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.

$98 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 5 - Sat, Sep 5

3:59 pm - 5:57 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 58mnonstop

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

2h 20mnonstop

$212American Airlines

Tue, Aug 25 - Tue, Sep 1

10:55 am - 12:15 pmLGA New York LaGuardia-MDW Chicago Midway

2h 20mnonstop

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

2h 05mnonstop

$217Southwest

Mon, Oct 5 - Tue, Oct 6

11:35 am - 6:23 pmEWR Newark-ORD Chicago O'Hare Intl

7h 48m1 stop Atlanta Hartsfield-Jackson

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

8h 11m1 stop Orlando

$217Frontier

Sat, Sep 5 - Tue, Sep 29

11:30 am - 11:08 pmEWR Newark-ORD Chicago O'Hare Intl

12h 38m1 stop Orlando

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

8h 11m1 stop Orlando

$217Frontier

Wed, Sep 2 - Sat, Sep 5

8:00 pm - 9:58 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 58mnonstop

5:27 pm - 9:00 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 33mnonstop

$217JetBlue

Wed, Sep 2 - Sat, Sep 5

8:00 pm - 9:58 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 58mnonstop

5:27 pm - 9:00 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 33mnonstop

$217JetBlue

Tue, Aug 25 - Sat, Aug 29

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

2h 46mnonstop

8:36 pm - 11:59 pmORD Chicago O'Hare Intl-EWR Newark

2h 23mnonstop

$217American Airlines

Thu, Oct 1 - Mon, Oct 5

3:38 pm - 11:08 pmEWR Newark-ORD Chicago O'Hare Intl

8h 30m1 stop Fort Lauderdale

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

8h 11m1 stop Orlando

$220Multiple Airlines

Fri, Oct 2 - Mon, Oct 5

3:38 pm - 11:08 pmEWR Newark-ORD Chicago O'Hare Intl

8h 30m1 stop Fort Lauderdale

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

8h 11m1 stop Orlando

$220Multiple Airlines

Wed, Aug 26 - Sat, Aug 29

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

2h 15mnonstop

6:00 am - 9:00 amMDW Chicago Midway-LGA New York LaGuardia

2h 00mnonstop

$222Southwest

Recent last minute flight deals from New York to Chicago

Wed, Aug 12 - Wed, Aug 26

5:00 pm - 7:12 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

3h 12mnonstop

6:00 am - 9:09 amORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 09mnonstop

$216Delta

Wed, Aug 12 - Wed, Aug 26

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

$216Delta

Wed, Aug 12 - Wed, Sep 2

10:29 pm - 8:02 amEWR Newark-ORD Chicago O'Hare Intl

10h 33m1 stop Atlanta Hartsfield-Jackson

1:59 pm - 9:28 pmORD Chicago O'Hare Intl-EWR Newark

6h 29m1 stop Atlanta Hartsfield-Jackson

$217Frontier

Wed, Aug 12 - Wed, Sep 2

10:29 pm - 9:51 amEWR Newark-MDW Chicago Midway

12h 22m1 stop Atlanta Hartsfield-Jackson

11:50 am - 1:03 amMDW Chicago Midway-EWR Newark

12h 13m1 stop Atlanta Hartsfield-Jackson

$223Frontier

Thu, Aug 13 - Fri, Sep 11

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

2h 46mnonstop

8:38 pm - 11:59 pmORD Chicago O'Hare Intl-EWR Newark

2h 21mnonstop

$257American Airlines

Tue, Aug 11 - Tue, Aug 11

8:27 am - 10:30 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

3h 03mnonstop

4:30 pm - 8:01 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 31mnonstop

$257American Airlines

Wed, Aug 12 - Wed, Aug 19

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

2h 15mnonstop

5:45 pm - 8:55 pmMDW Chicago Midway-LGA New York LaGuardia

2h 10mnonstop

$257Southwest

Thu, Aug 13 - Mon, Aug 17

8:00 pm - 9:58 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 58mnonstop

6:00 am - 9:17 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 17mnonstop

$265JetBlue

Thu, Aug 13 - Tue, Aug 18

6:55 am - 8:43 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 48mnonstop

6:00 am - 9:17 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 17mnonstop

$265JetBlue

Tue, Aug 11 - Tue, Aug 11

6:30 am - 11:50 amLGA New York LaGuardia-MDW Chicago Midway

6h 20m1 stop Lambert-St Louis

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

2h 05mnonstop

$267Southwest

Recent direct flight deals from New York to Chicago

Sat, Sep 5 - Sat, Sep 5

3:59 pm - 5:57 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 58mnonstop

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

2h 20mnonstop

$212American Airlines

Wed, Sep 2 - Sat, Sep 5

8:44 am - 10:30 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 46mnonstop

6:57 pm - 10:17 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 20mnonstop

$217American Airlines

Wed, Sep 2 - Sat, Sep 5

8:00 pm - 9:58 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 58mnonstop

5:27 pm - 9:00 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 33mnonstop

$217JetBlue

Wed, Sep 2 - Sat, Sep 5

8:00 pm - 9:58 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 58mnonstop

5:27 pm - 9:00 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 33mnonstop

$217JetBlue

Tue, Aug 25 - Tue, Sep 1

10:55 am - 12:15 pmLGA New York LaGuardia-MDW Chicago Midway

2h 20mnonstop

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

2h 05mnonstop

$217Southwest

Wed, Aug 26 - Sat, Aug 29

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

2h 15mnonstop

6:00 am - 9:00 amMDW Chicago Midway-LGA New York LaGuardia

2h 00mnonstop

$222Southwest

Tue, Sep 1 - Tue, Sep 1

7:30 am - 9:06 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 36mnonstop

2:25 pm - 5:47 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 22mnonstop

$227Delta

Sat, Aug 29 - Wed, Sep 2

5:55 pm - 7:57 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

3h 02mnonstop

8:12 pm - 11:44 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 32mnonstop

$227Delta

Tue, Aug 25 - Sat, Aug 29

2:25 pm - 4:09 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 44mnonstop

6:00 pm - 9:25 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 25mnonstop

$227United Airlines

Wed, Aug 26 - Wed, Sep 2

6:29 pm - 8:13 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 44mnonstop

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

2h 17mnonstop

$227United Airlines

Useful Info

Low season	January
High season	October
Cheapest flight	$98

Best time to beat the crowds with an average 17% drop in price.

Most popular time to fly and prices are also 12% lower on average.

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

Saint Joseph

Hammond

Portage

Lansing

Valparaiso

Munster

Chesterton

Schererville

Porter

Monticello

Saint John

Griffith

Everything you need to know for your flight to Chicago

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Complete your trip

Direct Flights

Flights to other cities

Origins

Other airports

Return flight deals

Cabin class types available on flights to New York

First Class flights to Chicagofrom $571

Business Class flights to Chicagofrom $598

Premium Economy Class flights to Chicagofrom $331

Economy Class flights to Chicagofrom $140

$98 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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High season

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