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.

$103 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, Nov 21 - Mon, Nov 23

1:03 pm - 7:47 pmBUF Buffalo-MDW Chicago Midway

7h 44m1 stop Orlando

8:42 pm - 8:24 pmMDW Chicago Midway-BUF Buffalo

22h 42m1 stop Orlando

$238Frontier

Wed, Nov 11 - Wed, Nov 18

2:00 pm - 11:47 pmBUF Buffalo-MDW Chicago Midway

10h 47m1 stop Atlanta Hartsfield-Jackson

6:08 am - 1:15 pmMDW Chicago Midway-BUF Buffalo

6h 07m1 stop Atlanta Hartsfield-Jackson

$238Frontier

Mon, Nov 9 - Wed, Nov 11

1:26 pm - 7:17 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

6h 51m1 stop Boston Logan Intl

1:00 pm - 7:59 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

5h 59m1 stop Boston Logan Intl

$246JetBlue

Tue, Nov 10 - Thu, Nov 12

6:40 am - 12:00 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

6h 20m1 stop Boston Logan Intl

1:00 pm - 9:29 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

7h 29m1 stop Boston Logan Intl

$246JetBlue

Sun, Nov 29 - Thu, Dec 3

6:56 am - 12:41 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

6h 45m1 stop Lambert-St Louis

9:30 am - 4:30 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

6h 00m1 stop Cleveland Hopkins Intl

$247American Airlines

Tue, Feb 2 - Tue, Feb 2

10:26 am - 2:00 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

4h 34m1 stop Detroit Metropolitan Wayne County

3:44 pm - 7:00 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 16mnonstop

$250American Airlines

Sat, Feb 13 - Mon, Feb 15

7:35 pm - 9:33 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 58mnonstop

6:10 pm - 9:45 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 35mnonstop

$251Delta

Wed, Nov 4 - Sun, Nov 8

3:24 pm - 5:20 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 56mnonstop

6:10 am - 9:27 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 17mnonstop

$251Delta

Wed, Nov 18 - Mon, Nov 23

5:55 am - 2:30 pmALB Albany Intl-MDW Chicago Midway

9h 35m2 stops Baltimore/Washington Atlanta Hartsfield-Jackson

6:30 pm - 7:55 amMDW Chicago Midway-ALB Albany Intl

12h 25m2 stops Lambert-St Louis Baltimore/Washington

$273Southwest

Mon, Nov 23 - Mon, Nov 23

7:25 am - 4:00 pmALB Albany Intl-MDW Chicago Midway

9h 35m1 stop Baltimore/Washington

6:30 pm - 7:55 amMDW Chicago Midway-ALB Albany Intl

12h 25m2 stops Lambert-St Louis Baltimore/Washington

$273Southwest

Recent last minute flight deals from New York to Chicago

Sat, Oct 17 - Tue, Oct 27

6:10 am - 11:32 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

6h 22m1 stop Atlanta Hartsfield-Jackson

10:40 am - 7:35 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

7h 55m1 stop Dallas/Fort Worth

$273Frontier

Tue, Oct 20 - Tue, Nov 3

4:59 pm - 11:43 pmLGA New York LaGuardia-MDW Chicago Midway

7h 44m1 stop Atlanta Hartsfield-Jackson

12:27 pm - 8:59 pmMDW Chicago Midway-LGA New York LaGuardia

7h 32m1 stop Dallas/Fort Worth

$294Frontier

Tue, Oct 20 - Thu, Oct 22

2:40 pm - 4:26 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 46mnonstop

6:00 am - 9:12 amORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 12mnonstop

$317Delta

Mon, Oct 19 - Thu, Oct 22

6:00 am - 7:36 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 36mnonstop

7:00 am - 10:17 amORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 17mnonstop

