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. Visit our flight page for the latest deals!>/a>

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. Visit our flight page for the latest deals!>/a>

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. Visit our flight page for the latest deals!>/a>

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. Visit our flight page for the latest deals!>/a>

$57 CHEAP FLIGHTS from New York State to Chicago

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

...and more

Travelers love KAYAK

41 299 237 searches in the past 7 days on KAYAK

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Filter your dealsChoose cabin class, free Wi-Fi and more.

Cheapest round-trip

$86

Typical prices: $147-$293

Frontier

Fri 1/30Sun 2/1

JFK - ORD • Non-stop

Cheapest one-way

$57

Typical prices: $98-$261

Spirit Airlines

Tue 12/16

LGA - ORD • 1 stop

Start a new search

KAYAK searches 100s of sites at once to find you the best travel deals.

We hope you love your trip to Chicago!

Flight Deals

Cheap Flights from New York to Chicago

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from New York to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

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

Fri, Jan 30 - Sun, Feb 1

4:29 pm - 6:29 pmJFK-ORD

3h 00mnonstop

11:55 am - 3:19 pmORD-JFK

2h 24mnonstop

$86Frontier

Find Deal

Thu, Dec 4 - Wed, Dec 10

8:41 pm - 10:11 pmLGA-ORD

2h 30mnonstop

4:38 pm - 7:42 pmORD-LGA

2h 04mnonstop

$86Spirit Airlines

Find Deal

Thu, Dec 4 - Sat, Dec 6

11:30 am - 1:01 pmEWR-MDW

2h 31mnonstop

6:00 am - 8:31 pmMDW-EWR

13h 31m1 stop

$111Multiple Airlines

Find Deal

Thu, Dec 11 - Thu, Dec 18

10:00 pm - 7:42 pmEWR-MDW

22h 42m1 stop

7:44 am - 10:45 amMDW-EWR

2h 01mnonstop

$117Multiple Airlines

Find Deal

Thu, Jan 15 - Sun, Jan 18

9:00 am - 10:40 amLGA-MDW

2h 40mnonstop

6:05 am - 9:10 amMDW-LGA

2h 05mnonstop

$138Southwest

Find Deal

Wed, Jan 28 - Sat, Jan 31

6:00 am - 7:40 amLGA-MDW

2h 40mnonstop

5:35 pm - 8:40 pmMDW-LGA

2h 05mnonstop

$139Southwest

Find Deal

Sat, Jan 17 - Sun, Jan 18

10:00 am - 5:43 pmBUF-ORD

8h 43m1 stop

7:45 am - 2:30 pmORD-BUF

5h 45m1 stop

$164JetBlue

Find Deal

Sat, Jan 17 - Sun, Jan 18

10:00 am - 5:44 pmBUF-ORD

8h 44m1 stop

7:45 am - 2:30 pmORD-BUF

5h 45m1 stop

$165JetBlue

Find Deal

Fri, Jan 23 - Sun, Jan 25

8:00 am - 9:44 amSYR-ORD

2h 44mnonstop

1:17 pm - 4:15 pmORD-SYR

1h 58mnonstop

$209United Airlines

Find Deal

Tue, Dec 16 - Tue, Dec 16

6:00 am - 7:42 amALB-ORD

2h 42mnonstop

6:00 pm - 9:14 pmORD-ALB

2h 14mnonstop

$269United Airlines

Find Deal

Useful Info

Low season	January
High season	November
Cheapest flight	$57

Best time to beat the crowds with an average 13% drop in price.

Most popular time to fly with an average 11% increase in price.

Flight from New York LaGuardia Airport to Chicago O'Hare Airport

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

Chesterton

Schererville

Munster

Porter

Monticello

Saint John

Griffith

Everything you need to know for your flight to Chicago

Cabin class

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 $297

Business Class flights to Chicagofrom $314

Prem Econ Class flights to Chicagofrom $287

Economy Class flights to Chicagofrom $56

$57 Find Cheap Flights from New York State to Chicago

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

Everything you should know

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

FAQs for booking flights from New York State to Chicago

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.

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