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.

$63 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

Wed, Oct 21 - Fri, Oct 23

1:44 pm - 11:43 pmBUF Buffalo-MDW Chicago Midway

10h 59m1 stop Atlanta Hartsfield-Jackson

6:15 am - 12:59 pmMDW Chicago Midway-BUF Buffalo

5h 44m1 stop Atlanta Hartsfield-Jackson

$230Frontier

Wed, Oct 21 - Fri, Oct 23

1:44 pm - 11:43 pmBUF Buffalo-MDW Chicago Midway

10h 59m1 stop Atlanta Hartsfield-Jackson

6:15 am - 12:59 pmMDW Chicago Midway-BUF Buffalo

5h 44m1 stop Atlanta Hartsfield-Jackson

$232Frontier

Wed, Jan 6 - Wed, Jan 6

10:19 am - 2:00 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

4h 41m1 stop Detroit Metropolitan Wayne County

4:37 pm - 7:53 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 16mnonstop

$250American 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

Mon, Nov 23 - Thu, Nov 26

6:05 am - 7:42 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 37mnonstop

10:06 am - 1:16 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 10mnonstop

$254Delta

Thu, Oct 29 - Wed, Nov 4

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

$266JetBlue

Thu, Oct 29 - Wed, Nov 4

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

$267JetBlue

Tue, Dec 1 - Thu, Dec 3

7:05 pm - 8:45 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 40mnonstop

11:35 am - 2:59 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 24mnonstop

$273Delta

Wed, Oct 21 - Fri, Oct 23

10:00 am - 2:26 pmALB Albany Intl-ORD Chicago O'Hare Intl

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

6:10 pm - 9:22 pmORD Chicago O'Hare Intl-ALB Albany Intl

2h 12mnonstop

$276United Airlines

Mon, Feb 8 - Fri, Feb 12

7:35 pm - 11:59 pmALB Albany Intl-ORD Chicago O'Hare Intl

5h 24m1 stop Washington, D.C. Dulles Intl

5:59 pm - 9:12 pmORD Chicago O'Hare Intl-ALB Albany Intl

2h 13mnonstop

$276United Airlines

Recent last minute flight deals from New York to Chicago

Sun, Oct 4 - Wed, Nov 4

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

12h 31m1 stop Atlanta Hartsfield-Jackson

6:16 am - 4:01 pmMDW Chicago Midway-LGA New York LaGuardia

8h 45m1 stop Atlanta Hartsfield-Jackson

$248Frontier

Wed, Oct 7 - Wed, Nov 4

6:15 am - 5:51 pmLGA New York LaGuardia-MDW Chicago Midway

12h 36m1 stop Atlanta Hartsfield-Jackson

6:16 am - 4:01 pmMDW Chicago Midway-LGA New York LaGuardia

8h 45m1 stop Atlanta Hartsfield-Jackson

$248Frontier

Sun, Oct 4 - Wed, Nov 4

6:00 am - 7:53 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 53mnonstop

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

2h 24mnonstop

$311American Airlines

Mon, Oct 5 - Mon, Oct 26

9:16 pm - 11:00 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 44mnonstop

8:05 am - 11:24 amORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 19mnonstop

$311American Airlines

Wed, Oct 7 - Sat, Oct 24

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

2h 36mnonstop

2:00 pm - 5:20 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 20mnonstop

$311Delta

Wed, Oct 7 - Wed, Oct 28

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

2h 36mnonstop

8:20 pm - 11:44 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 24mnonstop

$311Delta

Sun, Oct 4 - Tue, Nov 3

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

2h 39mnonstop

1:00 pm - 4:15 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 15mnonstop

$311United Airlines

Mon, Oct 5 - Mon, Oct 26

9:00 pm - 10:25 pmLGA New York LaGuardia-MDW Chicago Midway

2h 25mnonstop

5:10 am - 8:15 amMDW Chicago Midway-LGA New York LaGuardia

2h 05mnonstop

$311Southwest

Mon, Oct 5 - Tue, Oct 27

5:45 pm - 7:15 pmLGA New York LaGuardia-MDW Chicago Midway

2h 30mnonstop

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

2h 10mnonstop

$311Southwest

Sun, Oct 4 - Tue, Oct 6

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

2h 39mnonstop

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

2h 15mnonstop

$345United Airlines

Recent direct flight deals from New York to Chicago

Mon, Nov 23 - Thu, Nov 26

6:05 am - 7:42 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 37mnonstop

10:06 am - 1:16 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 10mnonstop

$254Delta

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

$268JetBlue

Thu, Oct 22 - Sat, Oct 24

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

2h 54mnonstop

6:10 am - 9:30 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 20mnonstop

$268JetBlue

Tue, Nov 10 - Tue, Nov 10

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 10 - Tue, Nov 10

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

Tue, Dec 1 - Thu, Dec 3

7:05 pm - 8:45 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 40mnonstop

11:35 am - 2:59 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 24mnonstop

$273Delta

Thu, Oct 22 - Mon, Oct 26

7:15 am - 8:35 amLGA New York LaGuardia-MDW Chicago Midway

2h 20mnonstop

5:10 pm - 8:15 pmMDW Chicago Midway-LGA New York LaGuardia

2h 05mnonstop

$277Southwest

Thu, Dec 31 - Tue, Jan 5

6:40 am - 8:05 amLGA New York LaGuardia-MDW Chicago Midway

2h 25mnonstop

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

2h 05mnonstop

$277Southwest

Tue, Oct 20 - Thu, Oct 22

10:46 am - 11:45 amBUF Buffalo-ORD Chicago O'Hare Intl

1h 59mnonstop

6:50 am - 9:29 amORD Chicago O'Hare Intl-BUF Buffalo

1h 39mnonstop

$277United Airlines

Sat, Dec 12 - Mon, Dec 14

5:40 pm - 6:54 pmBUF Buffalo-ORD Chicago O'Hare Intl

2h 14mnonstop

6:55 am - 9:44 amORD Chicago O'Hare Intl-BUF Buffalo

1h 49mnonstop

$277United Airlines

Useful Info

Low season	January
High season	July
Cheapest flight	$63

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 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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$63 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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