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.
Round-trip from | $132 (Priceline) |
---|---|
One-way from | $64 (FlightHub) |
Popular in | December |
Cheapest in | September |
Average price | $236 |
Good round-trip deal | $222 or less |
Good one-way deal | $134 or less |
Fly from
Fly to
Route
Depart
Return
Price
NewarkChicago
EWR - ORD
EWRORD
Newark
Thu 10/16
9:33 pm-11:10 pm
Nonstop2h 37m
Chicago O'Hare Intl
Sun 10/19
5:10 pm-8:28 pm
Nonstop2h 18m
NewarkChicago
EWR - ORD
EWRORD
Newark
Tue 7/29
11:04 am-4:38 pm
1 stop6h 34m
Chicago O'Hare Intl
Mon 8/4
4:37 pm-12:12 am
1 stop6h 35m
New YorkChicago
JFK - ORD
JFKORD
New York John F Kennedy Intl
Sat 8/30
9:29 am-11:18 am
Nonstop2h 49m
Chicago O'Hare Intl
Tue 9/2
11:35 am-2:58 pm
Nonstop2h 23m
New YorkChicago
LGA - MDW
LGAMDW
New York LaGuardia
Sat 8/30
7:30 am-8:50 am
Nonstop2h 20m
Chicago Midway
Tue 9/2
6:00 am-9:00 am
Nonstop2h 00m
New YorkChicago
LGA - ORD
LGAORD
New York LaGuardia
Mon 9/15
3:13 pm-4:51 pm
Nonstop2h 38m
Chicago O'Hare Intl
Fri 9/26
11:13 am-2:18 pm
Nonstop2h 05m
New YorkChicago
JFK - ORD
JFKORD
New York John F Kennedy Intl
Thu 7/31
6:59 am-3:27 pm
1 stop9h 28m
Chicago O'Hare Intl
Sat 8/2
5:07 pm-12:42 am
1 stop6h 35m
NewarkChicago
EWR - ORD
EWRORD
Newark
Sat 8/23
5:55 am-11:36 am
1 stop6h 41m
Chicago O'Hare Intl
Wed 8/27
2:40 pm-12:13 am
1 stop8h 33m
New YorkChicago
LGA - ORD
LGAORD
New York LaGuardia
Wed 7/23
6:30 am-4:04 pm
1 stop10h 34m
Chicago O'Hare Intl
Tue 7/29
8:09 am-5:30 pm
1 stop8h 21m
NewarkChicago
EWR - MDW
EWRMDW
Newark
Fri 9/19
11:15 am-3:58 pm
1 stop5h 43m
Chicago Midway
Mon 9/22
5:04 pm-12:34 am
1 stop6h 30m
New YorkChicago
LGA - MDW
LGAMDW
New York LaGuardia
Tue 9/9
6:30 am-3:58 pm
1 stop10h 28m
Chicago Midway
Sat 9/13
11:23 am-8:02 pm
1 stop7h 39m
To ensure you get the cheapest price possible for a flight from New York to Chicago, you should look to book at least 35 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 30% 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 (192 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (48 on average).
Crew
Overall
Comfort
Entertainment
Food
Boarding
Reviews
John,May 2025
PVD - BNA
Crew
Overall
Comfort
Entertainment
Food
Boarding
Reviews
John,May 2025
PVD - BNA
Crew
Overall
Comfort
Entertainment
Food
Boarding
Reviews
John,May 2025
PVD - BNA
Crew
Overall
Comfort
Entertainment
Food
Boarding
Reviews
John,May 2025
PVD - BNA
Crew
Overall
Comfort
Entertainment
Food
Boarding
Reviews
John,May 2025
PVD - BNA
Crew
Overall
Comfort
Entertainment
Food
Boarding
Reviews
John,May 2025
PVD - BNA
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$66 | Average$158 | FlexibilityNo cancel fee | On-time65% | |
Cheapest$84 | Average$230 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$98 | Average$280 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$118 | Average$329 | FlexibilityNo cancel fee | On-timeN/A | |
Cheapest$137 | Average$265 | FlexibilityNo cancel fee | On-time71% | |
Cheapest$147 | Average$297 | FlexibilityNo cancel fee | On-time69% | |
Cheapest$151 | Average$252 | FlexibilityNo cancel fee | On-time63% |