Q: What is the typical price of a round-trip flight between New York and Chicago?

Prices are currently low for flights on this route. Typical prices usually range from $124 to $238. The lowest price recently found on this route was $93.

Question 1

Which airline has the best punctuality record on New York to Chicago flights?

Accepted Answer

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 12% of their flights experiencing any sort of delay.

Question 2

How long does it take to fly to Chicago?

Accepted Answer

Average flight duration from New York to Chicago depends on which airport you fly into and out of. Flying from Newark to Chicago O'Hare Intl Airport is 2h 28m on average, while flying from New York to Chicago O'Hare Intl Airport is 2h 34m on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

Question 3

Which layover airport offers the lowest fares from New York to Chicago?

Accepted Answer

Flights via Atlanta (ATL) offer the lowest average round-trip price of $143.

Question 4

How have New York to Chicago flight prices changed over time?

Accepted Answer

As of January 2026, prices for New York to Chicago flights are approximately 26% cheaper when compared to flights at the same time last year.

Question 5

What is the typical price of a round-trip flight between New York and Chicago?

Accepted Answer

Prices are currently low for flights on this route.Typical prices usually range from $124 to $238.
The lowest price recently found on this route was $93.

Question 6

How many flights depart from New York to Chicago on average per week?

Accepted Answer

829 flights are operational weekly from New York to Chicago as of January 2026. The most popular departure day for this route is Wed, with 21% of flights per week taking off on this day.

Question 7

How often are flights from New York to Chicago delayed?

Accepted Answer

Historically, on average around 16% of flights between New York and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 159 minutes.

Question 8

Which layover airport has the shortest travel time from New York to Chicago?

Accepted Answer

Flights connecting via Pittsburgh (PIT) have the shortest average one-way travel time: 4h 20m.

Question 9

What day of the week experiences the fewest flight delays on this route?

Accepted Answer

Saturday is statistically the day of the week which experiences the fewest number of delays on this flight route. Thursday has historically seen more delays on average compared to the rest of the week.

Question 10

What is the cheapest New York to Chicago flight route?

Accepted Answer

Fly from New York John F Kennedy Intl to Chicago O'Hare Intl for the best New York - Chicago flight prices

Question 11

What is the cheapest month to fly to Chicago?

Accepted Answer

The month of January is, on average, the cheapest month to fly to Chicago from New York, with most prices found around $179. If you’re not able to fly to Chicago in January, then February is your next best option. Flight prices from New York to Chicago during February average around $192.

Question 12

Which layover airport has the shortest connection time from New York to Chicago?

Accepted Answer

Pittsburgh (PIT) has the shortest average layover time for this route: 0h 44m.

Question 13

What cabin class options are available on New York to Chicago flights?

Accepted Answer

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.

Question 14

What airlines fly to Chicago?

Accepted Answer

United Airlines, American Airlines and Spirit Airlines are the top three most popular airlines that fly to Chicago from New York according to our data. United Airlines is the first choice among our users, with 41% 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.

Question 15

Which airport is the most popular layover for flights between New York and Chicago?

Accepted Answer

Atlanta (ATL) was the most common stop: 50% of momondo users choosing 1-stop flights on this route connected there.

Question 16

Can stopping save me money on New York to Chicago flights?

Accepted Answer

No. A direct flight is the cheapest option for a flight between New York to Chicago.

Question 17

What is the cheapest airline that flies from New York to Chicago?

Accepted Answer

Spirit Airlines, United Airlines, and Frontier are the most popular carriers operating from New York to Chicago

Question 18

How far in advance should I book a flight to Chicago?

Accepted Answer

You are more likely to see cheaper flights to Chicago from New York when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $237 when searching 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 $168 on momondo.

Question 19

What is the cheapest day to depart on your flight to Chicago?

Accepted Answer

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $290. 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 $367.

Question 20

How many flights depart from New York to Chicago on average per day?

Accepted Answer

As of January 2026, 118 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 41% of daily flights taking off at noon.

Question 21

What is the cheapest time of day to depart on your flight to Chicago?

Accepted Answer

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 $268. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $364.

Question 22

What is the most punctual flight time for New York to Chicago flights?

Accepted Answer

Generally, flights departing in the morning tend to experience fewer delays. Flights at night have, in the past, seen delays more frequently in comparison.

Question 23

Is flying the fastest way to get from New York to Chicago?

Accepted Answer

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 00m 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.

Question 24

Is flying the cheapest way to get from New York to Chicago?

Accepted Answer

The cheapest way is to get a flight from New York to Chicago, which can be as cheap as $93. A train from New York to Chicago is more expensive than a flight, with prices starting at $150. A bus from New York to Chicago is also an option, with an average price of $197.

Question 25

When did momondo last update prices for flights from New York to Chicago?

Accepted Answer

Prices for flights from New York to Chicago are updated daily.

Question 26

How many operators does momondo search for flights from New York to Chicago?

Accepted Answer

As of January 2026, there are 7 operators available to choose from for flights from New York to Chicago.

Question 27

How old do you have to be to fly from New York to Chicago?

Accepted Answer

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.

Question 28

What documentation or ID do you need to fly to Chicago?

Accepted Answer

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.

Best Price Found	$97
Fastest flight time	2h 20m
Direct flights	Every day
Airports in Chicago	3 airports

Airline	Rating	Free Cancellation	Price
Frontier	PriceFrom $55	Free Cancellation	Rating 5.7 3,063 reviews	Search Frontier flights
Spirit Airlines	PriceFrom $65	Free Cancellation	Rating 6.3 8,285 reviews	Search Spirit Airlines flights
JetBlue	PriceFrom $85	Free Cancellation	Rating 7.2 2,896 reviews	Search JetBlue flights
Delta	PriceFrom $101	Free Cancellation	Rating 7.9 8,021 reviews	Search Delta flights
United Airlines	PriceFrom $118	Free Cancellation	Rating 7.4 9,138 reviews	Search United Airlines flights
American Airlines	PriceFrom $151	Free Cancellation	Rating 7.2 11,090 reviews	Search American Airlines flights
Southwest	PriceFrom $154	Free Cancellation	Rating 8.0 4,249 reviews	Search Southwest flights

Cheap flights from New York to Chicago from $53

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 2/19. 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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