Cheap flights from New York to Chicago from $38
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from New York to Chicago departing on 6/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
Discover deals from 900+ travel sites with momondo.
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.Price Alerts
Price Alerts
Not ready to book? to track prices.Find the cheapest flights from New York to Chicago
Cheap round-trip flights
Cheap one-way flights
Cheap last minute flights
Cheap direct flights
American Airlines flights from New York to Chicago
Our best American Airlines deals on New York to Chicago flight tickets
Spirit Airlines flights from New York to Chicago
Our best Spirit Airlines deals on New York to Chicago flight tickets
See travel insights to Chicago from
How to get the cheapest flight ticket from New York to Chicago
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly to Chicago?
The month of September is, on average, the cheapest month to fly to Chicago from New York, with most prices found around $177. If you’re not able to fly to Chicago in September, then January is your next best option. Flight prices from New York to Chicago during January average around $179.
What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $289. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from New York to Chicago for around $375.
What is the cheapest time of day to depart on your flight to Chicago?
Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from New York to Chicago during this time can be as low as $236. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $338.
What is the cheapest New York to Chicago flight route?
Fly from Newark to Chicago O'Hare Intl for the best New York - Chicago flight prices
How far in advance should I book a flight to Chicago?
You are more likely to see cheaper flights to Chicago from New York when booking 5 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $242 when searching 5 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from New York for as low as $202 on momondo.
What cabin class options are available on New York to Chicago flights?
There are 4 cabin classes available to choose from on New York to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
Can stopping save me money on New York to Chicago flights?
No. A direct flight is the cheapest option for a flight between New York to Chicago.
How have New York to Chicago flight prices changed over time?
As of May 2025, prices for New York to Chicago flights are approximately 45% cheaper when compared to flights at the same time last year.
What is the cheapest airline that flies from New York to Chicago?
Spirit Airlines, JetBlue, and Southwest are the most popular carriers operating from New York to Chicago
What airlines fly to Chicago?
American Airlines, United Airlines and Spirit Airlines are the top three most popular airlines that fly to Chicago from New York according to our data. American Airlines is the first choice among our users, with 35% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 7 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.
How many flights depart from New York to Chicago on average per day?
As of May 2025, 120 flights take off from New York and land in Chicago each day. The most common flight departure time for this route is 3:00PM, with 39% of daily flights taking off at noon.
How many flights depart from New York to Chicago on average per week?
840 flights are operational weekly from New York to Chicago as of May 2025. The most popular departure day for this route is Tue, with 22% of flights per week taking off on this day.
When to book flights from New York to Chicago
Cheap New York to Chicago (NYC to CHI) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from New York to Chicago
Is flying the fastest way to get from New York to Chicago?
The quickest way to travel this route is to take a flight from New York to Chicago, doing so can potentially save up to 17h 17m of travel time. While these options may take longer, booking a train from New York to Chicago or a bus from New York to Chicago may suit your needs if travel time is less of a factor in your decision making.
Is flying the cheapest way to get from New York to Chicago?
The cheapest way is to get a flight from New York to Chicago, which can be as cheap as $78. A train from New York to Chicago is more expensive than a flight, with prices starting at $180. A bus from New York to Chicago is also an option, with an average price of $165.
How far is New York to Chicago by plane?
Chicago is 710.8 mi away from New York. Typically, this will take 2h 15m by plane in normal conditions.
When did momondo last update prices for flights from New York to Chicago?
Prices for flights from New York to Chicago are updated daily.
How many operators does momondo search for flights from New York to Chicago?
As of May 2025, there are 7 operators available to choose from for flights from New York to Chicago.
How old do you have to be to fly from New York to Chicago?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from New York to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from New York to Chicago?
momondo data reveals that the most frequently booked plane model on the route from New York to Chicago is Boeing 737-800, representing 18.99% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 14.34%, Airbus A320neo at 7.38%, and Boeing 737-900 at 6.56%.
What is the most popular airline from New York to Chicago?
Based on momondo bookings for flights between New York and Chicago, the leading airline is Spirit Airlines, making up 28% of the total bookings. Other popular airlines include United Airlines with 25%, American Airlines with 25%, and Delta with 12%.
Best airlines flying from New York to Chicago
Compare and see reviews for airlines that fly from New York to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $66 | Free Cancellation | Rating 6.3 8,005 reviews | |||
| PriceFrom $68 | Free Cancellation | Rating 8.0 7,951 reviews | |||
| PriceFrom $84 | Free Cancellation | Rating 7.3 2,928 reviews | |||
| PriceFrom $97 | Free Cancellation | Rating 5.9 3,286 reviews | |||
| PriceFrom $138 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $147 | Free Cancellation | Rating 7.4 8,744 reviews | |||
| PriceFrom $150 | Free Cancellation | Rating 8.0 4,290 reviews |
Delta Flights From New York to Chicago
Delta flight deals from New York to Chicago start from $68 round-trip. Over the 74 Delta flights for this route in a normal week, average airfare is usually $325 round-trip - but some users have found much cheaper deals with momondo.
Southwest Flights From New York to Chicago
Another popular option for New York to Chicago flights is Southwest (8.0/10, 4,290 ratings). Southwest flies from New York to Chicago around 42 times per week, with deals starting from $150 round-trip and rising to an average price of around $248.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from New York to Chicago?
momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from New York to Chicago. Millions of users trust and use momondo every year so you are in good hands.
Can I find flights from New York to Chicago with flexible booking policies on momondo?
Flights from New York to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.
How can momondo help me find flights from New York to Chicago?
momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from New York to Chicago.
I’m not ready to book a flight from New York to Chicago right now. Can momondo alert me if prices change?
If you are not ready to book a flight from New York to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.