$54 Find Cheap Flights from New York State to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 3/14. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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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.

Recent round-trip flight deals from New York to Chicago

Wed, May 27 - Sat, May 30
Spirit Airlines Logo
6:15 pm - 7:57 pm
LGA
-
ORD
2h 42mnonstop
Spirit Airlines Logo
10:33 am - 1:43 pm
ORD
-
LGA
2h 10mnonstop
$86Spirit Airlines
Sun, Apr 12 - Wed, Apr 15
Spirit Airlines Logo
6:30 am - 8:01 am
LGA
-
ORD
2h 31mnonstop
Spirit Airlines Logo
2:09 pm - 5:20 pm
ORD
-
LGA
2h 11mnonstop
$87Spirit Airlines
Wed, Mar 25 - Tue, Mar 31
Frontier Logo
4:29 pm - 6:29 pm
JFK
-
ORD
3h 00mnonstop
Frontier Logo
8:06 am - 11:30 am
ORD
-
JFK
2h 24mnonstop
$89Frontier
Wed, Mar 25 - Tue, Mar 31
Frontier Logo
4:29 pm - 6:29 pm
JFK
-
ORD
3h 00mnonstop
Frontier Logo
8:06 am - 11:30 am
ORD
-
JFK
2h 24mnonstop
$90Frontier
Wed, Apr 15 - Wed, Apr 22
Multiple Airlines Logo
1:56 pm - 10:23 am
BUF
-
ORD
21h 27m
1 stop
Multiple Airlines Logo
6:08 pm - 11:40 am
ORD
-
BUF
16h 32m
1 stop
$138Multiple Airlines
Wed, Apr 15 - Wed, Apr 22
Multiple Airlines Logo
1:56 pm - 12:24 am
BUF
-
ORD
11h 28m
2 stops
Multiple Airlines Logo
11:07 am - 11:40 am
ORD
-
BUF
23h 33m
1 stop
$161Multiple Airlines
Thu, Aug 27 - Sun, Aug 30
Delta Logo
3:11 pm - 8:17 pm
SYR
-
ORD
6h 06m
1 stop
Delta Logo
8:15 am - 2:11 pm
ORD
-
SYR
4h 56m
1 stop
$249Delta
Tue, Mar 24 - Mon, Mar 30
JetBlue Logo
6:00 am - 10:10 am
SYR
-
ORD
5h 10m
1 stop
JetBlue Logo
6:20 pm - 10:57 pm
ORD
-
SYR
27h 37m
1 stop
$250JetBlue
Fri, Apr 10 - Mon, Apr 13
JetBlue Logo
6:10 am - 8:08 am
SYR
-
ORD
26h 58m
1 stop
JetBlue Logo
8:58 am - 10:57 pm
ORD
-
SYR
12h 59m
1 stop
$254JetBlue
Thu, Apr 9 - Sat, Apr 11
Delta Logo
6:16 pm - 11:54 pm
ROC
-
ORD
6h 38m
1 stop
Delta Logo
5:40 pm - 10:59 pm
ORD
-
ROC
4h 19m
1 stop
$315Delta
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Good to know

Low seasonJanuary
Cheapest flight$53
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly and prices are also 5% lower on average.
Flight from New York John F Kennedy Airport to Chicago O'Hare Airport

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?

Book flights to Chicago if you plan to visit one of these locations
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 types available on flights to New York

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.