Cheap flights from New York to Chicago from £24
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 1/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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JetBlue flights from New York to Chicago
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United Airlines flights from New York to Chicago
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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 typical price of a round-trip flight between New York and Chicago?
What is the cheapest month to fly to Chicago?
The cheapest month to fly to Chicago from New York is in September. Flight prices, which tend to average around £130, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of September, then book flights to Chicago from New York during January instead. Flights to Chicago in January, while not as cheap as those in September, still average around £132.
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 Tuesday when prices can be found for as low as £120. This is often the case because there is less demand to fly during this day of the week. The most expensive day to fly to Chicago is Thursday, with ticket prices averaging around £251.
What is the cheapest time of day to depart on your flight to Chicago?
Flying to Chicago from New York in the evening is the least expensive time of day to depart. momondo users have found prices as low as £116 when looking at flights departing in the evening. Flights in the afternoon are often more expensive, with an average ticket price of £276.
What is the cheapest New York to Chicago flight route?
Fly from New York LaGuardia 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 £177 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 £147 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 June 2025, prices for New York to Chicago flights are approximately 51% cheaper when compared to flights at the same time last year.
What is the cheapest airline that flies from New York to Chicago?
JetBlue, United Airlines, and Spirit Airlines are the most popular carriers operating from New York to Chicago
Which airlines fly to Chicago?
Spirit Airlines, American Airlines and JetBlue are the top three most popular airlines that fly to Chicago from New York according to our data. Spirit Airlines is the first choice among our users, with 46% of people opting to fly with this airline when travelling to Chicago. Keep in mind that there are 3 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?
The number of flights available between New York and Chicago is 134 per day as of June 2025. The most frequent departure time is 14:00, with 41% of daily flights leaving at midday.
How many flights depart from New York to Chicago on average per week?
As of June 2025, there are 939 flights per week flying from New York to Chicago. The most common day of the week flights depart is Thu, with 19% of flights 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?
Based on just travel duration our users have found a flight from New York to Chicago to be the fastest option to their destination at just 2h 30m. If travel time is less of a concern you may want to look into booking some alternative forms of transportation like a train from New York to Chicago or a bus from New York to Chicago.
Is flying the cheapest way to get from New York to Chicago?
Planning to book a flight from New York to Chicago can be a safe bet when looking for a low-cost deal to your destination. Currently, a train and a bus are priced higher than the cost of a flight. You can search prices for a train from New York starting at £132 to Chicago or a bus from New York to Chicago starting at £132 if that is your preferred method of transportation.
How far is New York to Chicago by plane?
New York and Chicago are 710.8 mi apart from one another. Typically, this will take 2h 30m 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?
The number of operators available for flights from New York to Chicago is 3 as of June 2025.
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 necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
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 19.81% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 14.04%, Airbus A321neo at 8.02%, and Boeing 737-900 at 7.34%.
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 49% of the total bookings. Other popular airlines include American Airlines with 17%, United Airlines with 14%, 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 £44 | Free Cancellation | Rating 6.3 8,054 reviews | |||
| PriceFrom £50 | Free Cancellation | Rating 7.3 2,925 reviews | |||
| PriceFrom £93 | Free Cancellation | Rating 7.2 10,000 reviews |
JetBlue Flights From New York to Chicago
JetBlue flight deals from New York to Chicago start from £68 round-trip. Over the 7 JetBlue flights for this route in a normal week, average airfare is usually £136 round-trip - but some users have found much cheaper deals with momondo.
American Airlines Flights From New York to Chicago
American Airlines (7.2/10 from 10,000 reviews) operates around 86 flights from New York to Chicago in any given week. The average American Airlines airfare for this route is around £217, with deals from around £127 rare but found on momondo. Referenced prices are for round-trip New York to Chicago flight searches in the last 72 hours.
Why use momondo?
Why should I use momondo to find a flight deal from New York to Chicago?
Finding the right flight to Chicago from New York is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.
Can I find flights from New York to Chicago with flexible booking policies on momondo?
Yes. momondo allows you to filter the results for New York to Chicago flights to just show those with flexible booking policies.
How can momondo help me find flights from New York to Chicago?
momondo helps you find the best flight between New York and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.
I’m not ready to book a flight from New York to Chicago right now. Can momondo alert me if prices change?
Yes momondo offers price alerts on flights to Chicago from New York. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.