Spirit's Big Front Seats offer 11 inches more legroom, ideal for comfort on short flights.
Spirit's self-service bag drop saves time; print your boarding pass in advance to avoid fees.
Most accurate provider | FlightHub 3 stars |
---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $106 (Cheapflightsfares) |
One-way from | $52 (FlightHub) |
Popular in | December |
Cheapest in | September |
Average price | $206 |
Good round-trip deal | $183 or less |
Good one-way deal | $99 or less |
Fly from
Fly to
Route
Depart
Return
Price
NewarkChicago
EWR - ORD
EWRORD
Newark
Tue 6/3
5:55 am-7:27 am
Nonstop2h 32m
Chicago O'Hare Intl
Sat 6/7
9:08 pm-12:29 am
Nonstop2h 21m
New YorkChicago
LGA - ORD
LGAORD
New York LaGuardia
Sat 5/31
6:30 pm-8:07 pm
Nonstop2h 37m
Chicago O'Hare Intl
Sat 6/7
5:51 am-9:00 am
Nonstop2h 09m
New YorkChicago
JFK - ORD
JFKORD
New York John F Kennedy Intl
Sun 5/25
8:00 pm-9:54 pm
Nonstop2h 54m
Chicago O'Hare Intl
Wed 5/28
4:03 pm-7:29 pm
Nonstop2h 26m
New YorkChicago
LGA - ORD
LGAORD
New York LaGuardia
Wed 4/23
10:57 am-12:20 am
1 stop14h 23m
Chicago O'Hare Intl
Thu 4/24
8:11 am-4:29 pm
1 stop7h 18m
New YorkChicago
JFK - ORD
JFKORD
New York John F Kennedy Intl
Sat 4/19
8:59 am-11:05 am
Nonstop3h 06m
Chicago O'Hare Intl
Fri 4/25
5:10 pm-8:30 pm
Nonstop2h 20m
New YorkChicago
LGA - MDW
LGAMDW
New York LaGuardia
Sat 4/19
7:15 am-8:40 am
Nonstop2h 25m
Chicago Midway
Sat 4/26
6:15 pm-9:25 pm
Nonstop2h 10m
New YorkChicago
LGA - ORD
LGAORD
New York LaGuardia
Sat 4/19
5:40 pm-7:29 pm
Nonstop2h 49m
Chicago O'Hare Intl
Tue 4/22
10:10 am-1:27 pm
Nonstop2h 17m
New YorkChicago
JFK - ORD
JFKORD
New York John F Kennedy Intl
Sat 5/3
8:00 am-9:55 am
Nonstop2h 55m
Chicago O'Hare Intl
Sat 5/10
6:18 pm-10:00 pm
Nonstop2h 42m
NewarkChicago
EWR - MDW
EWRMDW
Newark
Wed 5/28
1:05 pm-6:45 pm
1 stop6h 40m
Chicago Midway
Wed 6/4
4:15 pm-1:07 am
1 stop7h 52m
NewarkChicago
EWR - ORD
EWRORD
Newark
Sat 5/31
6:05 am-11:47 am
1 stop6h 42m
Chicago O'Hare Intl
Tue 6/3
3:57 pm-1:07 am
1 stop8h 10m
Provider | Price Accuracy | Trust Score* |
---|---|---|
Price Accuracy1 star | Trust Score*3 stars | |
Price Accuracy3 stars | Trust Score*3 stars | |
Price Accuracy3 stars | Trust Score*3 stars | |
Price Accuracy3 stars | Trust Score*2 stars | |
Price Accuracy1 star | Trust Score*3 stars | |
Price Accuracy1 star | Trust Score*3 stars | |
Price Accuracy- | Trust Score*3 stars | |
Price Accuracy3 stars | Trust Score*2 stars | |
Price Accuracy3 stars | Trust Score*3 stars | |
Price Accuracy3 stars | Trust Score*3 stars |
To ensure you get the cheapest price possible for a flight from New York to Chicago, you should look to book at least 61 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
Currently, August 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 March is currently the most expensive (average of $321). 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.
It’s typically best to fly out from New York to Chicago in the evening. Doing so could potentially save you 31% on the flight price compared to flying at noon, which is usually more expensive.
Travelers seeking maximum savings on their New York to Chicago flight should consider departing on Tuesday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
The most flights from NYC to CHI are scheduled on a Thursday (179 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (42 on average).
In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.
If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).
Overall
Boarding
Entertainment
Crew
Comfort
Food
Reviews
Cheri,Jan 2025
FAT - SEA
Overall
Boarding
Entertainment
Crew
Comfort
Food
Reviews
Cheri,Jan 2025
FAT - SEA
Overall
Boarding
Entertainment
Crew
Comfort
Food
Reviews
Cheri,Jan 2025
FAT - SEA
Overall
Boarding
Entertainment
Crew
Comfort
Food
Reviews
Cheri,Jan 2025
FAT - SEA
Overall
Boarding
Entertainment
Crew
Comfort
Food
Reviews
Cheri,Jan 2025
FAT - SEA
Overall
Boarding
Entertainment
Crew
Comfort
Food
Reviews
Cheri,Jan 2025
FAT - SEA
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.
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Cheapest$65 | Average$147 | FlexibilityNo cancel fee | On-time65% | |
Cheapest$68 | Average$323 | FlexibilityNo cancel fee | On-timeN/A | |
Cheapest$84 | Average$238 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$98 | Average$164 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$137 | Average$270 | FlexibilityNo cancel fee | On-time71% | |
Cheapest$148 | Average$248 | FlexibilityNo cancel fee | On-time63% | |
Cheapest$149 | Average$280 | FlexibilityNo cancel fee | On-time69% |