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.

$108 CHEAP FLIGHTS from New York State to Chicago

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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

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

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

$239Frontier

Sun, Nov 15 - Tue, Nov 17

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

5h 59m1 stop Boston Logan Intl

$263JetBlue

Sun, Nov 15 - Tue, Nov 17

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

5h 59m1 stop Boston Logan Intl

$263JetBlue

Thu, Nov 12 - Mon, Nov 16

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

2h 57mnonstop

2:44 pm - 10:29 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

6h 45m1 stop Detroit Metropolitan Wayne County

$263Delta

Fri, Nov 13 - Sat, Nov 14

4:25 pm - 10:45 pmLGA New York LaGuardia-MDW Chicago Midway

7h 20m1 stop Lambert-St Louis

7:35 am - 8:30 pmMDW Chicago Midway-LGA New York LaGuardia

11h 55m2 stops Baltimore/Washington Lambert-St Louis

$263Southwest

Thu, Jan 21 - Sun, Jan 24

2:00 pm - 11:00 pmLGA New York LaGuardia-MDW Chicago Midway

10h 00m1 stop Dallas Love Field

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

2h 00mnonstop

$263Southwest

Mon, Nov 23 - Tue, Dec 1

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

2h 57mnonstop

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

2h 20mnonstop

$267Delta

Sun, Nov 29 - Thu, Dec 3

8:35 am - 2:33 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

6h 58m1 stop Charlotte Douglas

4:59 pm - 11:37 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

5h 38m1 stop Washington, D.C. Reagan-National

$267American Airlines

Fri, Nov 20 - Wed, Nov 25

8:30 pm - 10:37 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

3h 07mnonstop

4:17 pm - 7:45 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 28mnonstop

$267American Airlines

Recent last minute flight deals from New York to Chicago

Wed, Oct 21 - Sat, Nov 7

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

6h 22m1 stop Atlanta Hartsfield-Jackson

10:29 am - 8:59 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

9h 30m1 stop Dallas/Fort Worth

$263Frontier

Wed, Oct 21 - Wed, Nov 4

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

6h 22m1 stop Atlanta Hartsfield-Jackson

8:59 am - 8:59 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

11h 00m1 stop Dallas/Fort Worth

$263Frontier

Tue, Oct 20 - Sat, Nov 7

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

Sat, Oct 24 - Sat, Nov 7

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

5h 59m1 stop Boston Logan Intl

$321JetBlue

Thu, Oct 22 - Thu, Nov 5

7:14 am - 9:05 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 51mnonstop

6:44 am - 10:09 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 25mnonstop

$331American Airlines

Wed, Oct 21 - Sat, Nov 7

4:30 pm - 6:20 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 50mnonstop

7:00 am - 10:20 amORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 20mnonstop

$331Delta

Wed, Oct 21 - Wed, Nov 4

4:30 pm - 6:20 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 50mnonstop

10:05 am - 1:26 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 21mnonstop

$331Delta

Thu, Oct 22 - Thu, Nov 5

8:10 am - 9:47 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 37mnonstop

5:00 pm - 8:19 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 19mnonstop

$331United Airlines

Thu, Oct 22 - Thu, Nov 5

10:45 am - 2:29 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

4h 44m1 stop Washington, D.C. Reagan-National

6:59 am - 10:19 amORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 20mnonstop

$341American Airlines

Tue, Oct 20 - Sat, Sep 4

8:10 am - 9:47 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 37mnonstop

2:00 pm - 5:09 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 09mnonstop

$346United Airlines

Recent direct flight deals from New York to Chicago

Thu, Nov 19 - Mon, Nov 23

2:00 pm - 2:50 pmBUF Buffalo-MDW Chicago Midway

1h 50mnonstop

7:50 am - 10:25 amMDW Chicago Midway-BUF Buffalo

1h 35mnonstop

$264Southwest

Thu, Jan 7 - Mon, Jan 11

1:55 pm - 3:00 pmBUF Buffalo-MDW Chicago Midway

2h 05mnonstop

8:10 am - 10:50 amMDW Chicago Midway-BUF Buffalo

1h 40mnonstop

$264Southwest

Fri, Nov 20 - Wed, Nov 25

8:30 pm - 10:37 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

3h 07mnonstop

4:17 pm - 7:45 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 28mnonstop

$267American Airlines

Mon, Nov 23 - Tue, Dec 1

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

2h 57mnonstop

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

2h 20mnonstop

$267Delta

Thu, Dec 31 - Wed, Jan 6

7:40 pm - 9:39 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 59mnonstop

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

2h 35mnonstop

$267Delta

Sun, Nov 8 - Mon, Nov 9

6:45 am - 8:10 amLGA New York LaGuardia-MDW Chicago Midway

2h 25mnonstop

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

2h 05mnonstop

$268Southwest

Sat, Nov 7 - Mon, Nov 9

2:59 pm - 4:55 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 56mnonstop

6:44 am - 10:09 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 25mnonstop

$277American Airlines

Fri, Jan 22 - Sun, Jan 24

4:13 pm - 6:05 pmALB Albany Intl-ORD Chicago O'Hare Intl

2h 52mnonstop

2:45 pm - 6:07 pmORD Chicago O'Hare Intl-ALB Albany Intl

2h 22mnonstop

$292United Airlines

Tue, Jan 5 - Thu, Jan 7

4:17 pm - 6:08 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 51mnonstop

3:00 pm - 6:15 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 15mnonstop

$297United Airlines

Thu, Nov 5 - Mon, Nov 9

11:26 am - 12:40 pmBUF Buffalo-ORD Chicago O'Hare Intl

2h 14mnonstop

7:00 pm - 9:37 pmORD Chicago O'Hare Intl-BUF Buffalo

1h 37mnonstop

$308Alaska Airlines

Useful Info

Low season	January
High season	July
Cheapest flight	$108

Best time to beat the crowds with an average 20% drop in price.

Most popular time to fly with an average 3% increase in price.

Flight from Buffalo to Chicago Midway 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

Chesterton

Schererville

Porter

Monticello

Saint John

Griffith

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$108 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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