare Intl-EWR Newark

2h 14mnonstop

$286United Airlines

Sun, Sep 6 - Tue, Oct 6

1:00 pm - 8:04 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

8h 04m1 stop Atlanta Hartsfield-Jackson

7:05 am - 10:33 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 28mnonstop

$293Multiple Airlines

Recent direct flight deals from New York to Chicago

Sun, Oct 4 - Thu, Oct 8

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

$230JetBlue

Mon, Oct 12 - Thu, Oct 15

7:00 am - 8:00 amBUF Buffalo-ORD Chicago O'Hare Intl

2h 00mnonstop

6:50 am - 9:29 amORD Chicago O'Hare Intl-BUF Buffalo

1h 39mnonstop

$237United Airlines

Thu, Oct 29 - Mon, Nov 2

11:26 am - 12:29 pmBUF Buffalo-ORD Chicago O'Hare Intl

2h 03mnonstop

8:00 am - 10:48 amORD Chicago O'Hare Intl-BUF Buffalo

1h 48mnonstop

$237American Airlines

Wed, Sep 30 - Sat, Oct 3

6:56 pm - 8:15 pmBUF Buffalo-ORD Chicago O'Hare Intl

2h 19mnonstop

7:20 pm - 10:10 pmORD Chicago O'Hare Intl-BUF Buffalo

1h 50mnonstop

$237American Airlines

Thu, Feb 11 - Mon, Feb 15

7:00 am - 7:48 amBUF Buffalo-ORD Chicago O'Hare Intl

1h 48mnonstop

2:12 pm - 4:47 pmORD Chicago O'Hare Intl-BUF Buffalo

1h 35mnonstop

$237United Airlines

Sat, Sep 19 - Sun, Sep 20

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

Wed, Dec 9 - Wed, Dec 9

7:30 am - 9:30 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

3h 00mnonstop

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

2h 37mnonstop

$265Delta

Tue, Sep 22 - Fri, Sep 25

6:00 am - 7:29 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 29mnonstop

8:15 pm - 11:39 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 24mnonstop

$265Delta

Mon, Nov 9 - Fri, Nov 13

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

2h 35mnonstop

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

2h 05mnonstop

$267Southwest

Wed, Nov 4 - Sun, Nov 8

3:15 pm - 5:00 pmLGA New York LaGuardia-MDW Chicago Midway

2h 45mnonstop

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

2h 05mnonstop

$267Southwest

Useful Info

Low season	January
High season	July
Cheapest flight	$89

Best time to beat the crowds with an average 15% drop in price.

Most popular time to fly with an average 8% 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

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 $159

$89 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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High season

Cheapest flight

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