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

Sun, Sep 27 - Thu, Oct 1

4:30 pm - 9:47 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

6h 17m1 stop Pittsburgh

7:46 am - 11:20 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 34mnonstop

$221American Airlines

Fri, Oct 23 - Mon, Oct 26

5:55 am - 7:02 pmEWR Newark-ORD Chicago O'Hare Intl

14h 07m1 stop Orlando

8:11 pm - 12:03 amORD Chicago O'Hare Intl-EWR Newark

26h 52m1 stop Orlando

$223Frontier

Mon, Nov 30 - Thu, Dec 3

8:30 pm - 10:37 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

3h 07mnonstop

9:00 am - 3:59 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

5h 59m1 stop Charlotte Douglas

$223American Airlines

Wed, Oct 7 - Fri, Oct 9

10:29 pm - 9:21 amEWR Newark-ORD Chicago O'Hare Intl

11h 52m1 stop Atlanta Hartsfield-Jackson

8:11 pm - 1:03 amORD Chicago O'Hare Intl-EWR Newark

27h 52m1 stop Orlando

$224Frontier

Fri, Sep 11 - Sun, Sep 13

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

2h 53mnonstop

6:00 am - 2:07 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

7h 07m1 stop Fort Lauderdale

$228JetBlue

Tue, Sep 29 - Sat, Oct 3

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

2h 48mnonstop

3:00 pm - 11:51 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

7h 51m1 stop Fort Lauderdale

$229JetBlue

Tue, Sep 15 - Wed, Sep 16

1:30 pm - 8:29 pmEWR Newark-ORD Chicago O'Hare Intl

7h 59m1 stop Dallas/Fort Worth

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

7h 06m1 stop Fort Lauderdale

$230Multiple Airlines

Fri, Oct 2 - Wed, Oct 7

3:38 pm - 11:08 pmEWR Newark-ORD Chicago O'Hare Intl

8h 30m1 stop Fort Lauderdale

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

8h 11m1 stop Orlando

$230Multiple Airlines

Wed, Oct 28 - Fri, Oct 30

5:58 pm - 7:02 pmBUF Buffalo-ORD Chicago O'Hare Intl

2h 04mnonstop

5:51 pm - 8:36 pmORD Chicago O'Hare Intl-BUF Buffalo

1h 45mnonstop

$236United Airlines

Tue, Sep 8 - Tue, Sep 8

8:05 am - 9:45 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 40mnonstop

3:00 pm - 6:25 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 25mnonstop

$237United Airlines

Recent last minute flight deals from New York to Chicago

Sat, Aug 29 - Thu, Sep 24

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

$227Frontier

Sat, Aug 29 - Fri, Sep 25

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

$227Frontier

Thu, Aug 27 - Mon, Sep 28

7:00 am - 8:46 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 46mnonstop

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

2h 27mnonstop

$257JetBlue

Sat, Aug 29 - Sat, Sep 19

7:00 am - 8:46 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 46mnonstop

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

2h 27mnonstop

$266JetBlue

Wed, Aug 26 - Wed, Sep 30

5:25 pm - 7:29 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

3h 04mnonstop

12:47 pm - 4:04 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 17mnonstop

$266American Airlines

Wed, Aug 26 - Mon, Sep 28

9:24 am - 11:12 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 48mnonstop

6:59 am - 10:10 amORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 11mnonstop

$266American Airlines

Sat, Aug 29 - Wed, Sep 23

2:30 pm - 4:15 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 45mnonstop

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

2h 15mnonstop

$272Delta

Sat, Aug 29 - Mon, Sep 21

2:30 pm - 4:15 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 45mnonstop

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

2h 15mnonstop

$272Delta

Sat, Aug 29 - Sat, Sep 5

1:25 pm - 3:09 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 44mnonstop

4:00 pm - 7:25 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 25mnonstop

$281United Airlines

Sat, Aug 29 - Sat, Sep 5

1:25 pm - 3:09 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 44mnonstop

4:00 pm - 7:25 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 25mnonstop

$285United Airlines

Recent direct flight deals from New York to Chicago

Tue, Sep 8 - Tue, Sep 8

6:55 am - 8:42 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 47mnonstop

6:23 pm - 9:59 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 36mnonstop

$230JetBlue

Wed, Oct 28 - Fri, Oct 30

5:58 pm - 7:02 pmBUF Buffalo-ORD Chicago O'Hare Intl

2h 04mnonstop

5:51 pm - 8:36 pmORD Chicago O'Hare Intl-BUF Buffalo

1h 45mnonstop

$236United Airlines

Wed, Jan 20 - Sat, Jan 23

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

2h 05mnonstop

8:03 am - 10:53 amORD Chicago O'Hare Intl-BUF Buffalo

1h 50mnonstop

$236American Airlines

Wed, Feb 3 - Sat, Feb 6

11:24 am - 12:29 pmBUF Buffalo-ORD Chicago O'Hare Intl

2h 05mnonstop

8:03 am - 10:53 amORD Chicago O'Hare Intl-BUF Buffalo

1h 50mnonstop

$236American Airlines

Thu, Sep 17 - Mon, Sep 21

7:59 am - 9:10 amBUF Buffalo-ORD Chicago O'Hare Intl

2h 11mnonstop

8:46 am - 11:39 amORD Chicago O'Hare Intl-BUF Buffalo

1h 53mnonstop

$237Alaska Airlines

Tue, Sep 15 - Wed, Sep 16

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

$237JetBlue

Tue, Sep 8 - Tue, Sep 8

8:05 am - 9:45 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 40mnonstop

3:00 pm - 6:25 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 25mnonstop

$237United Airlines

Tue, Sep 8 - Wed, Sep 16

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

3h 02mnonstop

10:25 am - 1:49 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 24mnonstop

$242Delta

Tue, Sep 8 - Mon, Sep 14

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

$242Delta

Fri, Sep 18 - Sun, Sep 20

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

2h 53mnonstop

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

2h 21mnonstop

$302Multiple Airlines

Useful Info

Low season	January
High season	July
Cheapest flight	$89

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 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

Saint Joseph

Hammond

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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Origins

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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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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