Popular in | June |
---|---|
Cheapest in | February |
Round-trip from | $222 |
One-way from | $73 |
Users have found that leaving on a Monday can be a cost-effective option. It’s possible to save up to 39% 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 48 days in advance, which can save you up to 76% on flights from New York to Chicago compared to booking the week you need them. Waiting 48 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 $302. For sooner than that we have options available in the next 3 days from $415.
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 $268 on average during February, but can be found for as low as $107.
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.
Fly from
Fly to
Budget
$89 - $195
Route
Depart
Return
Price
New York LaGuardiaChicago O'Hare Intl
LGA - ORD
LGAORD
New York LaGuardia
Thu 6/6
Nonstop2h 38m
Chicago O'Hare Intl
Wed 6/12
Nonstop2h 18m
New York LaGuardiaChicago O'Hare Intl
LGA - ORD
LGAORD
New York LaGuardia
Tue 5/7
1 stop9h 59m
Chicago O'Hare Intl
Tue 5/14
2 stops20h 47m
New York LaGuardiaChicago O'Hare Intl
LGA - ORD
LGAORD
New York LaGuardia
Sat 5/4
1 stop13h 23m
Chicago O'Hare Intl
Wed 5/8
1 stop6h 10m
New York LaGuardiaChicago O'Hare Intl
LGA - ORD
LGAORD
New York LaGuardia
Sat 5/11
Nonstop2h 37m
Chicago O'Hare Intl
Mon 5/13
Nonstop2h 09m
New York John F Kennedy IntlChicago O'Hare Intl
JFK - ORD
JFKORD
New York John F Kennedy Intl
Tue 5/28
Nonstop2h 50m
Chicago O'Hare Intl
Thu 5/30
Nonstop2h 28m
New York LaGuardiaChicago Midway
LGA - MDW
LGAMDW
New York LaGuardia
Tue 5/14
1 stop9h 25m
Chicago Midway
Wed 6/5
1 stop9h 49m
New York LaGuardiaChicago O'Hare Intl
LGA - ORD
LGAORD
New York LaGuardia
Tue 7/2
Nonstop2h 50m
Chicago O'Hare Intl
Tue 7/9
Nonstop2h 19m
New York John F Kennedy IntlChicago O'Hare Intl
JFK - ORD
JFKORD
New York John F Kennedy Intl
Wed 5/22
Nonstop3h 02m
Chicago O'Hare Intl
Wed 5/29
Nonstop2h 13m
New York John F Kennedy IntlChicago O'Hare Intl
JFK - ORD
JFKORD
New York John F Kennedy Intl
Wed 6/12
1 stop8h 49m
Chicago O'Hare Intl
Mon 6/17
1 stop13h 26m
Currently, February is the cheapest month in which you can book a flight from New York to Chicago (average of $245). Flying from New York to Chicago in June is currently the most expensive (average of $356). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
January
$248
February
$245
March
$280
April
$273
May
$282
June
$356
July
$336
August
$276
September
$258
October
$248
November
$270
December
$248
CHI Temperature | 23 - 73.4 °F |
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Entertainment
Boarding
Overall
Comfort
Crew
Food
Reviews
I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.
Entertainment
Boarding
Overall
Comfort
Crew
Food
Reviews
I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.
Entertainment
Boarding
Overall
Comfort
Crew
Food
Reviews
I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.
Entertainment
Boarding
Overall
Comfort
Crew
Food
Reviews
I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.
Entertainment
Boarding
Overall
Comfort
Crew
Food
Reviews
I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.
Entertainment
Boarding
Overall
Comfort
Crew
Food
Reviews
I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.
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.
7%of flight departures | Early morningMidnight to 6 am |
---|---|
35%of flight departures | Morning6 am to noon |
41%of flight departures | AfternoonNoon to 6 pm |
17%of flight departures | Evening6 pm to midnight |
Sunday | 147daily flights |
---|---|
Monday | 209daily flights |
Tuesday | 191daily flights |
Wednesday | 193daily flights |
Thursday | 187daily flights |
Friday | 204daily flights |
Saturday | 101daily flights |
Cheapflights helps you search for flights from New York to Chicago via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.
It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from New York to Chicago.
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Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Chicago from New York today and book when prices fit your budget.