$317Delta

Sat, Oct 17 - Mon, Nov 16

12:25 pm - 2:13 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 48mnonstop

2:31 pm - 5:59 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 28mnonstop

$321American Airlines

Sun, Oct 18 - Tue, Nov 3

7:01 am - 8:50 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 49mnonstop

11:05 am - 2:29 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 24mnonstop

$321American Airlines

Tue, Oct 20 - Tue, Nov 3

1:00 pm - 7:14 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

7h 14m1 stop Boston Logan Intl

1:00 pm - 9:29 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

7h 29m1 stop Boston Logan Intl

$321JetBlue

Fri, Oct 16 - Mon, Nov 16

8:15 pm - 10:10 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 55mnonstop

1:00 pm - 9:29 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

7h 29m1 stop Boston Logan Intl

$321JetBlue

Fri, Oct 16 - Tue, Oct 20

6:00 am - 7:39 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 39mnonstop

7:45 pm - 11:10 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 25mnonstop

$345United Airlines

Mon, Oct 19 - Thu, Oct 22

10:20 am - 11:59 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 39mnonstop

7:00 am - 10:17 amORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 17mnonstop

$345United Airlines

Recent direct flight deals from New York to Chicago

Sat, Feb 13 - Mon, Feb 15

7:35 pm - 9:33 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 58mnonstop

6:10 pm - 9:45 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 35mnonstop

$251Delta

Thu, Nov 5 - Sun, Nov 8

7:35 pm - 9:43 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

3h 08mnonstop

6:10 am - 9:27 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 17mnonstop

$251Delta

Wed, Nov 4 - Sun, Nov 8

3:24 pm - 5:20 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 56mnonstop

6:10 am - 9:27 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 17mnonstop

$251Delta

Thu, Dec 17 - Sat, Dec 19

8:05 pm - 10:00 pmALB Albany Intl-ORD Chicago O'Hare Intl

2h 55mnonstop

7:15 pm - 10:37 pmORD Chicago O'Hare Intl-ALB Albany Intl

2h 22mnonstop

$292American Airlines

Fri, Nov 6 - Sun, Nov 8

7:16 pm - 9:14 pmALB Albany Intl-ORD Chicago O'Hare Intl

2h 58mnonstop

8:16 am - 11:28 amORD Chicago O'Hare Intl-ALB Albany Intl

2h 12mnonstop

$292American Airlines

Sun, Dec 6 - Tue, Dec 8

6:00 am - 7:44 amALB Albany Intl-ORD Chicago O'Hare Intl

2h 44mnonstop

6:10 pm - 9:28 pmORD Chicago O'Hare Intl-ALB Albany Intl

2h 18mnonstop

$292United Airlines

Sat, Nov 7 - Sun, Nov 8

8:30 am - 10:15 amALB Albany Intl-ORD Chicago O'Hare Intl

2h 45mnonstop

6:15 pm - 9:33 pmORD Chicago O'Hare Intl-ALB Albany Intl

2h 18mnonstop

$292United Airlines

Sun, Dec 6 - Tue, Dec 8

6:50 pm - 8:20 pmALB Albany Intl-MDW Chicago Midway

2h 30mnonstop

6:25 pm - 9:20 pmMDW Chicago Midway-ALB Albany Intl

1h 55mnonstop

$292Southwest

Sun, Nov 15 - Thu, Nov 19

6:50 pm - 8:20 pmALB Albany Intl-MDW Chicago Midway

2h 30mnonstop

1:25 pm - 4:10 pmMDW Chicago Midway-ALB Albany Intl

1h 45mnonstop

$292Southwest

Fri, Nov 6 - Sun, Nov 8

7:16 pm - 9:14 pmALB Albany Intl-ORD Chicago O'Hare Intl

2h 58mnonstop

8:16 am - 11:28 amORD Chicago O'Hare Intl-ALB Albany Intl

2h 12mnonstop

$292American Airlines

Useful Info

Low season	January
High season	July
Cheapest flight	$103

Best time to beat the crowds with an average 19% drop in price.

Most popular time to fly with an average 4% increase in price.

Flight from Rochester to Chicago O'Hare Airport

MidnightFlew with American Airlines-Oct 2026

get there a few hours early. after getting through checking find you gate an stay there.

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

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$103 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

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More options for your flight to Chicago

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

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Flights from domestic origins to Chicago

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