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.

$117 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

Thu, Nov 19 - Mon, Nov 23

2:34 pm - 12:13 amBUF Buffalo-ORD Chicago O'Hare Intl

10h 39m1 stop Atlanta Hartsfield-Jackson

5:12 pm - 8:24 pmORD Chicago O'Hare Intl-BUF Buffalo

26h 12m1 stop Orlando

$230Frontier

Wed, Dec 9 - Thu, Dec 10

1:15 pm - 6:37 pmBUF Buffalo-ORD Chicago O'Hare Intl

6h 22m1 stop Atlanta Hartsfield-Jackson

5:24 pm - 1:44 pmORD Chicago O'Hare Intl-BUF Buffalo

19h 20m1 stop Orlando

$230Frontier

Tue, Jan 12 - Thu, Jan 21

9:00 am - 2:22 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

6h 22m1 stop Washington, D.C. Reagan-National

5:56 am - 12:58 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

6h 02m1 stop Washington, D.C. Reagan-National

$248American Airlines

Wed, Oct 21 - Sat, Oct 24

9:30 am - 11:24 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 54mnonstop

12:38 pm - 4:00 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 22mnonstop

$267JetBlue

Tue, Oct 20 - Wed, Oct 21

9:30 am - 11:24 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 54mnonstop

12:38 pm - 4:00 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 22mnonstop

$267JetBlue

Tue, Nov 3 - Tue, Nov 3

3:55 pm - 5:53 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 58mnonstop

8:00 pm - 11:25 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 25mnonstop

$272American Airlines

Fri, Jan 8 - Wed, Jan 13

7:40 am - 9:10 amALB Albany Intl-MDW Chicago Midway

2h 30mnonstop

6:25 am - 12:35 pmMDW Chicago Midway-ALB Albany Intl

5h 10m1 stop Baltimore/Washington

$276Southwest

Fri, Oct 23 - Mon, Oct 26

7:20 am - 8:30 amALB Albany Intl-MDW Chicago Midway

2h 10mnonstop

3:45 pm - 11:25 pmMDW Chicago Midway-ALB Albany Intl

6h 40m1 stop Orlando

$276Southwest

Fri, Oct 23 - Mon, Oct 26

6:03 am - 9:37 amALB Albany Intl-ORD Chicago O'Hare Intl

4h 34m1 stop Washington, D.C. Dulles Intl

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

2h 18mnonstop

$276United Airlines

Fri, Jan 8 - Wed, Jan 13

9:45 am - 2:11 pmALB Albany Intl-ORD Chicago O'Hare Intl

5h 26m1 stop Washington, D.C. Dulles Intl

1:59 pm - 5:21 pmORD Chicago O'Hare Intl-ALB Albany Intl

2h 22mnonstop

$276United Airlines

Recent last minute flight deals from New York to Chicago

Tue, Sep 29 - Wed, Oct 28

6:15 am - 11:51 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

6h 36m1 stop Atlanta Hartsfield-Jackson

7:15 am - 4:01 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

7h 46m1 stop Atlanta Hartsfield-Jackson

$239Frontier

Thu, Oct 1 - Sat, Oct 31

6:15 am - 5:46 pmLGA New York LaGuardia-MDW Chicago Midway

12h 31m1 stop Atlanta Hartsfield-Jackson

7:25 am - 4:01 pmMDW Chicago Midway-LGA New York LaGuardia

7h 36m1 stop Atlanta Hartsfield-Jackson

$240Frontier

Thu, Oct 1 - Wed, Oct 7

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

$285Multiple Airlines

Sat, Oct 3 - Wed, Oct 7

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

$286Multiple Airlines

Thu, Oct 1 - Sat, Oct 31

8:55 am - 10:25 amLGA New York LaGuardia-MDW Chicago Midway

2h 30mnonstop

4:05 pm - 7:10 pmMDW Chicago Midway-LGA New York LaGuardia

2h 05mnonstop

$301Southwest

Sun, Oct 4 - Thu, Nov 19

6:00 am - 7:30 amLGA New York LaGuardia-MDW Chicago Midway

2h 30mnonstop

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

2h 05mnonstop

$301Southwest

Tue, Sep 29 - Sat, Oct 10

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

$302JetBlue

Sat, Oct 3 - Wed, Oct 14

8:15 pm - 10:08 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 53mnonstop

12:38 pm - 4:00 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 22mnonstop

$302JetBlue

Tue, Sep 29 - Wed, Oct 28

5:57 pm - 8:00 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

3h 03mnonstop

6:50 am - 10:05 amORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 15mnonstop

$306American Airlines

Thu, Oct 1 - Tue, Oct 13

6:55 am - 8:48 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 53mnonstop

10:34 am - 1:59 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 25mnonstop

$311American Airlines

Recent direct flight deals from New York to Chicago

Wed, Oct 21 - Sat, Oct 24

9:30 am - 11:24 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 54mnonstop

12:38 pm - 4:00 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 22mnonstop

$267JetBlue

Tue, Oct 20 - Wed, Oct 21

9:30 am - 11:24 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 54mnonstop

12:38 pm - 4:00 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 22mnonstop

$267JetBlue

Tue, Nov 3 - Tue, Nov 3

10:40 am - 12:35 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 55mnonstop

4:31 pm - 8:03 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 32mnonstop

$272American Airlines

Tue, Nov 3 - Tue, Nov 3

3:55 pm - 5:53 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 58mnonstop

8:00 pm - 11:25 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 25mnonstop

$272American Airlines

Mon, Oct 26 - Thu, Oct 29

7:30 am - 9:27 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 57mnonstop

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

2h 17mnonstop

$277Delta

Sat, Nov 14 - Thu, Dec 3

3:21 pm - 5:20 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 59mnonstop

6:00 am - 9:20 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 20mnonstop

$277Delta

Wed, Nov 4 - Mon, Nov 9

7:29 pm - 9:20 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 51mnonstop

8:00 am - 11:12 amORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 12mnonstop

$277United Airlines

Sat, Oct 24 - Mon, Oct 26

7:29 pm - 9:13 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 44mnonstop

11:59 am - 3:14 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 15mnonstop

$277United Airlines

Thu, Oct 15 - Mon, Oct 19

8:55 am - 10:25 amLGA New York LaGuardia-MDW Chicago Midway

2h 30mnonstop

2:40 pm - 5:50 pmMDW Chicago Midway-LGA New York LaGuardia

2h 10mnonstop

$277Southwest

Tue, Nov 17 - Thu, Nov 19

10:00 am - 11:40 amLGA New York LaGuardia-MDW Chicago Midway

2h 40mnonstop

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

2h 05mnonstop

$277Southwest

Useful Info

Low season	January
High season	July
Cheapest flight	$117

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

Most popular time to fly with an average 6% 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

Schererville

Munster

Chesterton

Porter

Monticello

Saint John

Griffith

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$117 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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