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.

$93 CHEAP FLIGHTS from New York State to Chicago

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

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, Sep 30 - Sat, Oct 3

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

12h 36m1 stop Atlanta Hartsfield-Jackson

6:25 am - 4:00 pmMDW Chicago Midway-LGA New York LaGuardia

8h 35m1 stop Atlanta Hartsfield-Jackson

$228Frontier

Wed, Sep 30 - Wed, Oct 14

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

12h 36m1 stop Atlanta Hartsfield-Jackson

6:21 am - 4:14 pmMDW Chicago Midway-LGA New York LaGuardia

8h 53m1 stop Atlanta Hartsfield-Jackson

$228Frontier

Fri, Oct 30 - Mon, Nov 2

8:30 am - 3:20 pmLGA New York LaGuardia-MDW Chicago Midway

7h 50m1 stop Houston Hobby

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

2h 05mnonstop

$233Southwest

Fri, Nov 6 - Mon, Nov 9

6:45 pm - 1:10 amLGA New York LaGuardia-MDW Chicago Midway

7h 25m1 stop Dallas Love Field

7:15 pm - 10:20 pmMDW Chicago Midway-LGA New York LaGuardia

2h 05mnonstop

$233Southwest

Wed, Sep 30 - Sat, Oct 3

1:00 pm - 7:01 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

7h 01m1 stop Boston Logan Intl

9:38 am - 5:29 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

6h 51m1 stop Boston Logan Intl

$237JetBlue

Wed, Sep 30 - Wed, Oct 7

1:00 pm - 7:01 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

7h 01m1 stop Boston Logan Intl

10:59 am - 2:20 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 21mnonstop

$241JetBlue

Tue, Oct 6 - Sun, Oct 11

6:00 am - 9:38 amEWR Newark-ORD Chicago O'Hare Intl

4h 38m1 stop Washington, D.C. Dulles Intl

7:00 am - 11:48 amORD Chicago O'Hare Intl-EWR Newark

3h 48m1 stop Washington, D.C. Reagan-National

$242United Airlines

Tue, Sep 29 - Wed, Sep 30

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

$244Multiple Airlines

Wed, Sep 30 - Wed, Oct 14

1:00 pm - 6:23 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

6h 23m1 stop Atlanta Hartsfield-Jackson

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

2h 22mnonstop

$245Multiple Airlines

Thu, Dec 17 - Sun, Dec 27

2:59 pm - 6:50 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

4h 51m1 stop Washington, D.C. Dulles Intl

7:00 am - 10:11 amORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 11mnonstop

$264United Airlines

Recent last minute flight deals from New York to Chicago

Wed, Sep 16 - Wed, Sep 23

10:29 pm - 9:20 amEWR Newark-ORD Chicago O'Hare Intl

11h 51m1 stop Atlanta Hartsfield-Jackson

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

8h 11m1 stop Orlando

$244Frontier

Sat, Sep 19 - Wed, Sep 23

10:29 pm - 9:20 amEWR Newark-ORD Chicago O'Hare Intl

11h 51m1 stop Atlanta Hartsfield-Jackson

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

8h 11m1 stop Orlando

$244Frontier

Thu, Sep 17 - Tue, Oct 6

7:20 am - 9:00 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 40mnonstop

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

2h 17mnonstop

$286Delta

Sat, Sep 19 - Sat, Nov 21

7:20 am - 9:00 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 40mnonstop

6:26 pm - 9:59 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 33mnonstop

$286United Airlines

Sun, Sep 20 - Sat, Nov 21

7:20 am - 9:00 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 40mnonstop

3:00 pm - 6:19 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 19mnonstop

$286United Airlines

Thu, Sep 17 - Tue, Oct 6

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

2h 53mnonstop

7:22 am - 11:00 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 38mnonstop

$286American Airlines

Sat, Sep 19 - Tue, Sep 22

2:50 pm - 4:30 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 40mnonstop

5:40 pm - 9:00 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 20mnonstop

$293Delta

Thu, Sep 17 - Tue, Oct 6

8:29 am - 12:32 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

5h 03m1 stop Boston Logan Intl

1:31 pm - 5:00 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 29mnonstop

$296American Airlines

Wed, Sep 16 - Sat, Sep 26

1:00 pm - 6:23 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

6h 23m1 stop Atlanta Hartsfield-Jackson

7:00 am - 10:27 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 27mnonstop

$298Multiple Airlines

Wed, Sep 16 - Wed, Sep 23

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

$299Multiple Airlines

Recent direct flight deals from New York to Chicago

Wed, Oct 14 - Sun, Oct 18

9:05 pm - 10:30 pmLGA New York LaGuardia-MDW Chicago Midway

2h 25mnonstop

5:05 am - 8:10 amMDW Chicago Midway-LGA New York LaGuardia

2h 05mnonstop

$236Southwest

Wed, Dec 2 - Sun, Dec 6

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

2h 40mnonstop

5:15 pm - 8:20 pmMDW Chicago Midway-LGA New York LaGuardia

2h 05mnonstop

$236Southwest

Wed, Sep 30 - Wed, Oct 7

8:10 am - 9:58 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 48mnonstop

10:59 am - 2:20 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 21mnonstop

$258JetBlue

Tue, Oct 6 - Wed, Oct 7

8:10 am - 9:59 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 49mnonstop

10:59 am - 2:20 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 21mnonstop

$258JetBlue

Mon, Oct 5 - Tue, Oct 6

4:15 pm - 6:04 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 49mnonstop

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

2h 21mnonstop

$265Delta

Tue, Nov 10 - Wed, Nov 11

5:35 pm - 7:25 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 50mnonstop

11:30 am - 2:38 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 08mnonstop

$265Delta

Fri, Nov 6 - Fri, Nov 6

7:29 am - 9:30 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

3h 01mnonstop

2:31 pm - 6:00 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 29mnonstop

$267American Airlines

Sun, Nov 22 - Fri, Nov 27

7:45 am - 9:47 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

3h 02mnonstop

10:37 am - 2:00 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 23mnonstop

$267American Airlines

Sun, Jan 17 - Sat, Mar 20

3:25 pm - 5:16 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 51mnonstop

4:00 pm - 7:13 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 13mnonstop

$267United Airlines

Wed, Oct 7 - Thu, Oct 29

7:23 am - 9:00 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 37mnonstop

4:59 pm - 8:18 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 19mnonstop

$267United Airlines

Useful Info

Low season	January
High season	July
Cheapest flight	$93

Best time to beat the crowds with an average 16% drop in price.

Most popular time to fly with an average 9% increase in price.

Flight from New York LaGuardia Airport to Chicago Midway 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

Munster

Schererville

Chesterton

Porter

Monticello

Saint John

Griffith

More options for your flight to Chicago

Add a hotel or car rental

Cabin class

Direct Flights

Origins

Other airports

Other destinations

Return flight

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

Car rentals in Chicago

$93 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

Good to know

Low season

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?

More options for your flight to Chicago

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

Cabin class types available on flights to New York

Find direct flights for Chicago

Flights from domestic origins to Chicago

Choose which airport to fly into in Chicago

Flights to other popular destinations

Find deals for your return flight