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.

$73 CHEAP FLIGHTS from New York State to Chicago

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals

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

Thu, Sep 10 - Mon, Sep 14

2:58 pm - 4:46 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 48mnonstop

1:35 pm - 5:00 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 25mnonstop

$205American Airlines

Thu, Sep 10 - Mon, Sep 14

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

2h 48mnonstop

1:45 pm - 5:02 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 17mnonstop

$205American Airlines

Sat, Sep 12 - Fri, Sep 18

6:00 am - 4:40 pmLGA New York LaGuardia-MDW Chicago Midway

11h 40m2 stops Lambert-St Louis Baltimore/Washington

5:50 pm - 11:20 pmMDW Chicago Midway-LGA New York LaGuardia

4h 30m1 stop Lambert-St Louis

$207Southwest

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, Sep 11 - Sat, Sep 19

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

Fri, Sep 11 - Tue, Sep 22

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

Sun, Jan 17 - Mon, Jan 25

4:00 pm - 5:47 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 47mnonstop

5:00 pm - 8:15 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 15mnonstop

$208Delta

Sun, Jan 17 - Sat, Jan 23

2:30 pm - 4:12 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 42mnonstop

2:30 pm - 5:45 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 15mnonstop

$208Delta

Sat, Sep 12 - Sun, Sep 13

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

$209Multiple Airlines

Wed, Sep 9 - Wed, Sep 16

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

$209Multiple Airlines

Recent last minute flight deals from New York to Chicago

Sun, Aug 16 - Wed, Aug 19

10:29 pm - 9:51 amEWR Newark-MDW Chicago Midway

12h 22m1 stop Atlanta Hartsfield-Jackson

11:50 am - 9:28 pmMDW Chicago Midway-EWR Newark

8h 38m1 stop Atlanta Hartsfield-Jackson

$230Frontier

Sun, Aug 16 - Tue, Aug 25

10:29 pm - 9:51 amEWR Newark-MDW Chicago Midway

12h 22m1 stop Atlanta Hartsfield-Jackson

11:50 am - 9:28 pmMDW Chicago Midway-EWR Newark

8h 38m1 stop Atlanta Hartsfield-Jackson

$230Frontier

Thu, Aug 13 - Wed, Sep 16

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

2h 48mnonstop

1:45 pm - 5:02 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 17mnonstop

$245American Airlines

Sat, Aug 15 - Sat, Aug 29

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

$247American Airlines

Mon, Aug 17 - Sat, Aug 29

8:27 pm - 10:11 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 44mnonstop

6:29 pm - 9:54 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 25mnonstop

$247United Airlines

Mon, Aug 17 - Tue, Sep 1

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

2h 37mnonstop

7:05 am - 10:22 amORD Chicago O'Hare Intl-EWR Newark

2h 17mnonstop

$247United Airlines

Mon, Aug 17 - Wed, Sep 16

6:45 pm - 8:49 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

3h 04mnonstop

9:30 am - 12:49 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 19mnonstop

$257Delta

Mon, Aug 17 - Sat, Sep 19

6:45 pm - 8:49 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

3h 04mnonstop

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

2h 15mnonstop

$257Delta

Sat, Aug 15 - Sat, Aug 22

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

2h 58mnonstop

9:40 am - 12:59 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 19mnonstop

$265JetBlue

Sat, Aug 15 - Wed, Aug 19

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

2h 58mnonstop

6:30 pm - 10:06 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 36mnonstop

$267JetBlue

Recent direct flight deals from New York to Chicago

Thu, Sep 10 - Mon, Sep 14

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

2h 48mnonstop

1:45 pm - 5:02 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 17mnonstop

$205American Airlines

Thu, Sep 10 - Mon, Sep 14

2:58 pm - 4:46 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 48mnonstop

1:35 pm - 5:00 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 25mnonstop

$205American Airlines

Sun, Jan 17 - Mon, Jan 25

4:00 pm - 5:47 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 47mnonstop

5:00 pm - 8:15 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 15mnonstop

$208Delta

Sun, Jan 17 - Sat, Jan 23

2:30 pm - 4:12 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 42mnonstop

2:30 pm - 5:45 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 15mnonstop

$208Delta

Tue, Sep 1 - Thu, Sep 3

3:40 pm - 5:35 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 55mnonstop

6:00 am - 9:17 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 17mnonstop

$210JetBlue

Tue, Aug 25 - Wed, Sep 16

3:40 pm - 5:35 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 55mnonstop

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

2h 21mnonstop

$210JetBlue

Tue, Jan 19 - Fri, Jan 22

12:00 pm - 1:30 pmLGA New York LaGuardia-MDW Chicago Midway

2h 30mnonstop

2:05 pm - 5:10 pmMDW Chicago Midway-LGA New York LaGuardia

2h 05mnonstop

$211Southwest

Tue, Aug 25 - Wed, Sep 16

7:25 am - 8:45 amLGA New York LaGuardia-MDW Chicago Midway

2h 20mnonstop

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

2h 00mnonstop

$213Southwest

Sat, Aug 29 - Tue, Sep 1

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

2h 40mnonstop

6:00 pm - 9:25 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 25mnonstop

$213United Airlines

Sat, Aug 22 - Wed, Sep 2

6:33 pm - 8:17 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 44mnonstop

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

2h 25mnonstop

$213United Airlines

Useful Info

Low season	January
High season	October
Cheapest flight	$73

Best time to beat the crowds with an average 17% drop in price.

Most popular time to fly and prices are also 13% lower on average.

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

Chesterton

Schererville

Porter

Monticello

Saint John

Griffith

Everything you need to know for your flight to Chicago

Cabin class

Complete your trip

Direct Flights

Flights to other cities

Origins

Other airports

Return flight deals

Cabin class types available on flights to New York

First Class flights to Chicagofrom $577

Business Class flights to Chicagofrom $457

Premium Economy Class flights to Chicagofrom $246

Economy Class flights to Chicagofrom $147

$73 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

Good to know

Low season

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