Popular in | June |
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Cheapest in | February |
Round-trip from | $222 |
One-way from | $30 |
Users have found that leaving on a Monday can be a cost-effective option. It’s possible to save up to 41% on your flight compared to booking on days when demand is much higher.
When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 56 days in advance, which can save you up to 98% on flights from New York to Chicago compared to booking the week you need them. Waiting 56 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $282. For sooner than that we have options available in the next 3 days from $423.
Due to multiple factors, expect to potentially pay more when booking in June. For low rates, February can be a great choice for travel to Chicago. Flights to Chicago from New York in February are about $259 on average during February, but can be found for as low as $81.
It’s typically best to fly out from New York to Chicago in the evening. Doing so could potentially save you 17% on the flight price compared to flying in the afternoon, which is usually more expensive.
One of the most popular airlines traveling from New York to Chicago is Delta. Flights from Delta traveling this route typically cost $448.75 RT. This price is typically 28% cheaper than other airlines that offer New York to Chicago flights. When booking this route, the cheapest RT price found was $84. New York John F Kennedy Intl Airport is the most common New York airport to take off from when flying to Chicago. Chicago O'Hare Intl Airport is the most popular arrival airport in Chicago. When flying from New York to Chicago, Delta flights are 8% more popular than any other airline flying that same route.
If you’re traveling from New York to Chicago, one of the more common airlines traveling that route is United Airlines. Flights from United Airlines traveling this route typically cost $278.36 RT. This price is typically 53% more expensive than other airlines that offer New York to Chicago flights. When booking this route, the cheapest RT price found was $146. The most popular departure airport in New York when flying to Chicago is New York John F Kennedy Intl Airport. The most popular airport to fly into when visiting Chicago is Chicago O'Hare Intl Airport. When flying from New York to Chicago, United Airlines flights are 8% more popular than any other airline flying that same route.
Fly from
Fly to
Budget
$50 - $146
Route
Depart
Return
Price
New York LaGuardiaChicago O'Hare Intl
LGA - ORD
LGAORD
New York LaGuardia
Tue 9/10
Nonstop2h 39m
Chicago O'Hare Intl
Sat 9/14
Nonstop2h 11m
New York LaGuardiaChicago O'Hare Intl
LGA - ORD
LGAORD
New York LaGuardia
Tue 6/11
1 stop11h 25m
Chicago O'Hare Intl
Wed 6/12
Nonstop2h 18m
New York LaGuardiaChicago O'Hare Intl
LGA - ORD
LGAORD
New York LaGuardia
Wed 9/25
Nonstop2h 37m
Chicago O'Hare Intl
Sat 9/28
Nonstop2h 12m
New York LaGuardiaChicago O'Hare Intl
LGA - ORD
LGAORD
New York LaGuardia
Sat 9/14
Nonstop2h 37m
Chicago O'Hare Intl
Sat 9/21
Nonstop2h 11m
New York LaGuardiaChicago O'Hare Intl
LGA - ORD
LGAORD
New York LaGuardia
Tue 6/11
Nonstop2h 42m
Chicago O'Hare Intl
Sat 6/15
1 stop8h 08m
New York LaGuardiaChicago Midway
LGA - MDW
LGAMDW
New York LaGuardia
Tue 9/10
1 stop10h 53m
Chicago Midway
Sat 9/14
1 stop15h 00m
New York John F Kennedy IntlChicago O'Hare Intl
JFK - ORD
JFKORD
New York John F Kennedy Intl
Sat 8/24
Nonstop2h 45m
Chicago O'Hare Intl
Wed 8/28
Nonstop2h 19m
New York LaGuardiaChicago O'Hare Intl
LGA - ORD
LGAORD
New York LaGuardia
Sat 8/17
Nonstop2h 59m
Chicago O'Hare Intl
Wed 8/21
Nonstop2h 14m
NewarkChicago O'Hare Intl
EWR - ORD
EWRORD
Newark
Tue 7/2
Nonstop2h 35m
Chicago O'Hare Intl
Tue 7/2
Nonstop2h 20m
CHI Temperature | 23 - 73.4 °F |
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Boarding
Overall
Crew
Comfort
Entertainment
Food
Reviews
Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.
Boarding
Overall
Crew
Comfort
Entertainment
Food
Reviews
Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.
Boarding
Overall
Crew
Comfort
Entertainment
Food
Reviews
Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.
Boarding
Overall
Crew
Comfort
Entertainment
Food
Reviews
Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.
Boarding
Overall
Crew
Comfort
Entertainment
Food
Reviews
Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.
Boarding
Overall
Crew
Comfort
Entertainment
Food
Reviews
Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.
Chicago, with its dramatic location along the shores of Lake Michigan, is the professional, business, educational and cultural hub of the Midwest. When in Chicago, you have a wealth of choices, whether you prefer to tour architectural masterpieces, take in the top comedy improv groups in the country, attend a Chicago Cubs game at Wrigley Field, or just get some business done. Not surprisingly, it's easy to find flights between the first and third-largest cities in the United States: New York City and Chicago.
Whether you're traveling for business or vacation, Chicago is a friendly, welcoming town that combines high-end urban style with Midwestern hospitality. Take a cruise down the Chicago River to marvel at the architecture of this city's startling skyscrapers, or head to the suburbs to explore some of Frank Lloyd Wright's greatest designs. The Art Institute of Chicago is home to some of the greatest Impressionist paintings in the world, and the Magnificent Mile along Michigan Avenue satisfies even the most demanding shopper. Finish a day in Chicago with uproarious laughter at one of the many improv performances around town.
Your visit to Chicago can combine business and fun seamlessly. Just remember to bundle up against the wind that sweeps off Lake Michigan during all seasons. To find a cheap flight to Chicago from NYC at the perfect time of day, use our smart search engine.