New York City to Chicago Flight Route Information
| Travel Distance: | 738 Miles |
|---|---|
| Airlines Flying This Route: | American Airlines, United Airlines, Spirit Airlines |
| Weekly Flights: | 6 |
| Avg. Flight Duration: | 05.27 Hours |
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11/17/2026 Find Cheap Flights from New York City to Chicago (NYC to CHI)
NYC - New York City CHI - Chicago 
Find Cheap Flights from New York City to Chicago (NYC to CHI)
Fares Starting from $130
NYC - New York City CHI - Chicago Great deal! This is the lowest price we've seen for this one way route in the last 12 hours. Prices may change and aren't guaranteed for all flights or dates. Click on the price to continue your search and check the latest available fare. Ref. id 202609~Ref:08BUhseioUuwSitYxblY_g
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Cheap Flights from New York City to Chicago - Compare & Book Our Best Deals
With over 36 daily departures from New York City to Chicago, this route offers great flexibility for different travel plans. Browse one-way fares from $129.88, round-trip fares from $247.99, and other affordable options across different budgets. Compare flight choices, explore schedules, and book the best New York City to Chicago deals that fit your budget and travel preferences.
Top Airlines that fly from New York City to Chicago
Cheap Flight Deals from New York City to Chicago
NYC New York City Tue, Nov 17
CHI Chicago
from $130
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NYC New York City Wed, Oct 28
CHI Chicago
from $130
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NYC New York City Tue, Nov 3
CHI Chicago
from $130
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NYC New York City Wed, Nov 11
CHI Chicago
from $130
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NYC New York City Sat, Nov 14
CHI Chicago
from $130
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NYC New York City Tue, Nov 17
CHI Chicago
from $130
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NYC New York City Wed, Nov 18
CHI Chicago
from $130
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NYC New York City Wed, Nov 18
CHI Chicago
from $130
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NYC New York City Sat, Oct 31
CHI Chicago
from $134
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NYC New York City Tue, Dec 8
CHI Chicago
from $134
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*All fares above were last found on: Fares are one way/round trip. Fares incl. all fuel surcharges, taxes & fees and our service fees. Displayed fares are subject to change and cannot be guaranteed at the time of booking. See all booking terms and conditions. 202609~Ref:08BUhseioUuwSitYxblY_g
Insights about cheap flights from New York City to Chicago – Direct Flights, Duration & Best Travel Time
When it comes to booking cheap flights, having the right information at your fingertips can make all the difference. Dive into the insights for cheap flights from New York City to Chicago and enhance your travel experience!
Daily Flights
36
Cheapest Month
March
Avg. Flight Duration
05.27
Peak Season
July
Distance
738 miles
Direct Flights
1099
When is the Cheapest Time to Book Flights from NYC to CHI?
Explore data-powered insights and trends for flights from New York City to Chicago. Discover average fares, cheap months to fly, when to book, and plan smarter.
What’s the cheapest day of the week to fly from New York City to Chicago?‡
What is the cheapest month to fly from New York City to Chicago?‡
‡This information is based on historical data from the last 365 days.
Finding Affordable Flights from New York City to Chicago
- Plan Ahead - One of the keys to securing cheap flights from New York City to Chicago is to plan your trip well in advance. Airlines often offer lower prices for those who book tickets months ahead. Keep an eye on special promotions and sales events, which can yield significant savings.
- Flexibility is Key - Being flexible with your travel dates can also lead to substantial cost savings. Consider flying during off-peak seasons or on weekdays when prices tend to be lower.
- Set Price Alerts - To keep tabs on flight prices, consider setting up fare alerts. These alerts will notify you when fares from New York City to Chicago drop, giving you the opportunity to grab cheap deals.
- Consider Nearby Airports - If Chicago has multiple airports, check the prices at each one. Sometimes, flying into a nearby airport and then taking a short train or bus ride to your destination can be a much cheaper option.
- Bundle and Save - Booking your flight and accommodation together as a package can often result in significant savings. CheapOair offers these bundled deals, so make sure to explore this option.
When should I book flights from NYC to CHI? ‡
‡Got flexible travel dates? Use our flight data from the past year to discover ideal time to fly from New York City to Chicago. Find out which months and days typically offer lower fares and let CheapOair search for the best options.
CheapOair provides the predicted prices for one-way trips or round-trips with a duration of 7 days for domestic and 14 days for international trips based on historical data and available flight information. Graphs are estimates only. Prices are subject to change and can't be guaranteed until ticketed.
Estimated price for
Round-trip
‡Graphs are estimates only. Based on historical data and available flight information. Prices are subject to change and cannot be guaranteed until ticketed.
