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.

$102 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

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

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

$211JetBlue

Sat, Oct 31 - Tue, Nov 3

6:25 am - 12:02 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

6h 37m1 stop Atlanta Hartsfield-Jackson

2:03 pm - 8:53 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

5h 50m1 stop Atlanta Hartsfield-Jackson

$216Frontier

Tue, Oct 27 - Tue, Nov 3

6:25 am - 12:02 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

6h 37m1 stop Atlanta Hartsfield-Jackson

2:03 pm - 8:53 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

5h 50m1 stop Atlanta Hartsfield-Jackson

$216Frontier

Tue, Sep 22 - Fri, Sep 25

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

$220Multiple Airlines

Mon, Sep 21 - Sat, Sep 26

6:30 am - 1:45 pmEWR Newark-ORD Chicago O'Hare Intl

8h 15m1 stop Fort Lauderdale

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

8h 11m1 stop Orlando

$220Multiple Airlines

Wed, Sep 2 - Wed, Sep 2

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

2h 46mnonstop

1:15 pm - 4:39 pmORD Chicago O'Hare Intl-EWR Newark

2h 24mnonstop

$237American Airlines

Tue, Sep 1 - Wed, Sep 2

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

2h 52mnonstop

10:09 am - 1:30 pmORD Chicago O'Hare Intl-EWR Newark

2h 21mnonstop

$237American Airlines

Wed, Sep 2 - Wed, Sep 2

9:15 am - 10:58 amEWR Newark-ORD Chicago O'Hare Intl

2h 43mnonstop

7:45 pm - 11:07 pmORD Chicago O'Hare Intl-EWR Newark

2h 22mnonstop

$237United Airlines

Wed, Sep 2 - Wed, Sep 9

7:13 pm - 9:00 pmEWR Newark-ORD Chicago O'Hare Intl

2h 47mnonstop

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

2h 14mnonstop

$242United 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

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 - Tue, Sep 1

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

2h 46mnonstop

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

2h 19mnonstop

$262American Airlines

Sat, Aug 22 - Tue, Sep 1

5:29 am - 7:15 amEWR Newark-ORD Chicago O'Hare Intl

2h 46mnonstop

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

2h 19mnonstop

$262American 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

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

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

1:00 pm - 4:33 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 33mnonstop

$267Delta

Thu, Aug 20 - Wed, Nov 25

1:35 pm - 8:15 pmEWR Newark-ORD Chicago O'Hare Intl

7h 40m1 stop Dallas/Fort Worth

3:20 pm - 11:55 pmORD Chicago O'Hare Intl-EWR Newark

7h 35m1 stop Fort Lauderdale

$276Multiple Airlines

Sat, Aug 22 - Tue, Aug 25

6:20 pm - 8:07 pmEWR Newark-ORD Chicago O'Hare Intl

2h 47mnonstop

8:40 am - 11:58 amORD Chicago O'Hare Intl-EWR Newark

2h 18mnonstop

$287United Airlines

Recent direct flight deals from New York to Chicago

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

Tue, Sep 1 - Wed, Sep 2

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

2h 55mnonstop

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

2h 36mnonstop

$228JetBlue

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 - Wed, Sep 2

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

$237Delta

Wed, Sep 2 - Wed, Sep 2

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

2h 49mnonstop

8:25 pm - 11:45 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 20mnonstop

$237American Airlines

Tue, Sep 1 - Wed, Sep 2

4:00 pm - 5:57 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 57mnonstop

8:00 am - 11:16 amORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 16mnonstop

$237American Airlines

Wed, Sep 2 - Wed, Sep 2

9:15 am - 10:58 amEWR Newark-ORD Chicago O'Hare Intl

2h 43mnonstop

7:45 pm - 11:07 pmORD Chicago O'Hare Intl-EWR Newark

2h 22mnonstop

$237United Airlines

Wed, Sep 2 - Wed, Sep 2

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

2h 20mnonstop

12:25 pm - 3:30 pmMDW Chicago Midway-LGA New York LaGuardia

2h 05mnonstop

$237Southwest

Tue, Sep 1 - Wed, Sep 2

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

2h 15mnonstop

9:30 am - 12:35 pmMDW Chicago Midway-LGA New York LaGuardia

2h 05mnonstop

$237Southwest

Wed, Sep 2 - Sat, Sep 5

1:25 pm - 3:09 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

$242United Airlines

Useful Info

Low season	January
High season	July
Cheapest flight	$102

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 Rochester 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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Flights to other cities

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 $174

$102 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

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