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Insights About Flying from New York City to Chicago
Which is the high season to travel from New York City to Chicago?
The month of July is considered the high season for flying from NYC to CHI. Traveling during the high season can affect ticket prices and availability, making this data crucial for trip planning.
How many direct flights are available from NYC to CHI?
There are a total of 1099 direct flights from New York City to Chicago. For travelers seeking convenience and shorter travel times, this data is important when choosing flight options.
Which is the low season to travel from New York City to Chicago?
March is considered the low season for traveling from New York City to Chicago, Illinois. Travelers looking for cost-effective options and fewer crowds may consider traveling during this period.
How many daily flights are there between New York City to Chicago?
There are as many as 36 daily flights available for travelers between NYC to CHI. This data offers flexibility in choosing departure times that best suit your schedule.
At what time does the last flight depart to Chicago?
The last flight to Chicago typically departs between 10:00PM - 11:00PM. Travelers who prefer late-night departures will find this information valuable for planning their journey.
What percentage of travelers spent an average of 3 days in Chicago, Illinois?
Approximately 43.77% of travelers spent an average of 3 days exploring Chicago. This information can assist in planning the duration of your stay in Chicago
What percentage of NYC to CHI flyers traveled with kids under 14?
About 4% of passengers on flights from New York City to Chicago were accompanied by children under the age of 14. This information is useful if you're planning a family trip and want to know how common it is to travel with young children on this route.
What percentage of New York City to Chicago travelers were over 60 years old?
A notable 11% of travelers were aged 60 or older. This statistic provides insights for senior travelers or those seeking a mature travel demographic.
What percentage of NYC to CHI travelers were millennials?
Millennials make up a significant portion of travelers on this route, accounting for 44% of all passengers. If you're a millennial looking to connect with like-minded travelers, this statistic might interest you.
What percentage of New York City to Chicago travelers were female?
Almost half of the passengers, approximately 46% were female. Knowing the gender distribution can be useful for solo female travelers or those interested in gender-related travel insights.
What percent of New York City to Chicago travellers booked first or business class?
2% of travelers booked first or business class on this route.
At what time the earliest flight departs from New York City?
The earliest flight departs at 7:00AM - 8:00AM.
On which days one can have the most flight options in Chicago?
Monday offer the most flight options in Chicago.
§
All flight facts are based on last 3 months' data except the highest and lowest booking months that are based on last 3 months' data.
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Cheap Flights from New York City to Chicago
A trip to the Windy City offers something for every type of traveler. Whether you prefer to meander around museums or search for the best deep-dish in the city, a cheap ticket from New York City to Chicago unlocks endless possibilities. From history to sports, Chicago has a rich culture that surprises and captivates. And with CheapOair's tools for finding cheap flights from LGA to ORD, you may even have some leftover funds for the trip itself.
Why Purchase Cheap Flights From New York City To Chicago? 5 Attractions To Experience
Visit Millennium Park.
Your trip to Chicago would not be complete without a trip to Millennium Park. Here you will find �The Bean,� Chicago�s iconic reflective sculpture that has appeared in countless films and TV shows. Often, you can also catch a concert or festival while you are there.
Learn at the Field Museum.
History buffs can revel at Chicago�s famous natural history museum. Here you will find dinosaur bones, models of animals, and information about our planet�s past. This is a great destination for families and people of all ages.
Cheer on the Cubs at Wrigley Field.
This stadium is home to Chicago�s own Cubs, so grab some team gear and cheer like a local. As one of the most famous baseball fields in the U.S., Wrigley will be a blast for sports fans and sightseers alike.
Wander through Shedd Aquarium.
This must-see attraction sits on the banks of Lake Michigan, offering a glimpse of over 30,000 aquatic creatures. You are welcome to walk around and watch the animals, or you can opt for more interactive animal experiences.
Sightsee at Navy Pier.
History is alive in Chicago at Navy Pier. While strolling down the pier, you will see the large ferris wheel, beautiful carousel, and other attractions. Shop and eat at the shops along the pier or simply walk and enjoy the stunning views.
Have some laughs with Second City
Chicago is well known for having one of the most vibrant theater scenes in the country, and many comedy legends got their start at the city's famous Second City improv theater. Visit one of the many local comedy clubs and you might just see the next big late-night comedy star.
Looking for cheap flight tickets and deals to LGA (New York) to ORD (Chicago)? Whether you're going for business, pleasure, or to visit one of the area's many colleges and universities, CheapOair has you covered. Browse our discount ticket database, book your cheap flight, and get ready to experience this iconic Midwestern city.
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